2941-64-2

Usage

Uses

Used in Chemical Synthesis:
Ethyl chlorothioformate is used as an intermediate in the chemical synthesis of various organic compounds, particularly in the production of pharmaceuticals and agrochemicals. Its reactivity and versatility make it a valuable component in the synthesis of a wide range of products.
Used in Pesticide Production:
Ethyl chlorothioformate is used as a key component in the production of certain pesticides. Its ability to react with other chemicals and form new compounds makes it a useful building block for creating effective and targeted pest control agents.
Used in Rubber Industry:
In the rubber industry, ethyl chlorothioformate is used as a curing agent for certain types of rubber. Its chemical properties allow it to facilitate the cross-linking process, which is essential for the production of durable and high-quality rubber products.
Used in Pharmaceutical Industry:
Ethyl chlorothioformate is used as a reagent in the pharmaceutical industry for the synthesis of various drugs. Its ability to react with other compounds and form new molecules makes it a valuable tool in the development of new medications and therapies.
Used in Research and Development:
Due to its unique chemical properties and reactivity, ethyl chlorothioformate is also used in research and development laboratories. Scientists and researchers utilize Ethyl chlorothioformate to study its properties, explore its potential applications, and develop new methods for its synthesis and use in various industries.

Air & Water Reactions

Flammable. Insoluble in water. On contact with moisture Ethyl chlorothioformate produces highly corrosive and toxic fumes of hydrogen chloride gas.

Reactivity Profile

Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as sulfur oxides, hydrogen chloride, and carbon monoxide, may be formed when involved in fire.

Health Hazard

Exposure can cause irritation of eyes, nose and throat.

Potential Exposure

Used for making other chemicals. A pharmaceutical intermediate

Shipping

UN2826 Ethyl chlorothioformate, Hazard Class: 8; Labels: 8-Corrosive material, 6.1-Poison Inhalation Hazard, 3-Flammable liquid; Inhalation Hazard Zone B

Incompatibilities

Corrosive to metals. Flammable vapors may form explosive mixture with air. Contact with moisture releases highly corrosive and toxic hydrogen chloride gas. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Controlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices)

InChI:InChI=1/C3H5ClOS/c1-2-6-3(4)5/h2H2,1H3

Synthetic route

phosgene (75-44-5) + ethanethiol (75-08-1) → Ethyl chlorothioformate (2941-64-2)

ethyl isothiocyanate (542-90-5) + chloromalonyl dichloride (408321-65-3) → Ethyl chlorothioformate (2941-64-2)

bis(trichloromethyl) carbonate (32315-10-9) + ethanethiol (75-08-1) → Ethyl chlorothioformate (2941-64-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at -15 - 20℃; for 0.5h;
With triethylamine In tetrahydrofuran at -15 - 18℃; for 2h;

6-chloro-3-phenylpyridazin-4-ol (40020-01-7) + Ethyl chlorothioformate (2941-64-2) → O-[3-phenyl-6-chloro-4-pyridazinyl]S-ethyl thiocarbonate (88880-54-0)

Conditions	Yield
In sodium hydroxide; water; acetone	100%

4-hydroxy-2-methyl-5-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]pyridazin-3-one (1429870-80-3) + Ethyl chlorothioformate (2941-64-2) → [2-methyl-5-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]-3-oxo-pyridazin-4-yl]ethylsulfanylformate

Conditions	Yield
With triethylamine In tetrahydrofuran; ethyl acetate	100%

Ethyl chlorothioformate (2941-64-2) + N-(3-methylaminopropyl)carbamic acid tert-butyl ester (442514-22-9) → N-(3-((ethylsulfanylcarbonyl)(methyl)amino)propyl)carbamic acid tert-butyl ester (960010-13-3)

Conditions	Yield
With sodium hydroxide In diethyl ether at 0℃; for 0.5h;	99%

(α-(acetyloxy)benzyl)tributylstannane (1071508-40-1, 157339-06-5) + Ethyl chlorothioformate (2941-64-2) → Acetic acid ethylsulfanylcarbonyl-phenyl-methyl ester (82027-42-7)

Conditions	Yield
With CuCN In toluene at 75℃; for 21h;	98%

(1-(acetyloxy)-3-phenylpropyl) tributylstannane + Ethyl chlorothioformate (2941-64-2) → 1-((ethylthio)carbonyl)-3-phenylpropyl acetate

Conditions	Yield
With CuCN In toluene at 80℃; for 35h;	97%

1-(2,2-difluoroethyl)-3-[2-(trifluoromethyl)phenyl]-1H-pyrido[2,3-c][1,2]thiazin-4-ol 2,2-dioxide (1362698-64-3) + Ethyl chlorothioformate (2941-64-2) → O-{1-(2,2-difluoroethyl)-2,2-dioxido-3-[2-(trifluoromethyl)phenyl]-1H-pyrido[2,3-c][1,2]thiazin-4-yl} S-ethyl thiocarbonate

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 3h;	97%

1‐(tert‐butyl) 2‐methyl (R)‐5‐oxopyrrolidine‐1,2‐dicarboxylate (128811-48-3) + Ethyl chlorothioformate (2941-64-2) → (3rac, 5R)-1-(tert-butoxycarbonyl)-3-(thioethoxycarbonyl)-2-pyrrolidinon-5-carboxylic methyl ester (398476-14-7)

Conditions	Yield
Stage #1: 1‐(tert‐butyl) 2‐methyl (R)‐5‐oxopyrrolidine‐1,2‐dicarboxylate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Stage #2: Ethyl chlorothioformate In tetrahydrofuran at -78℃;	95%

aniline (62-53-3) + Ethyl chlorothioformate (2941-64-2) → phenylthiocarbamic acid S-ethyl ester (17425-24-0)

Conditions	Yield
With pyridine In dichloromethane	94%

2-methanesulfonylbenzothiazole (7144-49-2) + Ethyl chlorothioformate (2941-64-2) → S-ethyl 2-(benzo[d]thiazol-2-ylsulfonyl)ethanethioate (1357556-60-5) + 2-<(benzothiazol-2-ylmethyl)sulfonyl>benzothiazole (134792-21-5)

Conditions	Yield
Stage #1: 2-methanesulfonylbenzothiazole; Ethyl chlorothioformate With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 2h; Stage #2: With ammonium chloride In tetrahydrofuran; water	A 94% B 11%

4-nitro-phenol (100-02-7) + Ethyl chlorothioformate (2941-64-2) → S-ethyl O-(4-nitrophenyl) carbonothioate (320343-87-1)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	93.5%
With pyridine In dichloromethane at 0 - 20℃; for 16h; Condensation;	92%

3-methylisoquinoline (1125-80-0) + potassium cyanide (151-50-8) + Ethyl chlorothioformate (2941-64-2) → 1-cyano-2-<(ethylthio)carbonyl>-1,2-dihydro-3-methylisoquinoline

Conditions	Yield
With benzyltrimethylammonium chloride In dichloromethane; water for 2h;	93%

Geraniol (106-24-1) + Ethyl chlorothioformate (2941-64-2) → Thiocarbonic acid O-((E)-3,7-dimethyl-octa-2,6-dienyl) ester S-ethyl ester

Conditions	Yield
With pyridine for 16h; Ambient temperature;	93%

C10H12N6O6*ClH (903568-77-4) + Ethyl chlorothioformate (2941-64-2) → O2-(2,4-dinitrophenyl) 1-[4-(ethylmercaptocarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate (1163704-76-4)

Conditions	Yield
With triethylamine In dichloromethane	93%

phenylmethanethiol (100-53-8) + Ethyl chlorothioformate (2941-64-2) → S-Benzyl-S'-ethyl dithiocarbonate (79010-64-3)

Conditions	Yield
With triethylamine	90%

Ethyl chlorothioformate (2941-64-2) + 4-amino-n-butyric acid (56-12-2) → 4-(((ethylthio)carbonyl)amino)butanoic acid (78213-31-7)

Conditions	Yield
With potassium carbonate In water at 0 - 20℃; Inert atmosphere;	90%
With potassium carbonate In water at 0 - 20℃;	67%

3-amino-N-(2,6-dimethyl-4-(perfluoropropan-2-yl)phenyl)benzamide (847621-70-9) + Ethyl chlorothioformate (2941-64-2) → N-(2,6-dimethyl-4-heptafluoroisopropyl)phenyl-3-(ethylthiocarbonylamino)benzamide

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 2h;	89%

(5,5-difluoro-1,3,7,9-tetramethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2′,1′-f ][1,3,2]diazaborinin-10-yl)methanol (1256494-55-9) + Ethyl chlorothioformate (2941-64-2) → C17H21BF2N2O2S

Conditions	Yield
With pyridine In tetrahydrofuran at 40℃; for 19h; Inert atmosphere;	88%

1,1-dimethylethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate (1001397-21-2) + Ethyl chlorothioformate (2941-64-2) → S-ethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarbothioate (1001398-64-6)

Conditions	Yield
Stage #1: 1,1-dimethylethyl 4-({7-[2-fluoro-4-(methylsulfonyl)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 2h; Stage #2: Ethyl chlorothioformate With triethylamine In dichloromethane at 20℃; for 18h;	87%

2-(4-phenylphenoxy)-ethanol (19070-95-2) + Ethyl chlorothioformate (2941-64-2) → S-ethyl-2-(4-phenylphenoxy)-ethyl-thiolcarbonate

Conditions	Yield
In pyridine for 14h; Ambient temperature;	86%

ethylamine (75-04-7) + Ethyl chlorothioformate (2941-64-2) → S-ethyl N-ethylthiocarbamate (39078-37-0)

Conditions	Yield
In dichloromethane; water	85%

{α-(phthalimidoyl)octyl}tributylstannane (153942-88-2) + Ethyl chlorothioformate (2941-64-2) → S-ethyl 2-phthalimidononanethioate

Conditions	Yield
With CuCN In toluene at 75℃; for 70h;	85%

O2-(2,4-dinitrophenyl) 1-[4-homopiperazin-1-yl]diazen-1-ium-1,2-diolate hydrochloride (1163704-89-9) + Ethyl chlorothioformate (2941-64-2) → O2-(2,4-dinitrophenyl) 1-[4-(ethylmercaptocarbonyl)homopiperazin-1-yl]diazen-1-ium-1,2-diolate (1163704-84-4)

Conditions	Yield
With triethylamine In dichloromethane	84%

Ethyl chlorothioformate (2941-64-2) + N-(4-chlorophenyl)hydroxylamine (823-86-9) → N-(4-Chlor-phenyl)-N-ethylmercaptocarbonyl-hydroxylamin (14063-23-1)

Conditions	Yield
With potassium carbonate In diethyl ether at 0 - 20℃;	83%
With sodium hydrogencarbonate In 1,2-dichloro-ethane

5-phenyl-3H-[1,3,4]oxadiazol-2-one (1199-02-6) + Ethyl chlorothioformate (2941-64-2) → 2-phenyl-4-(ethylthio)carbonyl-1,3,4-oxadiazol-5(4H)-one (55084-82-7)

Conditions	Yield
With pyridine In toluene for 3h; Ambient temperature;	82%
With pyridine In benzene

N-methyl(p-chloroaniline) (932-96-7) + Ethyl chlorothioformate (2941-64-2) → N-methyl-N-p-chlorophenylcarbamate thioethyl ester

Conditions	Yield
With potassium carbonate In diethyl ether at 0 - 20℃;	82%

C23H19ClN6OS + Ethyl chlorothioformate (2941-64-2) → C26H23ClN6O2S2 (952300-53-7)

Conditions	Yield
With pyridine at 20 - 60℃; for 19h;	82%

6-methoxy-1,2,3,4-tetrahydroquinoline (120-15-0) + Ethyl chlorothioformate (2941-64-2) → S-ethyl 6-methoxy-3,4-dihydroquinoline-1(2H)-carbothioate

Conditions	Yield
Stage #1: 6-methoxy-1,2,3,4-tetrahydroquinoline With triethylamine In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: Ethyl chlorothioformate In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	82%

Ethyl chlorothioformate (2941-64-2) + triethyl phosphite (122-52-1) → S-ethyl diethylphosphonothiolformate (163678-85-1)

Conditions	Yield
at 0 - 20℃; for 3h;	81%
In toluene for 1h;	68%
In toluene at 20℃; for 3h; Substitution; Arbuzov reaction;

5-amino-3-trifluoromethyl-1,2,4-thiadiazole (35581-44-3) + Ethyl chlorothioformate (2941-64-2) → 5-(ethylthiolcarbamoyl)-3-trifluoromethyl-1,2,4-thiadiazole (75472-24-1)

Conditions	Yield
With K2CO3 at 56°C, 20 h, in presence of K2CO3;	81%
With potassium carbonate at 56°C, 20 h, in presence of K2CO3;	81%

2-(4-phenoxyphenoxy)-ethanol (63066-74-0) + Ethyl chlorothioformate (2941-64-2) → S-ethyl-2-(4-phenoxyphenoxy)-ethyl-thiocarbonate

Conditions	Yield
In pyridine for 14h; Ambient temperature;	80%

Upstream product

• 542-90-5 ethyl isothiocyanate 
• 408321-65-3 chloromalonyl dichloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 75-08-1 ethanethiol 
• 75-44-5 phosgene 

Downstream Products

• 32666-97-0 cyclohexyl-thiocarbamic acid S-ethyl ester 
• 121781-91-7 S-ethyl N-(4-methylphenyl)thiocarbamate 
• 17425-24-0 phenylthiocarbamic acid S-ethyl ester 
• 39078-66-5 allyl-thiocarbamic acid S-ethyl ester 
• 39078-45-0 propyl-thiocarbamic acid S-ethyl ester 
• 59300-32-2 prop-2-ynyl-propyl-thiocarbamic acid S-ethyl ester 
• 403-94-1 (3-fluoro-phenyl)-thiocarbamic acid S-ethyl ester 
• 55084-82-7 2-phenyl-4-(ethylthio)carbonyl-1,3,4-oxadiazol-5(4H)-one 
• 34654-07-4 2-ethylsulfanylcarbonylamino-benzoic acid 
• 66787-11-9 S-Aethyl-O-4-chlorphenylthiocarbonat 
• 28145-60-0 S-ethyl thio(4-methylbenzoate) 
• 36069-85-9 S-ethyl N-benzylcarbamothioate 
• 3326-52-1 Diphenylmethyl-aethyl-thiocarbonat 
• 66787-12-0 S-Aethyl-O-3-chlorphenylthiocarbonat 

Relevant academic research and scientific papers

ADENOSINE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

Disclosed here is an adenosine derivative prodrug that can have reverse transcriptase inhibitor activity in vivo. This disclosure is also directed to a pharmaceutical composition comprising the adenosine derivative that can be used for the treatment of HIV infection or RNA virus infection.

NOVEL DITHIOLOPYRROLONES AND THEIR THERAPEUTICAL APPLICATIONS

The present invention provides novel dithiolopyrrolone compounds and their salts, which promote production of white blood cells and are useful as prevention and treatments for microbial infections such as HIV infection and blood disorders such as neutropenia and other related diseases. The present invention also provides therapeutic compositions comprising particularly useful types of dithiolopyrrolones, the salts thereof, and methods and use in the manufacture of a medication for treatment of diseases.

Facile 'one-pot' preparation of phosphonothiolformates. Useful reagents for the synthesis of carbamoylphosphonates

A versatile and mild 'one-pot' reaction for the preparation of trialkyl phosphonothiolformates was accomplished by sequential reaction of phosgene solution with alkanethiols, and subsequent Arbuzov reaction with trialkyl phosphites.

The Kinetics and Mechanism of the Thallium(III) Ion-promoted Hydrolysis of Thiolurethanes in Aqueous Solution. A Metal Ion-promoted Elimination

The hydrolysis of thiolurethanes R1C6H4NHCOSC6H4R2 (1), in dilute aqueous perchloric acid, under conditions where the spontaneous hydrolysis is negligible, is promoted by Ti3+ ions.The organic products are the corresponding anilinium ion and the thalium salt of the thiophenol.The effects of substituent changes (R1,R2) of changes in +>, temperature, ionic strength, and of replacement of the NH proton by Me, are all compatible with hydrolysis occurring by elimination-addition mechanisms via the isocyanate as a reactive intermediate; thalium ion-promoted E1 cb and E2 routes are implicated.In effect the elimination-addition type of mechanism which is important for these esters at higher pH has been made available at low pH by complexation with Tl3+ ions.With the thiolurethanes RC6H4NHCOSEt, (2) which are less susceptible to the spontaneous and base-catalysed elimination-addition mechanisms of hydrolysis than are thiolurethanes (1), the presence of Tl3+ ions can also lead to promoted hydrolysis via elimination, but an AAc1-like route (with Tl3+ taking the role of H+) seems to be available to the N-Me derivatives.

NOVEL SYNTHESIS OF DISUBSTITUTED THIOLCARBAMATES VIA A SULFUR TRANSFER AGENT-POTASSIUM ALKYL OR BENZYL DITHIOCARBONATES

The reaction of N,N-disubstituted carbamoyl chlorides with potassium alkyl or benzyl dithiocarbonates afforded a novel synthesis of disubstituted thiolcarbamates.