18369-83-0

Basic information

• Product Name: METHYL CHLOROTHIOLFORMATE
• Synonyms: carbonochloridothioicacid,s-methylester;chloro-thioformicacimethylester;chlorothio-formicacis-methylester;Formic acid, chlorothio-, S-methyl ester;Methyl chlorothioformate;Methyl thiochloroformate;Methyl thiolchloroformate;methylchlorothioformate
• CAS NO: 18369-83-0
• Molecular Formula: C₂H₃ClOS
• Molecular Weight: 110.56
• EINECS: 242-244-2
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds
• Mol File: 18369-83-0.mol

Chemical Properties

• Boiling Point: 110 °C(lit.)
• Flash Point: 88 °F
• Appearance: /
• Density: 1.288 g/mL at 25 °C(lit.)
• Vapor Pressure: 26.9mmHg at 25°C
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL CHLOROTHIOLFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL CHLOROTHIOLFORMATE(18369-83-0)
• EPA Substance Registry System: METHYL CHLOROTHIOLFORMATE(18369-83-0)

Safety Data

• Hazard Codes: C
• Statements: 10-20/21/22-34-52/53
• Safety Statements: 16-26-27-36/37/39-45-61
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• RTECS: LQ7000000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 18369-83-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL CHLOROTHIOLFORMATE is used as a synthetic reagent for the production of Mitomycin C (M371900)-tethered phosphorothiaoate oligodeoxynucleotides, which serve as an anti-tumor antibiotic. This application is crucial in the development of treatments for cancer, as these oligodeoxynucleotides can help target and combat tumor growth.
Used in Agricultural Industry:
METHYL CHLOROTHIOLFORMATE is also used in the preparation of Brassinin (B676950) derivatives, which are plant metabolites with significant importance. Brassinin plays a dual role as an effective phytoalexin, providing plants with a natural defense against pathogens, and as an early biosynthetic precursor for the majority of phytoalexins. This application contributes to the development of more resilient and disease-resistant crops, ultimately benefiting the agricultural industry and food security.

InChI:InChI=1/C2H3ClOS/c1-5-2(3)4/h1H3

Upstream product

• 75-44-5 phosgene 
• 74-93-1 methylthiol 
• 2812-72-8 methyl chlorothioformate 
• 353-49-1 fluoroformyl chloride 
• 67-68-5 dimethyl sulfoxide 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 51861-05-3 S-Methyl N-cyclohexyl(thiocarbamate) 
• 99856-40-3 (2RS,3SR)-3-hydroxy-2-methylsulfanylcarbonylamino-3-phenyl-propionic acid 
• 100610-67-1 (2RS,3SR)-3-hydroxy-2-methylsulfanylcarbonylamino-3-phenyl-propionic acid ethyl ester 
• 60965-62-0 thiocarbonic acid O-((1R)-menthyl ester)-S-methyl ester 
• 18212-44-7 1-Methylthiocarbonylthio-2-phenyl-ethin 
• 39248-75-4 methyl m-xylenethiocarboxylate 
• 62353-90-6 methyl 3-phenylthiocarbazate 
• 5925-77-9 S-methyl 4-methylbenzothioate 
• 91133-79-8 S-Methyl-N-<4-ethoxycarbonyl-phenyl>-thiolcarbamat 
• 39274-34-5 methyl cumenethiocarboxylate 
• 701-50-8 methyl fluorobenzenethiocarboxylate 
• 4906-32-5 methyl bromobenzenethiocarboxylate 
• 39274-35-6 4-tert-Butyl-thiobenzoesaeure-S-methylester 
• 3326-53-2 Diphenylmethyl-methyl-thiocarbonat 

Relevant articles and documents

Synthesis of amides from Glycosmis species: Methylthiopropenoic acid, methylsulfonylpropenoic acid, thiocarbamic acid S-methyl ester, and senecioic acid amides

Representative samples of several types of naturally occurring amides from south and southeast Asian Glycosmis species were synthesized for proof of structures and for bioactivity testing. With one exception (senecioic acid) all these amides were characterized by sulfur containing acid components (methylthiopropenoic acid, methylsulfonylpropenoic acid, and thiocarbamic acid) in combination with phenethylamine derived amino moieties.

A General Strategy for Elaboration of the Dithiocarbonyl Functionality, -(C=O)SS-: Application to the Synthesis of Bis(chlorocarbonyl)disulfane and Related Derivatives of Thiocarbonic Acids

A variety of sulfenyl chlorides have been reacted with a variety of alkoxythiocarbonyl compounds to give adducts which then lose (spontaneously, or upon thermolysis, or in the presence of Lewis acid catalyst) the alkyl chloride to provide an assortment of dithiocarbonyl compounds in good to excellent yields.The preparations of bis(chlorocarbonyl)disulfane (1), ((trichloromethyl)dithio)carbonyl chloride (2), ((alkoxycarbonyl)dithio)carbonyl chlorides (3 and 4), and (((alkylthio)carbonyl)dithio)carbonyl chlorides (5 and 6) by this methodology were optimized; some of the (alkoxydichloromethyl)disulfanyl adducts, e.g., ROCCl2SS(C=O)Cl (10) and ROCCl2SS(C=O)OR'(54), were reasonable stable and could be isolated.All new compounds were characterized by analytical data, 1H and 13C NMR, IR, UV, and mass spectrometry, and high-yield derivatizations with alcohols or N-methylaniline.The reaction with N-methylaniline was also adapted to a rapid, convenient, and precise analytical-scale assay of mixtures of compounds containing acid chloride and/or sulfenyl chloride functionalities.The kinetics, mechanism, and stereochemistry of the dithiocarbonyl synthesis are discussed.

NOVEL SYNTHESIS OF DISUBSTITUTED THIOLCARBAMATES VIA A SULFUR TRANSFER AGENT-POTASSIUM ALKYL OR BENZYL DITHIOCARBONATES

The reaction of N,N-disubstituted carbamoyl chlorides with potassium alkyl or benzyl dithiocarbonates afforded a novel synthesis of disubstituted thiolcarbamates.