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928-51-8

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928-51-8 Usage

Description

4-Chloro-1-butanol, also known as Tetramethylene chlorohydrin, is an organic compound with the chemical formula C4H9ClO. It is a colorless liquid with a chlorohydrin functional group, which makes it a versatile intermediate in organic synthesis.

Uses

Used in Organic Synthesis:
4-Chloro-1-butanol is used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and functional group make it a valuable building block for the development of new molecules with potential applications in different industries.
Used in Pharmaceutical Analysis:
4-Chloro-1-butanol is employed as an internal standard in the analysis of genotoxic impurities in active pharmaceutical ingredients by the Gas Chromatography-Mass Spectrometry (GC-MS) technique. Its stability, volatility, and compatibility with GC-MS make it an ideal choice for accurate quantification and identification of genotoxic impurities, ensuring the safety and quality of pharmaceutical products.

Health Hazard

The toxicity of this compound is low. How ever, the acute toxic symptoms are those ofethylene and propylene chlorohydrins. Oralintake of this compound caused muscle con traction, gastrointestinal pain, ulceration, andliver injury in test animals.LD50 value, oral (mice): 990 mg/kgTetramethylene chlorohydrin caused tumorsin lungs in test animals. Its carcinogenicity,however, is not yet fully established.

Fire Hazard

Flammable; flash point 36°C (97°F); vapor density 3.7 (air = 1); the vapor forms an explosive mixture with air, range is not reported. Fire-extinguishing agent: “alcohol” foam; a water spray may be used to cool fire-exposed containers and to flush any spill. It decomposes to HCl and tetrahydrofuran on heating.

Safety Profile

Moderately toxic by ingestion. Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORIDES and ALCOHOLS.

Waste Disposal

Tetramethylene chlorohydrin is burned ina chemical incinerator equipped with anafterburner and scrubber.

Check Digit Verification of cas no

The CAS Registry Mumber 928-51-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,2 and 8 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 928-51:
(5*9)+(4*2)+(3*8)+(2*5)+(1*1)=88
88 % 10 = 8
So 928-51-8 is a valid CAS Registry Number.
InChI:InChI=1/C4H9ClO/c5-3-1-2-4-6/h6H,1-4H2

928-51-8 Well-known Company Product Price

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  • Alfa Aesar

  • (L04042)  4-Chloro-1-butanol, tech. 85%   

  • 928-51-8

  • 50g

  • 446.0CNY

  • Detail
  • Alfa Aesar

  • (L04042)  4-Chloro-1-butanol, tech. 85%   

  • 928-51-8

  • 250g

  • 1670.0CNY

  • Detail

928-51-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-chlorobutanol

1.2 Other means of identification

Product number -
Other names 4-CHLOROBUTANOL

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:928-51-8 SDS

928-51-8Synthetic route

1-chloro-4-tetrahydropyranyloxybutane
41302-05-0

1-chloro-4-tetrahydropyranyloxybutane

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
ammonium cerium(IV) nitrate In alkaline aq. solution; acetonitrile at 70℃; for 2h; pH=8; Decomposition;86%
4-Chlorobutyl acetate
6962-92-1

4-Chlorobutyl acetate

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol for 4h; Heating;85.4%
tetrahydrofuran
109-99-9

tetrahydrofuran

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
With hydrogenchloride for 5h; Heating;82%
With hydrogenchloride Heating;57%
With hydrogenchloride55%
Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
With pyridine; thionyl chloride at 80℃; for 1h;36%
With hydrogenchloride; bismuth(III) chloride; silica gel at 80℃;
With disulfur dichloride anfangs auf dem Wasserbad, danach auf 150grad;
With pyridine; thionyl chloride at 55℃;
With thionyl chloride In chloroform for 5h; Inert atmosphere;
oxirane
75-21-8

oxirane

chloroethane
75-00-3

chloroethane

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
With aluminium trichloride
tetrahydrofuran
109-99-9

tetrahydrofuran

A

silicic acid tetrakis-(4-chloro-butyl ester)
17898-52-1

silicic acid tetrakis-(4-chloro-butyl ester)

B

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
With hydrogenchloride; tetrachlorosilane
trichloroacetic 4-chlorobutyl ester
84273-54-1

trichloroacetic 4-chlorobutyl ester

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
With sodium hydroxide
3-butenyl chloride
927-73-1

3-butenyl chloride

A

4-chloro-2-butanol
2203-34-1

4-chloro-2-butanol

B

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
(i) B2H6, THF, H2O, (ii) NaOH, H2O2; Multistep reaction;
3-butenyl chloride
927-73-1

3-butenyl chloride

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
(i) bis-(2-methyl-butyl)-borane, THF, H2O, (ii) NaOH, H2O2; Multistep reaction;
1,4-dichlorobutane
110-56-5

1,4-dichlorobutane

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
(i) SbF5, SO2, (ii) acetone, (iii) Na2CO3, MeOH; Multistep reaction;
1-chloro-4-tetrahydropyranyloxybutane
41302-05-0

1-chloro-4-tetrahydropyranyloxybutane

A

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

B

5-hydroxy-pentanoic acid 4-chloro-butyl ester

5-hydroxy-pentanoic acid 4-chloro-butyl ester

Conditions
ConditionsYield
With aluminum oxide; Oxone; water In methanol at 50℃; Yield given; Yields of byproduct given;
tetrahydrofuran
109-99-9

tetrahydrofuran

hydrogenchloride
7647-01-0

hydrogenchloride

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

oxirane
75-21-8

oxirane

aluminium trichloride
7446-70-0

aluminium trichloride

chloroethane
75-00-3

chloroethane

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

pyridine
110-86-1

pyridine

thionyl chloride
7719-09-7

thionyl chloride

Butane-1,4-diol
110-63-4

Butane-1,4-diol

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
at 55℃;
hydrogenchloride
7647-01-0

hydrogenchloride

methanol
67-56-1

methanol

4-Chlorobutyl acetate
6962-92-1

4-Chlorobutyl acetate

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
at 40℃;
<4-chloro--acetate

<4-chloro--acetate

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
With hydrogenchloride; methanol at 40℃;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

disulfur dichloride

disulfur dichloride

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
zuletzt auf 150grad;
diethyl ether
60-29-7

diethyl ether

γ-chlorobutyric acid
627-00-9

γ-chlorobutyric acid

lithium alanate

lithium alanate

A

tetrahydrofuran
109-99-9

tetrahydrofuran

B

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

C

butan-1-ol
71-36-3

butan-1-ol

boron trichloride
10294-34-5

boron trichloride

A

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

B

bis(4-chlorobutyloxy)chloroborane
98997-54-7

bis(4-chlorobutyloxy)chloroborane

1-(4-chlorobutoxy)-2,2,6,6-tetramethylpiperidine

1-(4-chlorobutoxy)-2,2,6,6-tetramethylpiperidine

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Conditions
ConditionsYield
With acetic acid; zinc In tetrahydrofuran for 12h; Schlenk technique; Inert atmosphere;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

A

1,3-dichlorobutane
1190-22-3

1,3-dichlorobutane

B

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

C

bis-(4-chlorobutyl)ether
6334-96-9

bis-(4-chlorobutyl)ether

D

1,4-dichlorobutane
110-56-5

1,4-dichlorobutane

Conditions
ConditionsYield
With Tributylphosphine oxide; bis(trichloromethyl) carbonate at 50 - 60℃; Reagent/catalyst; Large scale;
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

2-methyldiphenylsilyl-1,3-dithiane
135746-47-3

2-methyldiphenylsilyl-1,3-dithiane

4-[1-(methyl-diphenyl-silyl)-2,6-dithiacyclohexyl]-1-butanol

4-[1-(methyl-diphenyl-silyl)-2,6-dithiacyclohexyl]-1-butanol

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃;100%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

aniline
62-53-3

aniline

N-phenylpyrrolidine
4096-21-3

N-phenylpyrrolidine

Conditions
ConditionsYield
With iron(III) chloride hexahydrate100%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

1-chloro-4-tetrahydropyranyloxybutane
41302-05-0

1-chloro-4-tetrahydropyranyloxybutane

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃;99%
pyridinium p-toluenesulfonate In dichloromethane for 8h; Ambient temperature;98%
With pyridinium p-toluenesulfonate In dichloromethane for 7h; Ambient temperature;97%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-(t-butyldimethylsiloxy)-1-chlorobutane
89031-83-4

4-(t-butyldimethylsiloxy)-1-chlorobutane

Conditions
ConditionsYield
Stage #1: 4-Chloro-1-butanol; tert-butyldimethylsilyl chloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
Stage #2: With 1H-imidazole In dichloromethane at 0℃; for 1.5h; Inert atmosphere;
99%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Substitution;93%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 4h;50%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-chlorobutyl 4-methylbenzenesulfonate
20999-32-0

4-chlorobutyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 1.5h;99%
With pyridine In chloroform at 0℃; for 2.5h;85%
With pyridine at 0℃; for 2h; Inert atmosphere;79%
With pyridine In tetrahydrofuran for 20h; Ambient temperature;49%
With pyridine at 0℃; for 3.5h;
2-(trimethylsilyl)-1,3-dithiane
13411-42-2

2-(trimethylsilyl)-1,3-dithiane

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

4-(2-Trimethylsilanyl-[1,3]dithian-2-yl)-butan-1-ol
78633-24-6

4-(2-Trimethylsilanyl-[1,3]dithian-2-yl)-butan-1-ol

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -78℃;99%
With lithium diisopropyl amide In tetrahydrofuran at -78℃;97%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

2-(phenylsulfonyl)tetrahydro-2H-pyran
96754-03-9

2-(phenylsulfonyl)tetrahydro-2H-pyran

1-chloro-4-tetrahydropyranyloxybutane
41302-05-0

1-chloro-4-tetrahydropyranyloxybutane

Conditions
ConditionsYield
With sodium hydrogencarbonate; magnesium bromide In tetrahydrofuran Ambient temperature; overnight (15-24 hrs);97%
With sodium hydrogencarbonate; magnesium bromide In tetrahydrofuran Ambient temperature;97%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

Tetramethylammonium hydrogen carbonate
58345-96-3

Tetramethylammonium hydrogen carbonate

butylene carbonate
4427-94-5

butylene carbonate

Conditions
ConditionsYield
In acetonitrile97%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

δ-chlorobutyl 4-nitrobenzoate
58168-12-0

δ-chlorobutyl 4-nitrobenzoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 2h;96%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;96%
With triethylamine In dichloromethane at 0 - 20℃; for 2h;96%
With triethylamine In chloroform for 18h; Ambient temperature;68%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

benzyl mesylate
55791-06-5

benzyl mesylate

[(4-chlorobutoxy)methyl]benzene
50873-93-3

[(4-chlorobutoxy)methyl]benzene

Conditions
ConditionsYield
With magnesium oxide; lithium trifluoromethanesulfonate; lithium tetrakis(pentafluorophenyl)borate In dichloromethane; cyclohexane at 20℃; for 24h;96%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

4-(methylthio)-1-butanol
20582-85-8

4-(methylthio)-1-butanol

Conditions
ConditionsYield
With sodium iodide In ethanol at 20℃; for 12h;95%
In water at 25℃; for 48h;72%
With ethanol
In water
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

acryloyl chloride
814-68-6

acryloyl chloride

4-chloro-1-butanol acrylate
2206-87-3

4-chloro-1-butanol acrylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃;95%
With triethylamine In benzene
With triethylamine In chloroform at 0℃;
With triethylamine In chloroform at 10℃; for 12h;
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

isobutene
115-11-7

isobutene

1-(tert-butoxy)-4-chlorobutane
104164-65-0

1-(tert-butoxy)-4-chlorobutane

Conditions
ConditionsYield
Amberlyst H-15 In hexane95%
With Amberlyst H-15 In hexane at 20℃; for 15h;95%
With Amberlyst 15 In hexane at 20℃; for 8h;95%
With sulfuric acid
Amberlyst H-15 In hexane Ambient temperature; Yield given;
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

L-phenylalanine
63-91-2

L-phenylalanine

L-phenylalanine 4-chlorobutyl ester hydrochloride
131326-15-3

L-phenylalanine 4-chlorobutyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 40℃; for 19h;95%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

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

1-(4-Fluorophenyl)piperazine

4-[4-(4-fluorophenyl)piperazin-1-yl]butan-1-ol
1156220-20-0

4-[4-(4-fluorophenyl)piperazin-1-yl]butan-1-ol

Conditions
ConditionsYield
With cesium hydroxide; sodium iodide at 60℃; for 0.05h; Microwave irradiation; Neat (no solvent); chemoselective reaction;95%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

4-chlorobutyl diphenylphosphinite
1346017-23-9

4-chlorobutyl diphenylphosphinite

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at -5℃; for 5h;95%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

4-chlorobutyraldehyde
6139-84-0

4-chlorobutyraldehyde

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In dichloromethane; water at 25℃; Electrolysis; Saturated solution;94%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78℃; Swern Oxidation; Inert atmosphere;90%
With oxalyl dichloride In dimethyl sulfoxide85%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

1-chloro-1-methylsiletane
2351-34-0

1-chloro-1-methylsiletane

1-(4-Chloro-butoxy)-1-methyl-siletane

1-(4-Chloro-butoxy)-1-methyl-siletane

Conditions
ConditionsYield
With urea at 50℃; for 4h;94%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

trimethylamine
75-50-3

trimethylamine

(4-hydroxy-butyl)-trimethyl-ammonium; chloride
125422-10-8

(4-hydroxy-butyl)-trimethyl-ammonium; chloride

Conditions
ConditionsYield
In water; acetonitrile at 70℃; for 18h; Inert atmosphere;94%
In water for 24h; Heating / reflux;94%
In water; acetonitrile at 70℃; for 14h;
TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

1-chloro-4-tetrahydropyranyloxybutane
41302-05-0

1-chloro-4-tetrahydropyranyloxybutane

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;94%
1-vinylimidazole
1072-63-5

1-vinylimidazole

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

C9H15N2O(1+)*Cl(1-)

C9H15N2O(1+)*Cl(1-)

Conditions
ConditionsYield
In water at 80℃;94%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

sodium 1-buthanethiolate
4779-86-6

sodium 1-buthanethiolate

n-butyl 4-hydroxybutyl sulfide
5331-34-0

n-butyl 4-hydroxybutyl sulfide

Conditions
ConditionsYield
In methanol for 2h; Heating;92%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

(4'-Chloro-1'-butyl)-3-oxobutanoate
91116-20-0

(4'-Chloro-1'-butyl)-3-oxobutanoate

Conditions
ConditionsYield
With dmap In cyclohexane for 16h; Heating;92%
With dmap In cyclohexane for 16h; Heating;92%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

para-thiocresol
106-45-6

para-thiocresol

4-(p-tolylthio)butan-1-ol
27975-48-0

4-(p-tolylthio)butan-1-ol

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 0 - 20℃;92%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

3-(4-hydroxybutyl)-1-methyl-1H-imidazol-3-ium chloride

3-(4-hydroxybutyl)-1-methyl-1H-imidazol-3-ium chloride

Conditions
ConditionsYield
at 80℃; for 4h; Neat (no solvent);92%
at 80℃; for 4h;92%
at 80℃; for 5h;89%
at 80℃; for 24h;
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

methylhydrazine
60-34-4

methylhydrazine

4-(1-methylhydrazinyl)butan-1-ol

4-(1-methylhydrazinyl)butan-1-ol

Conditions
ConditionsYield
In neat liquid at 20℃; for 24h; Inert atmosphere;92%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

ethyl vinyl ether
109-92-2

ethyl vinyl ether

1-Chlor-3-(1'-aethoxyaethoxy)-butan
52500-29-5

1-Chlor-3-(1'-aethoxyaethoxy)-butan

Conditions
ConditionsYield
With dichloro-acetic acid at 0℃; for 12h; Addition;90%
With trifluoroacetic acid for 24h; Ambient temperature;86%
With toluene-4-sulfonic acid at 0℃; for 1.5h;67%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

sodium thioethylate
811-51-8

sodium thioethylate

4-(ethylthio)-1-butanol
18721-62-5

4-(ethylthio)-1-butanol

Conditions
ConditionsYield
90%
4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

4-chlorobutanol-1-trifluoromethanesulfonate
103935-55-3

4-chlorobutanol-1-trifluoromethanesulfonate

Conditions
ConditionsYield
With dmap; potassium carbonate In dichloromethane at -50℃; for 1h;90%
1-(2-Methoxyphenyl)piperazine
35386-24-4

1-(2-Methoxyphenyl)piperazine

4-Chloro-1-butanol
928-51-8

4-Chloro-1-butanol

4-[4-(2-methoxyphenyl)piperazin-1-yl]butan-1-ol
40004-65-7

4-[4-(2-methoxyphenyl)piperazin-1-yl]butan-1-ol

Conditions
ConditionsYield
With cesium hydroxide; sodium iodide at 55℃; for 1h; Microwave irradiation; Neat (no solvent); chemoselective reaction;90%

928-51-8Relevant articles and documents

Fe(III)-Catalyzed Aerobic Intramolecular N-N Coupling of Aliphatic Azides with Amines

Zhang, Yue,Duan, Dongyu,Zhong, Ying,Guo, Xin-Ai,Guo, Jiawei,Gou, Jing,Gao, Ziwei,Yu, Binxun

supporting information, p. 4960 - 4965 (2019/09/03)

An Fe(III)-catalyzed intramolecular N-N coupling of aliphatic azidoamines that forms diverse five- and six-membered semisaturated diazoheterocycles using air as an oxidant is reported, providing an alternative to hydrazine-based methods. Mechanistic studies suggest that a N-radical induced intramolecular homolytic substitution (SH2) is involved in ring closure. The power of this N-N bond-forming method is also demonstrated by using it as the final step in a total synthesis of (-)-newbouldine.

Ru-Photoredox-Catalyzed Decarboxylative Oxygenation of Aliphatic Carboxylic Acids through N-(acyloxy)phthalimide

Zheng, Chao,Wang, Yuting,Xu, Yangrui,Chen, Zhen,Chen, Guangying,Liang, Steven H.

supporting information, p. 4824 - 4827 (2018/08/24)

Decarboxylative aminoxylation of aliphatic carboxylic acid derivatives with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) in the presence of ruthenium photoredox catalysis is reported. The key transformation entails a highly efficient photoredox catalytic cycle using Hantzsch ester as a reductant. The ensuing alkoxyamine can be readily converted to the corresponding alcohol in one pot, representing an alternative approach to access aliphatic alcohols under photoredox conditions.

Remarkable deprotection of THP and THF ethers catalysed by cerium ammonium nitrate (CAN) under neutral conditions

Marko, Istvan E.,Ates, Ali,Augustyns, Benoit,Gautier, Arnaud,Quesnel, Yannick,Turet, Laurent,Wiaux, Marianne

, p. 5613 - 5616 (2007/10/03)

The catalytic deprotection of a range of functionalised THP and THF ethers can be efficiently performed, under neutral conditions, using as little as 3 mol% CAN in MeCN/borate buffer (pH = 8).

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