Trichloromethanesulfenyl chloride

HCID 11666

Basic information

CAS
594-42-3
Standard SMILES
ClSC(Cl)(Cl)Cl
InChIKey
RYFZYYUIAZYQLC-UHFFFAOYSA-N
Molecular formula
CCl4S
Average molar mass
185.9 g/mol
Monoisotopic mass
183.84748172

Overview

Perchloromethyl mercaptan appears as a yellow oily liquid with an offensive odor. Insoluble in water. Density 1.72 g / cm3. Hence sinks in water. Nonflammable but supports combustion. Very toxic by inhalation or skin absorption.

Names & identifiers

Preferred name
Trichloromethanesulfenyl chloride
IUPAC
trichloromethyl thiohypochlorite
English name
Perchloromethylmercaptan
Molecular formula
CCl4S
Molecular weight
185.89

Names & synonyms

Perchloromethyl mercaptan594-42-3ClairsitTRICHLOROMETHANESULFENYL CHLORIDEPerchloromethylmercaptanMethanesulfenyl chloride, trichloro-PerchloromethanethiolTrichloromethylsulfenyl chloridePerchlormethylmerkaptan(Trichloromethane)sulfenyl chloridePerchlorinemethylmercaptanThiocarbonyl tetrachloride
Show more names
PCMPMMchlorothio-trichloro-methaneClairsit(TM)perchloromethylrcrawastenumberp118TRICHLOROMETHANETHIOL
RCRA waste number P118Trichloromethanesulphenyl chlorideTrichloromethane sulfenyl chlorideMercaptan methylique perchloreTrichlormethyl sulfur chlorideTrichloromethylsulphenyl chlorideTrichloromethyl sulfochlorideDTXSID6025854

Database identifiers

CAS
594-42-3
PubChem CID
11666
DTXSID
DTXSID6025854
ChEMBL
CHEMBL3188766
UNII
KK489OII9M
EC Number
209-840-4
Nikkaji
J6.775J

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
25.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesToxic Gases & Vapors -> Other Toxic Gases & Vapors
SpringerMaterials PropertiesSchoenflies notation
Odor · 2 items

STRONG UNPLEASANT

Unbearable, acrid odor.

Density · 6 items

1.6947 at 68 °F (EPA, 1998) - Denser than water; will sink

Sp gr: 1.7 at 20 °C

Relative density (water = 1): 1.7

1.69

1.6947 @ 20°C

1.69

Color/Form · 3 items

OILY, YELLOW LIQUID

YELLOW TO ORANGE-RED

Pale-yellow, oily liquid.

Solubility · 4 items

less than 1 mg/mL at 70 °F (NTP, 1992)

SOL IN ETHER; INSOL IN WATER

Solubility in water: none

Insoluble

Physicochemical properties

Boiling point
146 · 146-148 °C(lit.)
Density
1.7 g/mL · 1.7 g/mL at 25 °C(lit.)
vapor density
6.41 · 6.41 (vs air)
vapor pressure
2.02 psi · 2.02 psi ( 20 °C)
refractive index
20 · n20/D 1.537(lit.)
storage temp.
-20 °C · -20°C Freezer

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 79 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Hazard information

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 4 items

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

Status: No longer Valid Update: 24-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/6687

Perchloromethyl mercaptan: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison Inhalation Hazard
Fire Hazards · 3 items

Very irritating vapors formed from hot material; may form phosgene gas, hydrogen chloride, and sulfur dioxide. At high temperatures this compound 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. (EPA, 1998)

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialTHIS CMPD IS NEITHER FLAMMABLE NOR SERIOUS FIRE HAZARD, ALTHOUGH IT WILL SUPPORT COMBUSTION.
Health Hazards · 2 items

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. (EPA, 1998)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Safety & protection

Fire Fighting · 2 items

Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. Positive pressure breathing apparatus and special protective clothing should be worn.

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 items

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 items

Signs and Symptoms of Acute Perchloromethylmercaptan Exposure: Signs and symptoms of acute exposure to perchloromethylmercaptan may lead to liver, heart, and kidney damage. Respiratory effects include coughing, dyspnea (shortness of breath), painful breathing, and lung congestion. Tachycardia (rapid heart rate) is often observed. Nausea, vomiting, abdominal cramping, and diarrhea may also occur. Contact with perchloromethylmercaptan may result in severe dermatitis (red, inflamed skin), conjunctivitis (red, inflamed eyes), and burns with ulceration and severe pain.

General First Aid:

(General first aid procedures)

Safe StorageSeparated from food and feedstuffs. See Chemical Dangers. Well closed.
Exposure Control and Personal Protection · 2 items

· Wear positive pressure self-contained breathing apparatus (SCBA).

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Toxicology

Target OrgansEyes, skin, respiratory system, liver, kidneys
Environmental Fate · 3 items

TERRESTRIAL FATE: If trichloromethanesulfenyl chloride is released to soil, it will be expected to slowly hydrolyze(1). No data were located and no estimations could be made concerning biodegradation in, adsorption to or volatilization from soil(SRC). Based upon a measured vapor pressure of 3 mm Hg at 20 °C(2), volatilization from dry near-surface soil or surfaces may be significant processes(SRC).

AQUATIC FATE: If trichloromethanesulfenyl chloride is released to water, it will be expected to slowly hydrolyze(1). No data were located and no estimations could be made concerning bioconcentration, biodegradation, volatilization, and adsorption to sediment and suspended solids(SRC).

ATMOSPHERIC FATE: If trichloromethanesulfenyl chloride is released to the atmosphere, it will be expected to exist almost entirely in the vapor phase(1) based upon a reported vapor pressure of 3 mm Hg at 20 °C(2). It will be susceptible to photooxidation via vapor phase reaction with photochemically produced hydroxyl radicals. An atmospheric half-life of 8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm has been calculated for this process based upon an estimated rate constant(3,SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Signs and Symptoms · 5 items

Cough. Sore throat. Laboured breathing. Nausea. Vomiting. Convulsions.

Redness. Pain.

Redness. Pain.

Abdominal cramps. Further see Inhalation.

irritation eyes, skin, nose, throat; lacrimation (discharge of tears); cough, dyspnea (breathing difficulty), deep breath pain, coarse rales; vomiting; pallor, tachycardia; acidosis; anuria; liver, kidney damage

ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.

Regulatory information

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Perchloromethyl mercaptan is produced, as an intermediate or final product, by process units covered under this subpart.

CERCLA Reportable Quantities · 2 items

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Perchloromethylmercaptan is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

DHS Chemicals of Interest (COI) · 4 items

Perchloromethylmercaptan

1.00

10,000

Toxic chemical that can be released at a facility.

Safety data

F
13-21
OEB
C
OEL
TWA: 0.1 ppm (0.8 mg/m3)
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
IDLA
10 ppm

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used in the production of dyes and fungicides; [ACGIH]

Used as an intermediate for the synthesis of dyes & fungicides (Captan, Folpet).

... Has tear gas properties that have been of military interest.

Methods of Manufacturing · 2 items

CHLORINATION OF CARBON DISULFIDE, THIOPHOSGENE, OR METHYL THIOCYANATE.

The chlorination of carbon disulfide on a granular-charcoal column in the presence of difunctional carbonyl compounds, phosphonates, phosphorites, phosphites, phosphates or lead acetate.

Formulations/PreparationsGRADES OR PURITY: TECHNICAL: 97+%
General Manufacturing InformationMethanesulfenyl chloride, trichloro-: ACTIVE
Applications · 4 items

UsesOrganic synthesis, dye intermediate, fumigant.

UsesProduction of fungicides; vulcanizing accelerator in rubber industry

UsesPerchloromethyl Mercaptan is used as a reactant in the preparation of thio- and selenoesters of triflic acid via a route to thio- and selenosulfonates from disulfides and diselenides.

General DescriptionA yellow oily liquid with an offensive odor. Insoluble in water. Density 1.72 g / cm3. Hence sinks in water. Nonflammable but supports combustion. Very toxic by inhalation or skin absorption.

Related reactions

70 records

Compound notes

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