Malonic acid monomethyl ester
3-chloro-3-oxopropanoic acid methyl ester
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide In chloroform Heating; | 65% |
With phosphorus pentachloride In dichloromethane for 0.5h; Heating; | |
With thionyl chloride In dichloromethane | |
Stage #1: Malonic acid monomethyl ester In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; Cooling with ice; | |
With thionyl chloride at 80℃; for 2h; Inert atmosphere; |
monomethyl monopotassium malonate
3-chloro-3-oxopropanoic acid methyl ester
Conditions | Yield |
---|---|
With oxalyl dichloride In benzene | |
With thionyl chloride | |
With thionyl chloride In dichloromethane for 2h; Ambient temperature; | |
With hexachloroethane; triphenylphosphine In dichloromethane | |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; |
3-chloro-3-oxopropanoic acid methyl ester
Conditions | Yield |
---|---|
With thionyl chloride; diethyl ether unter Kuehlung mit Eis-Kochsalz-Gemisch; |
3-chloro-3-oxopropanoic acid methyl ester
methyl hydrogen succinate
3-chloro-3-oxopropanoic acid methyl ester
Conditions | Yield |
---|---|
With thionyl chloride In benzene for 1.5h; Reflux; |
3-chloro-3-oxopropanoic acid methyl ester
aniline
Methyl 2-(N-phenylaminocarbonyl)acetate
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 1h; | 100% |
With triethylamine In dichloromethane for 2h; Inert atmosphere; | 99% |
With triethylamine In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; | 99% |
3-chloro-3-oxopropanoic acid methyl ester
N-ethyl-N-phenylamine
methyl 3-(N-ethyl-N-phenylamino)-3-oxopropionate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 14h; Inert atmosphere; | 100% |
With triethylamine In acetone at 2 - 20℃; for 2h; Inert atmosphere; | 94% |
With pyridine | |
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; |
3-chloro-3-oxopropanoic acid methyl ester
2'-chloro-3,5-dimethyl-2-methylaminobenzophenone
methyl N-<2-(2-chlorobenzoyl)-4,6-dimethylphenyl>-N-methylmalonylamide
Conditions | Yield |
---|---|
With triethylamine In ethyl acetate for 1.5h; | 100% |
3-chloro-3-oxopropanoic acid methyl ester
ethanethiol
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; | 100% |
In dichloromethane at 0 - 20℃; for 15h; Inert atmosphere; | 100% |
4-Chloro-3-nitroaniline
3-chloro-3-oxopropanoic acid methyl ester
N-(4-chloro-3-nitro-phenyl)-malonamic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
3-chloro-3-oxopropanoic acid methyl ester
4-bromo-aniline
methyl 3-((4-bromophenyl)amino)-3-oxopropanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
Stage #1: 4-bromo-aniline With triethylamine In ethyl acetate at 10℃; Stage #2: 3-chloro-3-oxopropanoic acid methyl ester at 17℃; for 0.75h; | 122.75 g |
3-chloro-3-oxopropanoic acid methyl ester
p-aminoiodobenzene
methyl 3-((4-iodophenyl)amino)-3-oxopropanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 100% |
With triethylamine In ethyl acetate at 20℃; for 16h; Cooling with acetone-dry ice; | 99% |
With triethylamine In ethyl acetate at 10 - 15℃; for 0.5h; | 29.8 g |
4-fluoro-1-(3-methyl-butylamino)-1H-pyrrole-2-carboxylic acid allyl ester
3-chloro-3-oxopropanoic acid methyl ester
1-[(2-methoxycarbonyl-acetyl)-(3-methyl-butyl)-amino]-4-fluoro-1H-pyrrole-2-carboxylic acid allyl ester
Conditions | Yield |
---|---|
In 1,4-dioxane at 100℃; for 1h; | 100% |
3-chloro-3-oxopropanoic acid methyl ester
methyl 3-amino-3-phenylpropanoate
(RS)-(+/-)-N-(2-(methoxycarbonyl)-1-phenylethyl)malonamic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 16h; | 100% |
With triethylamine In dichloromethane at 20℃; for 2h; |
3-chloro-3-oxopropanoic acid methyl ester
(2S)-1-methylmalonyl-2-(1-carboxyethyl)pyrrolidine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 0.75h; | 100% |
(2S,4S)-4-methoxyhomoproline hydrochloride
3-chloro-3-oxopropanoic acid methyl ester
(2S,4S)-4-methoxy-1-methylmalonylhomoproline
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2.25h; | 100% |
3-chloro-3-oxopropanoic acid methyl ester
4-fluoroaniline
methyl 3-((4-fluorophenyl)amino)-3-oxopropanoate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 4h; | 100% |
With triethylamine In acetone at 20℃; for 5h; | 100% |
With sodium hydrogencarbonate In acetone at 20℃; for 12h; | 94% |
In dichloromethane at 20℃; for 8h; | |
With triethylamine In dichloromethane at 20℃; for 3h; |
3-chloro-3-oxopropanoic acid methyl ester
cyclohexylamine
Malonsaeure-methylester-cyclohexylamid
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; for 1h; | 100% |
In dichloromethane at 20℃; for 8h; |
(S)-tert-butyl 1-(4-(4-aminophenyl)-5-chloro-1H-imidazol-2-yl)-2-phenylethylcarbamate
3-chloro-3-oxopropanoic acid methyl ester
(S)-methyl 3-(4-(2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)-5-chloro-1H-imidazol-4-yl)phenylamino)-3-oxopropanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 4h; | 100% |
2-(2,3,4-trimethoxyphenyl)ethylamine
3-chloro-3-oxopropanoic acid methyl ester
N-[2-(2,3,4-trimethoxyphenyl)ethyl]methoxycarbonylacetamide
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane; water at 0℃; for 1h; Schotten-Baumann reaction; | 100% |
1.Introduction of Methyl malonyl chloride
Methyl malonyl chloride, with the register CAS NO 37517-81-0, is a kind of Light yellow to yellow clear liquid.It has synonyms of (Carbomethoxy)acetylchloride;(Methoxycarbonyl)acetyl chloride;2-Methoxycarbonylacetyl chloride and 3-Chloro-3-oxopropanoic acid methyl ester. Methyl malonyl chloride should sealed storage in shady and cool warehouse and keep away from sources of ignition.
2.Properties of Methyl malonyl chloride
EINECS: 253-540-6 (2)H bond acceptors: 3 (3)H bond donors: 0(4)Freely Rotating Bonds: 3 (5)Polar Surface Area: 43.37 Å2 (6)Index of Refraction: 1.424(7)Molar Refractivity: 27.23 cm3 (8)Molar Volume: 106.5 cm3 (9)Surface Tension: 35.2 dyne/cm(10)Density: 1.281 g/cm3 (11)Flash Point: 80 °C (12)Enthalpy of Vaporization: 40.4 kJ/mol(13)Boiling Point: 167.5 °C at 760 mmHg (14)Vapour Pressure: 1.69 mmHg at 25°C (15)Storage temp: 2-8°C
3.Structure descriptors of Methyl malonyl chloride
SMILES: O=C(OC)CC(Cl)=OInChI: InChI=1/C4H5ClO3/c1-8-4(7)2-3(5)6/h2H2,1H3InChIKey: UTBCRHAMJFMIIR-UHFFFAOYAEStd. InChI: InChI=1S/C4H5ClO3/c1-8-4(7)2-3(5)6/h2H2,1H3CopyStd. InChIKey: UTBCRHAMJFMIIR-UHFFFAOYSA-N
4.Safety profile of Methyl malonyl chloride
Hazard Codes: C
Risk Statements: 34-36/37
R34: Causes burns.
R36/37:I rritating to eyes and respiratory system.
Safety Statements: 26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR UN: 3265 8/PG 2
WGK Germany: 3
F: 8-10-19
Hazard Note: Corrosive/Lachrymatory/Keep Cold
HazardClass: 8
PackingGroup: II
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