Methyl 2-[(Cyanomethyl)thio]benzoate

Base Information

• Chemical Name: Methyl 2-[(Cyanomethyl)thio]benzoate
• CAS No.: 57601-89-5
• Molecular Formula: C₁₀H₉NO₂S
• Molecular Weight: 207.253
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID00380915
• Nikkaji Number: J2.440.061A
• Wikidata: Q82171415
• Mol file: 57601-89-5.mol

Synonyms:Methyl 2-[(Cyanomethyl)thio]benzoate;57601-89-5;methyl 2-(cyanomethylsulfanyl)benzoate;Methyl 2-((cyanomethyl)thio)benzoate;methyl 2-[(cyanomethyl)sulfanyl]benzoate;methyl 2-(cyanomethylthio)benzoate;Maybridge1_004679;SCHEMBL11083124;HMS554M15;DTXSID00380915;IZZWSNNLFRAPRY-UHFFFAOYSA-N;MFCD00068076;AKOS005091392;2-(2-carbomethoxyphenylthio)acetonitrile;2-(Cyanomethylthio)benzoic acid methyl ester;CS-0322899;FT-0628427;4F-942

Chemical Property of Methyl 2-[(Cyanomethyl)thio]benzoate

Chemical Property:

• Vapor Pressure: 9.69E-05mmHg at 25°C
• Melting Point: 121℃
• Boiling Point: 338.6°C at 760 mmHg
• Flash Point: 158.6°C
• PSA: 75.39000
• Density: 1.24g/cm³
• LogP: 2.08888
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 207.03539970
• Heavy Atom Count: 14
• Complexity: 246

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 2-[(cyanomethyl)thio]benzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Safety Statements: S36/37:Wear suitable protective clothing and gloves.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=CC=C1SCC#N

Technology Process of Methyl 2-[(Cyanomethyl)thio]benzoate

There total 5 articles about Methyl 2-[(Cyanomethyl)thio]benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

cyanomethyl bromide (590-17-0) + Methyl thiosalicylate (4892-02-8) → methyl 2-[(cyanomethyl)thio]benzoate (57601-89-5)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; for 8h; Heating;

DOI:10.1248/cpb.55.613

Reference yield:

methyl thiosalicylate (17999-25-6) + chloroacetonitrile (107-14-2) → methyl 2-[(cyanomethyl)thio]benzoate (57601-89-5)

Guidance literature:

In methanol;

Reference yield:

Thiosalicylic acid (147-93-3) → methyl 2-[(cyanomethyl)thio]benzoate (57601-89-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 5percent sulfuric acid / 18 h / Heating

2: potassium carbonate, potassium iodide / acetone

With sulfuric acid; potassium carbonate; potassium iodide; In acetone;

DOI:10.1002/jhet.5570280211

upstream raw materials:

chloroacetonitrile

Methyl thiosalicylate

cyanomethyl bromide

Thiosalicylic acid

Downstream raw materials:

3-hydroxy[1]benzothiophene-2-carbonitrile

O-(2-cyano-3-benzothienyl)glycolonitrile

4-chloro-2-phenyl<1>benzothieno<2',3':4,5>furo<3,2-d>pyrimidine

Refernces

• 1、 Sasaki,Tashima,Nakayama,Hirota. "Polycyclic N-hetero compounds. XXXVIII. Synthesis and evaluation of antidepressive activity of [1]benzothieno[2',3':4,5]furo[3,2-d]pyrimidines and their precursors". . p. 269 - 272. Retrieved 2007/10/02.
• 2、 Goerlitzer. "Reactions of beta-keto-nitriles". . p. 700 - 712. Retrieved 2007/10/08.