Dimethyl Sulfide

HCID 1068CAS 31533-72-9

Basic information

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

Overview

Dimethyl sulfide appears as a clear colorless to straw colored liquid with a disagreeable odor. Flash point less than 0 °F. Less dense than water and slightly soluble in water. Vapors are heavier than air.

Names & identifiers

Preferred name
Dimethyl Sulfide
IUPAC
methylsulfanylmethane
English name
Dimethyl sulfide
Molecular formula
C2H6S
Molecular weight
62.13

Names & synonyms

dimethyl sulfideMethyl sulfide75-18-3Methane, thiobis-Methyl thioetherdimethyl sulphidedimethylsulfide2-ThiapropaneDimethyl thioetherDimethylsulphideMethylthiomethaneMETHYLSULFANYLMETHANE
Show more names
Methyl sulphideDimethylsulfidThiobismethane(Methylsulfanyl)methaneMethyl monosulfideDimethyl monosulfide2-ThiopropaneMethanethiomethane

Database identifiers

CAS
31533-72-9、75-18-3
PubChem CID
1068
DTXSID
DTXSID9026398
ChEMBL
CHEMBL15580
ChEBI
CHEBI:17437
UNII
QS3J7O7L3U
EC Number
200-846-2
Nikkaji
J1.300.429C、J1.443E

Properties

Computed structural properties

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

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Sulfur Compounds

Flammable agents - 4th degree

SpringerMaterials PropertiesCoriolis coupling
FragrancesFragrance Ingredient (Dimethyl sulfide) -> IFRA transparency List
Pesticides · 2 items

Other Treatment

Active substance -> EU Pesticides database: Not approved

LogP0.84
OdorUNPLEASANT ODOR OF WILD RADISH, CABBAGE-LIKE

Physicochemical properties

Melting point
-98.3 °C · -98.3 °C
Boiling point
37.3 °C · 37.3 °C
Density
0.8483 g/cm3 · 0.8483 g/cm3
Symbol(GHS)
2 · GHS02
Signal word
Danger
Hazard statements
225 · H225

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225 (89.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1875 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

Hazard information

Regulatory Information · 6 items

Chemical: Methane, thiobis-

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

Methane, 1,1'-thiobis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, 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)

Reg. (EU) 2021/1451

Status: Active Update: 13-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13649

Methane, thiobis-: HSNO Approval: HSR001135 Approved with controls

DOT LabelFlammable Liquid
Fire Hazards · 3 items

Special Hazards of Combustion Products: Toxic and irritating sulfur dioxide is formed.

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

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

Fire PotentialHighly flammable
Health Hazards · 2 items

Inhalation causes moderate irritation of upper respiratory system. Contact of liquid with eyes causes moderate irritation. Repeated contact with skin may extract oils and result in irritation. 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

Liquid can cause first degree burns after short contact. [CHRIS] Decomposes on heating to release hydrogen sulfide and sulfur oxides; [ICSC] Low toxicity after skin or inhalation exposure; [HSDB] When applied to the skin, under a patch, for 48 hours, 1% dimethyl sulfide in petroleum jelly does not cause skin irritation. Dimethyl sulfide vapor can reach high concentrations at room temperature and act as a simple asphyxiant. It is a skin and respiratory tract irritant and can cause CNS depression after heavy inhalation exposure. From a case report, one worker in a storage tank died after exposure to about 500,000 ppm. The death was attributed to dimethyl sulfide toxicity and simple asphyxiation. [CHEMINFO]

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / 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. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). 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 · 2 items

INHALATION: move victim to fresh air at once; enforce rest, and keep warm; get medical attention immediately.

General First Aid:

Safe StorageFireproof. Separated from strong oxidants. Cool.
Firefighting HazardsAuto flammability: 205 °C at 1013 hPa

Toxicology

Body Burden · 1 item

Dimethyl sulfide was detected in expired air from 54 carefully selected healthy, nonsmokers as follows: 387 samples, 41.6% pos, mean concn 0.99 ng/l(1). It was detected in expired air from 6 out of 8 subjects at a range of measured expiration rates of 0.54-53.0 ug/hr(2). The concentration in breath samples collected from 14 persons exposed to organic reduced sulfur compounds in sulfate pulp mills ranged from 0.04 to 0.69 cu cm/cu m(3).

Interactions · 3 items

Tolerance against the rat lung edema response to ozone inhalation was not incr by intraperitoneal injection of dimethyl sulfide.

Dimethyl sulfoxide suppresses conversion of the prodrug sulindac to its bioactive sulfide metabolite (SD). During continuous iv infusions of sulindac (1 mg/kg/hr), plasma concn of SD at steady-state equilibrium were 80% lower when DMSO was infused concomitantly at 0.34 ml/kg/hr; whereas sulindac plasma concn were not significantly affected by DMSO. DMSO was only a weak inhibitor of SD oxidation in vitro and did not affect the rate of SD elimination in vitro. In contrast, dimethyl sulfide a metabolite of DMSO, was a potent inhibitor of SD oxidase in vitro.

Adult male rats were injected with sodium arsenite (4 mg/kg, sc) 10 min prior to injection of dimethyl sulfide. Neither compound caused mortality when given alone (n = 4). Dimethyl sulfide (320 mg S/kg, sc) resulted in no toxic signs or mortality with or without arsenite (n = 4).

Ecotoxicity Values · 2 items

LC50; Species: Daphnia pulex (Crustacea); Concentration: 150 mg/L for 24 hr (20 °C) /Conditions of bioassay not specified in source examined/

EC50; Species: Daphnia magna (Water flea); Concentration: 14300 ug/L for 24 hr; Effect: intoxication, immobilization /Conditions of bioassay not specified in source examined/

Environmental Fate · 4 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 6.3(SRC), determined from a water solubility of 22,000 mg/L(2) and a regression-derived equation(3), indicates that dimethyl sulfide is expected to have very high mobility in soil(SRC). Volatilization of dimethyl sulfide from moist soil surfaces is expected to be an important fate process(SRC) given a measured Henry's Law constant of 1.61X10-3 atm-cu m/mole(4). Dimethyl sulfide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 502 mm Hg at 25 °C(5). 100% degradation over 2 days in an aerobic test using a freshwater sediment inoculum(6) suggests that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 6.3(SRC), determined from a water solubility of 22,000 mg/L(2) and a regression-derived equation(3), indicates that dimethyl sulfide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a measured Henry's Law constant of 1.61X10-3 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 3 hours and 3 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 3.2(SRC), from a water solubility of 22,000 mg/L(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 100% degradation over 2 days in an aerobic test using a freshwater sediment inoculum(8) suggests that biodegradation 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), dimethyl sulfide, which has a vapor pressure of 502 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimethyl 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 3 days(SRC), calculated from its rate constant of 4.82X10-12 cu cm/molecule-sec at 25 °C(3). Dimethyl sulfide does not absorb light at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Role of organic sulfides in the atmosphere and emission rate of biogenic organic sulfides relative to that of hydrogen sulfide is not well understood. Absolute values of rate constants were detn for the reaction of ground-state oxygen atoms, O(3P), with dimethyl sulfide by using a phase shift technique in which O atoms were generated by Hg-sensitized decomposition of nitrous oxide and monitored by the chemiluminescence from their reaction with nitric oxide. Between 298 and K, the rate constants were represented by the following equation: k= (2.28 +/- 0.11)-12 exp((-2075 +/- 268)/T).

Food Survey Values · 1 item

Dimethyl disulfide has been detected in the volatile components of Beaufort cheese(1), of strawberries(2), of mutton, chicken, beef and pork(3), and of cooked mussels(4). Dimethyl disulfide has been detected in samples of various dried legumes at the following concentrations: lima beans, 8.6-176.7 ppb; pinto beans, 17.3-25.3 ppb; red kidney beans, 26.9 ppb; black beans, 15.2 ppb; navy beans, 401.7 ppb; mung beans, 47.7 ppb; soybeans, 48.5 ppb; split peas, 8.0 ppb; and lentils, 10.5-53.6 ppb(5). Dimethyl sulfide has been detected in the volatiles from popped popcorn at a concentration of 70 ug/kg dry weight(6). Dimethyl sulfide has been detected in the volatiles from stir-fried garlic at a concentration of 19.6% of the total analytes(7).

Adverse EffectsNeurotoxin - Other CNS neurotoxin

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. Dimethyl sulfide is produced, as an intermediate or a final product, by process units covered under this subpart.

Safety data

ridadr
UN 1164
Signal word
Danger
Symbol(GHS)
GHS02
hazard_class
3
packing_group
II
Hazard statements
H225

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

A single ip injection of 275 mg of dimethyl sulfoxide (DMSO) to rats effectively uncouples oxidative phosphorylation in liver mitochondria during the period from 2 hr to 5 days postinjection. Higher doses of DMSO are inhibitory to mitochondrial respiration. DMSO has, however, no uncoupling action on oxidative phosphorylation in vitro. Dimethyl sulfide, a known metabolite of DMSO, brings about the uncoupling effect in vitro. The uncoupling of oxidative phosphorylation by normal mitochondria could also be achieved if these are preincubated with postmitochondrial liver supernatant derived from rat injected with DMSO, 2-24 hr prior to sacrifice. These results provide an explanation for the observed uncoupling effect exerted by DMSO in vivo.

Biological Half-Life · 1 item

After overnight fasting, the concn of dimethyl sulfide in expired alveolar gas (ALV-DMS) was determined serially following ingestion of 2 g of dl-methionine in normal subjects and pt with liver diseases. ALV-DMS peaked in 30-90 min, declined markedly in 3 hr. Cirrhotics had t/2 longer than any other group.

Metabolism/Metabolites · 5 items

... To identify breath sulfur compounds causing halitosis induced by cysteamine therapy in patients with cystinosis. After the ingestion of 15 mg/kg cysteamine, whole blood (n = 4), urine (n = 4) and breath (n = 8) volatile sulfur compounds levels were measured every 60 min over a 360 min period by gas chromatography and the cysteamine plasma concentrations (n = 4) were measured by high-performance liquid chromatography. The expired air of cystinotic patients contained elevated concentrations of methanethiol (MT, median maximum value 0.5 (range 0-11) nmol/L) and, in particular, dimethyl sulfide (DMS, median maximum value 15 (range 2-83) nmol/L). DMS concentrations higher than 0.65 nmol/L are known to cause halitosis. Maximal plasma values of cysteamine (median 46 (range 30-52) umol/L) preceded those of MT and DMS, confirming that cysteamine is converted to MT and DMS. Less than 3% of the amount of cysteamine ingested was excreted as MT and DMS via expired air and 0.002% via urine. Halitosis induced by cysteamine intake is caused by DMS and to a lesser extent by MT, excreted via the expired air ...

Dimethylsulfoxide and dimethylsulfdioxide were found in rabbit urine following dimethyl sulfide administration.

The ip admin of dimethyl disulfide resulted in the appearance of dimethyl sulfide in expired breath of mice. Ip admin of methanethiol resulted in pulmonary excretion of dimethyl sulfide.

Methyl sulfide introduced into the mammalian system by ingestion or inhalation at low quantities can readily be metabolized. ... Methyl sulfide can also be formed as a degradation product from dimethyl sulfoxide. ... It is also formed from S-methylcysteine sulfoxide by intestinal bacteria.

A single ip injection of 275 mg of dimethyl sulfoxide (DMSO) to rats effectively uncouples oxidative phosphorylation in liver mitochondria during the period from 2 hr to 5 days postinjection. Higher doses of DMSO are inhibitory to mitochondrial respiration. DMSO has, however, no uncoupling action on oxidative phosphorylation in vitro. Dimethyl sulfide, a known metabolite of DMSO, brings about the uncoupling effect in vitro. The uncoupling of oxidative phosphorylation by normal mitochondria could also be achieved if these are preincubated with postmitochondrial liver supernatant derived from rat injected with DMSO, 2-24 hr prior to sacrifice. These results provide an explanation for the observed uncoupling effect exerted by DMSO in vivo.

Absorption, Distribution and Excretion · 4 items

Dimethyl sulfide is excreted by the lungs and the kidneys. Rats given oral or parenteral doses showed dimethyl sulfide in the breath. Dimethyl sulfide is also found in the breath of cats and mice given dimethylsulfoxide.

Dimethyl sulfide was detected in milk from mature cows in late lactation following ingestion of capsules containing either 60 or 80 g of D,L-methionine or 1,2,or 4 mL of dimethyl sulfide; no dimethyl sulfide was detected in the cows dosed with lower doses of D,L-methionine.

Excess methyl sulfide is exhaled with carbon dioxide, if it occurs in excess and in free form.

... The ip administration of dimethyl disulfide resulted in its appearance in the expired breath of mice and much smaller amounts of both methanethiol and dimethyl sulfide. The ip administration of methanethiol resulted in its pulmonary excretion and that of dimethyl sulfide. Administration of dimethyl sulfide led to its appearance alone in expired breath. Mice pretreated with ammonium acetate and then injected with dimethyl disulfide excreted the same 3 compounds via the lungs as above, but there were complex changes in the proportions and in the time sequence of their appearance. The absolute amounts of all 3 were increased, and the peak excretion for each was delayed. The amount excreted as dimethyl sulfide was particularly increased.

Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 6 items

Dimethyl sulfide is a common air pollutant of paper mills, sewage treatment plants, and oil refineries. It is used as a food flavoring agent. [ACGIH] Also used as a chemical intermediate, a sulfiding agent, an anti-coking agent, a gas odorant, and a mineral salt solvent; [CHEMINFO]

Petroleum Production and Refining [Category: Industry]

Reported uses (usual): alcoholic beverages 0.44 ppm; non-alcoholic beverages 0.73 ppm; condiments, relish 1.77 ppm; fats, oils 0.02 ppm; frozen dairy 0.74 ppm; imitation dairy 0.02 ppm; soft candy 1.16 ppm; hard candy 0.03 ppm; baked goods 4.34 ppm; chewing gum 12.83 ppm; gelatins and puddings 0.54 ppm; gravies 0.52 ppm; meat products 4.01 ppm. FEMA No 2746.

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

Dimethyl sulfide is used as a gas odorant, catalyst impregnator, and food flavoring agent.

Used as a chemical intermediate for the synthesis of dimethyl sulfoxide

ImpuritiesGas chromatographic analysis showed that dimethyl sulfide contained 710 ppm dimethyl disulfide, 355 ppm carbon disulfide, butyl ethyl sulfide, and 95 ppm allyl sulfide as impurities.
U.S. Production · 6 items

2023: 40,000,000 - <55,000,000 lb

(1972) Probably greater than 4.54x10+5 grams

(1976) Probably greater than 6.81x10+6 grams

Methane, 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#1109]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: methane, 1,1'-thiobis-. Aggreated National Production Volume: 10 to <50 million pounds.

Consumption PatternsAnnual: 10,183.33 lb
Consumer UsesIntermediate
Industry UsesProcessing aids, specific to petroleum production

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]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

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