Product Name

  • Name

    2-Chloroethyl ethyl sulfide

  • EINECS 211-742-1
  • CAS No. 693-07-2
  • Article Data16
  • CAS DataBase
  • Density 1.07
  • Solubility insoluble
  • Melting Point
  • Formula C4H9ClS
  • Boiling Point 156-157 ºC
  • Molecular Weight 124.634
  • Flash Point 52 ºC
  • Transport Information UN 1992
  • Appearance clear colourless to light yellow liquid
  • Safety Poison by ingestion and subcutaneous routes. Mutation data reported. A severe skin and eye irritant. See also ETHERS and SULFIDES. When heated to decomposition it emits very toxic fumes of Cl and SOx.
  • Risk Codes R10;R22;R36/37/38;R40   
  • Molecular Structure Molecular Structure of 693-07-2 (2-Chloroethyl ethyl sulfide)
  • Hazard Symbols
  • Synonyms Sulfide,2-chloroethyl ethyl (6CI,7CI,8CI);1-Chloro-2-(ethylsulfanyl)ethane;1-Chloro-2-(ethylthio)ethane;2-(Ethylthio)chloroethane;2-Chlorodiethylsulfide;2-Chloroethyl ethyl sulfide;2-Chloroethyl ethyl thioether;2-Ethylthioethyl chloride;Ethyl 2-chloroethyl sulfide;H-MG;Half-sulfurmustard;NSC 10977;
  • PSA 25.30000
  • LogP 1.97830

Synthetic route

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

ethanethiol
75-08-1

ethanethiol

A

1,2-bis(ethylthio)ethane
5395-75-5

1,2-bis(ethylthio)ethane

B

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

Conditions
ConditionsYield
Stage #1: ethanethiol With potassium hydroxide; hydrazine hydrate for 1h;
Stage #2: 1,2-dichloro-ethane at 50℃; for 2h;
A 68%
B 6%
ethene
74-85-1

ethene

Ethanesulfenyl chloride
1496-75-9

Ethanesulfenyl chloride

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

Conditions
ConditionsYield
at -10 - -5℃;
2-(ethylsulfanyl)ethanol
110-77-0

2-(ethylsulfanyl)ethanol

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

Conditions
ConditionsYield
With hydrogenchloride
With thionyl chloride; chloroform
With phosphorus trichloride
With thionyl chloride In chloroform Heating;
With thionyl chloride
1-ethylsulfanyl-2-butoxy-ethane
860213-87-2

1-ethylsulfanyl-2-butoxy-ethane

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

Conditions
ConditionsYield
With 1,4-dioxane; hydrogenchloride
1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

sodium thioethylate
811-51-8

sodium thioethylate

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

Conditions
ConditionsYield
With methanol
Ethyl-(2-ethylsulfanyl-ethyl)-(2-hydroxy-ethyl)-sulfonium

Ethyl-(2-ethylsulfanyl-ethyl)-(2-hydroxy-ethyl)-sulfonium

A

1,2-bis(ethylthio)ethane
5395-75-5

1,2-bis(ethylthio)ethane

B

chloroethane
75-00-3

chloroethane

C

2-(ethylsulfanyl)ethanol
110-77-0

2-(ethylsulfanyl)ethanol

D

6-oxa-3,9-dithiaundecane
5648-30-6

6-oxa-3,9-dithiaundecane

E

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

Conditions
ConditionsYield
With hydrogenchloride In water at 90℃; for 1h; Product distribution; Mechanism;A 2.4 % Chromat.
B 2.3 % Chromat.
C 44.9 % Chromat.
D 2.9 % Chromat.
E 44.9 % Chromat.
thionyl chloride
7719-09-7

thionyl chloride

3,6-dithiaoctan-1-ol
57830-41-8

3,6-dithiaoctan-1-ol

A

1,4-Dithiane
505-29-3

1,4-Dithiane

B

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

Conditions
ConditionsYield
at 100℃;
thionyl chloride
7719-09-7

thionyl chloride

3,6-dithiaoctan-1-ol
57830-41-8

3,6-dithiaoctan-1-ol

A

1,4-Dithiane
505-29-3

1,4-Dithiane

B

1-chloro-3,6-dithiaoctane
92569-22-7

1-chloro-3,6-dithiaoctane

C

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

Conditions
ConditionsYield
at 35℃;
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

vinyl ethylsulfide
627-50-9

vinyl ethylsulfide

Conditions
ConditionsYield
With potassium hydroxide; triisopropylsilanol In N,N-dimethyl-formamide Ambient temperature;100%
With potassium tert-butylate Kinetics;
With potassium hydroxide; triisopropylsilanol In N,N-dimethyl-formamide at 25℃;100 % Chromat.
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

2-chloroethyl ethyl sulfoxide
27998-62-5

2-chloroethyl ethyl sulfoxide

Conditions
ConditionsYield
With methanesulfonic acid; urea hydrogen peroxide adduct In methanol Flow reactor;98%
With N-(tert-butyl)-N-chloro-cyanamide In water; acetonitrile97%
With 1,8-diazabicyclo[5.4.0]undec-7-ene hydrobromide-perbromide In water; acetonitrile at 20℃; for 0.0166667h;94%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

[Me(C3H3N2)CH2CH2SEt]Cl

[Me(C3H3N2)CH2CH2SEt]Cl

Conditions
ConditionsYield
In diethyl ether at 0℃; for 24h; Inert atmosphere; Schlenk technique; Reflux;97%
In toluene Heating;
at 120℃; for 2h; Neat (no solvent); Inert atmosphere;
C6H10N2S
1253202-16-2

C6H10N2S

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

N-ethyl-methyl-sulfide-N'-ethyl-ethyl-sulfide imidazoliumchloride
1253202-03-7

N-ethyl-methyl-sulfide-N'-ethyl-ethyl-sulfide imidazoliumchloride

Conditions
ConditionsYield
at 120℃; for 2h;95%
trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI)

trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI)

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

C64H70Cl2N4O2RuS2

C64H70Cl2N4O2RuS2

Conditions
ConditionsYield
With oxygen In benzene-d6 at 20℃; under 760.051 Torr; for 504h;95%
1-(2’-thioethyl)ethylimidazole
27423-88-7

1-(2’-thioethyl)ethylimidazole

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

N,N'-bis(ethyl-ethyl-sulfide)imidazolium chloride
1253202-02-6

N,N'-bis(ethyl-ethyl-sulfide)imidazolium chloride

Conditions
ConditionsYield
at 120℃; for 2h;93%
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

N,N-bis(2-(ethylthio)ethyl)amine
81526-29-6

N,N-bis(2-(ethylthio)ethyl)amine

Conditions
ConditionsYield
With ammonia; sodium hydroxide In methanol; ethanol at -15 - 20℃; for 17h;92%
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

diethyl sulphide
352-93-2

diethyl sulphide

Conditions
ConditionsYield
With cyclopentylmagnesium bromide In diethyl ether; toluene at 70℃;91%
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

2-chloroethyl ethyl sulfone
25027-40-1

2-chloroethyl ethyl sulfone

Conditions
ConditionsYield
With m-chloroperoxybenzoic acid In dichloromethane90%
With 2,6-di-tert-butyl-pyridine; tert-butylammonium hexafluorophosphate(V) In water; acetonitrile for 12h; electrolysis at controlled potential;80%
With potassium permanganate; sulfuric acid In water; acetonitrile at 0℃; for 17h;80%
2-(ethylsulfanyl)ethanol
110-77-0

2-(ethylsulfanyl)ethanol

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

ethyl(2-(ethylthio)ethyl)(2-hydroxyethyl)sulfonium chloride
107327-28-6

ethyl(2-(ethylthio)ethyl)(2-hydroxyethyl)sulfonium chloride

Conditions
ConditionsYield
In water at 20℃;85%
N-(2,4,6-trimethylphenyl)imidazole
25364-44-7

N-(2,4,6-trimethylphenyl)imidazole

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

N-(2,4,6-trimethylphenyl)-N'-ethyl-ethyl-sulfide imidazolium iodide
1242931-12-9

N-(2,4,6-trimethylphenyl)-N'-ethyl-ethyl-sulfide imidazolium iodide

Conditions
ConditionsYield
With sodium iodide In toluene at 120℃; for 2h; Inert atmosphere;84%
(+/-)-3-(trans-3,4-dimethylpiperidinyl)phenol

(+/-)-3-(trans-3,4-dimethylpiperidinyl)phenol

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

(+/-)-3-{1-[2-(ethylsulfanyl)ethyl]-trans-3,4-dimethylpiperidinyl}phenol

(+/-)-3-{1-[2-(ethylsulfanyl)ethyl]-trans-3,4-dimethylpiperidinyl}phenol

Conditions
ConditionsYield
With sodium iodide; sodium hydrogencarbonate In N,N-dimethyl-formamide83%
ethylenediamine
107-15-3

ethylenediamine

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

S-2-(2-aminoethylamino)ethyl ethyl sulfide
70063-00-2

S-2-(2-aminoethylamino)ethyl ethyl sulfide

Conditions
ConditionsYield
Inert atmosphere;83%
3-thiapentan-1,5-dithiol
3570-55-6

3-thiapentan-1,5-dithiol

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

3,6,9,12,15-Pentathiaheptadecane
37460-05-2

3,6,9,12,15-Pentathiaheptadecane

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 1h; Heating;82%
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

sodium 3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-thiolate

sodium 3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-thiolate

6-(2-Ethylsulfanyl-ethylsulfanyl)-2H-[1,2,4]triazine-3,5-dione
184697-90-3

6-(2-Ethylsulfanyl-ethylsulfanyl)-2H-[1,2,4]triazine-3,5-dione

Conditions
ConditionsYield
In ethanol; water for 1h; Heating;82%
phenylmagnesium bromide

phenylmagnesium bromide

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

<2-(ethylthio)ethyl>benzene
22914-08-5

<2-(ethylthio)ethyl>benzene

Conditions
ConditionsYield
In diethyl ether; toluene at 70℃;82%
1-(2,6-diisopropylphenyl)-1H-imidazole
25364-47-0

1-(2,6-diisopropylphenyl)-1H-imidazole

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

C2H5SC2H4C3H2N2C6H3(CH(CH3)2)2H(1+)*I(1-)=C2H5SC2H4C3H2N2C6H3(C3H7)2HI
1242931-14-1

C2H5SC2H4C3H2N2C6H3(CH(CH3)2)2H(1+)*I(1-)=C2H5SC2H4C3H2N2C6H3(C3H7)2HI

Conditions
ConditionsYield
With sodium iodide In toluene at 120℃; for 2h; Inert atmosphere;81%
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

diethyl malonate
105-53-3

diethyl malonate

(2-ethylsulfanyl-ethyl)-malonic acid diethyl ester
100048-61-1

(2-ethylsulfanyl-ethyl)-malonic acid diethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Reflux;81%
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

A

2-chloroethyl ethyl sulfoxide
27998-62-5

2-chloroethyl ethyl sulfoxide

B

(2-chloroethyl)(ethyl)(2-(ethylthio)ethyl)sulfonium chloride

(2-chloroethyl)(ethyl)(2-(ethylthio)ethyl)sulfonium chloride

Conditions
ConditionsYield
With urea hydrogen peroxide adduct at 23℃;A 80%
B 20%
3,6-di(piperidin-1-yl)-9H-xanthene-9-thione

3,6-di(piperidin-1-yl)-9H-xanthene-9-thione

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

thiopyronin

thiopyronin

Conditions
ConditionsYield
In dichloromethane80%
2-mercapto-5-(1-methyl-5-nitro-2-imidazolyl)-1,3,4-thiadiazole
23092-56-0

2-mercapto-5-(1-methyl-5-nitro-2-imidazolyl)-1,3,4-thiadiazole

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

C11H14N4O2S3

C11H14N4O2S3

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 20℃;76%
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

3,6-dithiaoctan-1-ol
57830-41-8

3,6-dithiaoctan-1-ol

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 40℃; for 7h;73%
tetramethylammonium 2-oxo-2-thio-1,3,2-oxazaphosphorinan
84451-65-0

tetramethylammonium 2-oxo-2-thio-1,3,2-oxazaphosphorinan

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

2-(2-Ethylsulfanyl-ethylsulfanyl)-[1,3,2]oxazaphosphinane 2-oxide

2-(2-Ethylsulfanyl-ethylsulfanyl)-[1,3,2]oxazaphosphinane 2-oxide

Conditions
ConditionsYield
In benzene for 30h; Heating;71%
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

2-mercapto-5-(5-nitro-2-furyl)-1,3,4-thiadiazole
16865-27-3

2-mercapto-5-(5-nitro-2-furyl)-1,3,4-thiadiazole

C10H11N3O3S3

C10H11N3O3S3

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 20℃;70%
2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

2-ethylsulfanyl-ethanethiol
26750-44-7

2-ethylsulfanyl-ethanethiol

Conditions
ConditionsYield
With thiourea at 100℃;68%
With ethanol; potassium hydrosulfide
Stage #1: 2-Chloroethyl ethyl sulfide With thiourea In ethanol for 24h; Heating;
Stage #2: With potassium hydroxide for 5h; Heating;
sodium cyclopentadienide

sodium cyclopentadienide

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

1-(2-ethylsulfanyl-ethyl)-cyclopenta-1,3-diene
728880-40-8

1-(2-ethylsulfanyl-ethyl)-cyclopenta-1,3-diene

Conditions
ConditionsYield
In tetrahydrofuran for 4h; Heating;68%
5-(2-nitrophenyl)-1,3,4-thiadiazole-2-thiol
85103-35-1

5-(2-nitrophenyl)-1,3,4-thiadiazole-2-thiol

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

C12H13N3O2S3
1041361-26-5

C12H13N3O2S3

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 20℃;65%
4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide
38339-95-6

4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-ethylsulfanyl-ethoxy)-benzamide
122452-34-0

4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-ethylsulfanyl-ethoxy)-benzamide

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide 1.) Room temp., 16 h; 2.) 50 deg C, 2 h;61%
2-(4-nitrophenyl)-1,3,4-thiadiazole-5-thiol
81188-34-3

2-(4-nitrophenyl)-1,3,4-thiadiazole-5-thiol

2-Chloroethyl ethyl sulfide
693-07-2

2-Chloroethyl ethyl sulfide

C12H13N3O2S3
1041361-32-3

C12H13N3O2S3

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 20℃;61%

2-Chloroethyl ethyl sulfide Specification

  The IUPAC name of 2-Chloroethyl ethyl sulfide is 1-Chloro-2-ethylsulfanylethane , with the CAS registry number 693-07-2, it is also named as 1-Chloro-2-(ethylthio)ethane ; 2-(Ethylthio)chloroethane ; 2-Chloroethyl ethyl sulfide ; 2-Chloroethyl ethyl thioether ; 2-Chloroethyl(ethyl)sulfide ; 2-Ethylthioethyl chloride ; Chlordiethylsulfid ; Ethane, 1-chloro-2-(ethylthio)- . It belongs to the following product categories, such as Organic Building Blocks. This product must store at 0-6 °C. 2-Chloroethyl ethyl sulfide is clear colourless to light yellow liquid and is insoluble in water.

  2-Chloroethyl ethyl sulfide is harmful by inhalation, in contact with skin and if swallowed so we should rinse immediately with plenty of water and seek medical advice if contact with eyes. We must keep away from sources of ignition and no smoking because it is flammable. 2-Chloroethyl ethyl sulfide is also irritating to eyes, respiratory system and skin so we must wear suitable protective clothing, gloves and eye/face protection when contect with it .

Toxicity of 2-Chloroethyl ethyl sulfide is following:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LDLo subcutaneous 25mg/kg (25mg/kg)   National Technical Information Service. Vol. PB158-507,
rat LD50 oral 252mg/kg (252mg/kg)   "Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku," Marhold, J.V., Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha, Czechoslovakia, 1972Vol. -, Pg. 170, 1972.

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