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3153-36-4

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3153-36-4 Usage

Chemical Properties

clear yellow to brownish liquid

Uses

Different sources of media describe the Uses of 3153-36-4 differently. You can refer to the following data:
1. Ethyl 4-chlorobutyrate is a reagent used in the preparation of cyclopropane derivatives.
2. Ethyl 4-chlorobutyrate is used in organic synthesis. And also used for producting 4-Iodo-butyric acid ethyl ester.

Synthesis Reference(s)

Synthesis, p. 538, 1973 DOI: 10.1055/s-1973-22254

Check Digit Verification of cas no

The CAS Registry Mumber 3153-36-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,5 and 3 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3153-36:
(6*3)+(5*1)+(4*5)+(3*3)+(2*3)+(1*6)=64
64 % 10 = 4
So 3153-36-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H11ClO2/c1-2-9-6(8)4-3-5-7/h2-5H2,1H3

3153-36-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A11070)  Ethyl 4-chlorobutyrate, 98%   

  • 3153-36-4

  • 100g

  • 513.0CNY

  • Detail
  • Alfa Aesar

  • (A11070)  Ethyl 4-chlorobutyrate, 98%   

  • 3153-36-4

  • 500g

  • 2369.0CNY

  • Detail

3153-36-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 4-chlorobutanoate

1.2 Other means of identification

Product number -
Other names ethyl 4-chlorobutyrate

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:3153-36-4 SDS

3153-36-4Synthetic route

4-butanolide
96-48-0

4-butanolide

ethanol
64-17-5

ethanol

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride for 16h; Heating;80%
With hydrogenchloride
With hydrogenchloride
cyclobutanone
1191-95-3

cyclobutanone

oxovanadium(V) ethoxydichloride
1801-77-0

oxovanadium(V) ethoxydichloride

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With lithium chloride In diethyl ether for 13h; Ambient temperature;43%
ethyl 4-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

ethyl 4-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butanoate

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; 4-tert-Butylcatechol; 2-methoxybenzo[d][1,3,2]dioxaborole; trans-di-O-tert-butyl hyponitrite In methanol; dichloromethane; benzene at 70℃; for 16h; Inert atmosphere;30%
1,4-dioxane
123-91-1

1,4-dioxane

4-ethoxy-butyryl chloride
14077-66-8

4-ethoxy-butyryl chloride

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
at 70℃; Geschwindigkeit der Umlagerung verschiedener Konz.;
at 100℃; Geschwindigkeit der Umlagerung verschiedener Konz.;
4-butanolide
96-48-0

4-butanolide

ethanol
64-17-5

ethanol

A

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

B

4-(4-chloro-butyryloxy)-butyric acid ethyl ester

4-(4-chloro-butyryloxy)-butyric acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

ethanol
64-17-5

ethanol

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride
With sulfuric acid
With hydrogenchloride
With hydrogenchloride In dichloromethane at 8℃;
ethanol
64-17-5

ethanol

4-(4-nitrophenoxy)butanoic acid
28341-54-0

4-(4-nitrophenoxy)butanoic acid

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride zuletzt bei Siedetemperatur;
4-ethoxy-butyryl chloride
14077-66-8

4-ethoxy-butyryl chloride

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
at 100℃;
at 100℃;
at 50℃; Geschwindigkeit der Umlagerung;
at 100℃; Geschwindigkeit der Umlagerung;
4-ethoxybutanoic acid
10374-37-5

4-ethoxybutanoic acid

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With thionyl chloride
Multi-step reaction with 2 steps
1: hydrogen; SOCl2
2: 100 °C / Geschwindigkeit der Umlagerung
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; SOCl2
2: 100 °C
View Scheme
butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With tetrachloromethane; sulfuryl dichloride; dibenzoyl peroxide
γ-chlorobutyric acid
627-00-9

γ-chlorobutyric acid

ethanol
64-17-5

ethanol

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid
With thionyl chloride at 0℃; for 2h; Reflux;
With acetyl chloride at 20℃; for 24h; Inert atmosphere;
cyclobutanone
1191-95-3

cyclobutanone

oxovanadium(V) ethoxydichloride
1801-77-0

oxovanadium(V) ethoxydichloride

acrylonitrile
107-13-1

acrylonitrile

A

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

B

ethyl 6-chloro-6-cyanohexanoate
132960-08-8

ethyl 6-chloro-6-cyanohexanoate

Conditions
ConditionsYield
With copper dichloride 1.) dichloromethane, -75 deg C, 2.) a) -75 deg C, 2 h, b) room temperature, 14-19 h; Yield given. Multistep reaction. Yields of byproduct given;
cyclobutanone
1191-95-3

cyclobutanone

oxovanadium(V) ethoxydichloride
1801-77-0

oxovanadium(V) ethoxydichloride

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

A

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

B

ethyl 6-chloro-6-(methoxycarbonyl)heptanoate
132960-09-9

ethyl 6-chloro-6-(methoxycarbonyl)heptanoate

Conditions
ConditionsYield
With copper dichloride 1.) dichloromethane, -75 deg C, 2.) a) -75 deg C, 2 h, b) room temperature, 14-19 h; Yield given. Multistep reaction. Yields of byproduct given;
cyclobutanone
1191-95-3

cyclobutanone

oxovanadium(V) ethoxydichloride
1801-77-0

oxovanadium(V) ethoxydichloride

methacrylonitrile
126-98-7

methacrylonitrile

A

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

B

ethyl 6-chloro-6-cyanoheptanoate
132960-07-7

ethyl 6-chloro-6-cyanoheptanoate

Conditions
ConditionsYield
With copper dichloride Product distribution; multistep reaction; other olefins, or LiCl, other halogen source, other cyclic carbonyl compound; oxidative ring-opening reaction;
With copper dichloride 1.) dichloromethane, -75 deg C, 2 h, 2.) a) -75 deg C, 2 h, b) room temperature, 17 h; Yield given. Multistep reaction. Yields of byproduct given;
ethanol
64-17-5

ethanol

4-Chlorobutanoyl chloride
4635-59-0

4-Chlorobutanoyl chloride

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

tetrachloromethane
56-23-5

tetrachloromethane

sulfuryl dichloride
7791-25-5

sulfuryl dichloride

butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

A

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

B

ethyl 2-chlorobutyrate
7425-45-8

ethyl 2-chlorobutyrate

C

3-chloro-butyric acid ethyl ester
7425-48-1

3-chloro-butyric acid ethyl ester

thionyl chloride
7719-09-7

thionyl chloride

4-ethoxybutanoic acid
10374-37-5

4-ethoxybutanoic acid

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

5,11,17,23-tetra-tert-butyl-25,27-di(3-ethoxycarbonylpropoxy)-26,28-dihydroxycalix[4]arene
205995-80-8

5,11,17,23-tetra-tert-butyl-25,27-di(3-ethoxycarbonylpropoxy)-26,28-dihydroxycalix[4]arene

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
With titanium(IV) chloride tetrahydrofuran In toluene for 24h; Inert atmosphere; Reflux;
ethyl 3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-propionate
302577-73-7

ethyl 3-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolan-2-yl)-propionate

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: n-butyllithium / tetrahydrofuran; diethyl ether / 16 h / -100 - 20 °C / Inert atmosphere
2: trimethylsilyl trifluoromethanesulfonate; 4-tert-Butylcatechol; trans-di-O-tert-butyl hyponitrite; 2-methoxybenzo[d][1,3,2]dioxaborole / dichloromethane; benzene; methanol / 16 h / 70 °C / Inert atmosphere
View Scheme
ethyl acrylate
140-88-5

ethyl acrylate

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: copper(II) carbonate; copper(II) hydroxide; triphenylphosphine / water / 0.5 h / 20 °C / Inert atmosphere
1.2: 16 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; diethyl ether / 16 h / -100 - 20 °C / Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate; 4-tert-Butylcatechol; trans-di-O-tert-butyl hyponitrite; 2-methoxybenzo[d][1,3,2]dioxaborole / dichloromethane; benzene; methanol / 16 h / 70 °C / Inert atmosphere
View Scheme
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

ethyl 2-(benzylamino)acetate
6436-90-4

ethyl 2-(benzylamino)acetate

4-[benzyl(ethoxycarbonylmethyl)amino]butyric acid ethyl ester
63876-32-4

4-[benzyl(ethoxycarbonylmethyl)amino]butyric acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In toluene for 8h; Solvent; Reflux; Large scale;99.1%
With potassium carbonate In chloroform at 66 - 68℃; for 24h;
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-Methyl-N-methoxy-4-chlorobutanamide
64214-66-0

N-Methyl-N-methoxy-4-chlorobutanamide

Conditions
ConditionsYield
With trimethylaluminum In hexane; dichloromethane for 24h; Ambient temperature;99%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With dimethyl aluminium chloride In hexane; dichloromethane at 0 - 20℃; for 1h;
Stage #2: 4-chloro-butyric acid ethyl ester In dichloromethane for 1h;
82%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1-(3,4-dichloro)phenylpiperazine
57260-67-0

1-(3,4-dichloro)phenylpiperazine

ethyl 4-[4-(3,4-dichlorophenyl)piperazin-1-yl]butanoate
1061701-06-1

ethyl 4-[4-(3,4-dichlorophenyl)piperazin-1-yl]butanoate

Conditions
ConditionsYield
With cesium hydroxide; sodium iodide at 50℃; for 0.266667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;98%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1-(2,5-dimethylphenyl)piperazine
1013-25-8

1-(2,5-dimethylphenyl)piperazine

ethyl 4-[4-(2,5-dimethylphenyl)piperazin-1-yl]butanoate
1061701-76-5

ethyl 4-[4-(2,5-dimethylphenyl)piperazin-1-yl]butanoate

Conditions
ConditionsYield
With cesium hydroxide; sodium iodide at 50℃; for 0.266667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;97%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1-[3-(trifluoromethyl)phenyl]piperazine hydrochloride

1-[3-(trifluoromethyl)phenyl]piperazine hydrochloride

ethyl 4-[4-(3-(trifluoromethyl)phenyl)piperazin-1-yl]butanoate
108786-32-9

ethyl 4-[4-(3-(trifluoromethyl)phenyl)piperazin-1-yl]butanoate

Conditions
ConditionsYield
With cesium hydroxide; sodium iodide at 50℃; for 0.266667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;97%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

5-nitroguaiacol
636-93-1

5-nitroguaiacol

ethyl 4-(2-methoxy-5-nitrophenoxy) butyrate
1093798-74-3

ethyl 4-(2-methoxy-5-nitrophenoxy) butyrate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;96%
With potassium carbonate In N,N-dimethyl-formamide at 60℃;
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1,2,3-trimethoxybenzene
621-23-8

1,2,3-trimethoxybenzene

1-(4-chlorobutyl)-2,4,6-trimethoxybenzene

1-(4-chlorobutyl)-2,4,6-trimethoxybenzene

Conditions
ConditionsYield
With dimethylethylsilane; (μ3,η2,η3,η5-acenaphthylene)Ru3(CO)7 at 20℃; for 5h; Inert atmosphere; Neat (no solvent);96%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

octyl alpha-D-glucopyranoside
29781-80-4

octyl alpha-D-glucopyranoside

Octyl 6-O-4-chlorobutanoyl-α-D-glucopyranoside

Octyl 6-O-4-chlorobutanoyl-α-D-glucopyranoside

Conditions
ConditionsYield
With zeolite CaA at 40℃; for 48h; SP 435 lipase;95%
at 40℃; for 6h; Product distribution; lipase from Candida antarctica; other lipases, times; also in the presence of zeolite CaA;
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

ethyl 4-azidobutyrate
51453-79-3

ethyl 4-azidobutyrate

Conditions
ConditionsYield
With sodium azide; 15-crown-5 In acetonitrile for 12h; Heating;95%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1-(4-Fluorophenyl)piperazine
2252-63-3

1-(4-Fluorophenyl)piperazine

ethyl 4-<4-(4-fluorophenyl)-1-piperazinyl>butyrate
130933-88-9

ethyl 4-<4-(4-fluorophenyl)-1-piperazinyl>butyrate

Conditions
ConditionsYield
With cesium hydroxide; sodium iodide at 50℃; for 0.266667h; Microwave irradiation; Neat (no solvent); chemoselective reaction;95%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1,8-Naphthalimide
81-83-4

1,8-Naphthalimide

ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[d,e]isoquinolin-2-yl)butanoate
150705-10-5

ethyl 4-(1,3-dioxo-2,3-dihydro-1H-benzo[d,e]isoquinolin-2-yl)butanoate

Conditions
ConditionsYield
With caesium carbonate; sodium iodide In N,N-dimethyl-formamide at 70℃; for 0.166667h; Microwave irradiation;95%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

4-cyano-benzenebutanoic acid ethyl ester
131379-33-4

4-cyano-benzenebutanoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 4-chloro-butyric acid ethyl ester With tetrabutylammomium bromide; iodine; zinc In N,N-dimethyl acetamide at 80℃; for 12h;
Stage #2: 4-Cyanochlorobenzene; bis(triphenylphosphine)nickel(II) chloride In N,N-dimethyl acetamide Further stages.;
94%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

2-methoxyethyl 4-chlorobutanoate

2-methoxyethyl 4-chlorobutanoate

Conditions
ConditionsYield
With titanium(IV) isopropylate In toluene at 20℃; Dean-Stark;94%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1,3-dimethyl glycerol ether
623-69-8

1,3-dimethyl glycerol ether

1,3-dimethoxypropan-2-yl 4-chlorobutanoate

1,3-dimethoxypropan-2-yl 4-chlorobutanoate

Conditions
ConditionsYield
With titanium(IV) isopropylate In toluene at 20℃; Dean-Stark;94%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

4-chloro-1-butanol-1,1-d2
66502-79-2

4-chloro-1-butanol-1,1-d2

Conditions
ConditionsYield
With lithium aluminium deuteride In diethyl ether -15 deg C -> 15 deg C; 15 deg C , 30 min;93%
With lithium aluminium deuteride In diethyl ether at -10℃;
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

7-methyl-3,3-diphenylindoline

7-methyl-3,3-diphenylindoline

ethyl 4-(7-methyl-3,3-diphenylindolin-1-yl)butanoate

ethyl 4-(7-methyl-3,3-diphenylindolin-1-yl)butanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h;92%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

5-methoxy-2-(3-phenylisoxazol-5-yl)phenol
1186130-66-4

5-methoxy-2-(3-phenylisoxazol-5-yl)phenol

ethyl 4-(5-methoxy-2-(3-phenylisoxazol-5-yl)phenoxy)butanoate
1186130-80-2

ethyl 4-(5-methoxy-2-(3-phenylisoxazol-5-yl)phenoxy)butanoate

Conditions
ConditionsYield
With potassium carbonate In acetone Williamson type O-alkylation; Reflux;90.5%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1,4-bis(piperazin-1-yl)-2,3,5,6-tetrafluorobenzene

1,4-bis(piperazin-1-yl)-2,3,5,6-tetrafluorobenzene

4-(4-{4-[4-(3-ethoxycarbonyl-propyl)-piperazin-1-yl]-2,3,5,6-tetrafluoro-phenyl}-piperazin-1-yl)-butyric acid ethyl ester

4-(4-{4-[4-(3-ethoxycarbonyl-propyl)-piperazin-1-yl]-2,3,5,6-tetrafluoro-phenyl}-piperazin-1-yl)-butyric acid ethyl ester

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide Heating;90%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

5,5'-dimethyl-2,2'-dipyridyl diselenide
496043-96-0

5,5'-dimethyl-2,2'-dipyridyl diselenide

ethyl 2-(5-methyl)pyridylselenobutanoate
1124321-70-5

ethyl 2-(5-methyl)pyridylselenobutanoate

Conditions
ConditionsYield
Stage #1: 5,5'-dimethyl-2,2'-dipyridyl diselenide With sodium tetrahydroborate In ethanol Inert atmosphere;
Stage #2: 4-chloro-butyric acid ethyl ester In ethanol at 10 - 20℃; for 0.25h; Inert atmosphere;
90%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

diphenyl diselenide
1666-13-3

diphenyl diselenide

ethyl 4-(phenylselanyl)butanoate
25059-06-7

ethyl 4-(phenylselanyl)butanoate

Conditions
ConditionsYield
Stage #1: diphenyl diselenide With sodium tetrahydroborate In ethanol for 0.166667h;
Stage #2: 4-chloro-butyric acid ethyl ester In ethanol at 55 - 60℃; for 1.5h;
89%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1-(2-phenylethyl)-1H-imidazole
49823-14-5

1-(2-phenylethyl)-1H-imidazole

3-(4-ethoxy-4-oxobutyl)-1-phenethyl-1H-imidazol-3-ium chloride

3-(4-ethoxy-4-oxobutyl)-1-phenethyl-1H-imidazol-3-ium chloride

Conditions
ConditionsYield
In toluene at 80℃; for 0.333333h; Microwave irradiation; Green chemistry;89%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

phthalimide
136918-14-4

phthalimide

ethyl 4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butanoate
10294-97-0

ethyl 4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butanoate

Conditions
ConditionsYield
With caesium carbonate; sodium iodide In N,N-dimethyl-formamide at 70℃; for 0.166667h; Microwave irradiation;88%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

bis(diphenylmethyl) diselenide
24572-14-3

bis(diphenylmethyl) diselenide

ethyl 2-(diphenyl)methylselenobutanoate
1124321-77-2

ethyl 2-(diphenyl)methylselenobutanoate

Conditions
ConditionsYield
Stage #1: bis(diphenylmethyl) diselenide With sodium tetrahydroborate In ethanol Inert atmosphere;
Stage #2: 4-chloro-butyric acid ethyl ester In ethanol at 15 - 20℃; for 0.416667h; Inert atmosphere;
87%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

1-chloro-3-methoxy-benzene
2845-89-8

1-chloro-3-methoxy-benzene

ethyl 4-(3'-methoxyphenyl)butyrate
57816-01-0

ethyl 4-(3'-methoxyphenyl)butyrate

Conditions
ConditionsYield
With nickel(II) bromide dimethoxyethane; pyridine-2,6-bis(N-cyanocarboxamidine); lithium chloride; zinc In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;87%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

3-hydroxy-1-isopropyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile
371930-42-6

3-hydroxy-1-isopropyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile

ethyl 4-{[4-cyano-1-(propan-2-yl)-5,6,7,8-tetrahydroisoquinolin-3-yl]oxy}butanoate

ethyl 4-{[4-cyano-1-(propan-2-yl)-5,6,7,8-tetrahydroisoquinolin-3-yl]oxy}butanoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 75 - 80℃; for 2h;87%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

1-(3-chloropropyl)cyclopropanol
174790-32-0

1-(3-chloropropyl)cyclopropanol

Conditions
ConditionsYield
Stage #1: 4-chloro-butyric acid ethyl ester; ethylmagnesium bromide With titanium(IV) isopropylate In diethyl ether at 20℃; for 0.5h;
Stage #2: With sulfuric acid In diethyl ether
86%
Stage #1: 4-chloro-butyric acid ethyl ester; ethylmagnesium bromide With titanium(IV) isopropylate In diethyl ether at 20℃; Kulinkovich Hydroxycyclopropanation;
Stage #2: With sulfuric acid In diethyl ether
86%
With titanium(IV) isopropylate In diethyl ether Ambient temperature;85%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

2,2'-dipyridyldiselenide
59957-75-4

2,2'-dipyridyldiselenide

ethyl 2-pyridylselenobutanoate
1124321-67-0

ethyl 2-pyridylselenobutanoate

Conditions
ConditionsYield
Stage #1: 2,2'-dipyridyldiselenide With sodium tetrahydroborate In ethanol Inert atmosphere;
Stage #2: 4-chloro-butyric acid ethyl ester In ethanol at 10 - 20℃; for 0.5h; Inert atmosphere;
86%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

bis(2-naphthyl) diselenide
17932-23-9

bis(2-naphthyl) diselenide

ethyl 2-naphthylselenobutanoate
23763-12-4

ethyl 2-naphthylselenobutanoate

Conditions
ConditionsYield
Stage #1: bis(2-naphthyl) diselenide With sodium tetrahydroborate In ethanol Inert atmosphere;
Stage #2: 4-chloro-butyric acid ethyl ester In ethanol at 30 - 35℃; for 1.41667h; Inert atmosphere;
86%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

5-chloro-2-benzoxazolinone
95-25-0

5-chloro-2-benzoxazolinone

ethyl 4-(5-chloro-2(3H)-benzoxazolon-3-yl)butanoate
659724-36-4

ethyl 4-(5-chloro-2(3H)-benzoxazolon-3-yl)butanoate

Conditions
ConditionsYield
Stage #1: 5-chloro-2-benzoxazolinone With sodium ethanolate In ethanol
Stage #2: 4-chloro-butyric acid ethyl ester In N,N-dimethyl-formamide at 80℃; for 8h;
85%
4-chloro-butyric acid ethyl ester
3153-36-4

4-chloro-butyric acid ethyl ester

4-Fluorobenzyl bromide
459-46-1

4-Fluorobenzyl bromide

3-(4-piperidinyl)-1H-indole
17403-09-7

3-(4-piperidinyl)-1H-indole

4-{4-[1-(4-fluoro-benzyl)-1H-indol-3-yl]-piperidin-1-yl}-butyric acid

4-{4-[1-(4-fluoro-benzyl)-1H-indol-3-yl]-piperidin-1-yl}-butyric acid

Conditions
ConditionsYield
85%

3153-36-4Relevant articles and documents

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Noyce,Canfield

, p. 3630 (1954)

-

A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

André-Joyaux, Emy,Kuzovlev, Andrey,Renaud, Philippe,Tappin, Nicholas D. C.

, p. 13859 - 13864 (2020/06/10)

The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.

PYRAZOLYL DERIVATIVES AS SYK INHIBITORS

-

Page/Page column 134, (2014/01/09)

The present invention provides novel pyrazole derivatives of formula I which are potent inhibitors of spleen tyrosine kinase, and are useful in the treatment and prevention of diseases mediated by said enzyme, such as asthma, COPD, rheumatoid arthritis, and cancer.

Novel annelation methodology for the rapid and efficient construction of bicyclo [4.n.0] alkanols and alkenones

Markó, István E.,Ates, Ali

, p. 1033 - 1036 (2007/10/03)

The efficient assembly of a range of fused bicyclic alcohols and enones can be readily performed using a novel, orthoester-based, annelation methodology.

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