693-07-2

Basic information

• Product Name: 2-Chloroethyl ethyl sulfide
• Synonyms: 2-CHLOROETHYL ETHYL SULFIDE;2-CHLOROETHYLETHYLSULPHIDE;1-Chloro-2-(ethylsulfanyl)ethane;1-chloro-2-(ethylthio)-ethan;1-Chloro-2-(ethylthio)ethane;1-chloro-3-thiapentane;2-(Ethylthio)chloroethane;2-chlorodiethylsulfide
• CAS NO: 693-07-2
• Molecular Formula: C₄H₉ClS
• Molecular Weight: 124.63
• EINECS: 211-742-1
• Product Categories: Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 693-07-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 156-157 °C
• Flash Point: 52 °C
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.07 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.79mmHg at 25°C
• Refractive Index: 1.4875-1.4895
• Storage Temp.: 0-6°C
• Water Solubility: Insoluble
• CAS DataBase Reference: 2-Chloroethyl ethyl sulfide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroethyl ethyl sulfide(693-07-2)
• EPA Substance Registry System: 2-Chloroethyl ethyl sulfide(693-07-2)

Safety Data

• Hazard Codes: Xn,T
• Statements: 40-36/37/38-22-10-20/21/22-34-23/24-45
• Safety Statements: 36/37/39-26-16-45-27-53
• RIDADR: 1992
• WGK Germany: 3
• RTECS: WQ3250000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 693-07-2(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to light yellow liquid

General Description

2-Chloroethyl ethyl sulfide is a monofunctional analog of sulfur mustard (SM; 2,2′-dichloro diethyl sulfide). The mass diffusivity of 2-chloroethyl ethyl sulfide, a chemical warfare agent simulant, was studied.

Safety Profile

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 Cland SOx.

InChI:InChI=1/C4H9ClS/c1-2-6-4-3-5/h2-4H2,1H3

Synthetic route

1,2-dichloro-ethane (107-06-2) + ethanethiol (75-08-1) → 1,2-bis(ethylthio)ethane (5395-75-5) + 2-Chloroethyl ethyl sulfide (693-07-2)

Conditions	Yield
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) + Ethanesulfenyl chloride (1496-75-9) → 2-Chloroethyl ethyl sulfide (693-07-2)

Conditions	Yield
at -10 - -5℃;

2-(ethylsulfanyl)ethanol (110-77-0) → 2-Chloroethyl ethyl sulfide (693-07-2)

Conditions	Yield
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) → 2-Chloroethyl ethyl sulfide (693-07-2)

Conditions	Yield
With 1,4-dioxane; hydrogenchloride

1,2-dichloro-ethane (107-06-2) + sodium thioethylate (811-51-8) → 2-Chloroethyl ethyl sulfide (693-07-2)

Conditions	Yield
With methanol

Ethyl-(2-ethylsulfanyl-ethyl)-(2-hydroxy-ethyl)-sulfonium → 1,2-bis(ethylthio)ethane (5395-75-5) + chloroethane (75-00-3) + 2-(ethylsulfanyl)ethanol (110-77-0) + 6-oxa-3,9-dithiaundecane (5648-30-6) + 2-Chloroethyl ethyl sulfide (693-07-2)

Conditions	Yield
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) + 3,6-dithiaoctan-1-ol (57830-41-8) → 1,4-Dithiane (505-29-3) + 2-Chloroethyl ethyl sulfide (693-07-2)

Conditions	Yield
at 100℃;

thionyl chloride (7719-09-7) + 3,6-dithiaoctan-1-ol (57830-41-8) → 1,4-Dithiane (505-29-3) + 1-chloro-3,6-dithiaoctane (92569-22-7) + 2-Chloroethyl ethyl sulfide (693-07-2)

Conditions	Yield
at 35℃;

2-Chloroethyl ethyl sulfide (693-07-2) → vinyl ethylsulfide (627-50-9)

Conditions	Yield
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 sulfoxide (27998-62-5)

Conditions	Yield
With methanesulfonic acid; urea hydrogen peroxide adduct In methanol Flow reactor;	98%
With N-(tert-butyl)-N-chloro-cyanamide In water; acetonitrile	97%
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) + 2-Chloroethyl ethyl sulfide (693-07-2) → [Me(C3H3N2)CH2CH2SEt]Cl

Conditions	Yield
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) + 2-Chloroethyl ethyl sulfide (693-07-2) → N-ethyl-methyl-sulfide-N'-ethyl-ethyl-sulfide imidazoliumchloride (1253202-03-7)

Conditions	Yield
at 120℃; for 2h;	95%

trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI) + 2-Chloroethyl ethyl sulfide (693-07-2) → C64H70Cl2N4O2RuS2

Conditions	Yield
With oxygen In benzene-d6 at 20℃; under 760.051 Torr; for 504h;	95%

1-(2’-thioethyl)ethylimidazole (27423-88-7) + 2-Chloroethyl ethyl sulfide (693-07-2) → N,N'-bis(ethyl-ethyl-sulfide)imidazolium chloride (1253202-02-6)

Conditions	Yield
at 120℃; for 2h;	93%

2-Chloroethyl ethyl sulfide (693-07-2) → N,N-bis(2-(ethylthio)ethyl)amine (81526-29-6)

Conditions	Yield
With ammonia; sodium hydroxide In methanol; ethanol at -15 - 20℃; for 17h;	92%

2-Chloroethyl ethyl sulfide (693-07-2) → diethyl sulphide (352-93-2)

Conditions	Yield
With cyclopentylmagnesium bromide In diethyl ether; toluene at 70℃;	91%

2-Chloroethyl ethyl sulfide (693-07-2) → 2-chloroethyl ethyl sulfone (25027-40-1)

Conditions	Yield
With m-chloroperoxybenzoic acid In dichloromethane	90%
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-Chloroethyl ethyl sulfide (693-07-2) → ethyl(2-(ethylthio)ethyl)(2-hydroxyethyl)sulfonium chloride (107327-28-6)

Conditions	Yield
In water at 20℃;	85%

N-(2,4,6-trimethylphenyl)imidazole (25364-44-7) + 2-Chloroethyl ethyl sulfide (693-07-2) → N-(2,4,6-trimethylphenyl)-N'-ethyl-ethyl-sulfide imidazolium iodide (1242931-12-9)

Conditions	Yield
With sodium iodide In toluene at 120℃; for 2h; Inert atmosphere;	84%

(+/-)-3-(trans-3,4-dimethylpiperidinyl)phenol + 2-Chloroethyl ethyl sulfide (693-07-2) → (+/-)-3-{1-[2-(ethylsulfanyl)ethyl]-trans-3,4-dimethylpiperidinyl}phenol

Conditions	Yield
With sodium iodide; sodium hydrogencarbonate In N,N-dimethyl-formamide	83%

ethylenediamine (107-15-3) + 2-Chloroethyl ethyl sulfide (693-07-2) → S-2-(2-aminoethylamino)ethyl ethyl sulfide (70063-00-2)

Conditions	Yield
Inert atmosphere;	83%

3-thiapentan-1,5-dithiol (3570-55-6) + 2-Chloroethyl ethyl sulfide (693-07-2) → 3,6,9,12,15-Pentathiaheptadecane (37460-05-2)

Conditions	Yield
With sodium ethanolate In ethanol for 1h; Heating;	82%

2-Chloroethyl ethyl sulfide (693-07-2) + 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)

Conditions	Yield
In ethanol; water for 1h; Heating;	82%

phenylmagnesium bromide + 2-Chloroethyl ethyl sulfide (693-07-2) → <2-(ethylthio)ethyl>benzene (22914-08-5)

Conditions	Yield
In diethyl ether; toluene at 70℃;	82%

1-(2,6-diisopropylphenyl)-1H-imidazole (25364-47-0) + 2-Chloroethyl ethyl sulfide (693-07-2) → C2H5SC2H4C3H2N2C6H3(CH(CH3)2)2H(1+)*I(1-)=C2H5SC2H4C3H2N2C6H3(C3H7)2HI (1242931-14-1)

Conditions	Yield
With sodium iodide In toluene at 120℃; for 2h; Inert atmosphere;	81%

2-Chloroethyl ethyl sulfide (693-07-2) + diethyl malonate (105-53-3) → (2-ethylsulfanyl-ethyl)-malonic acid diethyl ester (100048-61-1)

Conditions	Yield
With potassium carbonate In acetonitrile Reflux;	81%

2-Chloroethyl ethyl sulfide (693-07-2) → 2-chloroethyl ethyl sulfoxide (27998-62-5) + (2-chloroethyl)(ethyl)(2-(ethylthio)ethyl)sulfonium chloride

Conditions	Yield
With urea hydrogen peroxide adduct at 23℃;	A 80% B 20%

3,6-di(piperidin-1-yl)-9H-xanthene-9-thione + 2-Chloroethyl ethyl sulfide (693-07-2) → thiopyronin

Conditions	Yield
In dichloromethane	80%

2-mercapto-5-(1-methyl-5-nitro-2-imidazolyl)-1,3,4-thiadiazole (23092-56-0) + 2-Chloroethyl ethyl sulfide (693-07-2) → C11H14N4O2S3

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃;	76%

2-Chloroethyl ethyl sulfide (693-07-2) + 2-hydroxyethanethiol (60-24-2) → 3,6-dithiaoctan-1-ol (57830-41-8)

Conditions	Yield
With sodium ethanolate In ethanol at 40℃; for 7h;	73%

tetramethylammonium 2-oxo-2-thio-1,3,2-oxazaphosphorinan (84451-65-0) + 2-Chloroethyl ethyl sulfide (693-07-2) → 2-(2-Ethylsulfanyl-ethylsulfanyl)-[1,3,2]oxazaphosphinane 2-oxide

Conditions	Yield
In benzene for 30h; Heating;	71%

2-Chloroethyl ethyl sulfide (693-07-2) + 2-mercapto-5-(5-nitro-2-furyl)-1,3,4-thiadiazole (16865-27-3) → C10H11N3O3S3

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃;	70%

2-Chloroethyl ethyl sulfide (693-07-2) → 2-ethylsulfanyl-ethanethiol (26750-44-7)

Conditions	Yield
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 + 2-Chloroethyl ethyl sulfide (693-07-2) → 1-(2-ethylsulfanyl-ethyl)-cyclopenta-1,3-diene (728880-40-8)

Conditions	Yield
In tetrahydrofuran for 4h; Heating;	68%

5-(2-nitrophenyl)-1,3,4-thiadiazole-2-thiol (85103-35-1) + 2-Chloroethyl ethyl sulfide (693-07-2) → C12H13N3O2S3 (1041361-26-5)

Conditions	Yield
With potassium hydroxide In ethanol; water at 20℃;	65%

4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (38339-95-6) + 2-Chloroethyl ethyl sulfide (693-07-2) → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-ethylsulfanyl-ethoxy)-benzamide (122452-34-0)

Conditions	Yield
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-Chloroethyl ethyl sulfide (693-07-2) → C12H13N3O2S3 (1041361-32-3)

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

Upstream product

• 110-77-0 2-(ethylsulfanyl)ethanol 
• 7719-09-7 thionyl chloride 
• 57830-41-8 3,6-dithiaoctan-1-ol 
• 107-06-2 1,2-dichloro-ethane 
• 75-08-1 ethanethiol 
• 811-51-8 sodium thioethylate 
• 860213-87-2 1-ethylsulfanyl-2-butoxy-ethane 
• 74-85-1 ethene 
• 1496-75-9 Ethanesulfenyl chloride 

Downstream Products

• 856375-36-5 1-ethylsulfanyl-2-benzoyloxy-ethane 
• 298-04-4 disulfoton 
• 109730-70-3 (2-ethylsulfanyl-ethyl)-phenyl-malonic acid diethyl ester 
• 101887-08-5 (2-ethylsulfanyl-ethyl)-benzyl-malonic acid diethyl ester 
• 640-15-3 S-2-ethylthioethyl O,O-dimethyl phosphorodithioate 
• 99986-14-8 2-(2-ethylsulfanyl-ethoxy)-benzoic acid amide 
• 27998-62-5 2-chloroethyl ethyl sulfoxide 
• 25027-40-1 2-chloroethyl ethyl sulfone 
• 19738-15-9 C₁₂H₂₆NPS₃ 
• 19738-16-0 C₁₄H₃₀NPS₃ 
• 188290-36-0 thiophene 
• 75-08-1 ethanethiol 
• 71-43-2 benzene 
• 32568-51-7 ethyl-vinyl sulfoxide 

Relevant articles and documents

New preparative procedure for the synthesis of chloroalkyl sulfides

Reaction of thiols with dihaloalkanes in the system hydrazine hydrate-base leads to alkyl(chloroalkyl) sulfides with different positions of the chlorine atom with respect to sulfur. The developed one-step procedure for the synthesis of such unsymmetrical sulfides is most suitable for arenethiols and alkanethiols having a long polymethylene chain. The reaction mechanism is discussed.

A POLYMERIC ANALOG OF DIMETHYL SULFOXIDE: SYNTHESIS OF CROSSLINKED POLYMERS WITH BOUND SULFOXIDE GROUPS

By using a sequence of functionalization reactions, a series of crosslinked polymers with pendant sulfoxide units of the P-(CH2SOCH2)nR type with n=1,2,3 and R= H, CH3, where P is poly(styrene-co-divinylbenzene) (content of the crosslinking component 1percent, 2percent) were prepared.The high reactivity of the crosslinked polymeric thiol P-CH2SH in alkylation reactions was used in the preparation.Conditions for the selective oxidation of polymeric sulfides to sulfoxides were checked.