Conditions | Yield |
---|---|
With titanium tetrachloride; acrylic acid methyl ester In dichloromethane at 20℃; for 0.0333333h; Inert atmosphere; | 96% |
With hydrogenchloride In water |
Conditions | Yield |
---|---|
F-4SK (H form) In dichloromethane at 41℃; for 15h; | 94% |
With iron(III) sulfate; sulfuric acid for 1h; Heating; | 94% |
With sulfuric acid for 6h; Fischer–Speier Esterification; Reflux; | 89% |
methyl diazoacetate
acrylic acid methyl ester
A
5-methoxycarbonyl-pyrazoline-3-carboxylic acid methyl ester
B
methyl chloroacetate
Conditions | Yield |
---|---|
With ethylaluminum dichloride In hexane; dichloromethane at 20℃; for 0.0666667h; Inert atmosphere; | A 90% B 5% |
With tin(IV) chloride In dichloromethane at 20℃; for 0.0333333h; Inert atmosphere; | A 10% B 85% |
methyl diazoacetate
acrylic acid methyl ester
A
5-methoxycarbonyl-pyrazoline-3-carboxylic acid methyl ester
B
dimethyl 1-(2-methoxy-2-oxoethyl)-4,5-dihydro-1H-pyrazole-3,5-dicarboxylate
C
methyl chloroacetate
Conditions | Yield |
---|---|
With gallium(III) trichloride In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; | A 15% B 76% C 5% |
methyl chloroacetate
Conditions | Yield |
---|---|
With hydrogenchloride In chloroform-d1 for 24h; Ambient temperature; | 72% |
Conditions | Yield |
---|---|
sulfuric acid In methanol Heating; | 51% |
Conditions | Yield |
---|---|
With silver tetrafluoroborate; lithium fluoride In methanol; diethyl ether at 0℃; for 0.5h; Yield given; | A n/a B 6% C 10% |
With silver tetrafluoroborate; lithium fluoride In methanol; diethyl ether at 0℃; for 0.5h; | A n/a B 6% C 10% |
With silver tetrafluoroborate; lithium fluoride In diethyl ether at 0℃; for 30h; | A n/a B 6% C 10% |
chloroform
methyl diazoacetate
A
methyl 2,3,3-trichloropropanoate
B
methyl chloroacetate
Conditions | Yield |
---|---|
UV-Licht.Irradiation; | |
im UV-Licht; |
methanol
(E)-1,2-dichloro-1-ethoxy-ethene
A
methyl chloroacetate
B
chloroacetic acid ethyl ester
Conditions | Yield |
---|---|
at 200℃; | |
With tetra(n-butyl)ammonium hydrogensulfate; sodium sulfate In water at 55℃; Methylation; esterification; |
magnesium methanolate
chloroacetyl chloride
methyl chloroacetate
Conditions | Yield |
---|---|
With Petroleum ether |
Conditions | Yield |
---|---|
With boron trifluoride |
methanol
2,3-Dichloroprop-1-ene
A
Methyl formate
B
methyl chloroacetate
Conditions | Yield |
---|---|
With ozone 1.) -78 deg C, 2.) room temperature, 15 h; Title compound not separated from byproducts; | A 66 % Spectr. B 80 % Spectr. |
methanol
2-chloro-2-propenal
A
Dimethyl oxalate
B
glycolic acid methyl ester
C
Methyl dimethoxyacetate
D
methyl chloroacetate
E
Glyoxilic acid
Conditions | Yield |
---|---|
With ozone at -78℃; Product distribution; ozonolysis; | A 18 % Spectr. B 14 % Spectr. C 44 % Spectr. D 1 % Spectr. E 18 % Spectr. |
methanol
3-chloro-but-3-en-2-one
A
Dimethyl oxalate
B
glycolic acid methyl ester
C
acetic acid methyl ester
D
methyl 2,2-dimethoxypropionate
E
methyl chloroacetate
Conditions | Yield |
---|---|
With ozone at -78℃; Product distribution; ozonolysis; |
methanol
chloroacetic acid 4-nitrophenyl ester
A
4-nitro-phenol
B
methyl chloroacetate
Conditions | Yield |
---|---|
pyridine at 25.1℃; Rate constant; also with other bases (3-methylpyridine, 4-methylpyridine, 2,6-dimethylpyridine, imidazole, 2-methylimidazole); kobs, k1, k2; |
methanol
2-chloro-1-hydroxyethyl 2-chloro-1-methoxyethyl peroxide
A
chloroacetaldehyde dimethyl acetal
B
methyl chloroacetate
Conditions | Yield |
---|---|
With hydrogenchloride In chloroform-d1 1.) 40 deg C, 16 h, 2.) 60 deg C, 12 h; Yield given. Yields of byproduct given; |
dichloro-acetic acid
A
dichloroacetic acid methyl ester
B
methyl chloroacetate
Conditions | Yield |
---|---|
1) CDCl3, 60 deg C, 7 d; 2) 30 min; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With ozone In ethyl acetate at -78℃; Rate constant; |
methanol
oxoproline TMS
chloroacetyl chloride
A
chloro-trimethyl-silane
B
N-chloroacetylpyroglutamic acid
C
methyl chloroacetate
D
methyl 5-oxopyrrolidine-2-carboxylate
Conditions | Yield |
---|---|
Product distribution; |
Conditions | Yield |
---|---|
acrylonitrile; triphenylphosphine at 25℃; for 0.5h; | 100 % Chromat. |
With HZnPS-1, porous sulfonated zinc phosphonate material at 24.84℃; for 24h; | 588 mg |
methanol
chloroacetic acid ethyl ester
A
ethanol
B
methyl chloroacetate
Conditions | Yield |
---|---|
With imobilized subtilisin on an alumina-phosphate In n-heptane at 22℃; Kinetics; | |
Stage #1: methanol; chloroacetic acid ethyl ester at 59.84℃; for 0.25h; Stage #2: With hybrid supermicroporous iron(III) phosphonate nanoparticle (HFeP-1-3) at 59.84℃; for 6h; |
3-methyl-1-p-tolyltriazene
chloroacetic acid
A
p-toluidine
B
methyl chloroacetate
Conditions | Yield |
---|---|
In acetone at 25℃; Rate constant; |
Conditions | Yield |
---|---|
With tetraethylammonium tosylate 1.) DMF, room temperature, electrolysis, 2.) DMF; Yield given. Multistep reaction; |
2-chloro-1-hydroxyethyl 2-chloro-1-methoxyethyl peroxide
A
chloroacetaldehyde dimethyl acetal
B
methyl chloroacetate
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; chloroform-d1 1.) 40 deg C, 16 h, 2.) 60 deg C, 12 h; Yield given. Yields of byproduct given; |
methyl chloroacetate
Conditions | Yield |
---|---|
With deuteromethanol; triphenylphosphine; 1,1,2,2-tetrachloroethane In chloroform-d1 at -60℃; | 92 % Spectr. |
(+)-2,2'-dihydroxy-1,1'-binaphthyl
(-)-2,2'-dihydroxy-1,1'-binaphthyl
C
methyl chloroacetate
Conditions | Yield |
---|---|
With methanol; lipase from Pseudomonas sp In di-isopropyl ether at 40℃; for 5.2h; Yield given. Title compound not separated from byproducts; | |
With methanol; lipase from Pseudomonas sp In di-isopropyl ether at 40℃; for 5.2h; Yield given; |
Conditions | Yield |
---|---|
With sodium iodide In acetone Finkelstein reaction; | 100% |
With ethanol; potassium iodide | |
With potassium iodide In acetone | |
With sodium iodide In acetone at 20℃; for 0.333333h; | |
With sodium iodide In acetone for 0.333333h; |
dimethyl formamidomalonate
methyl chloroacetate
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 0.5h; | 100% |
methyl chloroacetate
E-3-m-hydroxystyrylpyridine
4-[(E)-2-(3-Hydroxy-phenyl)-vinyl]-1-methoxycarbonylmethyl-pyridinium; chloride
Conditions | Yield |
---|---|
In methanol for 10h; Heating; | 100% |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 0.5h; | 100% |
4-hydroxy-benzaldehyde
methyl chloroacetate
methyl (4-formylphenoxy)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 5h; | 100% |
With potassium carbonate; sodium iodide In acetone for 12h; Heating / reflux; | 66.1% |
With iodine; potassium carbonate; toluene-4-sulfonic acid In water; toluene |
1-methylparabanic acid
methyl chloroacetate
N-methyl-N'-carbmethoxymethyl parabanic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 20℃; for 16h; Sonication; | 100% |
methyl chloroacetate
4-cyanobenzaldehyde
(Z)-2-chloro-3-(4-cyanophenyl)acrylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: methyl chloroacetate; 4-cyanobenzaldehyde With titanium tetrachloride In dichloromethane at 20℃; for 0.666667h; Aldol Condensation; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at 20 - 30℃; Aldol Condensation; Inert atmosphere; stereoselective reaction; | 100% |
N-((5-chloro-1H-indazol-3-yl)methyl)-1-(4-((2-oxopyridin-1(2H)-yl)methyl)benzyl)-1H-pyrazole-4-carboxamide
methyl chloroacetate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 50℃; | 100% |
methyl chloroacetate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 4h; Reflux; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetonitrile at 50℃; for 3h; | 100% |
2,6-dichloro-4-hydroxybenzaldehyde
methyl chloroacetate
methyl 2-(3,5-dichloro-4-formylphenoxy)acetate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 60℃; for 2h; | 99.9% |
methyl chloroacetate
1-(Trimethylsilyl)imidazole
Conditions | Yield |
---|---|
at 60℃; for 24h; | 99% |
at 60℃; for 24h; | 99.7% |
at 60℃; for 24h; | 99.7% |
In neat liquid at 60℃; for 24h; | 99.7% |
at 60℃; for 24h; Inert atmosphere; | 97% |
methyl chloroacetate
[1-(3,4-dichloro-phenyl)-propylamino]-acetic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 64h; | 99.7% |
With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 44h; | 99.7% |
With triethylamine In N,N-dimethyl-formamide at 20℃; for 64h; | 99.7% |
methyl chloroacetate
2,4-dichlorophenol
methyl 2,4-dichlorophenoxyacetate
Conditions | Yield |
---|---|
With potassium fluoride; potassium iodide at 120℃; for 24h; Reagent/catalyst; Time; | 99.2% |
Stage #1: 2,4-dichlorophenol With potassium carbonate In water; chlorobenzene at 125℃; for 2h; Stage #2: methyl chloroacetate In water; chlorobenzene at 120 - 146℃; for 4h; Reagent/catalyst; Temperature; Concentration; Solvent; | 98.5% |
Stage #1: 2,4-dichlorophenol With potassium carbonate In water; chlorobenzene at 125℃; for 2h; Stage #2: methyl chloroacetate In water; chlorobenzene at 120℃; for 4h; Solvent; Concentration; Reagent/catalyst; Temperature; | 98.5% |
Conditions | Yield |
---|---|
With sodium azide In N,N-dimethyl-formamide at 60℃; for 24h; | 99% |
With sodium azide In acetonitrile for 20h; Heating; | 93% |
With sodium azide In N,N-dimethyl-formamide at 20℃; for 4h; | 88% |
Conditions | Yield |
---|---|
at 20℃; for 1h; | 99% |
for 1h; Sonication; | 97% |
at 20℃; for 1.5h; |
methyl chloroacetate
4-bromo-benzaldehyde
(Z)-3-(4-bromophenyl)-2-chloroacrylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: methyl chloroacetate; 4-bromo-benzaldehyde With titanium tetrachloride In dichloromethane at 20℃; for 0.666667h; Aldol Condensation; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at 20 - 30℃; Aldol Condensation; Inert atmosphere; stereoselective reaction; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 3.5h; Inert atmosphere; | 99% |
methyl chloroacetate
Conditions | Yield |
---|---|
With caesium carbonate; triethylamine; potassium iodide In acetone at 20℃; for 24h; Microwave irradiation; | 99% |
potassium 1-naphtholate
methyl chloroacetate
(naphthalen-1-yloxy)acetic acid methyl ester
Conditions | Yield |
---|---|
at 120℃; for 2h; Time; | 98.9% |
Conditions | Yield |
---|---|
Stage #1: methyl chloroacetate; m-acetamide aniline With sodium carbonate at 90 - 100℃; for 2h; Stage #2: With sodium bromide; zinc at 105 - 110℃; for 2h; Catalytic behavior; Time; | 98.6% |
methyl chloroacetate
N-Benzoyl-m-phenylendiamin
Conditions | Yield |
---|---|
Stage #1: methyl chloroacetate; N-Benzoyl-m-phenylendiamin With sodium carbonate at 100 - 105℃; for 2h; Stage #2: With sodium bromide; zinc at 110 - 130℃; for 3h; | 98.4% |
Conditions | Yield |
---|---|
Stage #1: phenol With potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; 2-methyl-propan-1-ol; water at 138℃; for 1h; Stage #2: methyl chloroacetate In 5,5-dimethyl-1,3-cyclohexadiene; 2-methyl-propan-1-ol; water at 120 - 135℃; for 6h; Solvent; Temperature; Reagent/catalyst; | 98.15% |
With potassium carbonate at 150℃; for 10h; Temperature; Reagent/catalyst; | 97.6% |
Stage #1: phenol With sodium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; water; butan-1-ol at 140℃; for 1h; Stage #2: methyl chloroacetate at 146℃; for 6h; Solvent; Reagent/catalyst; Temperature; | 97.5% |
potassium ethyl xanthogenate
methyl chloroacetate
ethoxyrhiocarbonylsulfanylacetic acid methyl ester
Conditions | Yield |
---|---|
In acetonitrile at 0 - 20℃; for 2h; | 98% |
In acetone at 0 - 20℃; | 83% |
With ethanol |
saccharin sodium salt
methyl chloroacetate
methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide
Conditions | Yield |
---|---|
In DMF (N,N-dimethyl-formamide) at 115 - 120℃; for 1.5 - 2h; Industry scale; | 98% |
In N,N-dimethyl-formamide for 0.05h; Microwave irradiation; | 96.2% |
In N,N-dimethyl-formamide at 110 - 120℃; for 3h; | 96% |
4-nitrobenzaldehdye
methyl chloroacetate
Methyl trans-3-(4-nitrophenyl)oxirane-2-carboxylate
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; Darzens Condensation; | 98% |
With potassium tert-butylate In diethyl ether for 20h; | 69% |
With sodium methylate In methanol 1.) 0 deg C, 2 h, 2.) room temperature, 3 h; | 65% |
sodium p-chlorobenzenesulphinate
methyl chloroacetate
methyl 4-chlorophenylsulphinylacetate
Conditions | Yield |
---|---|
98% | |
In N,N-dimethyl-formamide at 120℃; for 3h; | 98% |
In N,N-dimethyl-formamide at 45 - 115℃; for 3h; | 98% |
2,2'-thiobis<4-methylphenol>
methyl chloroacetate
2,2'-sulfinyl bis[methy(4-methylphenoxyacetate)]
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone for 24h; Reflux; | 98% |
With potassium carbonate; potassium iodide In acetone for 24h; Reflux; | 98% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; | 95% |
With potassium carbonate; potassium iodide In acetone Heating; |
1,8-Naphthalimide
methyl chloroacetate
methyl (1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)acetate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 1h; | 98% |
Conditions | Yield |
---|---|
at 135℃; for 10h; | 98% |
IUPAC Name: Methyl 2-chloroacetate
Synonyms of Methyl chloroacetate (CAS NO.96-34-4): AI3-39185 ; Acetic acid, chloro-, methyl ester ; CCRIS 7749 ; Chloroacetic acid methyl ester ; EINECS 202-501-1 ; HSDB 5303 ; Methyl alpha-chloroacetate ; Methyl chloroethanoate ; Methyl monochloracetate ; Methyl monochloroacetate ; Methylester kyseliny chloroctove ; Methylester kyseliny chloroctove [Czech] ; Monochloroacetic acid methyl ester ; NSC 2635 ; Acetic acid, 2-chloro-, methyl ester ; Methyl chloroacetate [UN2295] [Poison] ; UN2295
CAS NO: 96-34-4
Molecular Formula of Methyl chloroacetate (CAS NO.96-34-4): C3H5ClO2
Molecular Weight: 108.5236
Molecular Structure:
Melting Point: -33 °C
ProductCategories: Organics ; Alpha sort ; H-MAlphabetic ; M ; META - METH ; Pesticides&Metabolites ;C2 to C5 ; Carbonyl Compounds ; Esters ; 500 Series Drinking Water Methods ; EPA ; Method 552
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.4
Molar Refractivity: 22.57 cm3
Molar Volume: 92.9 cm3
Surface Tension: 28.4 dyne/cm
Density of Methyl chloroacetate (CAS NO.96-34-4): 1.167 g/cm3
Flash Point: 51.7 °C
Enthalpy of Vaporization: 39.23 kJ/mol
Boiling Point: 132.2 °C at 760 mmHg
Vapour Pressure: 8.97 mmHg at 25°C
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mammal (species unspecified) | LD50 | oral | 240mg/kg (240mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974. | |
mouse | LC50 | inhalation | 1gm/m3/2H (1000mg/m3) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 82, 1982. | |
mouse | LD50 | oral | 240mg/kg (240mg/kg) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 82, 1982. | |
rat | LCLo | inhalation | 250ppm/7H (250ppm) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Toxicology and Applied Pharmacology. Vol. 19, Pg. 1, 1971. |
rat | LD16 | subcutaneous | 560mg/kg (560mg/kg) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 82, 1982. |
Methyl chloroacetate (CAS NO.96-34-4) Market Research Report 2009
Hazard Codes: T,Xi,F
Risk Statements: 10-23/25-41-40-36/37/38
R10: Flammable.
R23/25: Toxic by inhalation and if swallowed.
R41: Risk of serious damage to the eyes.
R40: Limited evidence of a carcinogenic effect.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39-45-36-16
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39: Wear suitable gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36: Wear suitable protective clothing.
S16: Keep away from sources of ignition.
RIDADR: UN 2295 6.1/PG 1
WGK Germany: 2
RTECS: AF9500000
F: 19
HazardClass: 6.1
PackingGroup: I
Hazardous Substances Data: 96-34-4(Hazardous Substances Data)
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