Conditions | Yield |
---|---|
at 0℃; | 96% |
1,1,1-triethoxy-2,2-dichloroethane
A
ethanol
B
ethyl acetate
C
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With acetic acid Heating; | A n/a B n/a C 95% |
ethanol
pentachloroacetone
A
chloroform
B
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With pyridine for 2h; Heating; | A 9.2 g B 82.2% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In N,N-dimethyl acetamide at 25℃; under 760.051 Torr; for 1h; chemoselective reaction; | 79% |
With 10% Pt/activated carbon; hydrogen In N,N-dimethyl acetamide at 25℃; under 760.051 Torr; for 1h; chemoselective reaction; | 79% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 28℃; for 72h; Irradiation; Inert atmosphere; | 70% |
ethanol
pentachloro-2-(trimethylsiloxy)propene
A
chloroform
B
ethyl trimethylsilyl ether
C
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With triethylamine for 8h; Heating; Yields of byproduct given; | A n/a B n/a C 71% |
With triethylamine for 8h; Heating; Yield given; | A n/a B n/a C 71% |
2,2-dichloro-3-oxo-propionic acid ethyl ester
A
ethyl 1,1-dichloroacetate
B
Formanilid
Conditions | Yield |
---|---|
With aniline In tetrachloromethane for 12h; Ambient temperature; | A 50% B 66% |
2,2-dichloro-3-oxo-propionic acid ethyl ester
aniline
A
ethyl 1,1-dichloroacetate
B
Formanilid
Conditions | Yield |
---|---|
In tetrachloromethane for 12h; Ambient temperature; | A 50% B 66% |
ethanol
Trichloroethylene
ethyl acetate
A
freon-121
B
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With chlorine monofluoride 1.) Freon 113; 2.) 20 - 25 deg C, 30 min.; Yield given. Multistep reaction; | A 65% B n/a |
dichloro-acetic acid
ethyl N-tert-butyl-4-nitrobenzenesulfonimidate
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
In dichloromethane Heating; | 58% |
Conditions | Yield |
---|---|
With phosphorus pentoxide; copper(II) sulfate; sodium sulfate for 2h; Heating; | 40% |
With hydrogenchloride | |
With sulfuric acid unter wiederholtem Abdestillieren des entstandenen Wassers mit Benzol; |
Conditions | Yield |
---|---|
at 100 - 120℃; |
Conditions | Yield |
---|---|
at 25℃; unter Lichtausschluss; |
ethanol
pentachloroacetone
aluminum ethoxide
A
chloroform
B
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With aluminum ethoxide |
Conditions | Yield |
---|---|
at 150℃; |
ethanol
2,2-diacetoxy-1,1,1-trichloro-ethane
potassium cyanide
A
ethyl acetate
B
ethyl 1,1-dichloroacetate
ethanol
2,2-diacetoxy-1,1,1-trichloro-ethane
potassium cyanide
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With sulfuric acid; potassium chloride |
Conditions | Yield |
---|---|
beim Chlorieren; |
(E)-1,2-dichloro-1-ethoxy-ethene
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With chlorine at 25℃; dann Behandeln mit Wasser; |
ethanol
ammonium acetate
2-acetoxy-3,3,3-trichloro-propionitrile
A
dichloroacetamide
B
ethyl 1,1-dichloroacetate
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With water In tetrahydrofuran |
Conditions | Yield |
---|---|
at 18 - 25℃; Yield given; |
1,1-dichloro-2,2-diethoxy-ethene
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With hydrogenchloride; water In [D3]acetonitrile |
Ethyl trichloroacetate
A
methylene chloride
B
dichloromethane
C
chloroacetic acid ethyl ester
D
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With hydrogen cation; tetranormalbutyl ammonium fluoride for 0.166667h; Product distribution; Ambient temperature; equilibrium; products determined by GC-MS; |
Ethyl trichloroacetate
A
tetrachloro-succinic acid diethyl ester
B
diethyl (Z)-2,3-dichlorobutenedioate
C
diethyl 2,3-dichlorofumarate
D
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With iron(II) chloride In acetonitrile at 25 - 82℃; Rate constant; Thermodynamic data; Product distribution; ΔH(excit.), ΔS(excit.), var. reagent conc., var. reaction time; |
N-nitrosoacetanilide
ethyl dichlorothionoacetate
A
ethyl (phenylhydrazono)chloroacetate
B
4-Chloro-2-phenyl-2H-[1,2,3]thiadiazol-5-one
C
diphenyldisulfane
D
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
In acetone at 20℃; for 20h; Yield given. Yields of byproduct given; |
ethyl dichlorothionoacetate
A
ethyl (phenylhydrazono)chloroacetate
B
4-Chloro-2-phenyl-2H-[1,2,3]thiadiazol-5-one
C
diphenyldisulfane
D
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With N-nitrosoacetanilide In acetone at 20℃; for 20h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With bis(tri-n-butyltin)oxide In benzene at 80℃; for 10h; other esters, other solvents, other temperatures and reaction times; | 100% |
With bis(tri-n-butyltin)oxide In benzene at 80℃; for 10h; | 100% |
With 2,2'-azobis(isobutyronitrile); bis(tri-n-butyltin)oxide In benzene at 80℃; for 1.5h; | 100 % Spectr. |
Conditions | Yield |
---|---|
In tetrahydrofuran | 100% |
hexanal
ethyl 1,1-dichloroacetate
2-Chloro-3-pentyl-oxirane-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium ethanolate In diethyl ether 0-5 deg C, 1 h; reflux, 3 h; | 98% |
With sodium ethanolate 1.) ether, 30 min, 2.) ether, reflux, 3 h; Multistep reaction; | |
With base In diethyl ether Darzens condensation; |
ethanethiol
ethyl 1,1-dichloroacetate
Bis(ethylthio)essigsaeure-ethylester
Conditions | Yield |
---|---|
With potassium carbonate; Aliquat 336 In toluene for 8h; Ambient temperature; | 98% |
isovaleraldehyde
ethyl 1,1-dichloroacetate
2-Chloro-3-isobutyl-oxirane-2-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With sodium ethanolate In diethyl ether 0-5 deg C, 1 h; reflux, 3 h; | 98% |
With base In diethyl ether Darzens condensation; |
Conditions | Yield |
---|---|
With hydrogenchloride In N,N-dimethyl-formamide | 97% |
(2R,3R)-2-benzylamino-3-(4-methylsulfonylphenyl)-propane-1,3-diol
ethyl 1,1-dichloroacetate
thiamphenicol
Conditions | Yield |
---|---|
Stage #1: (2R,3R)-2-benzylamino-3-(4-methylsulfonylphenyl)-propane-1,3-diol With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 20℃; for 2h; Stage #2: ethyl 1,1-dichloroacetate With triethylamine In methanol at 30℃; for 6h; Further stages.; | 96% |
(1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol
ethyl 1,1-dichloroacetate
Florfenicol
Conditions | Yield |
---|---|
Stage #1: (1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol With sulfuric acid; hydrogen; palladium on activated charcoal In ethanol at 20℃; for 2h; Stage #2: ethyl 1,1-dichloroacetate With triethylamine In methanol at 30℃; for 6h; Further stages.; | 96% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium carbonate In acetonitrile Reagent/catalyst; Solvent; Reflux; | 93.98% |
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 12h; | 93% |
(2-Benzylamino-ethyl)-phosphinic acid ethyl ester
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
for 12h; Heating; | 92% |
2-Methylbutyraldehyde
ethyl 1,1-dichloroacetate
(E)-ethyl 4-methylhex-2-enoate
Conditions | Yield |
---|---|
With manganese In tetrahydrofuran for 3h; Heating; | 92% |
With manganese In tetrahydrofuran for 3h; Reflux; Inert atmosphere; optical yield given as %de; stereoselective reaction; | 92% |
4-methoxy-benzaldehyde
ethyl 1,1-dichloroacetate
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With manganese In tetrahydrofuran for 3h; Heating; | 92% |
With manganese In tetrahydrofuran for 3h; Reflux; Inert atmosphere; optical yield given as %de; stereoselective reaction; | 92% |
ethyl 1,1-dichloroacetate
2,3-isopropylidene-glyceraldehyde
ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate
Conditions | Yield |
---|---|
With chromium dichloride In tetrahydrofuran at 75℃; for 3h; Inert atmosphere; optical yield given as %de; stereoselective reaction; | 91% |
acetophenone
ethyl 1,1-dichloroacetate
2-chloro-3-hydroxy-3-phenyl-butyric acid ethyl ester
Conditions | Yield |
---|---|
bronze-coloured C8K; silver(I) acetate; zinc(II) chloride In tetrahydrofuran at -20℃; for 0.666667h; | 90% |
With amalgamated magnesium; diethyl ether |
isobutyraldehyde
ethyl 1,1-dichloroacetate
ethyl 2-chloro-3-isopropyloxirane-2-carboxylate
Conditions | Yield |
---|---|
With sodium ethanolate In diethyl ether 0-5 deg C, 1 h; reflux, 3 h; | 90% |
With base In diethyl ether Darzens condensation; | |
With sodium ethanolate In diethyl ether; ethanol at 0℃; for 1h; |
3-phenyl-propenal
ethyl 1,1-dichloroacetate
(2E)-ethyl 5-phenylpenta-2,4-dienoate
Conditions | Yield |
---|---|
With manganese In tetrahydrofuran for 3h; Heating; | 90% |
ethyl 1,1-dichloroacetate
2,3,4,5-di-O-isopropylidenealdehydo-L-xylose
ethyl (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-L-xylo-hept-2-enonate
Conditions | Yield |
---|---|
With chromium dichloride In tetrahydrofuran at 75℃; for 3h; Inert atmosphere; optical yield given as %de; stereoselective reaction; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate; Aliquat 336 In toluene for 8h; Ambient temperature; | 89% |
isovaleraldehyde
ethyl 1,1-dichloroacetate
ethyl (E)-5-methylhex-2-enoate
Conditions | Yield |
---|---|
With manganese In tetrahydrofuran for 3h; Heating; | 89% |
With manganese In tetrahydrofuran for 3h; Reflux; Inert atmosphere; optical yield given as %de; stereoselective reaction; | 89% |
cyclopentanone
ethyl 1,1-dichloroacetate
chloro-(1-hydroxy-cyclohexyl)-acetic acid ethyl ester
Conditions | Yield |
---|---|
bronze-coloured C8K; silver(I) acetate; zinc(II) chloride In tetrahydrofuran at 0℃; for 1h; | 88% |
10-Undecenal
ethyl 1,1-dichloroacetate
ethyl (E)-trideca-2,12-dienoate
Conditions | Yield |
---|---|
With manganese In tetrahydrofuran for 3h; Heating; | 88% |
With manganese In tetrahydrofuran for 3h; Reflux; Inert atmosphere; optical yield given as %de; stereoselective reaction; | 88% |
4-chlorobenzaldehyde
ethyl 1,1-dichloroacetate
ethyl (E)-3-(4-chlorophenyl)prop-2-enoate
Conditions | Yield |
---|---|
With manganese In tetrahydrofuran for 3h; Heating; | 88% |
With manganese In tetrahydrofuran for 3h; Reflux; Inert atmosphere; optical yield given as %de; stereoselective reaction; | 88% |
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose
ethyl 1,1-dichloroacetate
ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate
Conditions | Yield |
---|---|
With chromium dichloride In tetrahydrofuran at 75℃; for 3h; Inert atmosphere; optical yield given as %de; stereoselective reaction; | 87% |
Conditions | Yield |
---|---|
With sodium ethanolate In diethyl ether 0-5 deg C, 1 h; reflux, 3 h; | 86% |
With sodium ethanolate 1.) ether, 30 min, 2.) ether, reflux, 3 h; Multistep reaction; | |
With base In diethyl ether Darzens condensation; |
ethyl 1,1-dichloroacetate
ethyl 2-chloro-2-deuterioacetate
Conditions | Yield |
---|---|
With tributyltin deuteride for 24h; Ambient temperature; | 86% |
2-acetyl-2-cyclohexen-1-one
ethyl 1,1-dichloroacetate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3h; | 86% |
phenylacetylene
ethyl 1,1-dichloroacetate
1,1-dichloro-4-phenylbut-3-yn-2-one
Conditions | Yield |
---|---|
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: ethyl 1,1-dichloroacetate With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at 20℃; for 2h; Further stages.; | 85% |
The Acetic acid,2,2-dichloro-, ethyl ester with CAS registry number of 535-15-9 is also known as Acetic acid, dichloro-, ethyl ester. The IUPAC name is Ethyl 2,2-dichloroacetate. It belongs to product categories of C2 to C5; Carbonyl Compounds; Esters. Its EINECS registry number is 208-611-6. In addition, the formula is C4H6Cl2O2 and the molecular weight is 157. What's more, This chemical can be used as solvent and medicine synthesis intermediates.
Physical properties about Acetic acid,2,2-dichloro-, ethyl ester are: (1)ACD/LogP: 1.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.52; (4)ACD/LogD (pH 7.4): 1.52; (5)ACD/BCF (pH 5.5): 8.45; (6)ACD/BCF (pH 7.4): 8.45; (7)ACD/KOC (pH 5.5): 160.34; (8)ACD/KOC (pH 7.4): 160.34; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 26.3Å2; (13)Index of Refraction: 1.441; (14)Molar Refractivity: 32.01 cm3; (15)Molar Volume: 121.1 cm3; (16)Polarizability: 12.69×10-24cm3; (17)Surface Tension: 32.9 dyne/cm; (18)Density: 1.295 g/cm3; (19)Flash Point: 55.6 °C; (20)Enthalpy of Vaporization: 38.8 kJ/mol; (21)Boiling Point: 151.1 °C at 760 mmHg; (22)Vapour Pressure: 3.72 mmHg at 25 °C.
Preparation of Acetic acid,2,2-dichloro-, ethyl ester: it is prepared by reaction of dichloroacetic acid with ethanol. The reaction needs reagents P2O5, CuSO4, Na2SO4 and other condition of heating for 2 hours. The yield is about 40%.
Uses of Acetic acid,2,2-dichloro-, ethyl ester: it is used to produce a-Chlor-cyclohexyl-essigsaeureaethylester by reaction with Cyclohexene. The reaction occurs with reagents Na2S2O4, NaHCO3 and solvent dimethylsulfoxide at 75 °C for 7 hours. The yield is about 65%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes and respiratory system. This chemical is Harmful by inhalation and in contact with skin. During using it, wear suitable protective clothing and do not breathe gas/fumes/vapour/spray. In case of contact with eyes, rinse immediately with plenty of water and seek medicl advice.
You can still convert the following datas into molecular structure:
1. SMILES: ClC(Cl)C(=O)OCC
2. InChI: InChI=1/C4H6Cl2O2/c1-2-8-4(7)3(5)6/h3H,2H2,1H3
3. InChIKey: IWYBVQLPTCMVFO-UHFFFAOYAQ
4. Std. InChI: InChI=1S/C4H6Cl2O2/c1-2-8-4(7)3(5)6/h3H,2H2,1H3
5. Std. InChIKey: IWYBVQLPTCMVFO-UHFFFAOYSA-N
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