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Ethyl chlorothioformate

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Name

Ethyl chlorothioformate

EINECS 220-928-1
CAS No. 2941-64-2 Density 1.239g/cm3
PSA 42.37000 LogP 2.09830
Solubility decomposes Melting Point -60 °C
Formula C3H5ClOS Boiling Point 132 °C at 760 mmHg
Molecular Weight 124.591 Flash Point 30.6 °C
Transport Information UN 2826 Appearance clear yellow or grey-greenish to purple liquid
Safety 16-25-28A-36/37/39-45 Risk Codes 10-22-26-34
Molecular Structure Molecular Structure of 2941-64-2 (Ethyl chlorothioformate) Hazard Symbols VeryT+; CorrosiveC
Synonyms

Formicacid, chlorothio-, S-ethyl ester (7CI,8CI);Ethyl chlorothioformate;Ethylthiochloroformate;Ethylthiocarbonyl chloride;Ethylthiol chloroformate;S-Ethyl carbonochloridothioate;S-Ethyl chlorothiocarbonate;S-Ethylchlorothioformate;S-Ethyl thiochloroformate;Thioethoxycarbonyl chloride;

 

Ethyl chlorothioformate Synthetic route

75-44-5

phosgene

75-08-1

ethanethiol

2941-64-2

Ethyl chlorothioformate

542-90-5

ethyl isothiocyanate

408321-65-3

chloromalonyl dichloride

2941-64-2

Ethyl chlorothioformate

32315-10-9

bis(trichloromethyl) carbonate

75-08-1

ethanethiol

2941-64-2

Ethyl chlorothioformate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -15 - 20℃; for 0.5h;
With triethylamine In tetrahydrofuran at -15 - 18℃; for 2h;
40020-01-7

6-chloro-3-phenylpyridazin-4-ol

2941-64-2

Ethyl chlorothioformate

88880-54-0

O-[3-phenyl-6-chloro-4-pyridazinyl]S-ethyl thiocarbonate

Conditions
ConditionsYield
In sodium hydroxide; water; acetone100%
1429870-80-3

4-hydroxy-2-methyl-5-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]pyridazin-3-one

2941-64-2

Ethyl chlorothioformate

[2-methyl-5-[2-methylsulfonyl-4-(trifluoromethyl)phenyl]-3-oxo-pyridazin-4-yl]ethylsulfanylformate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; ethyl acetate100%
2941-64-2

Ethyl chlorothioformate

442514-22-9

N-(3-methylaminopropyl)carbamic acid tert-butyl ester

960010-13-3

N-(3-((ethylsulfanylcarbonyl)(methyl)amino)propyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether at 0℃; for 0.5h;99%
1071508-40-1, 157339-06-5

(α-(acetyloxy)benzyl)tributylstannane

2941-64-2

Ethyl chlorothioformate

82027-42-7

Acetic acid ethylsulfanylcarbonyl-phenyl-methyl ester

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

(1-(acetyloxy)-3-phenylpropyl) tributylstannane

2941-64-2

Ethyl chlorothioformate

1-((ethylthio)carbonyl)-3-phenylpropyl acetate

Conditions
ConditionsYield
With CuCN In toluene at 80℃; for 35h;97%
1362698-64-3

1-(2,2-difluoroethyl)-3-[2-(trifluoromethyl)phenyl]-1H-pyrido[2,3-c][1,2]thiazin-4-ol 2,2-dioxide

2941-64-2

Ethyl chlorothioformate

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
ConditionsYield
With pyridine In dichloromethane at 20℃; for 3h;97%
128811-48-3

1‐(tert‐butyl) 2‐methyl (R)‐5‐oxopyrrolidine‐1,2‐dicarboxylate

2941-64-2

Ethyl chlorothioformate

398476-14-7

(3rac, 5R)-1-(tert-butoxycarbonyl)-3-(thioethoxycarbonyl)-2-pyrrolidinon-5-carboxylic methyl ester

Conditions
ConditionsYield
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%

Ethyl chlorothioformate Specification

The Ethyl chlorothioformate, with the CAS registry number 2941-64-2 and EINECS registry number 220-928-1, has the systematic name of S-ethyl carbonochloridothioate. It is a kind of clear yellow or grey-greenish to purple liquid, and belongs to the product category of Pharmaceutical Intermediates. And the molecular formula of the chemical is C3H5ClOS.

The characteristics of Ethyl chlorothioformate are as followings: (1)ACD/LogP: 2.02; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.02; (4)ACD/LogD (pH 7.4): 2.02; (5)ACD/BCF (pH 5.5): 20.21; (6)ACD/BCF (pH 7.4): 20.21; (7)ACD/KOC (pH 5.5): 299.33; (8)ACD/KOC (pH 7.4): 299.33; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 42.37 Å2; (13)Index of Refraction: 1.485; (14)Molar Refractivity: 28.82 cm3; (15)Molar Volume: 100.5 cm3; (16)Polarizability: 11.42×10-24cm3; (17)Surface Tension: 35.6 dyne/cm; (18)Density: 1.239 g/cm3; (19)Flash Point: 30.6 °C; (20)Enthalpy of Vaporization: 36.96 kJ/mol; (21)Boiling Point: 132 °C at 760 mmHg; (22)Vapour Pressure: 9.04 mmHg at 25°C.

Uses of Ethyl chlorothioformate: It can react with 5-fluoro-1H-pyrimidine-2,4-dione to produce 1-(ethylthio)carbonyl-5-fluorouracil. This reaction will need reagent triethylamine, and the menstruum pyridine. And the yield is about 40%.   

You should be cautious while dealing with this chemical. It is a kind of flammable chemical which is very toxic by inhalation, and may also cause burns. Therefore, you had better take the following instructions: Keep away from sources of ignition - No smoking; Avoid contact with eyes; Wear suitable protective clothing, gloves and eye/face protection; After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer); In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: ClC(=O)SCC
(2)InChI: InChI=1/C3H5ClOS/c1-2-6-3(4)5/h2H2,1H3
(3)InChIKey: QCMHWZUFWLOOGI-UHFFFAOYAP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LC50 inhalation 210mg/m3/4H (210mg/m3) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

LUNGS, THORAX, OR RESPIRATION: EMPHYSEMA

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"
National Technical Information Service. Vol. OTS0538464

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