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Diethylsulfid

Ethyl sulfide

HCID 9609
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Grundinformationen

CAS
352-93-2
Standard-SMILES
CCSCC
InChIKey
LJSQFQKUNVCTIA-UHFFFAOYSA-N
Summenformel
C4H10S
Durchschnittliche Molmasse
90,19 g/mol
Monoisotopische Masse
90,05032132

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Ethyl sulfide
IUPAC
ethylsulfanylethane
Lokaler Name
Diethylsulfid
Englischer Name
Diethyl sulfide
Summenformel
C4H10S
Molmasse
90.19

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,9
Polarare Oberfläche (TPSA)
25,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
2
Schwere Atome
5
Formalladung
0
Komplexität
11,1

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Sulfur Compounds

Flammable agents - 3rd degree

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

log Kow = 1.95

1.95

1.95

Odor · 2 Einträge

Garlic-like odor

Ethereal odor

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 2 Einträge

0.8362 g/cu cm at 20 °C

0.836-0.841

Flavoring AgentsEU Flavoring substances
Color/Form · 2 Einträge

Liquid

Colorless, oily liquid

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Regulatory Information · 5 Einträge

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 Einträge

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 Einträge

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

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

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 6 Einträge

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 Einträge

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 Einträge

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 Einträge

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HRID 88322als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
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Solubility · 6 Einträge

Soluble in ethanol, diethyl ether; slightly soluble in carbon tetrachloride.

Soluble in oxygenated solvents.

Miscible with alcohol, ether

In water, 3130 mg/L at 25 °C

3.13 mg/mL at 20 °C

insoluble in water; miscible in alcohol and oil

Flash Point · 2 Einträge

-6.7 °C

-10 °C (14 °F) closed cup

Boiling Point · 3 Einträge

92.1 °C

90.00 to 93.00 °C. @ 760.00 mm Hg

92 °C

Physikochemische Eigenschaften

Schmelzpunkt
100 °C · −100 °C(lit.)
Siedepunkt
90 · 90-92 °C(lit.)
Dichte
0.837 g/mL · 0.837 g/mL at 25 °C(lit.)
Dampfdruck
105 mm · 105 mm Hg ( 37.7 °C)
Brechungsindex
20 · n20/D 1.442(lit.)
FEMA
3825 · 3825 | DIETHYL SULFIDE
Flammpunkt
15 °F · 15 °F
Löslichkeit
2 O: · H2O: insoluble
Aggregatzustand
liquid
Wichte
0.837 · 0.837
Farbe
Colorless to Almost colorless
Geruch (Odor)
ethereal sulfurous
Geruchsart
sulfurous
Biologische Quelle
synthetic
Odor Threshold
0.000033 ppm · 0.000033ppm
Wasserlöslichkeit
Miscible with alcohol, ethanol and ether. Slightly miscible with carbon tetrachloride. Immiscible with water.
Spezifische Wärmekapazität
1.9 J/ · Cp(liquid): 1.9 J/(g·K); Cp(gas): 1.3 J/(g·K), at 25℃
JECFA Number
454 · 454
Merck
14 · 14,3854
BRN
1696909 · 1696909
Henry's Law Constant
3.5 · 3.5×10-3 mol/(m3Pa) at 25℃, Burkholder et al. (2019)
Dielectric constant
7.2 · 7.2(20℃)
Stabilität
Stable. Highly flammable. Incompatible with strong oxidizing agents.
Major Application
cleaning productscosmeticsfood and beveragespersonal care
InChI
1S/C4H10S/c1-3-5-4-2/h3-4H2,1-2H3
InChIKey
LJSQFQKUNVCTIA-UHFFFAOYSA-N
SMILES
CCSCC
LogP
1.95 at · 1.95 at 20℃
CAS Datenbank
352 · 352-93-2(CAS DataBase Reference)
NIST chemische Informationen
Diethyl sulfide(352-93-2)
EPA chemische Informationen
Diethyl sulfide (352-93-2)
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]
DOT ID and Guide2375 129
Reactive GroupSulfides, Organic
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 Eintrag

Organosulfides, such as DIETHYL SULFIDE, are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.

DOT Emergency Guidelines · 5 Einträge

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.

For more DOT Emergency Guidelines (Complete) data for 1,1'-Thiobisethane (8 total), please visit the HSDB record page.

DOT Hazard Classification · 4 Einträge

Diethyl sulfide

UN2375

Class 3 Flammable and combustible liquid (49 eCFR § 173.120)

PG II: the degree of danger presented by the material is medium

Sicherheit und Schutzausrüstung

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

· 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 Einträge

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 Einträge

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.
Cleanup Methods · 2 Einträge

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Contain spillage, and then collect with non-combustible absorbent material, (e.g. sand, earth, diatomaceous earth, vermiculite) and place in container for disposal according to local / national regulations.

Nonfire Spill ResponseExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Disposal Methods · 2 Einträge

Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Preventive MeasuresHandle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Choose body protection according to the amount and concentration of the dangerous substance at the work place.
Isolation and Evacuation · 2 Einträge

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

Immediate precautionary measure

Personal Protective Equipment (PPE) · 3 Einträge

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

Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Handle with gloves. Safety glasses

Toxikologische Informationen

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

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 Eintrag

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 Eintrag

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.

Natural Pollution SourcesDiethyl sulfide occurs naturally in petroleum deposits and can be formed by bacterial decomposition of plant and animal matter.
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Delayed toxicity may occur when the bioelectric activity of the respiratory muscles become impaired. Dermally, it is nonirritant, but is moderately irritant to the eye.
Artificial Pollution SourcesDiethyl sulfide's production and use as a solvent for anhydrous mineral salts, and as a raw material in gold and silver metal plating baths(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 2 Einträge

AEROBIC: Biodegradation data are not available for diethyl sulfide(SRC, 2009); however, data are available for the related dimethyl sulfide. Dimethylsulfide, present at 2.5 mg/L, showed 100% degradation in 2 days using a freshwater sediment inoculum(1). Based upon the structural similarity of diethyl sulfide to dimethyl sulfude, diethyl sulfide is expected to biodegrade repidly under aerobic conditions(SRC).

ANAEROBIC: Biodegradation data are not available for diethyl sulfide(SRC, 2009); however, data are available for the related dimethyl sulfide. Dimethylsulfide, present at 3.4 mg/L, showed 100% degradation in 8 days using a freshwater sediment inoculum under anoxic conditions(1). Dimethylsulfide, present at 0.3 mg/L, showed 100% degradation in 2 days using an anoxic salt marsh sediment as inoculum(2). Based upon the structural similarity of diethyl sulfide to dimethyl sulfude, diethyl sulfide is expected to biodegrade repidly under anaerobic conditions(SRC).

Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 9 was calculated in fish for diethyl sulfide(SRC), using a log Kow of 1.95(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration is aquatic organisms is low.

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for diethyl sulfide has been measured as 1.68X10-3 atm-cu m/mole(1). This Henry's Law constant indicates that diethyl sulfide is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 1.3 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 4 days(SRC). Diethyl sulfide's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of diethyl sulfide from dry soil surfaces may exist(SRC) based upon a vapor pressure of 60.2 mm Hg(3).

Sicherheitsdaten

F
13
wgk
3
tsca
TSCA listed
ridadr
UN 2375
hs_code
29309090
RTECS-Nr.
LC7200000
risk_code
11-38-36/38
hazard_code
F,Xi
safety_code
9-16-26-33-36
hazard_class
3
packing_group
II
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
352-93-2(Hazardous Substances Data)
Hazard Classifications
Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2

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 Einträge

All Other Basic Organic Chemical Manufacturing

Ethane, 1,1'-thiobis-: ACTIVE

Anwendungen · 3 Einträge

BeschreibungDiethylsulfid bildet eine farblose, wasserunlösliche Flüssigkeit mit ekelhaftem Geruch. Die Verbindung besitzt nur wissenschaftliches Interesse.

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

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

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Triethyloxoniumtetrafluoroborat(1-)Ethyl vinyl sulfideDiethylsulfoxid1-Chlor-2-(ethylthio)ethantert-ButyldimethylsilaneEthanthiol

Nachgelagerte Produkte

U-47319Thiophosphorsäure-O,O-bis(1-me-thylethyl)-S-(phenylmethyl)ester

Ergänzende Hinweise

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