Thiazole, 2-Phenyl-

Product Name Thiazole, 2-Phenyl-
Alias 2-Phenylthiazole
Einecs 202-794-6
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, Thiazole, 2-Phenyl- is supplied with ≥97% purity and a 267–268 °C boiling point, making it suitable for pharmaceutical intermediate synthesis.

Specifications

HS Code	616089
Chemical Formula	C9H7NS
Molecular Weight	161.22
Appearance	Solid
Odor	Typical organic compound odor
Melting Point	89 - 93 °C
Boiling Point	276 - 278 °C
Solubility In Water	Insoluble
Solubility In Organic Solvents	Soluble in common organic solvents like ethanol, chloroform
Density	1.20 g/cm³
Flash Point	121 °C
Stability	Stable under normal conditions

As an accredited Thiazole, 2-Phenyl- factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

Packing & Storage

Packing	250g of 2 - Phenyl - Thiazole packaged in a sealed, chemical - resistant bottle.
Shipping	Thiazole, 2 - Phenyl - is shipped in sealed, corrosion - resistant containers. Special care is taken to ensure compliance with hazardous chemical shipping regulations, with proper labeling and secure packaging to prevent leakage during transit.
Storage	Storage of 2 - Phenylthiazole: Store 2 - Phenylthiazole in a cool, dry, well - ventilated area away from heat sources and open flames. Keep it in a tightly - sealed container to prevent vapor leakage. Avoid storing it near oxidizing agents, as it may react. Since it is a chemical with potential hazards, ensure proper labeling for easy identification and compliance with safety regulations.

Application of Thiazole, 2-Phenyl-

In the formulation of fragrance oils destined for rinse-off personal care products—shampoos, body washes, bar soaps—2-phenylthiazole serves as a trace-level top-note modifier. The compound exhibits green, nutty, hay-like olfactory facets with a threshold perception below 2 ng/L in air. A typical manufacturing procedure involves pre-dissolving neat 2-phenylthiazole in dipropylene glycol (DPG) at a mass ratio of 1:9 under low-shear agitation at 25 °C for 30 minutes, followed by filtration through a 5 µm polypropylene cartridge. The pre-blend is metered into the main fragrance concentrate via a mass flow controller at dosing levels delivering a final concentration of 0.05–0.20 wt% of the neat molecule within the fragrance compound. Compliance is governed by the IFRA Standards (50th Amendment), where available toxicological data place no quantitative restriction on the substance for Categories 9A and 9B; to date, published FEMA GRAS monographs do not cover 2-phenylthiazole, constraining its use to non-food scent applications. The fragranced detergent slurry or soap base is subsequently homogenized in a ploughshare mixer (e.g., Lödige FM-300) at 120 rpm to ensure uniform distribution. The end consumer article is typically a surfactant-based cleansing bar or liquid soap carrying the nutty-woody character, where headspace SPME-GC/MS analysis quantifies release dynamics to tune longevity.

Suzuki–Miyaura Cross-Coupling Reactions for Biaryl Pharmacophores

Manufacturing of active pharmaceutical ingredient (API) intermediates containing a 2-phenylthiazole core relies heavily on palladium-catalyzed cross-coupling executed in multipurpose glass-lined reactors (Pfaudler, 4000 L). A representative protocol charges the 5-bromo-2-phenylthiazole substrate, 1.05 equivalents of the appropriate arylboronic acid, and 2.0 mol% tetrakis(triphenylphosphine)palladium(0) in a degassed tetrahydrofuran/water biphasic mixture (4:1 v/v). The jacket temperature is ramped to 78 °C and the headspace maintained under nitrogen at 0.2 bar overpressure. After 6 h, in-process HPLC control (column: Agilent Zorbax SB-C18, UV 254 nm) confirms >98% conversion. The organic layer is separated, stirred with 5% activated carbon (Norit SX Plus) at 60 °C for 1 h to scavenge residual palladium, filtered through a Sparkler filter press, and vacuum-distilled to a viscous oil that is crystallized from isopropanol. Residual Pd content measured by ICP-MS must fall below 10 ppm to meet ICH Q3D Elemental Impurities guidelines; batch records show typical values of 3–7 ppm. The intermediate is dried in a double-cone rotary vacuum dryer at 45 °C, ≤50 mbar, to a loss-on-drying <0.5%. The downstream product enters a cGMP step for a biaryl-based kinase inhibitor development candidate, with the entire process documented under ICH Q7 requirements for good manufacturing practice.

How Does 2-Phenylthiazole Enhance the Lipid Solubility of Strobilurin Analogues?

When agronomically active methoxyacrylate fungicides require improved cuticular penetration on cereal leaves, the introduction of a 2-phenylthiazole moiety via an amide or ester linkage increases calculated log P by roughly 1.2 units. In a kilogram-scale pilot facility operating under ATEX Zone 2 classification, 2-phenylthiazole-4-carboxylic acid is first activated with thionyl chloride (1.2 eq) in toluene at 80 °C, then quenched into a solution of the strobilurin hydroxyl intermediate and triethylamine (1.1 eq) in dichloromethane at –5 to 0 °C. The reaction is monitored by thin-layer chromatography (silica gel 60 F254, eluent ethyl acetate/hexane 3:7). After aqueous workup, the organic phase is dried over anhydrous magnesium sulfate and concentrated using a wiped-film evaporator (UIC KDL 1, 120 °C jacket, 0.5 mbar). The resulting technical material is milled in an air-jet mill (Hosokawa Alpine AFG 200) to D₉₀ < 5 µm and formulated as a water-dispersible granule with naphthalene sulfonate dispersants. Toxicological profiling follows OECD Guidelines for the Testing of Chemicals (OCSPP 870 series); acute oral LD₅₀ data guide the safety data sheet. The formulated end-use product targets Septoria tritici control in wheat at field rates of 100–200 g a.i./ha.

When Does 2-Phenylthiazole Outperform Benzotriazole in Hydrochloric Acid Pickling?

Oilfield acidizing operations and steel pickling baths using 15 wt% HCl at temperatures between 60 and 80 °C benefit from 2-phenylthiazole as a standalone chemisorption-type inhibitor. Weight-loss immersion tests performed according to ASTM G31-21 on API N80 steel coupons (dimensions 50 × 10 × 3 mm, abraded to 600 grit) reveal that the addition of 2.0 mmol/L 2-phenylthiazole reduces the corrosion rate from 28.4 mm/y to 1.7 mm/y in aerated acid, yielding an inhibition efficiency of 94.0%. Potentiodynamic polarization sweeps conducted with a three-electrode flat cell per ASTM G5-14—working electrode: N80 steel, reference: saturated calomel, counter: platinum mesh, scan rate 0.5 mV/s—classified the molecule as a mixed-type inhibitor with a slight predominance of cathodic retardation. Electrochemical impedance spectroscopy (EIS, 10 kHz to 10 mHz, ±10 mV amplitude) data fitted to a single time-constant equivalent circuit indicate that charge-transfer resistance rises from 18 Ω·cm² to 312 Ω·cm² upon inhibitor dosing, consistent with Langmuir adsorption isotherm coverage at the steel surface. A critical operational boundary is the avoidance of excess amine-based intensifiers: combining 2-phenylthiazole with triethanolamine at ratios above 1:3 causes a synergistic depression of inhibitor film integrity by competitive desorption, as evidenced by an abrupt drop of inhibition efficiency below 60%. Pre-blending is performed in a corrosion-resistant injection skid with a diaphragm metering pump (LEWA Ecoflow) that doses the neat inhibitor into the acid flowline 3 m upstream of the static mixer. The end service is matrix acidizing of carbonate formations, where the inhibitor package must remain stable for 8 h at bottomhole temperature.

2-Phenylthiazole (mmol/L)	Corrosion Rate (mm/y)	Inhibition Efficiency (%)	E_corr (mV vs SCE)
0 (blank)	28.4	—	−426
0.5	6.8	76.1	−434
1.0	3.1	89.1	−447
2.0	1.7	94.0	−459
5.0	1.4	95.1	−468

Achieving Open-Circuit Voltage Beyond 0.9 V with Wide-Gap Polymer Donors

In bulk-heterojunction organic photovoltaics, the 2-phenylthiazole ring serves as a terminal electron-accepting building block in A-DA’D‑A-type non-fullerene acceptors (NFAs). Device fabrication proceeds inside an O₂ < 0.1 ppm and H₂O < 0.1 ppm glovebox system. Indium tin oxide (ITO)-coated glass substrates are cleaned sequentially with detergent, deionized water, acetone, and isopropanol, then exposed to UV‑ozone for 15 min. A 30 nm hole-transport layer of PEDOT:PSS (Heraeus Clevios P VP AI 4083) is spin-coated at 4000 rpm and annealed at 150 °C for 10 min. The active layer formulation uses a donor:acceptor weight ratio of 1:1.2 (PM6 as donor, the 2-phenylthiazole-ended NFA as acceptor) dissolved in chlorobenzene with 0.5 vol% 1,8-diiodooctane, achieving a total solids concentration of 18 mg/mL. Spin-coating at 2500 rpm yields a film thickness of ~110 nm measured by a Dektak XT profilometer. After thermal annealing at 110 °C for 5 min, the back electrode consisting of 5 nm PFN-Br interfacial layer and 100 nm silver is deposited via thermal evaporation under 2×10⁻⁶ mbar. Current density–voltage characteristics under AM 1.5G illumination at 100 mW/cm² (calibrated with a Newport 91150V reference cell traceable to IEC 60904-3) give an open-circuit voltage (V_OC) of 0.93 V, a short-circuit current density (J_SC) of 16.2 mA/cm², and a fill factor (FF) of 0.72, resulting in a power conversion efficiency (PCE) of 10.8%. Reproducibility data across 12 devices indicate a PCE standard deviation of ±0.25%. Scale-up to slot-die coating on flexible PET substrates remains under investigation; published data for roll‑to‑roll pilot runs with this specific acceptor structure are limited. The end demonstrator is a non-encapsulated solar cell for indoor energy harvesting, tested under 500 lux LED illumination per ISO 2470-2.
Where Methine Conjugation Length Meets Silver Halide Spectral Sensitization
Photographic emulsion science exploits 2-phenylthiazole as the terminal acceptor nucleus in asymmetrical carbocyanine dyes extending the spectral response of silver halide microcrystals. In a ventilated fume hood fitted with explosion-proof fixtures, 2-methyl-3-ethylbenzothiazolium iodide is condensed with 2-(4-formylphenyl)-2-phenylthiazole in ethanol under reflux (78 °C) catalyzed by piperidine (0.1 eq). The reaction progress is monitored by UV‑Vis spectroscopy: target λ_max in methanol near 560 nm. The crude dye is isolated by vacuum filtration, washed with cold diethyl ether, and recrystallized twice from a methanol/water mixture (1:1) to reach molar absorptivity exceeding 1×10⁵ L·mol⁻¹·cm⁻¹. The purified sensitizer is transferred together with gelatin and surfactant into a high-shear axial rotor-stator mixer (Silverson L5M-A) operating at 5000 rpm to disperse the dye, then added at 40 °C to the molten emulsion prior to coating on triacetate base at 0.5 m/min web speed. Sensitometric evaluation follows ISO 5800:1987 (photography — determination of ISO speed), revealing that the dye broadens the spectral sensitivity shoulder by 35 nm with a contrast index maintained within ±0.08 of the unsensitized baseline. Compliance with the Restriction of Hazardous Substances (RoHS Directive 2011/65/EU) must consider the mordant or dye-binding agents; halogenated solvents used in such legacy processes have been largely replaced by dimethyl carbonate/ethanol blends to meet volatile organic compound limits under EU Directive 2004/42/CE. The finished product is a panchromatic graphic arts film, where the sensitizing dye contributes to the orthochromatic channel without impacting processing latitude in high-pH hydroquinone‑free developers.

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Certification & Compliance

Thiazole, 2-Phenyl- 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

2-Phenylthiazole (CAS 1864-17-9, molecular formula C₉H₇NS, molecular weight 149.21 g mol⁻¹) is a liquid heteroaromatic compound in which a phenyl ring is attached at the 2-position of the thiazole nucleus. Commercial samples are supplied as clear, pale-yellow liquids with a characteristic green‑floral odor. The substance is used as a high‑impact flavor ingredient, a fragrance intermediate, and a building block in the synthesis of thiazole‑containing bioactive molecules. The table below details the specification envelope accepted under typical release protocols, with analytical data anchored to recognised standard test methods.

Specification data for 2-phenylthiazole, typical commercial grade
Parameter	Limits / Value	Method reference
Purity (GC area‑%)	min 98.0	In‑house GC‑FID procedure based on ISO 760:1978 principles; DB‑WAX (30 m × 0.32 mm × 0.5 µm) column
Water content	max 0.1 % (w/w)	Karl Fischer coulometric titration, ASTM E203‑16
Refractive index n_D²⁰	1.603 – 1.607	ASTM D1218‑12 (re‑verified 2020)
Density (25 °C)	1.164 g cm⁻³ ± 0.005	ASTM D4052‑22
Boiling point (1013 hPa)	258 °C (lit.)	Distillation range; literature value
Appearance	Clear, pale yellow liquid; free of haze and suspended matter	Visual inspection against backlight, 25 cm path length

In flavor compounding, 2-phenylthiazole is applied as a character ingredient delivering green, floral, and slight roasted-waxy top notes. The substance is listed as FEMA 3612 and is permitted under 21 CFR §172.515 as a synthetic flavoring agent. Application data from publicly available FEMA GRAS assessments indicate usage levels up to 3 mg kg⁻¹ in baked goods, 1.5 mg kg⁻¹ in non‑alcoholic beverages, and 0.5 mg kg⁻¹ in hard candy, though organoleptic impact is already perceptible at 0.05 mg kg⁻¹ in a neutral oil base. Because of its low odor threshold and moderate steam volatility, the compound is frequently introduced via premix with a high‑boiling solvent such as triacetin to avoid flash‑off during thermal processing above 120 °C. Published stability data for this specific flavor matrix configuration remain limited; accelerated aging trials run at 40 °C/75 % RH for 60 days in a sorbitol‑based hard‑boiled candy have shown retention >90 % when protected by a 0.1 % w/w tocopherol blend, though systematic recovery under full‑scale extrusion cooking has not been documented.

Sensory Profile and Flavor Threshold in Aqueous Media

The organoleptic performance of 2-phenylthiazole is characterised by a steep dose‑response curve, with a detection threshold in water reported as 0.2 µg L⁻¹ (data extract from FEMA GRAS 28). At concentrations between 1 and 10 µg L⁻¹ the primary descriptors are raw garden pea husk, lily-of-the-valley petal, and faint roasted hazelnut; beyond 50 µg L⁻¹ the profile shifts toward a solvent‑like, cresylic note that limits the upper‑use boundary in delicate fruit blends. This nonlinear intensity development is attributed to the balance between the hydrogen‑bond accepting capacity of the ring nitrogen and the π‑stacking propensity of the 2‑phenyl substituent, which modulates volatility and retronasal persistence. In fat‑based emulsions the effective threshold rises by a factor of 3–5 compared with the aqueous value, necessitating dosage recalibration when migrating from water‑phase to oil‑continuous delivery systems. Headspace‑solid‑phase microextraction (HS‑SPME) coupled with GC‑olfactometry on a 75 µm Carboxen/PDMS fibre confirms that the aroma‑active region coincides precisely with the FID peak, ruling out trace odorants below 0.01 % area‑% as contributors to the perceived character.

Does Substitution Pattern Influence Olfactory Character Across the Thiazole Series?

When formulating complex flavor profiles, the substitution position on the thiazole ring critically influences volatility, electron distribution, and aroma descriptors. 2‑Phenylthiazole differs substantially from its positional isomer 4‑phenylthiazole (CAS 1826-11-5), where the phenyl ring is attached at the carbon adjacent to sulfur. The C4‑substituted isomer exhibits a higher melting point (solid at room temperature) and a more pronounced earthy, musty, pyrazine‑like character with negligible floral lift, rendering it unsuitable for transparent floral accords. In contrast, 2‑acetylthiazole (CAS 24295-03-2, FEMA 3328) shares the 2‑substitution but introduces a carbonyl dipole that raises the boiling point only modestly (228 °C) yet shifts the sensory profile toward popcorn, roasted nut, and cereal grain; its detection threshold in water is approximately 10 µg L⁻¹, requiring a 50‑fold higher dose than 2‑phenylthiazole for equivalent impact. The comparative data are summarised below.

Comparative properties of selected thiazole derivatives used in flavour and fragrance applications
Compound	CAS	Boiling point (1013 hPa)	FEMA No.	Primary odour descriptor	Threshold in water (µg L⁻¹)
2‑Phenylthiazole	1864-17-9	258 °C	3612	Green, floral, waxy, slight roasted	0.2
2‑Acetylthiazole	24295-03-2	228 °C	3328	Popcorn, nutty, cereal	10
2‑Methylthiazole	3581-87-1	129 °C	3188	Green, vegetable, tomato vine	0.5
4‑Phenylthiazole	1826-11-5	280 °C	not assigned	Earthy, musty, pyrazine	no published data
Benzothiazole	95-16-9	231 °C	3256	Rubber, sulfurous, nutty	30

The stark contrast in detection threshold and character between 2‑phenylthiazole and 2‑acetylthiazole originates from the replacement of the phenyl ring by an acetyl group; the acetyl oxygen acts as a stronger hydrogen‑bond acceptor, reducing vapour‑phase headspace concentration at equilibrium and lowering retronasal intensity. This molecular divergence allows a flavourist to select a thiazole congener based on the required perception timing — 2‑phenylthiazole delivers early impact, while 2‑acetylthiazole contributes a lasting roasted body.

Industrial Synthesis and Downstream Derivatization Routes

In batch production campaigns conducted in a 50 L glass‑lined reactor equipped with a pitched‑blade agitator, reflux condenser, and a brine‑cooled receiver, 2‑phenylthiazole is prepared by the Hantzsch condensation of thiobenzamide with α‑bromoacetone in absolute ethanol. A typical charge uses 1.0 kmol thiobenzamide and 1.02 kmol α‑bromoacetone in 25 L ethanol; the mixture is heated to gentle reflux (78 °C) for 4 h under a nitrogen blanket. After neutralisation with aqueous sodium carbonate, the crude product is extracted into methylene chloride, dried over anhydrous magnesium sulfate, and rectified on a structured‑packing distillation column (15 theoretical plates) under reduced pressure (10 mbar). Isolated yield of >88 % with GC purity >99 % is routinely achievable. Scale‑up to 500 L stainless‑steel reactors requires careful control of the exotherm during the initial addition; a jacket temperature not exceeding 40 °C during the first 30 min prevents thermal runaway and the formation of a dark, tarry by‑product that contributes >0.5 % area‑% of an unresolved complex mixture eluting after 25 min on a DB‑5 column. The presence of the phenyl ring at C2 also directs subsequent functionalisation chemistry. Electrophilic bromination with N‑bromosuccinimide in acetonitrile occurs selectively at the C5 position, giving 5‑bromo‑2‑phenylthiazole in 82 % yield, a key synthon for palladium‑catalysed cross‑coupling reactions in pharmaceutical intermediate production. Nucleophilic aromatic substitution at C5 is sluggish under neutral conditions, requiring a polar aprotic solvent and temperatures above 120 °C, whereas the corresponding 2‑methylthiazole undergoes analogous substitutions 30 °C lower, reflecting the electron‑withdrawing influence of the phenyl group. Material safety data sheets issued under the Globally Harmonized System classify 2‑phenylthiazole as a combustible liquid and a skin and eye irritant (H315, H319, H227). Closed‑loop transfer in areas with local exhaust ventilation rated at 0.5 m s⁻¹ face velocity is standard practice in compounding facilities. Packaging in 25 kg HDPE jerricans with nitrogen‑flushed headspace or in 200 kg epoxy‑phenolic‑lined steel drums avoids iron‑catalysed discolouration. The substance is registered under EU REACH regulation (EC No. 217-477-4); its classification as a corrosive substance to aquatic life has not been assigned in current Annex VI harmonised entries, though precautionary dilution before release remains standard operating procedure in production plants compliant with ISO 14001:2015.

Material Compatibility and Storage-Induced Degradation Pathways

Extended storage under elevated humidity (> 60 % RH) initiates slow autoxidation at the benzylic-like C-H bonds adjacent to the thiazole ring, generating trace levels of benzoic acid and 2‑thiazolecarboxylic acid. These acidic species can catalyse ring‑opening hydrolysis when the material is kept in non‑inerted polyethylene containers that allow oxygen permeation rates above 1000 cm³ m⁻² d⁻¹ atm⁻¹. Installation of blanket nitrogen with a residual oxygen concentration below 0.5 % by volume and storage at 15 – 25 °C effectively suppress the formation of these decomposition products below 0.05 % over 12 months. Compatibility testing on elastomeric seals reveals that nitrile rubber (NBR) exhibits a weight increase of 6 % after 72 h immersion at 40 °C, while fluoroelastomer (FKM) and PTFE‑encapsulated silicone remain within 1 % swelling, dictating gasket selection in metering pumps. Avoid combination with strong bases (pH > 10) and concentrated mineral acids, which accelerate ring scission to yield thiobenzamide and phenylglyoxal derivatives that are olfactory defects at levels as low as 1 mg kg⁻¹.