Methanesulfenic acid chloride

Base Information

• Chemical Name: Methanesulfenic acid chloride
• CAS No.: 5813-48-9
• Molecular Formula: CH3ClS
• Molecular Weight: 82.5538
• Mol file: 5813-48-9.mol

Synonyms:Methanesulfenylchloride;

Chemical Property of Methanesulfenic acid chloride

Chemical Property:

• Vapor Pressure: 191mmHg at 25°C
• Refractive Index: 1.466
• Boiling Point: 62.4°C at 760 mmHg
• Flash Point: 7.3°C
• PSA: 25.30000
• Density: 1.172g/cm³
• LogP: 1.50320

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methanesulfenic acid chloride

There total 8 articles about Methanesulfenic acid chloride 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: 81.0%

Dimethyldisulphide (624-92-0) + dichloromethylsulfonium hexachloroantimonate(V) → Methanesulfenyl chloride (5813-48-9) + Methylthio(bismethylthio)sulfonium hexachloroantimonate (56648-69-2)

Guidance literature:

In dichloromethane; 6 mmol of the Sb compound suspended in CH2Cl2; addn. of 12 mmol Me2S2 i CH2Cl2 at -65°C; ppt. filtered off at -65°C, washed with CH2Cl2, and dried;

Reference yield:

methylthio radical (7175-75-9) + chlorine (7782-50-5) → Methanesulfenyl chloride (5813-48-9) + clorine (14700-96-0,14835-24-6,15723-23-6,16547-50-5,16885-04-4,16887-00-6,16904-11-3,16904-12-4,16999-02-3,20337-89-7,20499-73-4,22537-15-1,22537-27-5,22541-73-7,22541-74-8,24203-47-2,33944-49-9,34937-26-3,37352-90-2)

Guidance literature:

In gas; room temp., 0.3 Torr; Kinetics;

DOI:10.1016/0009-2614(88)80305-1

Reference yield:

dichloromethane (75-09-2) + trichloro-methyl-λ4-sulfane (661-38-1) + diphenyldisulfane (882-33-7) → Methanesulfenyl chloride (5813-48-9) + benzenesulfenyl chloride (931-59-9)

Guidance literature:

DOI:10.1021/ja01156a091

upstream raw materials:

dichloromethane

trichloro-methyl-λ⁴-sulfane

diphenyldisulfane

S-methyl thiolacetate

Downstream raw materials:

trans-1-chloro-2-(methylthio)cyclohexane

4-methylthio-o-cresol

4-Chloro-2-(Methylthio)-Phenol

bis-(diethylamino)methane

Refernces

The Reaction of Sulfenyl Chlorides with Trialkyl Phosphites1

10.1021/ja01606a062

The study investigates the reaction of sulfenyl chlorides with trialkyl phosphites, resulting in the formation of esters of monothiophosphoric acid. Various alkyl and aromatic sulfenyl chlorides, such as methanesulfenyl chloride, benzenesulfenyl chloride, and p-chloroethanesulfenyl chloride, were reacted with triethyl phosphite, tri-n-propyl phosphite, and tri-n-butyl phosphite. The reactions were rapid, even at Dry Ice temperatures, indicating a nucleophilic displacement of chloride accompanied by the elimination of alkyl chloride. The study also compared the reactivity of these sulfenyl chlorides with that of sulfur monochloride and noted that the sulfenyl chlorides reacted at least as readily as acyl halides, which are known to react exothermally with tertiary phosphites. The compounds synthesized were used for biological testing in cancer chemotherapy studies, with particular interest in the 6-chloro thioester as a potential mustard analog.

5-chloro-3-methylthio-1,2,4-thiadiazol-2-ium chlorides as useful synthetic precursors to a variety of 6aλ⁴-thiapentalene systems

10.1002/hc.10106

The study focuses on the synthesis and chemical behavior of 5-chloro-1,2,4-thiadiazol-2-ium chlorides (salts 3), which are useful precursors to a variety of 6aλ4-thiapentalene systems. These salts were obtained by treating formimidoyl isothiocyanates (1) with an excess of methanesulfenyl chloride. The salts exhibited interesting chemical behavior towards several nitrogen and carbon nucleophiles, leading to the formation of diverse polyheterapentalene systems. Key chemicals used in the study include isothioureas, acetamide, p-toluidine, phenyl isothiocyanate, and active methylene compounds like methyl cyanoacetate and dimethyl malonate. These reagents served to displace the 5-chlorine atom of the salts, leading to the formation of various heterocyclic compounds such as 1H,6H-6aλ4-thia-1,3,4,6-tetraazapentalenes (7), 6H-6aλ4-thia-1-oxa-3,4,6-triazapentalene (9), and other thiapentalene derivatives. The study utilized IR and NMR spectroscopic data for structural assignments and received additional support from X-ray analysis of substrate 16a. The purpose of these chemicals was to explore the reactivity of the thiadiazolium salts and to synthesize new hypervalent sulfur compounds through nucleophilic substitution reactions.