937-63-3

Basic information

• Product Name: P-TOLYL CHLOROTHIONOFORMATE
• Synonyms: Chlorothioformic acid p-tolyl ester;p-Tolyl chlorothionoformate,98%;p-Tolyl Chlorthioformate;O-p-tolyl carbonochloridothioate;4-TOLYLCHLOROTHIONOFORMATE;4-METHYLPHENYL CHLOROTHIOFORMATE;P-TOLYL CHLOROTHIOFORMATE;P-TOLYL CHLOROTHIONOCARBONATE
• CAS NO: 937-63-3
• Molecular Formula: C₈H₇ClOS
• Molecular Weight: 186.66
• EINECS: 213-333-3
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds
• Mol File: 937-63-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 245 °C(lit.)
• Flash Point: 205 °F
• Appearance: clear yellow liquid
• Density: 1.225 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0466mmHg at 25°C
• Refractive Index: n20/D 1.573(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with common organic solvents.
• Sensitive: Moisture Sensitive
• BRN: 1448986
• CAS DataBase Reference: P-TOLYL CHLOROTHIONOFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLYL CHLOROTHIONOFORMATE(937-63-3)
• EPA Substance Registry System: P-TOLYL CHLOROTHIONOFORMATE(937-63-3)

Safety Data

• Hazard Codes: T,Xi
• Statements: 23-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 13-19
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 937-63-3(Hazardous Substances Data)

Usage

Description

P-TOLYL CHLOROTHIONOFORMATE is an organic compound that serves as a reagent in various chemical reactions. It is known for its ability to facilitate dehydration reactions through cyclic elimination of thiocarbonate esters, making it a valuable component in the synthesis of complex organic molecules.

Uses

Used in Organic Synthesis:
P-TOLYL CHLOROTHIONOFORMATE is used as a catalyst for the synthesis of alfa-L-2'-deoxythreofuranosyl nucleoside analogs and alkenes from hindered alcohols. Its role in these reactions is crucial for the formation of the desired products, showcasing its importance in the field of organic chemistry.
Used in Dehydration Reactions:
In the dehydration reactions, P-TOLYL CHLOROTHIONOFORMATE is used as a catalyst to promote the cyclic elimination of thiocarbonate esters. This ability to act as a catalyst in such reactions highlights its utility in creating new compounds and advancing chemical research.

InChI:InChI=1/C8H7ClOS/c1-6-2-4-7(5-3-6)10-8(9)11/h2-5H,1H3

Upstream product

• 106-44-5 p-cresol 
• 463-71-8 thiophosgene 

Downstream Products

• 39170-77-9 Thiocarbonic acid O-bicyclo[3.3.1]non-1-yl ester O-p-tolyl ester 
• 68270-46-2 Hiba-14-on-15α-p-tolylthionocarbonat 
• 68270-48-4 Hiba-14α-ol-15β-p-tolylthionocarbonat 
• 68270-49-5 Hiba-14α,15α-di-p-tolylthionocarbonat 
• 68270-47-3 Hiba-14α-ol-15α-p-tolylthionocarbonat 
• 57717-08-5 Thiocarbonic acid O-[3-(3,5-di-tert-butyl-4-hydroxy-phenyl)-2,2-dimethyl-propyl] ester O-p-tolyl ester 
• 39170-76-8 Thiocarbonic acid O-spiro[5.5]undec-7-en-1-yl ester O-p-tolyl ester 
• 67876-95-3 Thiocarbonic acid O-((2S,5S)-2-isopropyl-5-methyl-cyclopentylmethyl) ester O-p-tolyl ester 
• 39170-75-7 (-)-(1R,6R)-trans,trans-Spiro<4,4>nonan-1,6-diol-bis-<4-methyl-phenyl-thion-kohlensaeureester> 
• 3288-96-8 5-(4-methylphenyloxy)-1,2,3,4-thiatriazole 
• 16241-02-4 O-(4-methylphenyl) N,N-dimethylthiocarbamate 
• 92103-38-3 3.4-Dichlor-thiocarbanilsaeure-<4-methyl-phenyl-ester> 
• 130255-55-9 5-p-Tolyloxy-[1,2,4]dithiazol-3-ylideneamine; hydrochloride 
• 145593-90-4 9-(2',3'-Dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl)-N²-isobutyrylguanin 

Relevant articles and documents

Radical OfC transposition: A metal-free process for conversion of phenols into benzoates and benzamides

We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the CdS moiety. This addition step, analogous to the first step of the Barton-McCombie reaction, produces a carbon radical which undergoes 1,2 OfC transposition through an O-neophyl rearrangement. The usually unfavorable equilibrium in the reversible rearrangement step is shifted forward via a highly exothermic C-S bond scission in the O-centered radical, which furnishes the final benzoic ester or benzamide product. The metal-free preparation of benzoic acid derivatives from phenols provides a potentially useful alternative to metal-catalyzed carbonylation of aryl triflates.

Episulfidation of strained cycloalkenes in the thermolysis of 5-aryloxy-1,2,3,4-thiatriazoles

The thermolysis of 5-aryloxythiatriazoles 1 in the presence of norbornene (2a) and trans-cyclooctene (trans-2b) affords the corresponding thiiranes 3a and trans-3b in moderate yields. First-order kinetics are observed, suggesting that a sulfur intermediate, presumably dinitrogen sulfide, is generated in the fragmentation process of 1, which then serves as the active sulfur atom donor.