ChemicalBook >> CAS DataBase List >>1,2-Ethanedithiol

1,2-Ethanedithiol

CAS No.
540-63-6
Chemical Name:
1,2-Ethanedithiol
Synonyms
EDT;ethane-1,2-dithiol;ETHANEDITHIOL;EDT(L);L k Vadehra;Ethylenedithiol;1,2-dithioethane;dimercaptoethane;1,2-Ethandithiol;1,2-DIMERCAPTOETHANE
CBNumber:
CB3742510
Molecular Formula:
C2H6S2
Molecular Weight:
94.2
MDL Number:
MFCD00004892
MOL File:
540-63-6.mol
MSDS File:
SDS
Last updated:2024-12-18 14:08:52

1,2-Ethanedithiol Properties

Melting point -41 °C (lit.)
Boiling point 144-146 °C (lit.)
Density 1.123 g/mL at 25 °C (lit.)
vapor density >1 (vs air)
vapor pressure 4.8 mm Hg ( 20 °C)
refractive index n20/D 1.558(lit.)
FEMA 3484 | 1,2-ETHANEDITHIOL
Flash point 122 °F
storage temp. Store below +30°C.
pka pK1:8.96;pK2:10.54 (25°C)
form Liquid
color Clear slightly colored
Odor at 0.01 % in propylene glycol. sulfury meaty
Odor Type sulfurous
Water Solubility insoluble
Sensitive Air Sensitive
Merck 14,3725
JECFA Number 532
BRN 505946
Stability Stable. Flammable. Incompatible with oxidizing agents, bases, reducing agents, alkali metals.
InChIKey VYMPLPIFKRHAAC-UHFFFAOYSA-N
LogP 1.31
Substances Added to Food (formerly EAFUS) 1,2-ETHANEDITHIOL
CAS DataBase Reference 540-63-6(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 92T634FLAR
NIST Chemistry Reference 1,2-Ethanedithiol(540-63-6)
EPA Substance Registry System 1,2-Ethanedithiol (540-63-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS02,GHS06
Signal word  Danger
Hazard statements  H226-H301-H310+H330
Precautionary statements  P210-P262-P280-P301+P310+P330-P302+P352+P310-P304+P340+P310
Hazard Codes  T,Xn,F
Risk Statements  10-23/24/25-23/25-21-36-23-21/22-36/37/38-20/21/22
Safety Statements  36/37/39-45-26-16-36/37-36-7/9
RIDADR  UN 3071 6.1/PG 2
WGK Germany  3
RTECS  KI3325000
10-13-23
TSCA  Yes
HazardClass  3
PackingGroup  III
HS Code  29309070
Hazardous Substances Data 540-63-6(Hazardous Substances Data)
Toxicity LD50 orally in Rabbit: 120 mg/kg LD50 dermal Rabbit 197 mg/kg
NFPA 704
2
4 1

1,2-Ethanedithiol price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.00795 1,2-Ethanedithiol for synthesis 540-63-6 100mL $180 2024-03-01 Buy
Sigma-Aldrich 8.00795 1,2-Ethanedithiol for synthesis 540-63-6 500mL $378 2024-03-01 Buy
Sigma-Aldrich 02390 1,2-Ethanedithiol ≥98.0% (GC) 540-63-6 25ml $61.6 2024-03-01 Buy
Sigma-Aldrich 02390 1,2-Ethanedithiol ≥98.0% (GC) 540-63-6 100ml $112 2024-03-01 Buy
TCI Chemical E0032 1,2-Ethanedithiol >99.0%(GC) 540-63-6 25g $37 2024-03-01 Buy
Product number Packaging Price Buy
8.00795 100mL $180 Buy
8.00795 500mL $378 Buy
02390 25ml $61.6 Buy
02390 100ml $112 Buy
E0032 25g $37 Buy

1,2-Ethanedithiol Chemical Properties,Uses,Production

Description

1,2-Ethanedithiol (EDT) is a colorless liquid with a characteristic odor that resembles that of rotten cabbage. It is widely used as a building block in organic synthesis, and it is also an effective ligand for metal ions. 1,2-ethanedithiol if applied as a flavoring agent and it is available in a variety of animal foods, in cooked beef and chicken.

Chemical and Physical properties

1, 2-ethanedithiol (C2H6S2) has a molecular weight of 94.19 g/mol, a monoisotopic mass of 93.991 g/mol and an exact mass of 93.991 g/mol. It has a heavy atom count of 4, a topographical surface area of 2 A^2, and a complexity of 6. EDT has a hydrogen bond donor and acceptor count of 2 and 2 respectively.
EDT gas a boiling point of 146 deg C at 760 mm Hg and a melting point of -41.2 °C. It dissolves in benzene, acetone, ether, ethanol and oxygenated solvents, while it is sparingly soluble in alkali. EDT dissolves in water at 1.12X10+4 mg/L at 25 deg C (est).
1,2-ethanedithiol has an extrapolated vapor pressure of 5.61 mm Hg at 25 deg C. When heated, EDT decomposes to emit toxic fumes comprising of sulfur oxides. Its odor is mild at 31 ppb and it gets more noticeable at 5.6 ppm.

Preparation

1,2-ethanedithiol can be synthesized by reacting an alkali metal hydrosulfide with an alkylene halide. However, this method does not yield a good amount of EDT due to the formation of by-products such as polymeric materials. The formation of these by-products could be reduced by conducting the reaction in an autoclave where the pressure is regulated to H 8. EDT can also be prepared through the decomposition of thiourea and the isothiuronium salt of ethylene bromide. This method yields slightly higher dithiol yields as indicated in the general formula where n is equal to or more than 3, for instance, 1,4-butanedithiol and 1,3-propanedithiol. However, this method also imposes significant constraints in the preparation of lower members of the dithiol series, such as 1,2-ethanedithiol. An additional method for the preparation of the compound entails the reaction between ethylene sulfide and H 8 in methanol, which yields approximately 49% of 1,2-ethanedithiol. However, this method also yields products with a relatively high molecular weight, which account for about 20% of the total products. There is a wide range of other methods that have been suggested for the synthesis of 1,2-ethanedithiol but they have been disqualified based on certain justifications.
The process highlighted below entails three major steps: 1) the generation of ethylene sulfide, 2) reaction of ethylene sulfide with hydrosulfide and 3) the liberation of 1,2-ethanedithiol through acid treatment. Z-mercaptoethy-lcarbonate is added to an alkaline solution in the portions highlighted above over a 30-minute period, the pH of the alkaline solution should be above 6.8, where the base is indicated with the general formula MOH, where M indicates an alkali-metal hydroxides such as potassium, lithium or sodium. The contents should also include 1-2 moles of the reacting ammonium hydrosulfide per mole of the alkyl 2-mercaptoethylcarbonate. Stir the reaction contents while maintaining the temperature at -100 C while adding the alkyl portions. The solution can be saturated with hydrogen sulfide by passing the gas through the reaction contents for about 2 hours. The contents should be stirred for a period of 10-20 hours or more while maintaining the temperature at 15300 C. The solution is cooled and reacted with an acid such as phosphoric, sulfuric or hydrochloric acids, and 1,2-ethanedithiol is separated from the mixture through conventional means such as extraction using a volatile solvent such as benzene or chloroform, or by distillation. This step is followed by the evaporation of the contents to remove the solvent. A combination of both processes could be more effective, where the dried product is taken through fractional distillation. This method involving ammonium hydrosulfide and ethyl Z-mercaptoethyl carbonate is highly preferred for the preparation of 1,2-ethanedithiol.

Precautions

One should wash their hands thoroughly after contact with 1,2-ethanedithiol. It is not recommended to smoke, eat or drink while handling EDT. If ingested, one should contact a doctor immediately or the poison center. In the event of a fire, one should use appropriate apparatus to extinguish the fire. If the chemical comes into contact with one’s clothes or skin, they should take off the clothes and rinse their skin with plenty of water.

Hazard Statements

1,2-ethanedithiol is a flammable liquid. EDT is toxic when ingested and it may result in acute toxicity. It may cause acute dermal toxicity upon contact with the skin. EDT may result in serious eye irritation/damage and it may also cause acute toxicity upon inhalation.
Inhalation of EDT vapours may cause severe nausea or headaches.

Chemical Properties

Clear colorless solid

Chemical Properties

1,2-Ethanedithiol has a repulsive odor.

Occurrence

Reported found in beef (boiled, cooked) and chicken (cooked)

Uses

Metal-complexing agent. Reverses the inhibition by α-keto aldehydes on mitosis in E. coli.

Uses

1,2-Ethanedithiol is used as a reagent in organic synthesis to convert carbonyl compounds to thioacetals (1,3-dithiolanes). It replaces the toxic reagent arsenic tirchloride, which is involved in the synthesis of membrane-permeant fluorogenic biarsenicals from precursor dyes fluorescein and resorufin. It acts bidendate ligand to form complexes with metal ions.

Preparation

Prepared by reacting ethanol, thiourea and ethylene dibromide and subsequent alkaline hydrolysis of the ethylenediisothiuronium bromide

Aroma threshold values

Detection: 30 ppb

General Description

1,2-Ethanedithiol (1,2-Dimercaptoethane, Dithioglycol, Ethylene mercaptan) is an organo sulfur compound. It affords monomeric, dimeric and polymeric complexes on reaction with Pt(PPh3)4, Pd(PPh3)4 and Ni(PPh3)4. It has been synthesized by refluxing 1,2-dichloroethane with thiourea in ethanol.

Hazard

Vapors cause severe headache and nausea.

Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. When heated to decomposition it emits very toxic fumes of SOx. See also MERCAPTANS .

5769-02-8
540-63-6
98-86-2
Synthesis of 1,2-Ethanedithiol from Acetophenone ethane-1,2-diyl dithioacetal
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1,2-Ethanedithiol pictures 2024-12-18 1,2-Ethanedithiol
540-63-6
US $6.00 / kg 1kg More than 99% 2000KG/Month Hebei Longbang Technology Co., Ltd
1,2-Ethanedithiol  pictures 2024-12-18 1,2-Ethanedithiol
540-63-6
US $6.00 / kg 1kg 99% 2000KG/Month HebeiShuoshengImportandExportco.,Ltd
1,2-Ethanedithiol pictures 2024-12-17 1,2-Ethanedithiol
540-63-6
US $0.00-0.00 / kg 1kg 98%+ 10000kgs per Month Shanghai Qyubiotech Co., Ltd.
  • 1,2-Ethanedithiol pictures
  • 1,2-Ethanedithiol
    540-63-6
  • US $6.00 / kg
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1,2- B twoMercaptan Ethylene dithioglycol Ethylene glycol, dithio- ethylenedithioglycol ethylhydropersulfide s-Ethylene dimercaptan s-ethylenedimercaptan DITHIOETHYLENE GLYCOL DITHIOGLYCOL ETHYLENE MERCAPTAN ETHYLENE DIMERCAPTAN FEMA 3484 1,2-ETHANEDITHIOL FOR SYNTHESIS 1,2-dithiolethane 1,2-Ethanethiol 1,2-Ethyldimercaptan EDT)1,2-Ethane 1,2-Ethanedithiol >=98.0% (GC) 1,2-Ethanedithiol technical grade, >=90% 1,2-Ethanedithiol, 95%, SpcSeal a-ethylenedimercaptan alpha-Ethylene dimercaptan alpha-ethylenedimercaptan dimercaptanethylenique dithio-ethyleneglyco 1,2-ETHANEDITHIOL 1,2-ETHANEDITHIOL, TECH., 90+% 1 2-ETHANEDITHIOL 98% (GC) 1 2-ETHANEDITHIOL 98+% 1,2-ETHANEDITHIOL 98% MIN 1,2-Ethanedithiol,95+% Dithio ethyl alcohol 1,2-Ethanedithiol, 95+% (Assay) 1,2-Ethanedithiol,1,2-dimercaptoethane 1-ETHANEDITHIOL Ethan-1,2-dithiol EDT 1,2-Ethanedithiol EDT, 98% MIN. 1,2-Dimercaptoethane, Dithioglycol, Ethylene mercaptan 2-Mercaptoethanethiol 1,2-Ethane-bisthiol Ethane-1,2-bisthiol Ethylone diMercaptan 1,2-Ethanedithiol,1,2-Dimercaptoethane, Dithioglycol, Ethylene mercaptan 1,2-Ethanedithiol, 98.5% EDT (liquid) 1,2-Ethanedithiol 1,2-Ethanedithiol, 98.5%, for synthesis 1,2-Ethanedithiol, 97%, for synthesis 1,2-Ethanedithiol> 1,2-Ethanedithiol, 95%, for synthesis 1,2-Ethanedithiol USP/EP/BP EDT125ml 1,2-Ethanedithiol ex Manufacturer Supply Pharmaceutical Intermediate, 1, 2-Ethanedithiol CAS 540-63-6 High Purity 540-63-6 "1,2-Ethanedithiol D4" 1,2-Ethanedithiol extrapure, 98.5% ethane-1,2-dithiol