Ethanethiol

HCID 6343CAS 75-08-1

Basic information

Standard SMILES
CCS
InChIKey
DNJIEGIFACGWOD-UHFFFAOYSA-N
Molecular formula
C2H6S
Average molar mass
62.14 g/mol
Monoisotopic mass
62.01902119

Overview

Ethyl mercaptan appears as a clear colorless low-boiling liquid (boiling point 97 °F) with an overpowering, garlic-like/skunk-like odor. Flash point -55 °F. Less dense than water and very slightly soluble in water. Vapors are heavier than air. Vapors may irritate nose and throat. May be toxic if swallowed, by inhalation or by contact. Added to natural gas as an odorant. Used as a stabilizer for adhesives.

Names & identifiers

Preferred name
Ethanethiol
IUPAC
ethanethiol
English name
Ethanethiol
Molecular formula
C2H6S
Molecular weight
62.13

Names & synonyms

EthanethiolETHYL MERCAPTAN75-08-1MercaptoethaneEthyl sulfhydrateThioethanolEthyl thioalcoholThioethyl alcoholEthyl hydrosulfideAethylmercaptanEtilmercaptanoAethanethiol
Show more names
C2H5SHEthanthiolMERCAPTAN C21-ETHANETHIOLEM RTEM(TM) RT
Etantiolo1-MercaptoethaneEthaanthiolEthylmercaptaanEthylmerkaptanethyl-mercaptanLPG ethyl mercaptan 1010M439R54A1D

Database identifiers

CAS
75-08-1
PubChem CID
6343
DTXSID
DTXSID9026394
ChEBI
CHEBI:46511
UNII
M439R54A1D
EC Number
200-837-3
Nikkaji
J1.439G

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
3

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Thiols

Flammable agents - 4th degree

SpringerMaterials PropertiesSchoenflies notation
Pesticides · 2 items

Rodenticides

Active substance -> EU Pesticides database: Not approved

LogP1.5
Odor · 3 items

Leek-like odor

Penetrating garlic-like odor

Strong, skunk-like odor.

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Physicochemical properties

Melting point
-148 °C · -148 °C
Boiling point
35 °C · 35 °C(lit.)
Density
0.839 g/mL · 0.839 g/mL at 25 °C(lit.)
vapor density
2.1 · 2.1 (vs air)
vapor pressure
8.51 psi · 8.51 psi ( 20 °C)
refractive index
20 · n20/D 1.4306(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H224: Extremely flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P317, P303+P361+P353, P304+P340, P316, P321, P330, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H225 (93.1%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P317, P303+P361+P353, P304+P340, P317, P330, P370+P378, P391, P403+P235, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Chemical: Ethanethiol

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanethiol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanethiol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 16-02-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/2123

Ethanethiol: HSNO Approval: HSR001043 Approved with controls

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 LabelFlammable Liquid
Fire Hazards · 3 items

Special Hazards of Combustion Products: Irritating fumes of sulfur dioxide are generated.

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Extremely flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Fire Potential · 4 items

Dangerous, when exposed to heat or flame or oxidizers.

Minimum ignition temperature in air: 299 °C; in oxygen: 261 °C

Can react vigorously with oxidizing materials.

Extremely flammable.

Health Hazards · 2 items

Inhalation of vapor causes muscular weakness, convulsions, respiratory paralysis. High concentrations may cause pulmonary irritation. Liquid irritates eyes and skin. Ingestion causes nausea and irritation of mouth and stomach. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

Hazards Summary · 1 item

Its toxicity in rats and mice is similar to that of butyl mercaptan. Acutely, it is about 1/5 as toxic as hydrogen sulfide. Human volunteers exposed to 1mg/m3 (0.5 ppm) experienced no symptoms, while those exposed to 10 mg/m3 (4 ppm) complained of mucous membrane irritation and fatigue. [ACGIH] Liver necrosis occurs in animals receiving sublethal doses. [HSDB] See THIOLS.

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Use powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Rinse skin with plenty of water or shower. Rinse skin with plenty of water or shower.

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

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

Excerpt from NIOSH Pocket Guide for Ethyl mercaptan:

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants and strong acids. Cool.
Firefighting HazardsVapor is heavier than air and may travel long distance to a source of ignition and flash back; containers may explode in a fire.

Toxicology

Body BurdenSmall amounts of ethyl mercaptan are components of human breath(1).
Interactions... It supplements the effect of UV light on the epidermis by increasing the skin's histidase activity.
Target OrgansEyes, respiratory system, liver, kidneys, blood
Ecotoxicity Values · 2 items

EC50 Daphnia magna (Waterflea, <24 hr old) 90-280 mg/L/48 hr; static, 20 °C, hardness: 250 mg/L CaCO3, dissolved oxygen: >6.5 mg/L, pH 8.2

LC50 Daphnia magna (Water flea) 170 ug/L/48 hr; static /formulated product/

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a water solubility of 1.56X10+4 mg/L(2) and a regression-derived equation(3), indicates that ethyl mercaptan is expected to have very high mobility in soil(SRC). Volatilization of ethyl mercaptan from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.53X10-3 atm-cu m/mole(4). Ethyl mercaptan is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 529 mm Hg(5). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a water solubility of 1.56X10+4 mg/L(2) and a regression-derived equation(3), indicates that ethyl mercaptan is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 4.53X10-3 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.4 hours and 3.2 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 2.7(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl mercaptan, which has a vapor pressure of 529 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl mercaptan is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 hours(SRC), calculated from its rate constant of 4.68X10-11 cu cm/molecule-sec at 25 °C(3). Ethyl mercaptan does not absorb light at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight.

Food Survey ValuesEthyl mercaptan was qualitatively detected in the volatile components of raw chicken breast muscle(1). The compound has been identified as a beef volatile(2). Ethyl mercaptan occurs naturally in some vegetables such as cabbage(3).

Regulatory information

DHS Chemicals of Interest (COI) · 4 items

Ethyl mercaptan

1

10000

Flammable chemical that can be released at a facility.

Safety data

F
13
OEL
Ceiling: 0.5 ppm (1.3 mg/m3) [15-minute]
wgk
3
IDLA
500 ppm
tsca
TSCA listed
rtecs
KI9625000

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 5 items

A membrane bound enzymatic activity found in rabbit liver microsomes which catalyzes transmethylation from s-adenosylmethionine to series of c1-c3 alkane thiols. Methane and ethane thiols are endogenous toxins. Methylation could play role in metabolic detoxification.

Metabolism of ethyl mercaptan studied in rabbits. Ethyl methyl sulfide and diethyl sulfide were detected in blood and expired air.

... In dogs ... and ... guinea pigs in vitro ... ethanethiol is oxidatively metabolized to the sulfate probably via a sulfonic intermediate. One of the intermediate products is also postulated to involve ethylmethionine with a S-adenosylthionine enzyme as a mediator.

Mercaptans ... in small amount, occur naturally in urine, and appear to be related to nature of diet. ... Mercaptans also result from reduction of disulfides and may undergo methylation to form methyl alkyl sulfides, which are oxidized to corresponding sulfones. However, most of these sulfur compounds are metabolized eventually into sulfate.

For more Metabolism/Metabolites (Complete) data for ETHYL MERCAPTAN (6 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 3 items

In rabbits after inhalation of 30 ppm for 25 min, trace amounts were detected in blood, while inhalation of 10,000 ppm for 60 min resulted in significant amount of gas in blood. After exposure ended, amount present was very small and diminished rapidly.

Ethylmercaptan is rapidly absorbed, but also readily excreted by the mammalian system. Even in a normal subject, 5.9 ug/cu m of the thiol is exhaled.

Rabbits that inhaled 30 ppm for 25 min had trace amounts of ethyl mercaptan in the blood. Inhalation of 10,000 ppm for 60 min resulted in significant amounts in the blood. After the exposure ended, the amount present in the blood was very small and diminished very rapidly.

Uses & manufacturing

Uses · 3 items

Used as an odorant for natural gas; used as an intermediate in the plastic, pesticide, and organic chemical industries; [ACGIH]

Odorant for natural gas; intermediate and starting material in manufacture of plastics, insecticides, antioxidants.

Intermediate in production of acaricides, defoliants, pharmaceuticals, and adhesives

U.S. Production · 3 items

2023: 7,000,000 - <8,500,000 lb

Ethanethiol is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1991) Exceeded 5000 lb or US $5000 in value

Consumer UsesFuel
Industry UsesFuel
Methods of Manufacturing · 4 items

... From sodium ethylsulfate and KSH /potassium thiol/; ... catalytically from ethanol and hydrogen sulfide.

By saturating potassium hydroxide solution with hydrogen sulfide, mixing with calcium ethylsulfate solution and distilling on water bath.

Ethanethiol is prepared from ethylene and hydrogen sulfide in the gas phase over aluminum oxide catalysts containing potassium tungstate or nickel and tungsten oxides.

... Ethanethiol is obtained from ethylene and hydrogen sulfide in the liquid phase in the presence of azobisisobutyronitrile and tributylphosphine.

Formulations/PreparationsGrades or purity: 98.5+%
Applications · 5 items

DescriptionEthane thiol, commonly known as ethyl mercaptan, is a colorless gas or clear liquid with a distinct odor. It is an organosulfur compound with the formula CH3CH2SH. Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with S instead of O. The odor of EtSH is infamous. Ethanethiol is more volatile than ethanol due to a diminished ability to engage in hydrogen bonding. Ethanethiol is toxic. It occurs naturally as a minor component of petroleum, and may be added to other wise odorless gaseous products such as liquefied petroleum gas (LPG) to help warn of gas leaks. At these concentrations, ethanethiol is not harmful.

UsesEthanethiol is used as an intermediate inthe manufacture of insecticides, plastics, andantioxidants; and as an additive to natural gasto give odor. It occurs in illuminating gas andin petroleum distillates.

UsesStenching agent for liquefied petroleum gases; adhesive stabilizer; manufacture of plastics, insecticides, and antioxidants

UsesLPG odorant, adhesive, stabilizer, chemical intermediate.

General DescriptionA clear colorless low-boiling liquid (boiling point 97°F) with an overpowering, garlic-like/skunk-like odor. Flash point -55°F. Less dense than water and very slightly soluble in water. Vapors are heavier than air. Vapors may irritate nose and throat. May be toxic if swallowed, by inhalation or by contact. Added to natural gas as an odorant. Used as a stabilizer for adhesives.

Preparation methods · 1 item

PreparationEthanethiol is prepared by the reaction of ethylene with hydrogen sulfide over a catalyst. The various producers utilize different catalysts in this process. It is also be prepared commercially by the reaction of ethanol with hydrogen sulfide gas over an acidic solid catalyst, such as alumina. Ethanethiol was originally reported by Zeiss in 1834 . Zeise treated calcium ethyl sulfate with a suspension of barium sulfide saturated with hydrogen sulfide. He is credited with naming the C2H5S- group as mercaptum. Ethanethiol can also be prepared by a halide displacement reaction, where ethyl halide is reacted with aqueous sodium bisulfide. This conversion was demonstrated as early as 1840 by Henri Victor Regnault.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
山东旭晨化工科技有限公司0533-15715337262 15715337262 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]
常州市紫东联化进出口有限公司0519-85560282 13656141470 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Ethanethiol is an alkanethiol that is ethane substituted by a thiol group at position 1. It is added to odorless gaseous products such as liquefied petroleum gas (LPG) to provide a garlic scent which helps warn of gas leaks. It has a role as a rodenticide.

Related reactions

1,187 records

Linked notes

Loading…