Ethyl sulfide

HCID 9609CAS 352-93-2

Basic information

Standard SMILES
CCSCC
InChIKey
LJSQFQKUNVCTIA-UHFFFAOYSA-N
Molecular formula
C4H10S
Average molar mass
90.19 g/mol
Monoisotopic mass
90.05032132

Overview

Diethyl sulfide appears as a colorless oily liquid with a garlic-like odor. Less dense than water. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.

Names & identifiers

Preferred name
Ethyl sulfide
IUPAC
ethylsulfanylethane
English name
Diethyl sulfide
Molecular formula
C4H10S
Molecular weight
90.19

Names & synonyms

Diethyl sulfideEthyl sulfide352-93-2ethylsulfanylethaneEthyl thioetherEthylthioethaneDiethyl thioetherEthane, 1,1'-thiobis-Diethylsulfid(ethylsulfanyl)ethane1-(Ethylsulfanyl)ethaneDTXSID5027146
Show more names
diethylsulfanethioetherFEMA 3825Ethanethiolate1,1'-thiobisethaneTwo.Sulfodor(C2H5)2S
9191Y76OTCNSC-75157DTXCID507146FEMA NO. 3825CHEBI:27710RefChem:587283CHEBI:23996206-526-9

Database identifiers

CAS
352-93-2
PubChem CID
9609
DTXSID
DTXSID5027146
ChEMBL
CHEMBL117181
ChEBI
CHEBI:27710
UNII
9191Y76OTC
EC Number
206-526-9
Nikkaji
J2.577A

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
25.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
5

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Sulfur Compounds

Flammable agents - 3rd degree

SpringerMaterials PropertiesSchoenflies notation
FragrancesFragrance Ingredient (Diethyl sulfide) -> IFRA transparency List
LogP · 3 items

log Kow = 1.95

1.95

1.95

Odor · 2 items

Garlic-like odor

Ethereal odor

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

Physicochemical properties

Melting point
100 °C · −100 °C(lit.)
Boiling point
90 · 90-92 °C(lit.)
Density
0.837 g/mL · 0.837 g/mL at 25 °C(lit.)
vapor pressure
105 mm · 105 mm Hg ( 37.7 °C)
refractive index
20 · n20/D 1.442(lit.)
FEMA
3825 · 3825 | DIETHYL SULFIDE

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1476 reports by companies from 7 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 5 items

Chemical: Ethane, 1,1'-thiobis-

Ethane, 1,1'-thiobis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethane, 1,1'-thiobis- 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: 19-11-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/11953

Ethane, 1,1'-thiobis-: HSNO Approval: HSR001126 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 · 2 items

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

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

Fire PotentialA very dangerous fire hazard when exposed to heat, flame, or sparks
Health Hazards · 2 items

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

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

Hazards SummaryEmergency treatment: Irritants; [HSDB] Safe when used as a flavoring agent in food; [JECFA] A mild eye and moderate skin irritant; [RTECS] A skin and severe eye irritant; [Alfa Aesar MSDS]

Safety & protection

Fire FightingExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
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 · 2 items

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

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 3 items

For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water.

To fight fire, use water spray or mist, dry chemical, carbon dioxide, foam.

Wear self contained breathing apparatus for fire fighting if necessary.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Store in cool place.

Toxicology

Ecotoxicity ValuesLC50; Species: Lebistes reticulatus (Guppy); Concentration: 500 mg/L for 96 hr /Conditions of bioassay not specified in source examined/
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a log Kow of 1.95(2) and a regression-derived equation(3), indicates that diethyl sulfide is expected to have very high mobility in soil(SRC). Volatilization of diethyl sulfide from moist soil surfaces is expected to be an important fate process(SRC) given a measured Henry's Law constant of 1.68X10-3 atm-cu m/mole(4). Diethyl sulfide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 60.2 mm Hg at 25 °C(SRC). Although biodegradation data on diethyl sulfide are not available(SRC, 2009), the closely related compound dimethyl sulfide showed 100% degradation over 2 days in an aerobic test using freshwater sediment(6); this suggests that biodegradation of diethyl sulfide is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 50(SRC), determined from a log Kow of 1.95(2) and a regression-derived equation(3), indicates that diethyl sulfide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 1.68X10-3 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 1.3 hours and 4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 9(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Although biodegradation data on diethyl sulfide are not available(SRC, 2009), the closely related compound dimethyl sulfide showed 100% degradation over 2 days in an aerobic test using freshwater sediment(8); this suggests that biodegradation of 1,1'thiobisethane is an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethyl sulfide, which has a vapor pressure of 60.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethyl sulfide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(3); the half-life for this reaction in air is estimated to be about 26 hours(SRC), calculated from its rate constant of 1.50X10-11 cu cm/molecule-sec at 25 °C(3). Diethyl sulfide does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey ValuesDiethyl sulfide was detected in samples of beer at concentrations ranging from 3 to 30 ppb(1); it is a byproduct of yeast fermentation of grains. Diethyl sulfide has been detected in samples of chicken and beef(2).
Ecotoxicity Excerpts/PLANTS/ Vapor is phytotoxic ...
Effluent Concentrations · 1 item

Diethyl sulfide was detected in 1 of 63 industrial waste-water samples collected from unspecified locations in the US at a concentration of less than 10 ug/L(1). Diethyl sulfide was not detected in air samples collected from a highway tunnel in western Pennsylvania in August-September 1979(2).

Soil Adsorption/Mobility · 1 item

The Koc of diethyl sulfide is estimated as 50(SRC), using a log Kow of 1.95(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diethyl sulfide is expected to have very high mobility in soil.

Safety data

F
13
wgk
3
tsca
TSCA listed
rtecs
LC7200000
ridadr
UN 2375
hs_code
29309090

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 6 items

Used for chemical synthesis, as a solvent for anhydrous mineral salts, and in plating baths for coating metals with gold or silver; [HSDB] Used as flavoring agent; [JECFA]

Electroplating [Category: Plate]

For diethyl sulfide (USEPA/OPP Pesticide Code: 125101) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Reported uses (ppm): (Flavor and Extract Manufacturers' Association, 2005)

Diethyl sulfide is used as a chemical intermediate and in electroplating.

Solvent for anhydrous mineral salts; in plating baths for coating metals with gold or silver.

U.S. Production · 4 items

2023: <50,000 lb

Ethane, 1,1'-thiobis- 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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5437]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Ethane, 1,1'-thiobis-. Aggregated National Production Volume: 500,000 to <1 million pounds.

Industry UsesOther
Methods of Manufacturing · 3 items

Derivation: Heating sodium ethyl sulfate and potassium sulfide with subsequent distillation.

Ethylene + hydrogen sulfide (addition).

Made by distillation of sodium ethyl sulfate with a solution of K2S.

Use Classification · 6 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

Ethane, 1,1'-thiobis-: ACTIVE

Applications · 5 items

OccurrenceReported found in cabbage, sauerkraut, mustard, egg, chicken, beef, pork, beer (0.0002 to 0.0017 ppm), grape brandy (cognac, armagnac, weinbrand).

UsesDiethyl sulfide is used as a solvent for anhydrous mineral salts and in plating baths for coating metals with gold or silver. It is used as a flavoring agent. It is also used in the addition reaction with platinum dichloride to prepare platinum ethynyl dimers and polymers with pendant ferrocenyl group. Further, it is used in the preparation of triethylsulfoniuim ethylsulfate by reaction with sulfuric acid diethyl ester. In addition to this, it is used in the quantification procedure of volatile sulfur compounds by solid-phase microextraction.

UsesDiethyl sulfide may be used as an analytical standard for the determination of the analyte in wastewater, wines, and beer by gas chromatography (GC) based techniques.

UsesSolvent for Anhydrous mineral salts; in plating baths for coating metals with gold or silver.

General DescriptionA colorless oily liquid with a garlic-like odor. Less dense than water. Flash point 20°F. Vapors heavier than air. May irritate skin and eyes. Used to make other chemicals.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
三门峡奥科化工有限公司0398-3711988 13525866741 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes

DefinitionChEBI: Diethyl sulfide is an ethyl sulfide compound having two ethyl groups attached to a sulfur atom.

Related reactions

21 records

Linked notes

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