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Ethyl chloracetate

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Name

Ethyl chloracetate

EINECS 203-294-0
CAS No. 105-39-5 Density 1.119 g/cm3
PSA 26.30000 LogP 0.78830
Solubility 20 g/L (20 ºC) Melting Point -27 ºC
Formula C4H7ClO2 Boiling Point 147.6 ºC at 760 mmHg
Molecular Weight 122.551 Flash Point 65.6 ºC
Transport Information UN 1181 6.1/PG 2 Appearance colourless liquid
Safety 45-61-7/9-16 Risk Codes 23/24/25-50-10
Molecular Structure Molecular Structure of 105-39-5 (Ethyl chloroacetate) Hazard Symbols ToxicT; DangerousN
Synonyms

Aceticacid, chloro-, ethyl ester (6CI,8CI,9CI);(Ethoxycarbonyl)methyl chloride;2-Chloroacetic acid ethyl ester;Chloroacetic acid ethyl ester;Ethyl 2-chloroacetate;Ethyl 2-monochloroacetate;Ethyl monochloracetate;Ethyl a-chloroacetate;NSC 8833;

Article Data 114

Ethyl chloracetate Synthetic route

64-17-5

ethanol

79-11-8

chloroacetic acid

105-39-5

chloroacetic acid ethyl ester

Conditions
ConditionsYield
With Candida antarctica lipase B at 20℃; for 36h; Enzymatic reaction;97%
at 105℃; for 3h; Temperature; Molecular sieve;97.4%
F-4SK (H form) In tetrachloromethane at 80℃; for 5h;95%
79-11-8

chloroacetic acid

105-39-5

chloroacetic acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride In ethanol; dichloromethane for 0.583333h; Cooling with ice;83%
623-33-6

glycine ethyl ester hydrochloride

79-04-9

chloroacetyl chloride

105-39-5

chloroacetic acid ethyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; toluene at 20℃; for 13h; Cooling with ice;80%
623-73-4

diazoacetic acid ethyl ester

105-39-5

chloroacetic acid ethyl ester

Conditions
ConditionsYield
With tertiary butyl chloride; [HB(3,5-(CF3)2Pz)3]Ag(THF)73%
With hydrogenchloride
With hydrogenchloride; diethyl ether
623-81-4

diethyl sulphite

79-11-8

chloroacetic acid

105-39-5

chloroacetic acid ethyl ester

Conditions
ConditionsYield
sulfuric acid In ethanol Heating;66%
141-97-9

ethyl acetoacetate

105-39-5

chloroacetic acid ethyl ester

Conditions
ConditionsYield
With potassium bromate; hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 12h;63%
623-73-4

diazoacetic acid ethyl ester

A

105-39-5

chloroacetic acid ethyl ester

B

1520-50-9

but-2-enedioic acid diethyl ester

Conditions
ConditionsYield
With tertiary butyl chloride; bis(μ2-2,2,2',2'-tetramethyl-1,3-benzene-di(propanoato-O,O'))rhodium-bismuth at 39.84℃; for 2h; Inert atmosphere;A 46%
B n/a
623-73-4

diazoacetic acid ethyl ester

140-29-4

phenylacetonitrile

A

74185-57-2

2-benzyl-5-ethoxy-1,3-oxazole

B

105-39-5

chloroacetic acid ethyl ester

Conditions
ConditionsYield
aluminium trichloride In neat (no solvent) at 25℃;A 31%
B n/a
7064-36-0

4-chloro-5-methyl-isoxazole

64-17-5

ethanol

A

141-78-6

ethyl acetate

B

105-39-5

chloroacetic acid ethyl ester

Conditions
ConditionsYield
With pyridine for 5h; Heating;A n/a
B 25%
623-73-4

diazoacetic acid ethyl ester

507-20-0

tertiary butyl chloride

A

98551-46-3

2-chloro-3,3-dimethyl-butyric acid ethyl ester

B

105-39-5

chloroacetic acid ethyl ester

Conditions
ConditionsYield
Photolysis;
Irradiation.mit UV-Licht;

Ethyl chloracetate Consensus Reports

Reported in EPA TSCA Inventory.

Ethyl chloracetate Standards and Recommendations

DOT Classification:  6.1; Label: Poison

Ethyl chloracetate Specification

The CAS registry number of Ethyl chloracetate is 105-39-5. Its EINECS registry number is 203-294-0. The IUPAC name is ethyl 2-chloroacetate. In addition, the molecular formula is C4H7ClO2. What's more, it is a kind of colourless liquid and can be used as a pharmaceutical intermediate. It is incompatible with acids, bases, oxidizing agents and reducing agents.

Physical properties about this chemical are: (1)ACD/LogP: 0.94; (2)ACD/LogD (pH 5.5): 0.94; (3)ACD/LogD (pH 7.4): 0.94; (4)ACD/BCF (pH 5.5): 3.05; (5)ACD/BCF (pH 7.4): 3.05; (6)ACD/KOC (pH 5.5): 77.3; (7)ACD/KOC (pH 7.4): 77.3; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 26.3 Å2; (11)Index of Refraction: 1.411; (12)Molar Refractivity: 27.2 cm3; (13)Molar Volume: 109.4 cm3; (14)Polarizability: 10.78 ×10-24cm3; (15)Surface Tension: 29.2 dyne/cm; (16)Density: 1.119 g/cm3; (17)Flash Point: 65.6 °C; (18)Enthalpy of Vaporization: 40.43 kJ/mol; (19)Boiling Point: 147.6 °C at 760 mmHg; (20)Vapour Pressure: 4.39 mmHg at 25°C.

Preparation of Ethyl chloracetate: it can be prepared by chloroacetic acid and ethanol. This reaction will need reagents P2O5, CuSO4 and Na2SO4. The reaction time is 2 hours by heating. The yield is about 45%.

Ethyl chloracetate can be prepared by chloroacetic acid and ethanol

Uses of Ethyl chloracetate: it can react with 1-(N-phenylamino)-3-butoxypropane-2-thiol to get (1-butoxymethyl-2-phenylamino-ethylsulfanyl)-acetic acid ethyl ester. This reaction will need reagent NaOH and solvent H2O. The reaction time is 1 hours at reaction temperature of 30-40 °C. The yield is about 32%.

Ethyl chloracetate can react with 1-(N-phenylamino)-3-butoxypropane-2-thiol to get (1-butoxymethyl-2-phenylamino-ethylsulfanyl)-acetic acid ethyl ester

When you are using this chemical, please be cautious about it as the following:
This chemical is flammable. And it is toxic by inhalation, in contact with skin and if swallowed. Moreover, it is very toxic to aquatic organisms. During using it, you should keep away from sources of ignition. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). In addition, you should avoid release to the environment and you can refer to special instructions/safety data sheets. Besides, keep container tightly closed and in a well-ventilated place after using it.

You can still convert the following datas into molecular structure:
(1)SMILES: ClCC(=O)OCC
(2)InChI: InChI=1/C4H7ClO2/c1-2-7-4(6)3-5/h2-3H2,1H3
(3)InChIKey: VEUUMBGHMNQHGO-UHFFFAOYAS

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 350mg/kg (350mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 30(5), Pg. 59, 1986.
mouse LD50 subcutaneous 250mg/kg (250mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Japanese Journal of Pharmacology. Vol. 3, Pg. 99, 1954.
rabbit LD50 skin 230mg/kg (230mg/kg)   Toxicology and Applied Pharmacology. Vol. 42, Pg. 417, 1977.
rat LC50 inhalation 3330uL/m3/4H (3.33mL/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
BG Chemie: Toxicological Evaluations, Five Potential Health Hazards of Existing Chemicals. Vol. 5, Pg. 71, 1993.
rat LD50 oral 180mg/kg (180mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
BG Chemie: Toxicological Evaluations, Five Potential Health Hazards of Existing Chemicals. Vol. 5, Pg. 71, 1993.
rat LD50 skin 161mg/kg (161mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
BG Chemie: Toxicological Evaluations, Five Potential Health Hazards of Existing Chemicals. Vol. 5, Pg. 71, 1993.

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