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S-propyl chlorothioformate

HCID 26323
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
13889-92-4
Standard SMILES
CCCSC(=O)Cl
InChIKey
FYOPSYJKEHWOBR-UHFFFAOYSA-N
Molecular formula
C4H7ClOS
Average molar mass
138.62 g/mol
Monoisotopic mass
137.9906137

Overview

Blackish-brown liquid. (NTP, 1992)

Names & identifiers

Preferred name
S-propyl chlorothioformate
IUPAC
S-propyl chloromethanethioate
English name
n-Propyl chlorothioformate
Molecular formula
C4H7ClOS
Molecular weight
138.62

Names & synonyms

S-PROPYL CHLOROTHIOFORMATEPropyl chlorothioformateCarbonochloridothioic acid, S-propyl estern-Propyl thiochloroformatePropyl chlorothiolformaten-Propyl chlorothiolformateS-(n-propyl)chlorothioformic acidCCRIS 6097HSDB 6155S-(n-Propyl) carbonochloridothioateEINECS 237-656-4NSC 72086
Show more names
propylchlorothioformatepropylchlorothiolformateS-PROPYL THIOCHLOROFORMATEn-Propyl chlorothioformate1-(Chloroformylthio)propanen-propylthiochloroformate[qr](PROPYLTHIO)CARBONYL CHLORIDES-Propyl chlorothioformate 96%
BRN 1633747AI3-52665NSC-72086S-propyl carbonochloridothioateS-PROPYL CHLOROTHIOFORMATE [HSDB]nPropyl chlorothioformatenPropyl thiochloroformateSPropyl thiochloroformate

Database identifiers

CAS
13889-92-4

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
42.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
7
Formal charge
0
Complexity
64.7

Experimental & physicochemical properties

Chemical ClassesToxic Gases & Vapors -> Acid Halides
pHpH 0.2-1.5 (1:1:1 vol - % n-propl chlorothioformate:acetone:water)
SpringerMaterials PropertiesMolecular structure
OdorPenetrating
Density · 2 items

1.053 at 66 °F (NTP, 1992) - Denser than water; will sink

1.1

Viscosity4 cps at 20 °C
Color/FormAmber-colored liquid
Solubility · 3 items

less than 1 mg/mL at 68 °F (NTP, 1992)

INSOL IN WATER

Soluble in dichloroethane.

Flash Point · 3 items

144 °F (NTP, 1992)

63 °C

63 °C

Boiling Point155 °C

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P330, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

DOT LabelCorrosive Flammable Liquid
Fire HazardsThis chemical is combustible. (NTP, 1992)
Fire PotentialThis material is considered combustible.
Health HazardsACUTE/CHRONIC HAZARDS: This compound may be corrosive and may cause lachrymation. (NTP, 1992)
Hazards SummaryLachrymator; May hydrolyze after inhalation releasing HCl; Causes acute pulmonary edema in animal inhalation experiments; [HSDB] Harmful if ingested; Causes burns; Lachrymator; [MSDSonline]
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Special ReportsITC/USEPA; Information Review #331 (Draft) S-(n-propyl) Chlorothioformate (1983)
TSCA RequirementsReported in TSCA inventory
Reactivity Profile

Chemistry & industry

Uses & manufacturing

Uses · 4 items

Used to make thiocarbamate pesticides and herbicides; [HSDB]

Manufacture of thiocarbamate pesticides.

Synthetic intermediate used to produce derivatives of thiolformate.

Compound is used as an intermediate in the manufacture of herbicides.

U.S. Production1-10 million pounds produced in 1977; current annual production is 1-10 million pounds.
Formulations/PreparationsThe pesticide products, which appear to be vernolate and pebulate, are marketed by Stauffer under the trade names Vernam and PEBC, respectively.
General Manufacturing InformationCarbonochloridothioic acid, S-propyl ester: INACTIVE

Applications

General DescriptionBlackish-brown liquid.

Suppliers10 total

常州金和生物科技有限公司18796930758 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海相辉医药科技有限公司13761987713; 13761987713 · [email protected]
宝鸡缔都医药化工有限公司029-81145305 17791533577 · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
26323
DTXSID
DTXSID8025963
ChEMBL
CHEMBL1469099
UNII
S8YPJ4718Q
EC Number
237-656-4
Nikkaji
J23.980A
Vapor Density
4.8 (AIR= 1)
Vapor Pressure · 3 items

178.8 mmHg at 100 °F (NTP, 1992)

6.27 [mmHg]

6.27 mm Hg at 25 °C.

Physicochemical properties

Boiling point
37 °C/ · 37 °C/ 8 mmHg
Density
1.149 g/mL · 1.149 g/mL at 25 °C
refractive index
20 · n 20/D 1.4807
Flash point
49 °C · 49 °C
storage temp.
2 · 2-8°C
InChI
1S/C4H7ClOS/c1-2-3-7-4(5)6/h2-3H2,1H3
InChIKey
FYOPSYJKEHWOBR-UHFFFAOYSA-N
SMILES
CCCSC(Cl)=O
FDA UNII
8 YPJ4718Q · S8YPJ4718Q
EPA Substance Registry System
S-Propyl chlorothioformate (13889-92-4)
UNSPSC Code
12352100 · 12352100
Symbol(GHS)
2 · GHS02,GHS05,GHS07
Signal word
Danger
Hazard statements
226 · H226-H302-H314
Precautionary statements
280 · P280-P305+P351+P338-P310
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes
C
Risk Statements
10 · 10-22-34
Safety Statements
28 · 28-36/37/39-45
RIDADR
2920 · UN 2920 8/PG 2
WGK Germany
3 · 3
RTECS
7005000 · LQ7005000
TSCA
TSCA listed
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
4 OralEye · Acute Tox. 4 OralEye Dam. 1Flam. Liq. 3Skin Corr. 1B
Hazardous Substances Data
13889 · 13889-92-4(Hazardous Substances Data)
· 1 item

S-(N-PROPYL)CHLOROTHIOFORMIC ACID reacts exothermically with acids. May generate hydrogen sulfide with acids. Strong oxidizing agents may cause vigorous reactions that are sufficiently exothermic to ignite the reaction products. Reacts exothermically with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides.

Air and Water ReactionsSensitive to moisture (NTP, 1992). Slowly hydrolyzed. Insoluble in water.
NFPA Hazard Classification · 3 items

2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.

2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.

0 - Materials that in themselves are normally stable, even under fire conditions.

Toxic Combustion ProductsUnder fire conditions ... will decompose to give off toxic materials.

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Firefighting HazardsVapors are extremely irritating to the respiratory tract and may cause breathing difficulty and pulmonary edema. Symptoms may be delayed several hours or longer depending on exposure.
Fire Fighting Procedures · 1 item

Use water, dry chemicals, foam or carbon dioxide. If drums are not leaking, keep cooled with a water spray. High pressure water hose may spread product from broken containers increasing contamination hazards. Use of contaminated buildings, areas and equipment must be prevented until they are properly decontaminated.

Storage ConditionsContainers should be stored in a cool, dry, well-ventilated area. Store away from flammable materials, sources of heat and flame and foodstuffs. Exercise due caution to prevent damage to or leakage from the container.
Cleanup Methods · 1 item

Soak up pooled liquid with a suitable neutralizing absorbent, such as dry calcium hydroxide. Exercise caution during the neutralization as considerable heat may be generated. Place the absorbed material into a suitable chemical waste container. Apply diethanolamine (DEA) to the spill area and allow to stand for 5 min. Using wet towels, wipe up the DEA. Flush the spill area to remove residual DEA.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Personal Protective Equipment (PPE) · 2 items

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

Firefighters should wear full-face, self-contained breathing apparatus and impervious clothing such as gloves, hoods, suits and rubber boots.

Toxicology

Environmental Fate · 3 items

Atmospheric: photolysis and hydrolysis in water droplets should rapidly destroy the cmpd in the atmosphere.

S-(n-propyl) chlorothioformate is likely to have minimal environmental release. The manufacture of the cmpd should take place in a closed system. Use of this cmpd as an intermediate in preparation of pesticides is likely to also occur in a closed system.

Atmospheric: ... based on its estimated volatility the cmpd could move into the atmosphere.

Adverse EffectsDermatotoxin - Skin burns.
Environmental BioconcentrationBased on its octanol/water partition coefficient S-(n-propyl) Chlorothioformate is not expected to bioconcentrate.
Non-Human Toxicity Excerpts · 4 items

Propyl mercaptan, a hydrolysis product of s-(n-propyl)chlorothioformate caused severe irritation to the eye of a rabbit at 83 mg. /propyl mercaptan/

S-(n-propyl) chlorothioformate may act as ... a vesicant and, after inhalation, may produce respiratory tract effects due to release of HCl by hydrolysis and acylation of tissue nucleophiles.

A single oral dose of 566 mg/kg did not produce signs of toxicity in male or female rats. Signs of toxicity at larger, /not specified/, doses included decreased physical activity, lacrimation, piloerection and weakened righting and placement reflexes.

A single one-hr inhalation exposure of 1.3 mg/l (nominal concn) produced ataxia, gasping, lacrimation and 70% mortality in rats. Necropsy revealed pulmonary edema, and congested liver and/or lungs.

Environmental Abiotic Degradation · 2 items

Hydrolysis rate constant of s-(n-propyl) chlorothioformate is 29.6 x 10-4; half-life (min) 3.9 in water at 4.6 °C.

S-(n-propyl) chlorothioformate hydrolyzes to produce n-propyl mercaptan.

Antidote and Emergency Treatment · 4 items

Ingestion: do not induce vomiting. Immediately give large quantities of water. If vomiting does occur, give fluids again. Never give anything by mouth to an unconscious person.

Skin contact; Immediately remove contaminated clothing, wiping away excess material from the skin. Under a safety shower, flush all affected areas with large amounts of water for at least 15 min. Do not attempt to neutralize with chemical agents.

Eye contact: Immediately flush the eyes with large quantities of water for a minimum of 15 min. Hold the eyelids apart during the flushing to ensure rinsing of the entire surface of the eye and lids with water. Do not attempt to neutralize with chemical agents. Obtain medical attention as soon as possible. Oils or ointments should not be used. Continue the flushing for an additional 15 minutes if the physician is not immediately available.

Inhalation: Remove from contaminated atmosphere. If breathing has ceased, clear the victim's airway and start mouth-to-mouth artificial respiration, which may be supplemented by the use of a bag-mask respirator or a manually-triggered, oxygen supply capable of delivering one l/sec or more. If the victim is breathing, oxygen may be delivered from a demand-type or continuous-flow inhalator, preferably with a physician's advice

Toxicity DataLCLo (rat) = 1,300 mg/m3
Non-Human Toxicity Values · 2 items

LD50 rat po 1129 mg/kg; toxic effects: eye, skin, and behavioral symptoms

LD50 rabbit dermal 4500 mg/kg

Regulatory information

TSCA RequirementsReported in TSCA inventory

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
LQ7005000
ridadr
UN 2920 8/PG 2
risk_code
10-22-34
Signal word
Danger
Symbol(GHS)
GHS02,GHS05,GHS07
hazard_code
C
safety_code
28-36/37/39-45
Storage Class
3 - Flammable liquids
Hazard statements
H226-H302-H314
Hazard Classifications
Acute Tox. 4 OralEye Dam. 1Flam. Liq. 3Skin Corr. 1B
Precautionary statements
P280-P305+P351+P338-P310
Hazardous Substances Data
13889-92-4(Hazardous Substances Data)
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
许昌峰飞新材料科技有限公司19713077352; 19713077352 · [email protected]
河南奥诗曼生物科技有限公司13761588971 17719817155 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]