59463-56-8

Basic information

• Product Name: CYANOMETHYL ETHANETHIOATE
• Synonyms: CYANOMETHYL ETHANETHIOATE;ACETYLMERCAPTO METHYLCYANID;ACETYLTHIOACETONITRILE;ACETYLTHIOACETONITRILE 97%;acetylmercaptomethylcyanide;ACETYLMERCAPTOACETONITRILE;Ethanethioic acid, S-(cyanoMethyl) ester;S-(Cyanomethyl) ethanethioate, (Acetylthio)acetonitrile
• CAS NO: 59463-56-8
• Molecular Formula: C₄H₅NOS
• Molecular Weight: 115.15
• Mol File: 59463-56-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 226-227 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.176 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.367mmHg at 25°C
• Refractive Index: n20/D 1.495(lit.)
• CAS DataBase Reference: CYANOMETHYL ETHANETHIOATE(CAS DataBase Reference)
• NIST Chemistry Reference: CYANOMETHYL ETHANETHIOATE(59463-56-8)
• EPA Substance Registry System: CYANOMETHYL ETHANETHIOATE(59463-56-8)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: 20/21/22
• Safety Statements: 36/37
• RIDADR: 3276
• WGK Germany: 3
• Hazardous Substances Data: 59463-56-8(Hazardous Substances Data)

Usage

General Description

CYANOMETHYL ETHANETHIOATE, also known as S-Methyl cyanoacetate or 3-(cyanothio)methyl propanoate, is a chemical compound with the molecular formula C5H7NO2S. It is a clear, colorless to pale yellow liquid with a pungent odor and is commonly used as an intermediate in organic synthesis and pharmaceutical manufacturing. The compound is highly reactive and can undergo various chemical reactions, including esterification, hydrolysis, and addition to double bonds. It is classified as a hazardous substance and should be handled with care, as it can cause irritation to the skin and eyes, and may be harmful if swallowed or inhaled. Overall, cyanomethyl ethanethioate is an important chemical in the production of pharmaceuticals and other organic compounds, but caution must be exercised in its handling and use.

InChI:InChI=1/C4H5NOS/c1-4(6)7-3-2-5/h3H2,1H3

Upstream product

• 107-14-2 chloroacetonitrile 
• 507-09-5 tiolacetic acid 
• 42177-19-5 chloromethyl Thioacetate 
• 143-33-9 sodium cyanide 
• 10387-40-3 potassium thioacetate 

Downstream Products

• 132575-27-0 3-amino-2-cyano-4<(S)-2,3-isopropylidenedioxypropyl>thiophene 
• 132575-34-9 3-amino-2-cyano-4-(3,4-isopropylidenedioxybutyl)thiophene 
• 54524-31-1 2-mercaptoacetonitrile 
• 54524-32-2 mercaptoacetonitrile sodium salt 
• 97518-57-5 2-(2-benzyloxycarbonylamino-4-thiazolyl)-4-benzyloxycarbonyl-2-butenoic acid 
• 1370007-66-1 4-[(3aS,4S,6R,6aR)-6-[(tert-butyl(diphenyl)silyl)oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3-amino-thiophene-2-carbonitrile 
• 885593-51-1 C₃₀H₃₆N₂O₄SSi 
• 911048-26-5 (3bS,4aR)-3,4,4-trimethyl-3b,4,4a,5-tetrahydrocyclopropa[3,4]cyclopenta[1,2-c]thiophene-1-carbonitrile 

Relevant articles and documents

PPAR (peroxisome proliferator-activated receptor) agonist and application thereof to treatment of senile dementia and other diseases

The invention relates to a compound, namely a gamma-subtype peroxisome proliferator-activated receptor (PPAR) agonist. In addition, the invention discloses a medicinal component and a preparation containing the compound and application of such the gamma-subtype PPAR agonist.

Toxin-targeted design for anticancer therapy. I: Synthesis and biological evaluation of new thioimidate heterobifunctional reagents

In an effort to obtain a more potent and specific immunotoxin for cancer therapy, we designed a series of heterobifunctional linkers characterized by a thioimidate group linked to a S-acetyl thiol (4, 5) or substituted aryldithio group (6-10). These ligands were synthesized by a Pinner-type process from the corresponding nitrile derivatives obtained by thiol- disulphide exchange reaction, reaction with substituted benzene-sulphenyl chloride, or other known procedures. To check the reagent of choice for immunoconjugate preparation, we studied thioldisulphide exchange kinetics between the intermediate nitrile derivatives and cysteine. Among the tested aryldithio derivatives (6-10), we selected ethyl 3-(4-carboxamido- phenyldithio)propionthioimidate (CDPT, 9) for further studies. By analyzing the rate of incorporation of the linkers 4, 5, and 9 in a model immunoglobulin G protein, we found similar results with CDPT 9 and ethyl S- acetyl 3-mercaptopropionthioimidate ester hydrochloride (AMPT, 5) because both reagents showed a linear correlation between the number of introduced thiol groups and factors such as time and protein and reagent concentrations. Comparison of the two acetylthio-derivative ligands 4 and 5 showed that AMPT 5 was more stable toward deacetylation than ethyl S-acetyl 2- mercaptopropionthioimidate ester hydrochloride (AMAT, 4). By comparing the kinetic and biological parameters of seven new thioimidate linkers, we found that two of these (CDPT and AMPT) could be superior ligands for protein- protein conjugation. They offer advantages over the commercially available compounds, such as minimal perturbation of the protein structure, controlled reactivity, and good stability.