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535-15-9

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535-15-9 Usage

Uses

Ethyl dichloroacetate may be used in the synthesis of α-halo-carboxylic acid ester.

General Description

Ethyl dichloroacetate is an ester and its base catalyzed hydrolysis has been reported.

Purification Methods

Shake the ester with aqueous 3% NaHCO3 to remove free acid, wash with distilled water, dry for 3 days with CaSO4 and distil it under reduced pressure. [Beilstein 2 IV 501.]

Check Digit Verification of cas no

The CAS Registry Mumber 535-15-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 5 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 535-15:
(5*5)+(4*3)+(3*5)+(2*1)+(1*5)=59
59 % 10 = 9
So 535-15-9 is a valid CAS Registry Number.
InChI:InChI=1/C4H6Cl2O2/c1-2-8-4(7)3(5)6/h3H,2H2,1H3

535-15-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl Dichloroacetate

1.2 Other means of identification

Product number -
Other names Ethyl 2,2-dichloroacetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:535-15-9 SDS

535-15-9Synthetic route

trichloroethylene epoxide
16967-79-6

trichloroethylene epoxide

ethanol
64-17-5

ethanol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
at 0℃;96%
1,1,1-triethoxy-2,2-dichloroethane
54567-92-9

1,1,1-triethoxy-2,2-dichloroethane

A

ethanol
64-17-5

ethanol

B

ethyl acetate
141-78-6

ethyl acetate

C

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With acetic acid Heating;A n/a
B n/a
C 95%
ethanol
64-17-5

ethanol

pentachloroacetone
1768-31-6

pentachloroacetone

A

chloroform
67-66-3

chloroform

B

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With pyridine for 2h; Heating;A 9.2 g
B 82.2%
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
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
64-17-5

ethanol

pentachloro-2-(trimethylsiloxy)propene
87651-34-1

pentachloro-2-(trimethylsiloxy)propene

A

chloroform
67-66-3

chloroform

B

ethyl trimethylsilyl ether
1825-62-3

ethyl trimethylsilyl ether

C

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
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
86164-39-8

2,2-dichloro-3-oxo-propionic acid ethyl ester

A

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

B

Formanilid
103-70-8

Formanilid

Conditions
ConditionsYield
With aniline In tetrachloromethane for 12h; Ambient temperature;A 50%
B 66%
2,2-dichloro-3-oxo-propionic acid ethyl ester
86164-39-8

2,2-dichloro-3-oxo-propionic acid ethyl ester

aniline
62-53-3

aniline

A

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

B

Formanilid
103-70-8

Formanilid

Conditions
ConditionsYield
In tetrachloromethane for 12h; Ambient temperature;A 50%
B 66%
ethanol
64-17-5

ethanol

Trichloroethylene
79-01-6

Trichloroethylene

ethyl acetate
141-78-6

ethyl acetate

A

freon-121
354-14-3

freon-121

B

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
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
79-43-6

dichloro-acetic acid

ethyl N-tert-butyl-4-nitrobenzenesulfonimidate
1569262-64-1

ethyl N-tert-butyl-4-nitrobenzenesulfonimidate

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
In dichloromethane Heating;58%
dichloro-acetic acid
79-43-6

dichloro-acetic acid

ethanol
64-17-5

ethanol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
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;
1,1,2,2-tetrachloroethylene
127-18-4

1,1,2,2-tetrachloroethylene

sodium ethanolate
141-52-6

sodium ethanolate

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
at 100 - 120℃;
diethyl ether
60-29-7

diethyl ether

dichloro-acetyl iodide

dichloro-acetyl iodide

A

ethyl iodide
75-03-6

ethyl iodide

B

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
at 25℃; unter Lichtausschluss;
ethanol
64-17-5

ethanol

pentachloroacetone
1768-31-6

pentachloroacetone

aluminum ethoxide
555-75-9

aluminum ethoxide

A

chloroform
67-66-3

chloroform

B

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethanol
64-17-5

ethanol

pentachloroacetone
1768-31-6

pentachloroacetone

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With aluminum ethoxide
ethanol
64-17-5

ethanol

2-acetoxy-3,3-dichloro-acrylonitrile
861794-62-9

2-acetoxy-3,3-dichloro-acrylonitrile

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
at 150℃;
ethanol
64-17-5

ethanol

2,2-diacetoxy-1,1,1-trichloro-ethane
24298-56-4

2,2-diacetoxy-1,1,1-trichloro-ethane

potassium cyanide
151-50-8

potassium cyanide

A

ethyl acetate
141-78-6

ethyl acetate

B

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethanol
64-17-5

ethanol

2,2-diacetoxy-1,1,1-trichloro-ethane
24298-56-4

2,2-diacetoxy-1,1,1-trichloro-ethane

potassium cyanide
151-50-8

potassium cyanide

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethanol
64-17-5

ethanol

potassium dichloroacetate
19559-59-2

potassium dichloroacetate

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With sulfuric acid; potassium chloride
ethanol
64-17-5

ethanol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
beim Chlorieren;
(E)-1,2-dichloro-1-ethoxy-ethene
42345-82-4

(E)-1,2-dichloro-1-ethoxy-ethene

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With chlorine at 25℃; dann Behandeln mit Wasser;
ethanol
64-17-5

ethanol

potassium cyanide
151-50-8

potassium cyanide

chloral
75-87-6

chloral

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethanol
64-17-5

ethanol

ammonium acetate
631-61-8

ammonium acetate

2-acetoxy-3,3,3-trichloro-propionitrile
86164-43-4

2-acetoxy-3,3,3-trichloro-propionitrile

A

dichloroacetamide
683-72-7

dichloroacetamide

B

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

dichloroacethyl chloride
79-36-7

dichloroacethyl chloride

ethanol
64-17-5

ethanol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

C4H5Cl2O2(1-)*Cl(1-)*Zn(2+)

C4H5Cl2O2(1-)*Cl(1-)*Zn(2+)

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With water In tetrahydrofuran
perchloroethylene oxide
16650-10-5

perchloroethylene oxide

ethanol
64-17-5

ethanol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
at 18 - 25℃; Yield given;
1,1-dichloro-2,2-diethoxy-ethene
54567-93-0

1,1-dichloro-2,2-diethoxy-ethene

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With hydrogenchloride; water In [D3]acetonitrile
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

A

methylene chloride
74-87-3

methylene chloride

B

dichloromethane
75-09-2

dichloromethane

C

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

D

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With hydrogen cation; tetranormalbutyl ammonium fluoride for 0.166667h; Product distribution; Ambient temperature; equilibrium; products determined by GC-MS;
Ethyl trichloroacetate
515-84-4

Ethyl trichloroacetate

A

tetrachloro-succinic acid diethyl ester
3875-96-5

tetrachloro-succinic acid diethyl ester

B

diethyl (Z)-2,3-dichlorobutenedioate
15649-41-9

diethyl (Z)-2,3-dichlorobutenedioate

C

diethyl 2,3-dichlorofumarate
15649-40-8

diethyl 2,3-dichlorofumarate

D

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
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
938-81-8

N-nitrosoacetanilide

ethyl dichlorothionoacetate
112260-88-5

ethyl dichlorothionoacetate

A

ethyl (phenylhydrazono)chloroacetate
28663-68-5

ethyl (phenylhydrazono)chloroacetate

B

4-Chloro-2-phenyl-2H-[1,2,3]thiadiazol-5-one
112260-89-6

4-Chloro-2-phenyl-2H-[1,2,3]thiadiazol-5-one

C

diphenyldisulfane
882-33-7

diphenyldisulfane

D

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
In acetone at 20℃; for 20h; Yield given. Yields of byproduct given;
ethyl dichlorothionoacetate
112260-88-5

ethyl dichlorothionoacetate

A

ethyl (phenylhydrazono)chloroacetate
28663-68-5

ethyl (phenylhydrazono)chloroacetate

B

4-Chloro-2-phenyl-2H-[1,2,3]thiadiazol-5-one
112260-89-6

4-Chloro-2-phenyl-2H-[1,2,3]thiadiazol-5-one

C

diphenyldisulfane
882-33-7

diphenyldisulfane

D

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With N-nitrosoacetanilide In acetone at 20℃; for 20h; Yield given. Yields of byproduct given;
ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

dichloro-acetic acid
79-43-6

dichloro-acetic acid

Conditions
ConditionsYield
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.
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

C12H18N4O2(2+)*2Cl(1-)

C12H18N4O2(2+)*2Cl(1-)

Conditions
ConditionsYield
In tetrahydrofuran100%
hexanal
66-25-1

hexanal

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

2-Chloro-3-pentyl-oxirane-2-carboxylic acid ethyl ester
111055-67-5

2-Chloro-3-pentyl-oxirane-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
75-08-1

ethanethiol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Bis(ethylthio)essigsaeure-ethylester
20461-95-4

Bis(ethylthio)essigsaeure-ethylester

Conditions
ConditionsYield
With potassium carbonate; Aliquat 336 In toluene for 8h; Ambient temperature;98%
isovaleraldehyde
590-86-3

isovaleraldehyde

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

2-Chloro-3-isobutyl-oxirane-2-carboxylic acid ethyl ester
111055-66-4

2-Chloro-3-isobutyl-oxirane-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium ethanolate In diethyl ether 0-5 deg C, 1 h; reflux, 3 h;98%
With base In diethyl ether Darzens condensation;
1,3-difluoro-5-nitrobenzene
2265-94-3

1,3-difluoro-5-nitrobenzene

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethyl 2-chloro-2-(2,6-difluoro-4-nitrophenyl)ethanoate

ethyl 2-chloro-2-(2,6-difluoro-4-nitrophenyl)ethanoate

Conditions
ConditionsYield
With hydrogenchloride In N,N-dimethyl-formamide97%
(2R,3R)-2-benzylamino-3-(4-methylsulfonylphenyl)-propane-1,3-diol
895570-99-7

(2R,3R)-2-benzylamino-3-(4-methylsulfonylphenyl)-propane-1,3-diol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

thiamphenicol
15318-45-3

thiamphenicol

Conditions
ConditionsYield
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
895571-10-5

(1R,2S)-1-(4-methylsulfonylphenyl)-2-benzylamino-3-fluoro-1-propanol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Florfenicol
73231-34-2

Florfenicol

Conditions
ConditionsYield
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%
1H-imidazole
288-32-4

1H-imidazole

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

C10H12N4O2

C10H12N4O2

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In acetonitrile Reagent/catalyst; Solvent; Reflux;93.98%
(1R,2S)-2-amino-1-(4-chlorophenyl)-3-fluoropropan-1-ol

(1R,2S)-2-amino-1-(4-chlorophenyl)-3-fluoropropan-1-ol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

C11H11Cl3FNO2

C11H11Cl3FNO2

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 12h;93%
(2-Benzylamino-ethyl)-phosphinic acid ethyl ester
126227-04-1

(2-Benzylamino-ethyl)-phosphinic acid ethyl ester

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

{2-[Benzyl-(2,2-dichloro-acetyl)-amino]-ethyl}-phosphinic acid ethyl ester

{2-[Benzyl-(2,2-dichloro-acetyl)-amino]-ethyl}-phosphinic acid ethyl ester

Conditions
ConditionsYield
for 12h; Heating;92%
2-Methylbutyraldehyde
96-17-3, 57456-98-1

2-Methylbutyraldehyde

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

(E)-ethyl 4-methylhex-2-enoate
78023-52-6

(E)-ethyl 4-methylhex-2-enoate

Conditions
ConditionsYield
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
123-11-5

4-methoxy-benzaldehyde

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
24393-56-4

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
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
535-15-9

ethyl 1,1-dichloroacetate

2,3-isopropylidene-glyceraldehyde
15186-48-8

2,3-isopropylidene-glyceraldehyde

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate
64520-58-7

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Conditions
ConditionsYield
With chromium dichloride In tetrahydrofuran at 75℃; for 3h; Inert atmosphere; optical yield given as %de; stereoselective reaction;91%
acetophenone
98-86-2

acetophenone

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

2-chloro-3-hydroxy-3-phenyl-butyric acid ethyl ester
91767-65-6

2-chloro-3-hydroxy-3-phenyl-butyric acid ethyl ester

Conditions
ConditionsYield
bronze-coloured C8K; silver(I) acetate; zinc(II) chloride In tetrahydrofuran at -20℃; for 0.666667h;90%
With amalgamated magnesium; diethyl ether
isobutyraldehyde
78-84-2

isobutyraldehyde

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethyl 2-chloro-3-isopropyloxirane-2-carboxylate
21806-21-3, 78058-54-5

ethyl 2-chloro-3-isopropyloxirane-2-carboxylate

Conditions
ConditionsYield
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
104-55-2

3-phenyl-propenal

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Conditions
ConditionsYield
With manganese In tetrahydrofuran for 3h; Heating;90%
ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

2,3,4,5-di-O-isopropylidenealdehydo-L-xylose
120522-10-3

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
1310802-46-0

ethyl (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-L-xylo-hept-2-enonate

Conditions
ConditionsYield
With chromium dichloride In tetrahydrofuran at 75℃; for 3h; Inert atmosphere; optical yield given as %de; stereoselective reaction;90%
thiophenol
108-98-5

thiophenol

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethyl α,α-bis(phenylthio)acetate
20461-96-5

ethyl α,α-bis(phenylthio)acetate

Conditions
ConditionsYield
With potassium carbonate; Aliquat 336 In toluene for 8h; Ambient temperature;89%
isovaleraldehyde
590-86-3

isovaleraldehyde

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethyl (E)-5-methylhex-2-enoate
34993-63-0

ethyl (E)-5-methylhex-2-enoate

Conditions
ConditionsYield
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
120-92-3

cyclopentanone

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

chloro-(1-hydroxy-cyclohexyl)-acetic acid ethyl ester
114091-86-0

chloro-(1-hydroxy-cyclohexyl)-acetic acid ethyl ester

Conditions
ConditionsYield
bronze-coloured C8K; silver(I) acetate; zinc(II) chloride In tetrahydrofuran at 0℃; for 1h;88%
10-Undecenal
112-45-8

10-Undecenal

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethyl (E)-trideca-2,12-dienoate
148118-58-5

ethyl (E)-trideca-2,12-dienoate

Conditions
ConditionsYield
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
104-88-1

4-chlorobenzaldehyde

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethyl (E)-3-(4-chlorophenyl)prop-2-enoate
24393-52-0

ethyl (E)-3-(4-chlorophenyl)prop-2-enoate

Conditions
ConditionsYield
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
23558-05-6

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate
108788-49-4

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

Conditions
ConditionsYield
With chromium dichloride In tetrahydrofuran at 75℃; for 3h; Inert atmosphere; optical yield given as %de; stereoselective reaction;87%
pentanal
110-62-3

pentanal

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

Ethyl 2-chloro-2,3-epoxyheptanoate
111055-65-3

Ethyl 2-chloro-2,3-epoxyheptanoate

Conditions
ConditionsYield
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
535-15-9

ethyl 1,1-dichloroacetate

ethyl 2-chloro-2-deuterioacetate
125951-38-4

ethyl 2-chloro-2-deuterioacetate

Conditions
ConditionsYield
With tributyltin deuteride for 24h; Ambient temperature;86%
2-acetyl-2-cyclohexen-1-one
52784-38-0

2-acetyl-2-cyclohexen-1-one

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

3-Methyl-4-oxo-4,5,6,7-tetrahydro-isobenzofuran-1-carboxylic acid ethyl ester

3-Methyl-4-oxo-4,5,6,7-tetrahydro-isobenzofuran-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 3h;86%
phenylacetylene
536-74-3

phenylacetylene

ethyl 1,1-dichloroacetate
535-15-9

ethyl 1,1-dichloroacetate

1,1-dichloro-4-phenylbut-3-yn-2-one
52293-00-2

1,1-dichloro-4-phenylbut-3-yn-2-one

Conditions
ConditionsYield
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%

535-15-9Relevant articles and documents

-

Gupta

, p. 4081,4082 (1973)

-

Mixed-ligand complexes of paddlewheel dinuclear molybdenum as hydrodehalogenation catalysts for polyhaloalkanes

Tsurugi, Hayato,Hayakawa, Akio,Kando, Shun,Sugino, Yoshitaka,Mashima, Kazushi

, p. 3434 - 3439 (2015/05/27)

We developed a hydrodehalogenation reaction of polyhaloalkanes catalyzed by paddlewheel dimolybdenum complexes in combination with 1-methyl-3,6-bis(trimethylsilyl)-1,4-cyclohexadiene (MBTCD) as a non-toxic H-atom source as well as a salt-free reductant. A mixed-ligated dimolybdenum complex Mo2(OAc)2[CH(NAr)2]2 (3a, Ar = 4-MeOC6H4) having two acetates and two amidinates exhibited high catalytic activity in the presence of nBu4NCl, in which [nBu4N]2[Mo2{CH(NAr)2}2Cl4] (9a), derived by treating 3a with ClSiMe3 and nBu4NCl, was generated as a catalytically-active species in the hydrodehalogenation. All reaction processes, oxidation and reduction of the dimolybdenum complex, were clarified by control experiments, and the oxidized product, [nBu4N][Mo2{CH(NAr)2}2Cl4] (10a), was characterized by EPR and X-ray diffraction studies. Kinetic analysis of the hydrodehalogenation reaction as well as a deuterium-labelling experiment using MBTCD-d8 suggested that the H-abstraction was the rate-determining step for the catalytic reaction. This journal is

SNAAP sulfonimidate alkylating agent for acids, alcohols, and phenols 1

Maricich, Tom J.,Allan, Matthew J.,Kislin, Brett S.,Chen, Andrea I-T.,Meng, Fan-Chun,Bradford, Christine,Kuan, Nai-Chia,Wood, Jeremy,Aisagbonhi, Omonigho,Poste, Alethea,Wride, Dustin,Kim, Sylvia,Santos, Therese,Fimbres, Michael,Choi, Dianne,Elia, Haydi,Kaladjian, Joseph,Abou-Zahr, Ali,Mejia, Arturo

, p. 3361 - 3368 (2014/01/06)

Stable, crystalline ethyl N-tert-butyl-4-nitrobenzenesulfonimidate has been prepared in high yield by direct O-ethylation of N-tert-butyl-4- nitrobenzenesulfonamide with iodoethane and silver(I) oxide in dichloromethane. This sulfonimidate directly ethylates various acids to esters; the stronger the acid, the faster it alkylates and in higher yield. It readily ethylates alcohols and phenols to ethers at room temperature in the presence of tetrafluoroboric acid catalyst without molecular rearrangements or racemization. We have defined these reactions as SNAAP alkylations: [substitution, nucleophilic of acids, alcohols and phenols]. The hard sulfonimidate alkylating agent is chemoselective, preferring oxygen > nitrogen > sulfur. The sulfonamide byproduct of alkylation is readily recycled to the sulfonimidate. Georg Thieme Verlag Stuttgart . New York.

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