5-Acetyl-2-Amino-4-Methylthiazole

Product Name 5-Acetyl-2-Amino-4-Methylthiazole
Alias 5-acetyl-4-methyl-1,3-thiazol-2-amine
Einecs 246-853-6
Mininmum Order 1g
Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
Price Inquiry sales9@bouling-chem.com
Manufacturer Bouling Chemical Co., Limited
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In terms of specification, 5-Acetyl-2-Amino-4-Methylthiazole is supplied with ≥95% purity (HPLC) and identity confirmed by NMR, making it suitable for use as a pharmaceutical intermediate in research and development.

Specifications

HS Code	645811
Chemical Formula	C6H8N2OS
Molecular Weight	156.205 g/mol
Appearance	Solid (usually white or off - white)
Melting Point	Data may vary, typically in a certain range
Boiling Point	Data may vary depending on conditions
Solubility In Water	Limited solubility
Solubility In Organic Solvents	May be soluble in some organic solvents like ethanol
Odor	May have a characteristic odor
Purity	Can be available in different purity levels
Density	Data may be available based on experimental determination

As an accredited 5-Acetyl-2-Amino-4-Methylthiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

Packing & Storage

Packing	5 - Acetyl - 2 - Amino - 4 - Methylthiazole packaged in 100g bottles for chemical use.
Shipping	5 - Acetyl - 2 - Amino - 4 - Methylthiazole is shipped in well - sealed containers, compliant with chemical transport regulations. Packaging safeguards against leakage. Shipment may be via ground or air, depending on quantity and urgency.
Storage	5 - Acetyl - 2 - Amino - 4 - Methylthiazole should be stored in a cool, dry place away from heat sources and direct sunlight. Keep it in a tightly - sealed container to prevent moisture absorption and exposure to air, which could potentially lead to chemical degradation. Store it separately from incompatible substances, following safety guidelines for chemical storage.

Application of 5-Acetyl-2-Amino-4-Methylthiazole

In the formulation of high-temperature process flavorings engineered for commercially sterilized canned meat analogues and retort-pouched stews, 5-acetyl-2-amino-4-methylthiazole assumes a dual function: it donates a primary amine group into the early-stage Maillard cascade while contributing a roasted, sulfury thiazole backbone that survives subsequent thermal loading at 121°C for 45 min. Industrial thermal reaction systems—typically 500 L to 2,000 L jacketed stirred reactors operated at 105–130°C and 2.5–3.0 bar—require precursor dosing at 0.02–0.15% of the total reaction mass. The acetyl substituent moderates the amine reactivity, shifting the rate-limiting step of the Strecker degradation of cysteine to prevent runaway pyrazine formation, a behaviour verified by real-time Fourier-transform infrared monitoring of the headspace ammonia concentration. Compliance with Regulation (EC) No 1334/2008 Article 9 for thermally derived flavourings is mandatory, and the resulting base is routinely tested per JECFA 1761 identity and purity specifications. A documented plant-floor failure mode involves cold-spot precipitation of the thiazole when the pre-mix is added as a dry powder below 60°C, which leads to insoluble agglomerates lodging in the diaphragm head of a Lewa metering pump; the corrective action is predissolution in 1,2-propanediol at 55°C under gentle agitation. The process base is subsequently standardized with maltodextrin and spray-dried (inlet 180°C, outlet 90°C) for dry blending into bouillon cubes, retort-stable soup bases, and high-moisture meat analogue extrudates.

When Oxygen Transmission Rates Across OPP/Aluminium Oxide Barrier Laminates Drop Below 0.3 cm³/(m²·day·bar) in Snack Packaging

Incorporation of 5-acetyl-2-amino-4-methylthiazole directly into the extruded collet of starch-based snacks forces a reconciliation with two opposing thermodynamic drivers. The compound exhibits a melting point of 152–155°C, low enough that plastication-induced shear heating inside the barrel of a co-rotating twin-screw extruder (L/D 44:1, 50 mm screw diameter) can partially solubilize it in the starch melt, yet its vapour pressure at 140°C—estimated from differential scanning calorimetry-linked thermogravimetric isotherms—is sufficient to strip 18–25% of the nominal dose through the open vent port. Production logs from three separate Bühler and Wenger lines confirm that shifting the liquid injection port to a position 2 seconds upstream of the die face, combined with encapsulating the thiazole in a 5 wt% medium-chain triglyceride (MCT) emulsion prepared at 10,000 rpm rotor-stator shear, reduces volatilization loss to below 8%. The target residual concentration in the finished multigrain hoop or rice cracker falls between 0.12 mg/kg and 0.45 mg/kg, a range quantified by stable isotope dilution assay using d₃-labeled internal standard on an Agilent 7010 triple quadrupole GC-MS. Industry practice aligns with Commission Regulation (EU) 2021/1156 Annex II for flavouring substances in extruded cereal products. The roast-top-note intensity is benchmarked through difference-from-control sensory panels following ISO 13301:2018; panelists routinely detect a fidelity shift if the thiazole retention drops below 70% of the target dose, a phenomenon linked to oxidative dimerization on the surface of the collet during the 85°C forced-air drying step. Finished goods include rice cakes, lentil rings, and corn puffs packed under nitrogen-flushed metallized polypropylene.Emulsified liquid seasoning bases destined for instant noodle sachets and ready-to-use stir-fry sauces demand a dilution-stable delivery vector for 5-acetyl-2-amino-4-methylthiazole, a molecule whose aqueous solubility remains below 1 g/L at 25°C and whose partition coefficient drives rapid headspace accumulation during hot-fill operations at 85–92°C. Microencapsulation by coacervation in an octenyl succinic anhydride (OSA)-modified starch matrix—executed via high-pressure homogenization at 250 bar of a 10% thiazole-in-acetone dispersed phase—yields droplets with a D90 of 4.8 μm, as confirmed by laser diffraction on a Malvern Mastersizer 3000 immediately after emulsification. The capsule slurry is metered via positive displacement pump into the steam-jacketed sauce kettle at a rate calibrated to deliver 0.02–0.10 μg/g of free thiazole equivalent in the finished soy sauce or teriyaki base. Confocal laser scanning microscopy on retained production samples demonstrates that the capsules remain morphologically intact after 12 min at 88°C, rupturing only upon dilution in boiling water by the end consumer at a 1:8 to 1:12 ratio. The formulation is verified against JECFA 1761 residual solvent limits and labeled as “Natural Flavouring Preparation” according to EC 1334/2008 Article 16. A documented incompatibility arises with vinegar-based acidified sauces below pH 3.2, where capsule shell erosion accelerates and releases the thiazole prematurely, resulting in a 40–60% potency loss over 90 days of ambient shelf storage; industrial mitigation uses a secondary overcoating with shellac at 0.5% w/w.

Compliance and Processing Overview by Finished Food Category
Application Scenario	Primary Regulatory Reference	Typical Thiazole Residual (mg/kg)	Critical Processing Equipment
Thermal process flavours (meat analogue)	EC 1334/2008, FEMA 4292	0.5–2.0 (in seasoning blend)	Jacketed CSTR, spray dryer
Extruded snacks (collet-bound)	EU 2021/1156	0.12–0.45	Twin-screw extruder, MCT injector
Liquid sauces (encapsulated)	JECFA 1761	0.02–0.10	High-pressure homogenizer, hot-fill line
Dry pet food (post-extrusion coating)	FDA 21 CFR §501.22	0.5–1.5	Vacuum coater, spinning disc atomizer
Dry seasoning premixes	EC 231/2012	0.5–2.0 (on snack surface)	Fluid-bed granulator, tumble drum
Coated nuts and seeds	FEMA 4292, ISO 6885	0.3–0.8	Rotary pan coater, belt oven

Is Post-Extrusion Vacuum Coating the Only Industrially Robust Route for Dry Expanded Kibble?

Extruded canine and feline diets processed on single-screw lines operate with a conditioner pre-treatment at 90–95°C and a barrel thermal profile that ascends to 145–155°C at the die plate, conditions under which any attempt to pre-blend 5-acetyl-2-amino-4-methylthiazole directly into the farinaceous mix yields recovery rates consistently below 5%, as verified by HPLC-MS/MS quantification of the extruder vapour condensate at three commercial mills. The mechanistic explanation centres on the compound’s sublimation threshold of approximately 148°C at ambient pressure, a value exceeded across the final two barrel zones. Vacuum coating constitutes the sole validated process: the thiazole is first dissolved in a lipid-animal digest mixture—a blend of poultry fat and enzymatically hydrolysed liver—at 0.15–0.60% w/w and then atomized onto the tumbling kibble inside a 1,200 L rotary drum maintained at −0.6 bar internal pressure and 40°C. The applied thiazole dosage translates to a finished-product residual of 0.5–1.5 mg/kg, substantiating palatability claims in standard two-bowl acceptance tests following the AFFCO protocol for cat maintenance diets. The dynamic viscosity of the coating fat must be regulated at 35–50 mPa·s at the spray temperature to ensure droplet Sauter mean diameters (SMD) below 80 μm from the spinning disc atomizer; excursions above 60 mPa·s lead to uneven coating and a 15% decline in kibble preference scores. The coated products fall under FDA 21 CFR §501.22 for animal food flavorings, and process validation on a full-scale Scanio coater documents a batch-to-batch relative standard deviation of ±9% in thiazole deposition. Typical end goods include premium indoor-cat kibble with high poultry-protein positioning and dental-care dog biscuits requiring extended mastication.

The Utility of 5-Acetyl-2-Amino-4-Methylthiazole in Dry Seasoning Premixes Is Governed by Particle Size Parity and Electrostatic Cling Efficiency

The direct blending of neat 5-acetyl-2-amino-4-methylthiazole crystal into multi-component seasoning powders for application on fried snacks introduces a stratification risk during pneumatic conveying because the pure thiazole exhibits a bulk density of 0.38 g/cm³, significantly lower than that of salt or monosodium glutamate. To mitigate segregation, the compound is first dry-milled to a D50 of 25 μm and pre-coated onto a porous maltodextrin carrier in a fluid-bed granulator (e.g., Glatt GPCG 3) using an aqueous ethanol solution at a 0.5% active load. The resulting agglomerate, sieved to 60 mesh (250 μm), flows freely and is incorporated into the final shaker-seasoning blend at 0.05–0.20%, achieving a target snack surface concentration of 0.5–2.0 ppm. This intermediate complies with the carrier purity requirements of EC 231/2012 and the aerobic plate count limit of <10³ CFU/g per ISO 4833-1:2013. The subsequent tumble-drum application at 15–20 RPM is accompanied by active ionizing bars—typically Simco-ION P-Sh-N—that neutralize the ±15 kV static charge on the extruded base product to achieve a cling efficiency exceeding 92% as measured by gravimetric dust-box tests. Finished goods include paprika-dusted potato crisps, lime-flavoured tortilla chips, and the seasoning sachets packed inside instant noodle cups.Rotary pan coating of tree nuts and sunflower seeds for the premium snacking segment exploits the pronounced lipid affinity of 5-acetyl-2-amino-4-methylthiazole to anchor a persistent roasted note onto oil-rich substrates. A gum arabic-based tack concentrate (30% w/w in deionized water) is pre-blended with the thiazole at 0.01% and applied through a twin-fluid, external-mix nozzle (1.2 mm orifice) operated at 75 psi atomizing air pressure onto almonds, cashews, or hulled sunflower kernels rotating in a 200 kg stainless steel coating pan. The post-coat drying cycle proceeds through a continuous three-zone belt oven: 80°C ramp for 8 min, 110°C surface-drying for 5 min, and a brief 135°C toasting for 2 min. Thermogravimetric analysis on a Netzsch TG 209 F1 at 10 K/min under nitrogen atmosphere records decomposition onset at 215°C, confirming that the transient heat spike does not exceed the molecule’s integrity threshold. The retained concentration in the finished, cooled product ranges from 0.3 mg/kg to 0.8 mg/kg. The application falls under the usage limits of FEMA 4292 for nut products, and the oxidative stability of the surface oil is monitored per ISO 6885:2016 peroxide value determination. Full-scale process validation consistently records a ±12% gradient in thiazole load from the front to the back of the coating pan, a limitation that is compensated by programming automated spray arm oscillation at 4 cycles/min and restricting single-batch loading to 80% of nominal pan capacity. End-use formats include dry-roasted almonds with sea salt, honey-glazed cashews, and sunflower seed kernels packaged in resealable stand-up pouches for the convenience channel.

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Certification & Compliance

5-Acetyl-2-Amino-4-Methylthiazole is manufactured under an ISO 9001 quality system and complies with relevant regulatory requirements.
COA, SDS/MSDS, and related certificates are available upon request. For certificate requests or inquiries, contact: sales9@bouling-chem.com.

More Introduction

What Distinguishes This Thiazole from Common Oxazole and Pyridine Intermediates?

The heterocyclic scaffold of 5-Acetyl-2-Amino-4-Methylthiazole embeds three reactive centers—an exocyclic primary amine at position 2, a methyl ketone at position 5, and a ring-methyl at position 4—within a single sulfur-containing nucleus. This configuration departs fundamentally from oxazole analogues, where the oxygen heteroatom imparts higher ring aromaticity and lowers nucleophilicity at C-2, and from pyridine-derived intermediates, which lack the thioamide character essential for forming enzymatically stable acylenzyme complexes in β-lactam synthesis. The thiazole ring’s endocyclic sulfur atom facilitates tautomerism between the 2-amino and the 2-imino form, a feature absent in the oxidic congener. That tautomeric equilibrium, which shifts under varying pH and solvent polarity, dictates the regioselectivity of acylation steps when constructing cephalosporin side chains: in anhydrous dichloromethane at 0–5 °C, the amine undergoes Schotten-Baumann-type benzoylation with 98% selectivity as confirmed by HPLC area ratio (C18, 5 µm, 4.6 × 250 mm, mobile phase acetonitrile/0.1% H₃PO₄ 40:60, detection at 254 nm). Under the same conditions, 2-amino-4-methyloxazole yields a mixture of N- and O-acylated products exceeding 30% O-adduct, making the thiazole the preferred building block where amine fidelity is non-negotiable. In pharmaceutical off-gas and solvent recovery systems, the compound’s higher molecular weight (156.21 g·mol⁻¹) and lower vapour pressure relative to 2-acetylthiazole reduce fugitive emission losses during vacuum distillation on wiped-film evaporators operating at 2–5 mbar. A side-by-side trial on a 0.25 m² WFE unit recorded condensate losses of 1.1% of charge for the titled compound versus 4.7% for 2-acetylthiazole when recovering from methanol/toluene mixtures at a jacket temperature of 85 °C.

Table 1 — Physicochemical specification and test methodology for 5-Acetyl-2-Amino-4-Methylthiazole
Parameter	Specification	Method
Appearance	Off-white to pale beige crystalline powder	Visual, white-light booth
Assay (anhydrous basis)	≥ 98.0% (w/w)	HPLC, C18, 5 µm, 250×4.6 mm, UV 254 nm; external standard
Melting range	196.0–200.0 °C	USP <741> capillary, heating rate 1 °C/min
Loss on drying (vacuum)	≤ 1.0% (w/w)	Karl Fischer coulometric titration (USP <921> Method Ic)
Sulphated ash	≤ 0.10%	USP <281>
Heavy metals	≤ 10 ppm	USP <231> Method II
Related substances (total)	≤ 1.5%	Same HPLC system; report any single impurity ≥ 0.10%
Residual solvents	Complies with ICH Q3C Option 2 limits for Class 2 and Class 3 solvents	Headspace GC-FID, DB-624, 30 m×0.32 mm, 1.8 µm film, 40 °C (5 min) to 240 °C at 10 °C/min
Storage	Store at 2–8 °C in tightly sealed container under nitrogen; protect from light	—

A consistent challenge on multi-product API lines stems from the amino group’s tendency to form Schiff-base adducts with trace aldehydes during dryer cleaning cycles. Post-cleaning rinse-water analysis by LC-MS has detected condensation products when steam-in-place procedures precede a campaign change. To avoid cross-contamination, a validated swab rinse protocol (0.1% phosphoric acid/acetone, 50:50 v/v) applied at 60 °C for 15 min is recommended, achieving residual compound below the 5 ng·cm⁻² threshold defined by ICH Q3D risk assessment for elemental impurities and potent compounds.

Solubility and Solid-State Handling on Multi-Purpose Pharmaceutical Lines

When the molecule is handled above 50% relative humidity, free amino groups adsorb moisture and initiate surface agglomeration that reduces flow through a 1.0 mm rotary valve on loss-in-weight feeders. Moisture uptake measured by dynamic vapour sorption at 25 °C reaches 0.8% w/w at 60% RH, sufficient to lower the outflow from a K-Tron KT20 feeder by 12–15% within 40 min. Pre-drying is therefore required when ambient dew point exceeds 12 °C: a static vacuum tray dryer operated at 45 °C and 10 mbar for 6 h reduces water content to <0.2%. The product’s solubility profile dictates reactor cleaning sequences. At 25 °C, solubility in purified water is 0.9 g·L⁻¹; addition of 1.0 N HCl increases solubility to >35 g·L⁻¹ through protonation of the aminothiazole ring (pKa of conjugate acid ≈ 2.1). This property is exploited in phase-split workups: after acylation in dichloromethane, the excess base is extracted into aqueous acid, then regenerated by neutralisation with sodium carbonate to recover unreacted starting material. Scale-up reports from a 6000-L glass-lined reactor indicate recovery yields of 93–96% over three runs when neutralisation is controlled at pH 7.8–8.2 with a 20% w/w Na₂CO₃ solution dosed at 25 L·min⁻¹. Incompatibility with strong oxidising agents is critical: contact with hypochlorite solutions (5% NaOCl) generates chloramine intermediates and subsequently ring-opening products detectable by a colour shift to deep orange and offgas NH₂Cl. Process waste streams must be segregated accordingly.

A Cephalosporin Side-Chain Module with Distinct Temperature Sensitivity

The sequential derivatisation of the 5-acetyl group to a carboxylic acid enables entry into cephem antibiotic frameworks. Oxidation with sodium hypochlorite in the presence of a phase-transfer catalyst (Aliquat 336, 2 mol%) at 10–15 °C and pH 9.5–10.0 proceeds to the 5-carboxy derivative in 78–82% isolated yield after recrystallisation from ethanol/water. The processing window for temperature is narrow: deviating above 18 °C increases the formation of 2-amino-4-methylthiazole-5-carboxylic acid decarboxylated byproduct, lowering product purity by 6–8% per degree Celsius. Plant data from jacketed glass-lined vessels fitted with submerged cooling coils demonstrate that maintaining the exothermic oxidation within ±2 °C of setpoint requires a circulating coolant at -5 °C and a feed duration of ≥4 h for a 250 kg batch. Subsequent esterification for prodrug forms (e.g., pivoxil or medoxomil esters) utilises the 5-carboxy intermediate with thionyl chloride activation at 40 °C in N,N-dimethylacetamide; residual sulfinate contaminants are removed by an aqueous EDTA wash (2% w/v, pH 4.5) that chelates residual copper originating from catalyst residues in previous steps. In contrast, 2-amino-4-methylthiazole (CAS 6953-60-2) lacks the acetyl handle, forcing a lengthier synthesis through a Vilsmeier formylation or lithium-halogen exchange to introduce the C-5 carbon. When 5-Acetyl-2-Amino-4-Methylthiazole is directly oxidised to the acid, the step-count reduction from 5 to 3 synthetic stages compared to the unsubstituted analogue lowers the process mass intensity by 34% and the E-factor from 47 to 28, based on reported kilo-lab campaigns for a generic cefditoren intermediate. Flavour perception is governed by a different set of structure-activity boundaries. The roasted, nutty, slightly meaty aroma character requires very low odour thresholds: detection in water occurs at 0.1–0.5 µg·L⁻¹, and recognition at 1.0–1.5 µg·L⁻¹. Organoleptic panels (PanelCheck v1.4.0, significance at α = 0.05) distinguish this compound from the more popcorn-prone 2-acetylthiazole (FEMA 3328) and the peanut-like 2-amino-4-methylthiazole. The amino group reduces vapour pressure but improves substantivity in dry-blend flavour carriers; GC-headspace analysis over a 12-week storage at 40 °C/75% RH on a 20% plated maltodextrin carrier shows retention of 87% versus 54% for thiazole without the amine. This differential is attributed to hydrogen bonding with the carbohydrate matrix. Nevertheless, the compound is susceptible to Maillard-driven losses in high-temperature extrusion (twin-screw, 120 °C barrel, L/D 44:1, screw speed 350 rpm): under those conditions, residual acetyl groups condense with reducing sugars, and flavour intensity drops by 3.5 log dilution units unless the extrudate is cooled immediately in a post-gelatinisation zone to <70 °C. A further distinguishing feature surfaces in heterocycle cascade chemistry. With malononitrile and ethanolic potassium hydroxide under reflux, the 5-acetyl group undergoes Knoevenagel condensation to yield 2-[2-amino-4-methylthiazol-5-yl]-2-oxoethylidenemalononitrile, a precursor for pyridothiazole libraries. In comparative trials with 2-amino-4,5-dimethylthiazole, the isolated yield climbs from 62% to 88% due to the enhanced electrophilicity of the α,β-unsaturated carbonyl intermediate stabilised by the adjacent sulfur. The reaction is run in absolute ethanol with 2.5 equivalents of malononitrile at reflux (78 °C) for 4 h; published data indicate that replacement of the methyl group at C-4 by a hydrogen in this condensation leads to a 19% drop in conversion under identical conditions, underscoring the role of the electron-donating methyl in polarising the acetyl carbonyl.

Table 2 — Comparative reactivity and application properties of selected C-5 substituted aminothiazoles
Compound	Melting range (°C)	Acylation product ratio (N:O) with benzoyl chloride^a	Knoevenagel yield^b (%)	Sensory character
5-Acetyl-2-amino-4-methylthiazole	196.0–200.0	>98:2	88–92	Roasted, nutty, meaty
2-Amino-4-methylthiazole	42.0–44.5	—^c	—	Peanut, green
2-Amino-4,5-dimethylthiazole	103.0–106.0	97:3	58–65	Burnt, nutty
2-Acetylthiazole (no amine)	22.0–24.0	Not applicable	71–78^d	Popcorn, roasted grain

^aDichloromethane, 0–5 °C, 2 eq. Et₃N, 1 h; determined by HPLC area % at 254 nm.
^bMalononitrile, piperidine catalyst, EtOH reflux, 4 h.
^cNo acetyl group present; formylation gives mixtures.
^dReaction at carbonyl carbon affected by absence of amine. Integration into a continuous flow platform for the malononitrile condensation has been demonstrated on a Corning G1 reactor with a heart-shaped channel (volume 8.25 mL) operating at 160 °C and 12 bar back-pressure, achieving 97% conversion within a residence time of 3.2 min. The product slurry, upon cooling to 25 °C, is filtered and washed with cold ethanol to deliver material of 99.2 area% purity without column chromatography. Published work indicates that 2-amino-4-methylthiazole-5-carbaldehyde, a competitive intermediate for the same downstream pyridothiazole, suffers from thermal dimerisation above 50 °C, limiting its use in flow chemistry and highlighting the titled compound’s thermal stability in demanding conditions. No dimer or oligomer peaks are observed in LC-MS after 3 h at 180 °C in dimethyl sulfoxide solution for the acetyl derivative, whereas the aldehyde analogue generates 4.3% area of dimeric species. When formulating for captive intermediate supply in an API network governed by ICH Q7 and EU GMP Part II, the compound’s status as a non-sterile, non-critical starting material is commonly documented in the site’s Qualified Suppliers List with a certificate of analysis reflecting Table 1 parameters. Retest periods of 24 months under recommended storage are supported by accelerated stability data at 40 °C/75% RH for 6 months, showing assay reduction of <0.3% and no appearance of new impurity peaks exceeding 0.10%. This contrasts with many aminoheterocycles that undergo deamination or ring hydrolysis under similar stress conditions, a differential credited to the electron-withdrawing acetyl group that deactivates the thiazole ring toward hydrolytic attack.