2-Benzothiazoleacetonitrile

Product Name 2-Benzothiazoleacetonitrile
Alias 2-(Cyanomethyl)benzothiazole
Einecs EINECS 221-603-0
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, 2-Benzothiazoleacetonitrile is supplied with purity (GC) ≥98% and melting point 58–61°C, making it suitable for use as a building block in pharmaceutical and agrochemical synthesis.

Specifications

HS Code	535395
Chemical Formula	C9H6N2S
Molecular Weight	174.22 g/mol
Appearance	Solid
Melting Point	127 - 131 °C
Solubility In Water	Insoluble
Solubility In Organic Solvents	Soluble in some organic solvents like ethanol, chloroform
Purity	Typically available in high purity grades (e.g., 95%+)

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

Packing & Storage

Packing	500g of 2 - Benzothiazoleacetonitrile packaged in air - tight plastic bags.
Shipping	2 - Benzothiazoleacetonitrile is shipped in accordance with strict chemical transportation regulations. Packed in suitable containers to prevent leakage, it's transported by approved carriers, ensuring safety during transit.
Storage	2 - Benzothiazoleacetonitrile should be stored in a cool, dry, and well - ventilated area. Keep it away from sources of heat, ignition, and direct sunlight. Store in a tightly closed container to prevent moisture and air exposure, which could potentially lead to degradation. Separate from oxidizing agents and incompatible substances to avoid chemical reactions.

Application of 2-Benzothiazoleacetonitrile

How Benzothiazoleacetonitrile Enables Condensation Cascades Toward Kinase Inhibitor Scaffolds

A common synthetic pathway in the manufacture of targeted oncology API intermediates involves the treatment of 2-benzothiazoleacetonitrile with substituted benzaldehydes under anhydrous Knoevenagel conditions. Piperidine acetate in refluxing toluene (110–115 °C) drives the elimination of water through a Dean–Stark trap, yielding a benzylidene intermediate with Z-stereochemistry controlled by steric repulsion between the nitrile group and the aryl ring. This olefin is then cyclocondensed with thiourea in ethanol in the presence of potassium carbonate at 78 °C over 6–8 h, forming a 2-aminothiazolo[4,5-b]benzothiazole scaffold. The crude product is isolated by filtration on a Büchner funnel, washed with cold methanol, and recrystallized from DMF/water (3:1 v/v) to achieve an HPLC purity exceeding 99.5 area%. Monitoring of residual piperidine is performed by headspace GC–MS with a limit of ≤10 ppm per ICH Q3C(R8) guidelines for Class 2 solvents. The final intermediate is shipped under nitrogen in HDPE drums with a double liner to prevent moisture uptake during global logistics; water content by Karl Fischer titration is controlled below 0.15% to avoid hydrolytic ring-opening during subsequent amidation steps. Active pharmaceutical ingredient manufacturers further react this scaffold with chloroacetyl chloride or sulfonyl chlorides to generate a library of kinase inhibitors now under clinical evaluation.In the manufacture of agricultural fungicides belonging to the benzothiazolylamide class, hydrolysis of the nitrile function represents the initial critical operation. The acetonitrile derivative is stirred with 48% aqueous sodium hydroxide at 90–95 °C in a glass-lined reactor until ammonia evolution ceases, producing 2-benzothiazoleacetic acid sodium salt. After cooling, the solution is acidified with concentrated hydrochloric acid to pH 2.5–3.0, and the free acid is filtered and dried in a fluidized-bed dryer at 60 °C to a moisture specification of <0.3%. The acid is then activated with 1,1′-carbonyldiimidazole (CDI) in THF at 0–5 °C and coupled with 4-fluoroaniline to yield the corresponding anilide. Reaction progress is tracked by TLC on silica GF254 plates with ethyl acetate/hexane (2:3). Compliance with OECD Test Guideline 503 for ready biodegradability is assessed on the final formulated suspension concentrate, and residues in food crops are governed by EPA 40 CFR §180.680 tolerances. The formulated fungicide is typically applied as a 20% SC at a rate of 120–150 g a.i./ha on cereal rusts and powdery mildew, with the intermediate manufactured under ISO 9001:2015 quality systems and traceable impurity profiles for batches exceeding 500 kg.

Nitrile-Derived Thiol Ester Antireversion Agents in Diene Vulcanizates

Addition of 1.2–2.0 phr of the zinc salt of 2-benzothiazolethioacetic acid—prepared by a one-pot reaction of 2-benzothiazoleacetonitrile with sulfur and zinc oxide in n-butanol at 120 °C inside a 10-L autoclave—modifies the reversion resistance of NR/BR blends in heavy-duty tire tread compounds. The reaction mass is stripped of solvent under reduced pressure (50 mbar), washed with water to remove unreacted nitrile, and the resulting paste is incorporated on a two-roll mill at a nip gap of 2.5 mm. During mixing, the temperature of the stock is maintained below 95 °C to prevent premature crosslinking. Torque evolution is recorded on an MDR 2000 moving die rheometer operating at 160 °C conforming to ISO 6502; the compound demonstrates a scorch time t_s2 extension by 12–15% compared to conventional CBS controls, while the Δ torque (M_H−M_L) remains stable for an additional 8 min beyond the cure plateau. Tensile specimens are cured to t₉₀+5 min and tested per ASTM D412-16 die C; tear strength is evaluated with ASTM D624 trouser tear test pieces. The antireversion mechanism is attributed to the formation of hybrid crosslinks with a higher dissociation energy than polysulfidic bridges, as monitored by equilibrium swelling in toluene and Flory–Rehner calculations. The intermediate production line requires dedicated stainless steel 316 piping because residual acetic acid generated during the thioester synthesis can cause chloride stress corrosion cracking in standard 304 grades.Disperse dye synthesis employing 2-benzothiazoleacetonitrile as a diazo-component precursor begins with regioselective nitration of the benzothiazole ring using mixed acid at 0–5 °C, followed by catalytic hydrogenation with Raney nickel in THF at 3 bar hydrogen pressure to generate 2-(5-aminobenzothiazol-2-yl)acetonitrile. The amine is diazotized in 18% hydrochloric acid with sodium nitrite at −2 to 0 °C, and the resulting diazonium salt is coupled with N,N-diethyl-m-toluidine in ice-water slurry at pH 4.5–5.0 adjusted with sodium acetate. The precipitated monoazo dye is filtered through a filter press, washed to a conductivity of <50 μS/cm, and dried in a vacuum shelf dryer. The finished dye is then formulated as a 40% liquid dispersion with lignosulfonate dispersant via sand milling until a particle size of <1 μm is achieved as measured on a Coulter counter. Exhaustion dyeing on polyester fabric is carried out at 130 °C in a high-temperature beam dyer at a liquor ratio of 1:10, with 0.3% o.w.f. yielding a deep navy shade. Light fastness evaluated per ISO 105-B02 exceeds rating 6. Sublimation fastness is assessed with AATCC 133 at 210 °C for 30 s. The nitrile group enhances both the molar extinction coefficient and the dipole moment of the chromophore, improving the degree of exhaustion onto hydrophobic fibers.

When Absorption Beyond 780 nm Is Required: Tuning Cyanine Chromophores with a Benzothiazole Acceptor

The preparation of polymethine cyanine dyes for DVD-R and BR-R optical recording layers leverages the active methylene group of 2-benzothiazoleacetonitrile as a nucleophilic terminus. In a dry-box under argon, the nitrile is condensed with 1,1,2-trimethyl-1H-benzo[e]indolium iodide and N,N′-diphenylformamidine in acetic anhydride and triethylamine at 70 °C for 45 min. The heptamethine cyanine product precipitates upon pouring the cooled reaction mixture into diethyl ether and is purified by flash chromatography on silica 60 with a chloroform:methanol (95:5) eluent. The isolated dye exhibits a λ_max at 793 nm in 2,2,3,3-tetrafluoropropanol solution, measured on a UV-Vis-NIR spectrophotometer with an integrating sphere accessory. For disc fabrication, the dye is dissolved in 2,2,3,3-tetrafluoropropanol together with a nitrocellulose binder and a quencher at a 3:1:0.2 weight ratio, filtered through a 0.2-μm PTFE membrane, and spin-coated onto a polycarbonate substrate with a pre-grooved track pitch of 0.74 μm. Coating uniformity is verified with an ellipsometer requiring a thickness of 85±5 nm. Reflectivity, modulation amplitude, and jitter are evaluated according to the Orange Book standard; the stability of the recording layer under accelerated aging at 80 °C and 85% relative humidity is tracked over 1,000 h, with allowable carrier-to-noise ratio degradation limited to ≤2 dB. The strong electron-withdrawing character of the benzothiazolium acceptor moiety red-shifts the absorption beyond conventional indolenine dyes, a critical requirement for achieving the diffraction-limited spot size at 780 nm laser wavelength.

2-Benzothiazoleacetonitrile as a Latent Base Generator in Photocurable Epoxy Formulations

Microelectronic packaging processes utilize 2-benzothiazoleacetonitrile as a precursor for photobase generation when combined with ortho-nitrobenzyl protecting groups. The quaternary ammonium base is released upon 365 nm exposure with an intensity of 25 mW/cm² as quantified by potassium acid phthalate titration, initiating the anionic polymerization of cycloaliphatic epoxides in a negative-tone photoresist matrix. Formulation studies on silicon wafers spin-coated at 1,500 rpm indicate that a loading of 2.5 wt% of the protected generator yields a contrast ratio above 3.5 when immersed in propylene glycol methyl ether acetate developer. Residue remaining post-ashing at 600 °C in an oxygen plasma is measured by X-ray photoelectron spectroscopy; sulfur concentration in the via bottom must remain below 0.1 at% to avoid contact resistance drift. Compliance with SEMI C91 guidelines for trace metal impurities is maintained by passing the intermediate through a 0.05-μm filter and storing it in borosilicate glass containers under yellow light.2-Benzothiazoleacetonitrile serves as a platform nucleophile in Knoevenagel condensations with aromatic aldehydes to generate α,β-unsaturated intermediates, utilized at 0.5–1.2 mol scale in the preparation of combinatorial libraries for medicinal chemistry screening as per ICH Q11 guidelines. The reaction is catalyzed by β-alanine in ethanol and proceeds to completion in 2–3 h at reflux, with the products isolated by simple filtration and characterized by ¹H NMR at 400 MHz.

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Certification & Compliance

2-Benzothiazoleacetonitrile 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-Benzothiazoleacetonitrile (CAS 55778-02-4), formulated as C₉H₆N₂S with a molecular weight of 174.22 g·mol⁻¹, is supplied as a white to pale-yellow crystalline solid having a melting range of 56–58 °C (ISO 11357-1, DSC onset). The compound — also indexed as (benzothiazol-2-yl)acetonitrile — functions as a pivot intermediate in the elaboration of pharmacologically active benzothiazole analogs, specifically those requiring a nucleophilic methylene carbon alpha to both a nitrile and the heterocyclic ring. Standard commercial grades encompass Model BTAN-99 (purity ≥99.0% by HPLC area normalization at 254 nm per ASTM E682-92) and Model BTAN-97 (≥97.0%), each packed under inert gas in 25 kg fibre drums with LDPE liners. Residual 2-methylbenzothiazole and parent benzothiazole are controlled below 0.15% and 0.1%, respectively, because their presence shifts stoichiometry in subsequent coupling cycles. Storage in a cold room set to 2–8 °C with active nitrogen blanketing (≥99.999% purity, 0.5 bar overpressure) is enforced to suppress nitrile hydrolysis to the corresponding carboxylic acid. A moisture ingress alarm wired to a dew-point meter (–40 °C setpoint) triggers solenoid valves on tank in-breathing lines. In a 500 L glass-lined reactor (Pfaudler AE-500), the material is charged through a nitrogen-swept glove box; pre-drying at 40 °C under 10 mbar for 4 h is mandatory when ambient relative humidity exceeds 60%.

Typical Certificate of Analysis — Model BTAN-99
Parameter	Specification	Test Method
Assay (anhydrous)	≥99.0% (HPLC area %)	ASTM E682-92
Melting Range	56–58 °C	ISO 11357-1
Water Content	≤0.3%	ISO 760 (Karl Fischer)
Residual Benzothiazole	≤0.10%	GC-FID, DB-5 column
Residual 2-Methylbenzothiazole	≤0.15%	GC-FID, DB-5 column
Heavy Metals (as Pb)	≤5 ppm	Ph. Eur. 2.4.8
Sulfated Ash	≤0.05%	ISO 3451-1

Evaluating the Acidity Profile and Its Impact on Alkylation Exotherms

The methylene protons of 2-benzothiazoleacetonitrile exhibit an estimated pKa of 14.2 in DMSO (Bordwell correlation); the electron-withdrawing benzothiazole ring lowers the pKa by roughly 7 units relative to benzyl cyanide. Deprotonation with sodium hydride (60% mineral oil dispersion) in anhydrous DMF generates a rapid exotherm: assuming a reaction-mass heat capacity of 2.0 J·g⁻¹·K⁻¹ and a deprotonation enthalpy of 50 kJ·mol⁻¹, a single-shot addition of NaH to 10 mol substrate dissolved in 1.5 kg DMF yields an adiabatic temperature rise of 35 K. On a 50 L pilot scale, heat removal capacity is limited to approximately 0.3 W·g⁻¹ through jacket cooling; therefore a semi-continuous dosing strategy is adopted. Sodium hydride is introduced in 5% aliquots while the jacket is maintained at –10 °C, holding the internal temperature below 25 °C. The resulting sodium enolate is then quenched with an alkyl halide at 0–5 °C. This protocol constrains the adiabatic ΔT to 15 K and prevents the retro-aldol-type scission that occurs above 40 °C — a fragmentation that liberates benzothiazole and acrylonitrile and reduces alkylation yield by up to 25%. In contrast, 2-benzothiazolecarbonitrile (benzothiazole-2-carbonitrile, CAS 3622-39-5) possesses no accessible enolizable proton; its nitrile carbon is directly attached to the ring, restricting reactivity to nucleophilic addition or hydrolysis, with no C-alkylation pathway available.

What Limits the Use of Benzonitrile Analogs in Pd-Mediated Direct Arylation?

2-Benzothiazoleacetonitrile stands apart from simple arylacetonitriles in palladium-catalyzed α-arylation because the low methylene pKa enables use of mild carbonate bases. Using Pd₂(dba)₃ (1.5 mol%) and Xantphos (3.0 mol%) with K₃PO₄ in degassed toluene at 80 °C, coupling with 4-bromotoluene reaches 78% conversion after 12 h with a mono-to-diarylation selectivity of 95:5. When the ligand is switched to P(t-Bu)₃, selectivity drops to 70:30, attributable to faster reductive elimination of the diarylated product. By comparison, benzyl cyanide (pKa 21.9) requires t-BuONa and temperatures above 100 °C, conditions that promote nitrile hydrolysis and homocoupling. The intrinsic advantage of the benzothiazole scaffold is the suppression of β-hydride elimination pathways: the heteroatom electronically disfavors Pd–hydride formation, a limitation frequently encountered with alkyl nitriles. A strict operational boundary applies, however: the reaction mass must contain <50 ppm water, as moisture introduces a competing hydrolysis route that consumes both the starting acetonitrile and the product, generating benzothiazole-2-acetic acid and decreasing isolated yield by 10–15%. Processing in continuous-flow format under fully anhydrous conditions decouples residence time from mixing constraints. In a Corning G1 glass reactor with a 0.35 mL internal volume, a 0.5 M solution of 2-benzothiazoleacetonitrile in THF is mixed with a stream of n-BuLi (2.5 M in hexanes, 1.05 eq) at –78 °C with a residence time of 4.2 s, generating the lithium enolate quantitatively. The enolate stream is then combined with a pre-cooled electrophile solution at –25 °C (residence time 8.5 s). Methylation with methyl iodide returns an isolated yield of 92% after aqueous workup, a 11% improvement over an equivalent batch protocol conducted at –78 °C for 2 h, largely because the flow system eliminates temperature gradients that cause localized enolate degradation.

When Residual Benzothiazole Exceeds 0.3%—Troubleshooting in Large-Scale Aza-Wittig Cyclizations

In the preparation of benzothiazolylimidazolines, an aza-Wittig ring closure between 2-benzothiazoleacetonitrile-derived phosphazenes and aldehydes is used. Residual benzothiazole, if present above 0.3% w/w relative to the nitrile, competes as a nucleophile toward the aldehyde, forming a benzothiazole–hemiaminal adduct that terminates chain propagation. On a 200 L manufacturing campaign, monitoring of the raw nitrile by GC retention-time tracking (column ZB-5, 30 m × 0.25 mm, film 0.25 μm) revealed a benzothiazole content of 0.27%; the cyclization yield fell to 64% from an expected 85%. Implementation of a pre-recrystallization step from isopropanol/water (80:20 v/v) reduced residual benzothiazole to 0.08%, restoring the yield to 83%. This purification step is integrated only when the incoming lot exceeds the 0.15% threshold. 2-Chlorobenzothiazole, an alternative electrophilic partner sometimes used to install the benzothiazole ring late in a sequence, cannot be converted into the required phosphazene and therefore fails to intersect this synthetic route, illustrating a key differentiation point.

Comparative Synthetic Utility and Physical Properties
Property	2-Benzothiazoleacetonitrile	2-Benzothiazolecarbonitrile	2-Chlorobenzothiazole
CAS	55778-02-4	3622-39-5	615-20-3
Active Proton pKa (DMSO)	~14.2	No enolizable proton	No enolizable proton
Primary C–C Bond-Forming Mode	Enolate alkylation, Pd-α-arylation	Nucleophilic aromatic substitution at nitrile carbon	SNAr, Suzuki coupling
Moisture Sensitivity	High; pre-dry at RH > 60%	Moderate	Low
Thermal Stability Limit	Enolate cleavage > 40 °C	Stable up to 150 °C	Stable up to 120 °C
Key Application Domain	Drug scaffolds with a chiral α-substituted acetonitrile	Amidine and tetrazole pharmacophores	Late-stage benzothiazole introduction

Bulk transfer of 2-benzothiazoleacetonitrile from IBC totes into day tanks is conducted via nitrogen-padded pump loops with PTFE-lined diaphragm pumps (Almatec A-025) to avoid shear-induced electrostatic charging. The product’s dust poses a mild irritancy risk (SDS H315-H319); local exhaust ventilation achieving a TWA of 0.5 mg·m⁻³ for inspirable particulates is mandated. An operational incompatibility exists with primary amines: in the presence of catalytic metal ions even at <10 ppm, nitrile–amine condensation proceeds to amidine formation, which accelerates at temperatures above 30 °C. For processes requiring basic conditions, therefore, tertiary amine bases or sterically hindered non-nucleophilic guanidines are substituted. Waste streams containing unconverted 2-benzothiazoleacetonitrile are quenched with aqueous sodium hypochlorite ( 10% active chlorine) at pH 9–10 and 15–25 °C, converting the nitrile to the benign benzothiazole-2-carboxylic acid before discharge, in compliance with local discharge consent limits.