594-42-3

Basic information

• Product Name: Perchloromethylmercaptan
• Synonyms: (Trichloromethyl)sulfenyl chloride;carbonsulfoperchloride;Clairsit;Mercaptan methylique perchlore;mercaptanmethyliqueperchlore;mercaptanmethyliqueperchlore(french);PCM;Perchlormethylmerkaptan
• CAS NO: 594-42-3
• Molecular Formula: CCl₄S
• Molecular Weight: 185.89
• EINECS: 209-840-4
• Mol File: 594-42-3.mol

Chemical Properties

• Boiling Point: 146-148 °C(lit.)
• Appearance: Clear yellow/Liquid
• Density: 1.7 g/mL at 25 °C(lit.)
• Vapor Density: 6.41 (vs air)
• Vapor Pressure: 2.02 psi ( 20 °C)
• Refractive Index: n20/D 1.537(lit.)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: Perchloromethylmercaptan(CAS DataBase Reference)
• NIST Chemistry Reference: Perchloromethylmercaptan(594-42-3)
• EPA Substance Registry System: Perchloromethylmercaptan(594-42-3)

Safety Data

• Hazard Codes: T,T+,N
• Statements: 23/24/25-34-26-25-21-52/53
• Safety Statements: 26-36/37/39-45-7/9-28A-25-61
• RIDADR: UN 1670 6.1/PG 1
• WGK Germany: 3
• RTECS: PB0370000
• F: 13-21
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 594-42-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Perchloromethylmercaptan is used as a reactant in the preparation of thioand selenoesters of triflic acid via a route to thioand selenosulfonates from disulfides and diselenides.
Used in Dye Industry:
Perchloromethylmercaptan is used as a dye intermediate, contributing to the production of various dyes.
Used in Fumigation:
Perchloromethylmercaptan is employed as a fumigant, utilized for its effectiveness in controlling pests and maintaining the quality of stored products.
Used in Rubber Industry:
In the rubber industry, Perchloromethylmercaptan is used as a vulcanizing accelerator, enhancing the process of rubber vulcanization and improving the properties of the final product.
Used in Fungicide Production:
Perchloromethylmercaptan is used as a reactant in the production of fungicides, playing a crucial role in the development of these agricultural chemicals to protect crops from fungal infections.

Synthesis Reference(s)

Tetrahedron, 48, p. 8065, 1992 DOI: 10.1016/S0040-4020(01)80477-4

Air & Water Reactions

Insoluble in water. Slowly decomposed by moisture in the air. Reacts with hot water to give carbon dioxide, hydrochloric acid and sulfur.

Reactivity Profile

Perchloromethylmercaptan is incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Reacts readily with oxidizing agents.

Health Hazard

May cause death or permanent injury after short exposure to small quantities, strong irritant to eyes and skin. Inhalation may cause severe irritation of the upper respiratory tract. It also is a strong irritant to the eyes and skin. Brief exposure to lower concentrations may produce central nervous system depression and lung, liver, and heart congestion. Severe exposures may be fatal. Exposure of eyes may lead to severe conjunctivitis or corneal damage. The liquid is irritating to the skin, and may be absorbed through the skin in quantities sufficient to cause general toxic effects. Ingestion may cause damage to mucous membranes and result in pain and burning of the mouth and throat, nausea, vomiting, cramps, and diarrhea. In severe cases, tissue ulceration and CNS depression may occur.

Fire Hazard

Very irritating vapors formed from hot material; may form phosgene gas, hydrogen chloride, and sulfur dioxide. At high temperatures Perchloromethylmercaptan will decompose to carbon tetrachloride, sulfur chloride, heavy oil polymers, phosgene gas, hydrogen chloride, and sulfur dioxide. Reacts with iron or steel, evolving carbon tetrachloride. Corrosive to most metals. Reacts with water only when hot to give carbon dioxide, hydrochloric acid, and sulfur. Hazardous polymerization may not occur.

Safety Profile

Poison by ingestion, inhalation, and intravenous routes. A severe skin, eye, and mucous membrane irritant. When heated to decomposition it emits very toxic fumes of Cland SOx. See also MERCAPTANS

Potential Exposure

Perchloromethyl mercaptan is used as an intermediate for the synthesis of dyes and fungicides, such as Captan and Folpet. This chemical has been considered as a warfare tear gas because of its highly irritant properties.

Shipping

UN1670 Perchloromethyl mercaptan, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Inhalation Hazard Zone B.

Incompatibilities

Water contact forms HCl, sulfur and carbon dioxide. Reacts with alkalies, amines, hot water; alcohols, oxidizers, reducing agents; iron, and steel. Attacks most metals.

Waste Disposal

Incineration together with a flammable solvent in a furnace equipped with afterburner and scrubber.

InChI:InChI=1/CCl4S/c2-1(3,4)6-5

Upstream product

• 75-15-0 carbon disulfide 
• 56-23-5 tetrachloromethane 
• 463-71-8 thiophosgene 
• 75-18-3 dimethylsulfide 
• 7553-56-2 iodine 
• 7782-50-5 chlorine 
• 556-64-9 methyl thiocyanate 
• 7732-18-5 water 
• 2532-50-5 perchlorodimethyltrisulfane 
• 16396-68-2 allyl trichloromethyl sulfoxide 
• 51737-74-7 fluorobis(trifluoromethylsulfanyl)methanesulfenyl chloride 
• 67-66-3 chloroform 
• 74128-90-8 2,2,2',2'-Tetrachlor-1,1'-diphenyl-2,2'-trithiobis(ethanon) 
• 98-86-2 acetophenone 

Downstream Products

• 25726-97-0 1-trichloromethanesulfenyl-1H-pyrazole 
• 109069-46-7 trichloro-methanesulfenic acid-(2-chloro-1-phenyl-ethyl ester) 
• 90155-06-9 3-trichloromethanesulfenyl-oxazolidine-2,4-dione 
• 13029-17-9 2-trichloromethyldisulfanyl-benzothiazole 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 52739-89-6 trithiocarbonic acid bis-benzothiazol-2-yl ester 
• 98334-15-7 (+/-)-trichloromethanesulfenic acid-(trans-2-chloro-cyclohexyl ester) 
• 53743-19-4 3-Trichlormethylthio-5,5-diphenyl-hydantoin 
• 98556-42-4 trichloro-methanesulfenic acid-(4-cyano-phenyl ester) 
• 16188-40-2 N-(4-methylphenyl)-1,1,1-trichloromethanesulfenamide 
• 88693-68-9 trichloro-methanesulfenic acid-(4-chloro-anilide) 
• 2284-20-0 4-Methoxyphenyl isothiocyanate 
• 5440-98-2 N,N',N''-tribenzyl-guanidine 
• 1009-03-6 (+/-)-(trans-2-chloro-cyclohexyl)-trichloromethyl sulfide 

Relevant articles and documents

A FUNGICIDAL COMPOUND AND PROCESS OF PREPARATION THEREOF

The present invention relates to a fungicidal sulfenyl phthalimide compound of formula (I) and a compound of formula (II) wherein said compound of formula (I) and formula (II) are substantially free from unwanted impurity. Particularly the present invention relates to a process of preparation of compounds of formula (I) and (II) substantially free from unwanted impurity.

Synthetic method of perchloromethyl mercaptan

The invention discloses a synthetic method of perchloromethyl mercaptan. According to the synthetic method, trichloromethane and sulfur dichloride are used as reaction raw materials, and organic alkali is used as a catalyst and an acid-binding agent to prepare the perchloromethyl mercaptan. The method has the advantages of simple operation, strong operability, avoidance of the use of carbon disulfide and chlorine, effective solving of potential safety hazards caused by the use of carbon disulfide and chlorine and high safety; and the obtained perchloromethyl mercaptan appears to be yellow oilyliquid, has yield of 85% or above and density of 1.69 or above, meets use requirements, and presents industrial application value.

Radical Aromatic Trifluoromethylthiolation: Photoredox Catalysis vs. Base Mediation

Trifluoromethyl aryl sulfides (Ar-SCF3) constitute highly attractive building blocks due to their exceptional lipophilicity and chemical properties. Related protocols of radical aromatic trifluoro-methylthiolation of arenediazonium salts were developed that are based on the facile generation of intermediate aryl radicals. Their reactions with commercial F3CS-SCF3 under very mild conditions afforded a diverse set of Ar-SCF3 (3]Cl2} with the weak base-mediated dark reaction documented higher synthetic efficiency of the former but higher operational simplicity of the latter strategy.

One-Step Conversion of Methyl Ketones to Acyl Chlorides

Treatment of aromatic and heteroaromatic methyl ketones with sulfur monochloride and catalytic amounts of pyridine in refluxing chlorobenzene leads to the formation of acyl chlorides. Both electron-rich and electron-poor aryl methyl ketones can be used as starting materials. The resulting C1-byproduct depends on the precise reaction conditions chosen.

PROCESS FOR SYNTHESIS FIPRONIL

The present disclosure relates to a process for trifluoromethylsulfinyl pyrazole compound of formula I, from a compound of formula III, wherein, R, R1 and R2 represent a group containing halogen group respectively and R3 represents a perhaloalkyl.

PROCESS FOR SYNTHESIS OF FIPRONIL

A process for preparation of a trifluoromethylsulfinyl pyrazole compound of formula (I) from a compound of formula (III) is provided, wherein R, R1 and R2 represent a group containing halogen respectively and R3 represents a perhaloalkyl.

MODULATORS OF MUSCARINIC RECEPTORS

The present invention relates to modulators of muscarinic receptors. The present invention also provides compositions comprising such modulators, and methods therewith for treating muscarinic receptor mediated diseases.

SPIRO CONDENSED PIPERIDNES AS MODULATORS OF MUSCARINIC RECEPTORS

The present invention relates to modulators of muscarnic receptors of formula (I). The present invention also provides impositions comprising such modulators, and methods therewith for treating muscarinic receptor mediated diseases.

Preparation of α, α-difluoroalkanesulfonic acids

Chlorodifluoromethanesulfonic acid (1) was prepared using a new procedure starting from perchloromercaptan, which is readily obtained from chlorination of CS2. Modified Swarts reaction transformed N, N-diethyl trichloromethanesulfenamide into N, N-diethyl chlorodifluoromethanesulfenamide, and the latter species was further oxidized and hydrolyzed into chlorodifluoromethanesulfonic acid. The preparations of other two new α,α-difluoroalkanesulfonic acids, phenyl difluoromethanesulfonic acid (2) and 2-phenyl-1,1,2,2, -tetrafluoroethanesulfonic acid (3), are also disclosed. The acids 2 and 3 are stable in the forms of sodium (lithium) salts or in aqueous solutions; however, the pure forms of 2 and 3 can readily undergo defluorinations. 1-3 and their salts have potential applications as superacid catalysts and lithium battery electrolytes.

Organic Heterocyclothiazenes. Part 13. Rotational Synthesis and Chemistry of 1,3,5,2,4-Trithiadiazines

1,3,5,2,4-Trithiadiazines, previously formed from tetrasulphur tetranitride and diazoalkanes, are synthesised from 1,1-bis-sulphenyl chlorides (1; R = H, Cl), (5), (11) and bis(trimethylsilyl)sulphurdiimide (2), and this reaction extends to trithiadiazines with functional groups on carbon.Bis-sulphenyl chlorides (5a-d) are formed in one step from malonic esters and amides and sulphur dichloride.Pentathiepane (lenthionine) (14), prepared from di-iodomethane and disodium disulphide, gives methanebis(sulphenyl chloride) on chlorinolysis and hence, with (2), the parenttrithiadiazine (3; R = H).Similarly the pentathiepane (16) is converted into bis-sulphenyl chloride (11) and the spirotrithiadiazine (12).The sensitivity of the heterocyclic ring towards strongly polar reagents precluded the generation of the trithiadiazine cation (17) and anion (19), but the radical (18) is formed on treatment with benzoyl peroxide and benzoyl t-butyl nitroxide (22), resulting in the benzoyloxy and amino-oxy derivatives (21) and (24). m-Chloroperbenzoic acid or nitrogen tetroxide convert trithiadiazine into the S-oxide (25).