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100-46-9 Usage

Chemical Description

Benzylamine is an organic compound with the formula C6H5CH2NH2.

Chemical Description

Benzylamine is an organic compound containing an amine group and a benzyl group.

Chemical Description

Benzylamine and sodium cyanoborohydride are used in the reductive amination step to form piperidinones.

Chemical Description

Benzylamine is an organic compound with the formula C6H5CH2NH2, while benzyl chloroformate is a derivative of chloroformic acid with the formula C6H5CH2OC(O)Cl.

Chemical Description

Benzylamine is an organic compound containing an amine group and a benzene ring.

Check Digit Verification of cas no

The CAS Registry Mumber 100-46-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 100-46:
(5*1)+(4*0)+(3*0)+(2*4)+(1*6)=19
19 % 10 = 9
So 100-46-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2/p+1

100-46-9 Well-known Company Product Price

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  • TCI America

  • (B0406)  Benzylamine  >99.0%(GC)

  • 100-46-9

  • 25mL

  • 80.00CNY

  • Detail
  • TCI America

  • (B0406)  Benzylamine  >99.0%(GC)

  • 100-46-9

  • 500mL

  • 190.00CNY

  • Detail
  • Alfa Aesar

  • (A10997)  Benzylamine, 98+%   

  • 100-46-9

  • 250g

  • 224.0CNY

  • Detail
  • Alfa Aesar

  • (A10997)  Benzylamine, 98+%   

  • 100-46-9

  • 500g

  • 331.0CNY

  • Detail
  • Alfa Aesar

  • (A10997)  Benzylamine, 98+%   

  • 100-46-9

  • 1000g

  • 632.0CNY

  • Detail
  • Alfa Aesar

  • (A10997)  Benzylamine, 98+%   

  • 100-46-9

  • 5000g

  • 2735.0CNY

  • Detail
  • Sigma-Aldrich

  • (13180)  Benzylamine  for GC derivatization, ≥99.0%

  • 100-46-9

  • 13180-10X1ML

  • 957.06CNY

  • Detail
  • Sigma-Aldrich

  • (13180)  Benzylamine  for GC derivatization, ≥99.0%

  • 100-46-9

  • 13180-100ML

  • 304.20CNY

  • Detail
  • Sigma-Aldrich

  • (13180)  Benzylamine  for GC derivatization, ≥99.0%

  • 100-46-9

  • 13180-500ML

  • 786.24CNY

  • Detail

100-46-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzylamine

1.2 Other means of identification

Product number -
Other names Phenylmethanamine

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:100-46-9 SDS

100-46-9Synthetic route

benzyl azide
622-79-7

benzyl azide

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran for 0.25h; Reduction; Heating;100%
With sodium tetrahydroborate; tin bis(1,2-benzenedithiolate) In tetrahydrofuran; phosphate buffer at 10℃; for 0.5h; pH=10; Product distribution; Further Variations:; pH-values; Solvents; Reduction;100%
With (Sn(SPh)3)(Et3N) In benzene at 15℃; for 0.0833333h;99%
benzonitrile
100-47-0

benzonitrile

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With lithium borohydride; 9-methoxy-9-BBN In diethyl ether at 25℃; for 5h; Product distribution; rate of reduction;100%
With borane N-ethyl-N-isopropylaniline complex In tetrahydrofuran for 0.1h; Heating;100%
With hydrogen; palladium In methanol at 20℃; for 432h;100%
benzyl carbamic acid allyl ester
104669-74-1

benzyl carbamic acid allyl ester

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With diethylamine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile for 0.166667h; Ambient temperature;100%
Allylbenzylamine
4383-22-6

Allylbenzylamine

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With Thiosalicylic acid; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 60℃; for 0.5h; effect of temperature on deprotection of various primary and secondary allylamines;100%
With Thiosalicylic acid; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 60℃; for 0.5h;100%
With polymethylhydrosiloxane; zinc(II) chloride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;92%
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); diisobutylaluminium hydride In toluene for 1h; Ambient temperature;66%
N,N-di-2-propenylbenzylamine
4383-26-0

N,N-di-2-propenylbenzylamine

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With Thiosalicylic acid; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 60℃; for 0.5h;100%
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); diisobutylaluminium hydride In toluene for 1h; Ambient temperature;79%
N-tert-butoxycarbonylbenzylamine
42116-44-9

N-tert-butoxycarbonylbenzylamine

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With methanol; Acetyl bromide In dichloromethane at 25℃; for 0.333333h;100%
With 3-butyl-l-methyl-1H-imidazol-3-iumtrifloroacetate In 1,4-dioxane; water at 80 - 82℃; for 4h;98%
With nitric acid In dichloromethane at 0℃; for 1h;95%
N-benzyl-2,4-dinitro-benzenesulfonamide

N-benzyl-2,4-dinitro-benzenesulfonamide

A

S-(2,4-Dinitrophenyl)-cystein
3165-76-2

S-(2,4-Dinitrophenyl)-cystein

B

sulfur dioxide
7446-09-5

sulfur dioxide

C

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
In aq. phosphate buffer for 0.5h; pH=7.4;A n/a
B 100%
C n/a
(benzylimino)triphenylphosphorane
52826-45-6

(benzylimino)triphenylphosphorane

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With phenylsilane In toluene at 111℃; for 12h;100%
benzaldehyde
100-52-7

benzaldehyde

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With ammonia; hydrogen In methanol at 90℃; under 15001.5 Torr; for 4h; Solvent; Temperature; Pressure; Autoclave;99.7%
With Candida boidinii formate dehydrogenase; Geobacillus stearothermophilus ε‐deaminating L‐lysine dehydrogenase variant 1; nicotinamide adenine dinucleotide In aq. buffer at 30℃; for 24h; pH=8.5; Reagent/catalyst; Enzymatic reaction;99%
With ammonium hydroxide; hydrogen In ethanol at 130℃; under 7500.75 Torr; for 12h; Autoclave;96.9%
N-benzyl-p-toluenesulfonamide
1576-37-0

N-benzyl-p-toluenesulfonamide

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
Stage #1: N-benzyl-p-toluenesulfonamide With n-butyllithium In tetrahydrofuran at 0℃;
Stage #2: With naphthalene; lithium In tetrahydrofuran at -78 - 20℃;
99%
Stage #1: N-benzyl-p-toluenesulfonamide With n-butyllithium In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: With naphthalene; lithium In tetrahydrofuran at -78 - 25℃;
Stage #3: With water In tetrahydrofuran
99%
With naphthalene; water; lithium 1.) THF, -78 deg C, 2 h; Yield given. Multistep reaction;
4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine
383865-57-4

4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine

A

1-Benzyl-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-urea

1-Benzyl-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-urea

B

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
A 99%
B n/a
N-benzylformamide
6343-54-0

N-benzylformamide

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With sodium ethanolate In methanol at 80℃; for 2h;99%
With sodiumsulfide nonahydrate In water at 100℃; for 12h;86%
Multi-step reaction with 2 steps
1: 3 h / Reflux
2: triphenylphosphine; triethylamine / dichloromethane; tetrachloromethane / 4 h / Reflux; Inert atmosphere
View Scheme
1-nitro-1-phenylmethane
622-42-4

1-nitro-1-phenylmethane

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; ammonium formate In methanol under 2068.65 Torr; Flow reactor;98%
With palladium on activated charcoal; tetrabutylammomium bromide; water; sodium hydroxide; silicon at 100℃; for 6h; Reagent/catalyst;94%
With hydrazine hydrate In dichloromethane at 20℃; for 1h;71%
benzylammonium O-ethylstyrylphosphonate
122954-29-4

benzylammonium O-ethylstyrylphosphonate

A

styrylphosphonic acid ethylester
5849-49-0

styrylphosphonic acid ethylester

B

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 0.5h;A 98%
B 83%
1-phenyl-N-tritylethanamine
3378-73-2

1-phenyl-N-tritylethanamine

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; water; acetic acid In dichloromethane at 20℃; for 7.5h; Inert atmosphere;98%
With water; ytterbium(III) triflate In tetrahydrofuran at 20℃; Product distribution; Further Variations:; Catalysts; Reagents; Hydrolysis;93%
2-(benzylamino-methylene)-malonic acid diethyl ester
54535-21-6

2-(benzylamino-methylene)-malonic acid diethyl ester

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With ethylenediamine In ethanol at 20℃; for 0.75h;98%
N-benzyl-3,3-dimethoxypropylsulfonamide

N-benzyl-3,3-dimethoxypropylsulfonamide

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
Stage #1: N-benzyl-3,3-dimethoxypropylsulfonamide With p-toluenesulfonic acid monohydrate In water; acetone at 0 - 20℃; for 6h;
Stage #2: With sodium hydroxide In methanol; water; acetone at 0 - 20℃; for 1.08333h;
98%
Benzaldoxime
932-90-1

Benzaldoxime

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With sodium hydrogensulfate monohydrate; molybdenum(V) chloride; sodium cyanoborohydride In N,N-dimethyl-formamide for 1.5h; Reflux;96%
With sodium tetrahydroborate at 20℃; for 0.0333333h; neat (no solvent, solid phase);94%
With iron oxide; zirconium(IV) chloride; sodium cyanoborohydride In neat (no solvent) at 75 - 80℃; for 0.25h; Reagent/catalyst; Temperature;93%
benzyl alcohol
100-51-6

benzyl alcohol

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With sodium azide; triphenylphosphine In dichloromethane; N,N-dimethyl-formamide at 90℃; for 4h; Substitution; Mitsunobu reaction; Staudinger reaction;96%
With ammonia In toluene at 110℃; under 5250.53 Torr; for 20h;91%
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tert-Amyl alcohol at 140℃; for 20h; Inert atmosphere; Cooling;87%
4-allyloxy-benzonitrile
33148-47-9

4-allyloxy-benzonitrile

A

4-cyanophenyl propyl ether
60758-84-1

4-cyanophenyl propyl ether

B

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal; ethylenediamine In tetrahydrofuran at 20℃; for 24h; atmospheric pressure;A 96%
B n/a
benzyl bromide
100-39-0

benzyl bromide

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With 5-methyl-1,3,4-thiadiazol-2-amine; triethylamine In ethanol; water at 25℃; for 1h;96%
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / Inert atmosphere
1.2: 8 h / Inert atmosphere
1.3: 2 h / 60 °C / Inert atmosphere
2.1: titanium(III) chloride; water / tetrahydrofuran / pH 10 / Reflux; Alkaline aq. solution; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C
2: hydrogenchloride / water / 3 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / 1 h / Milling
1.2: 1 h / Milling
2.1: ethylenediamine / neat (no solvent) / Milling
View Scheme
methyl N-benzylcarbamate
5817-70-9

methyl N-benzylcarbamate

A

methanol
67-56-1

methanol

B

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With C25H19BrMnN2O2P; potassium tert-butylate; hydrogen In toluene at 130℃; under 15001.5 Torr; for 48h;A 98 %Spectr.
B 96%
N-benzyl-2,2,2-trifluoroacetamide
7387-69-1

N-benzyl-2,2,2-trifluoroacetamide

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With potassium hydroxide at 20℃; for 0.25h;95%
2-hydroxy-N-(benzyl)benzylamine
5001-26-3

2-hydroxy-N-(benzyl)benzylamine

A

C21H18O3

C21H18O3

B

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
at 220℃; under 10 Torr; for 0.0833333h; Product distribution; pyrolysis without solvent, isolated as sulfate;A n/a
B 95%
1-naphthylmethyl N-benzyl carbamate

1-naphthylmethyl N-benzyl carbamate

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With ammonium formate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In dimethyl sulfoxide at 80℃; for 12h; deprotection;95%
ethyl N-benzylcarbamate
2621-78-5

ethyl N-benzylcarbamate

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With ammonium bromide; 3-azapentane-1,5-diamine at 110℃; for 5h; Temperature; Microwave irradiation;95%
N-benzylphthalimide
2142-01-0

N-benzylphthalimide

A

phthalyl alcohol
612-14-6

phthalyl alcohol

B

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With [RuCl2(2-(diphenylphosphino)-N-((6-((diphenylphosphino)methyl)pyridin-2-yl)methyl)ethan-1-amine)]; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 20h; Catalytic behavior; Autoclave; chemoselective reaction;A 95%
B 87%
With C25H19BrMnN2O2P; potassium tert-butylate; hydrogen In tetrahydrofuran at 130℃; under 22502.3 Torr; for 48h; Mechanism; Inert atmosphere; Glovebox; Autoclave; Green chemistry;A 94%
B 92%
With [Ru(PtBuNNHtBu)H(CO)Cl]; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 15001.5 Torr; for 24h; Autoclave;
With C25H19BrMnN2O2P; potassium tert-butylate; hydrogen In 1,4-dioxane at 130℃; under 22502.3 Torr; for 48h; Catalytic behavior; Solvent; Reagent/catalyst; Pressure; Inert atmosphere; Glovebox; Autoclave; Green chemistry;A 92 %Spectr.
B 97 %Spectr.
benzyl chloride
100-44-7

benzyl chloride

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 3h;94%
With 5-methyl-1,3,4-thiadiazol-2-amine; triethylamine In ethanol; water at 25℃; for 1h; Reagent/catalyst;94%
With hydrogenchloride; potassium hydride; 1,1,3,3-tetramethyldisilazane In tetrahydrofuran at 0 - 25℃; multistep selective monoamination reaction of various alkyl halides;88%
N-benzyl-2,2,6,6-tetramethyl-2,6-disilapiperidine
119592-74-4

N-benzyl-2,2,6,6-tetramethyl-2,6-disilapiperidine

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
In hydrogenchloride for 8h; Heating;94%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

benzylamine
100-46-9

benzylamine

N-benzyl-3-oxobutanamide
882-36-0

N-benzyl-3-oxobutanamide

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃;100%
In dichloromethane at 0 - 20℃;100%
In dichloromethane at 0 - 20℃;100%
4-butanolide
96-48-0

4-butanolide

benzylamine
100-46-9

benzylamine

N-benzyl-4-hydroxybutanamide
19340-88-6

N-benzyl-4-hydroxybutanamide

Conditions
ConditionsYield
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;100%
Stage #1: benzylamine With diisobutylaluminium hydride In tetrahydrofuran; toluene
Stage #2: 4-butanolide In tetrahydrofuran at 20℃; for 0.5h;
98%
In benzene for 12h; Reflux;98%
furfural
98-01-1

furfural

benzylamine
100-46-9

benzylamine

N-benzyl-1-(furan-2-yl)methanimine
4393-11-7

N-benzyl-1-(furan-2-yl)methanimine

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In water at 20℃; for 0.0166667h;100%
In water at 20℃; for 2h;93%
In dichloromethane Inert atmosphere; Molecular sieve;81%
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

benzylamine
100-46-9

benzylamine

rac-(1R,2R)-2-(benzylamino)cyclohexanol
40571-86-6, 40571-87-7, 51925-39-4, 131164-07-3, 141553-09-5

rac-(1R,2R)-2-(benzylamino)cyclohexanol

Conditions
ConditionsYield
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation;100%
at 150℃; Neat (no solvent);99%
With zinc(II) perchlorate hexahydrate at 80℃; for 1h;97%
pivaloyl chloride
3282-30-2

pivaloyl chloride

benzylamine
100-46-9

benzylamine

N-benzyl-2,2-dimethylpropanamide
26209-45-0

N-benzyl-2,2-dimethylpropanamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 25℃; for 1h;100%
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;100%
With 1-methyl-1H-imidazole In dichloromethane at 0℃; Inert atmosphere;99%
cyclohexanone
108-94-1

cyclohexanone

benzylamine
100-46-9

benzylamine

N-benzylcyclohexylamine
4383-25-9

N-benzylcyclohexylamine

Conditions
ConditionsYield
With formic acid; Cp*IrCl(N-(phenyl(pyridin-2-yl)methyl)methanesulfonamide)complex In ethyl acetate at 40℃; for 18h; Reagent/catalyst; Inert atmosphere;100%
Stage #1: cyclohexanone; benzylamine With formic acid; chlorido(8-quinolinolato-k2N,O)(η5-pentamethylcyclopentadienyl)iridium(III) In ethyl acetate at 0 - 40℃; Inert atmosphere; Schlenk tube; Cooling with ice;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate Product distribution / selectivity;
98%
With 4 A molecular sieve; borane pyridine complex In methanol for 16h;96%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

benzylamine
100-46-9

benzylamine

N-benzyl-p-tolylmethanimine
24431-15-0

N-benzyl-p-tolylmethanimine

Conditions
ConditionsYield
In chloroform at 20℃; for 1h;100%
for 6h; Kinetics; Molecular sieve; Reflux;100%
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;65%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

benzylamine
100-46-9

benzylamine

N-(4-chlorobenzylidene)benzylamine
130517-96-3, 13540-93-7

N-(4-chlorobenzylidene)benzylamine

Conditions
ConditionsYield
for 6h; Molecular sieve; Reflux;100%
In ethanol at 20℃;94%
In dichloromethane at 20℃; for 16h; Molecular sieve;92%
terephthalaldehyde,
623-27-8

terephthalaldehyde,

benzylamine
100-46-9

benzylamine

1,4-bis(benzyliminomethyl)benzene
20941-14-4

1,4-bis(benzyliminomethyl)benzene

Conditions
ConditionsYield
In methanol at 20℃;100%
In methanol at 20℃;80%
Benzyl isothiocyanate
622-78-6

Benzyl isothiocyanate

benzylamine
100-46-9

benzylamine

dibenzyl thiourea
1424-14-2

dibenzyl thiourea

Conditions
ConditionsYield
In hexane at 20℃; for 2h;100%
In dichloromethane at 20℃;98%
In chloroform for 0.5h; Heating;88%
benzaldehyde
100-52-7

benzaldehyde

benzylamine
100-46-9

benzylamine

N-benzylidene benzylamine
780-25-6

N-benzylidene benzylamine

Conditions
ConditionsYield
In toluene at 120℃; for 24h;100%
With magnesium sulfate In dichloromethane for 3h; Reflux;100%
With aluminum oxide at 20℃; for 2.5h;99%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

benzylamine
100-46-9

benzylamine

N-(4-methoxylbenzylidene)benzylamine
622-72-0

N-(4-methoxylbenzylidene)benzylamine

Conditions
ConditionsYield
In chloroform at 20℃; for 1h;100%
With sodium sulfate In dichloromethane at 20℃;99%
In chloroform at 20℃; for 1h;96.8%
benzoyl chloride
98-88-4

benzoyl chloride

benzylamine
100-46-9

benzylamine

N-benzylbenzamide
1485-70-7

N-benzylbenzamide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;100%
With sodium hydroxide In 1,2-dimethoxyethane; water at 25℃; for 0.5h; pH 10.45;99%
Stage #1: benzoyl chloride; benzylamine With triethylamine In dichloromethane at 20℃; for 0.333333h;
Stage #2: With poly{trans-bicyclo[2.2.1]hept-5-ene-2,3-di(chlorocarbonyl)} In dichloromethane at 20℃; for 0.5h;
99%
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

benzylamine
100-46-9

benzylamine

1-benzyl-3-phenylthiourea
726-25-0

1-benzyl-3-phenylthiourea

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h;100%
In acetonitrile at 25℃; for 0.166667h; Milling;99%
With C64H52CaN6 In neat (no solvent) at 60℃; for 12h; Schlenk technique; Glovebox; Inert atmosphere;98%
benzylamine
100-46-9

benzylamine

N-benzylformamide
6343-54-0

N-benzylformamide

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate In toluene for 2h; Concentration; Reflux;100%
With H-β-zeolite In neat (no solvent) at 80℃; for 24h; Green chemistry;99%
at 20 - 120℃; for 15h;99%
isobutyraldehyde
78-84-2

isobutyraldehyde

benzylamine
100-46-9

benzylamine

isobutylidenebenzylamine
22483-21-2

isobutylidenebenzylamine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; Inert atmosphere;100%
With aluminum oxide at 20℃; for 7h;90%
In water Condensation;65.12%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

benzylamine
100-46-9

benzylamine

3-benzylamino-propionic acid methyl ester
23574-01-8

3-benzylamino-propionic acid methyl ester

Conditions
ConditionsYield
at -40℃; for 12h;100%
With [HP(HNCH2CH2)3N]NO3 In acetonitrile at 20℃; for 48h; Michael addition;98%
copper In methanol at 20℃; for 0.3h; Aza-Michael Addition;98%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

benzylamine
100-46-9

benzylamine

bis(2-methoxycarbonylethyl)benzylamine
793-19-1

bis(2-methoxycarbonylethyl)benzylamine

Conditions
ConditionsYield
In methanol at 20℃; for 8h; Reflux;100%
In methanol Reflux;99%
In methanol at 34℃; for 72h; Inert atmosphere;99%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

benzylamine
100-46-9

benzylamine

N-benzyl-2-chloroacetamide
2564-06-9

N-benzyl-2-chloroacetamide

Conditions
ConditionsYield
In dichloromethane100%
With triethylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;98%
With potassium carbonate In dichloromethane Heating;97%
2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

benzylamine
100-46-9

benzylamine

N-benzyl-2-bromoacetamide
2945-03-1

N-benzyl-2-bromoacetamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 2h;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 16h;99%
In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;98%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

benzylamine
100-46-9

benzylamine

N-benzylbenzenesulfonamide
837-18-3

N-benzylbenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane 1) 0 deg C, 1 h, 2) room temperature;100%
With sodium hydroxide In water at 25℃; for 2h; pH 9.6;99.9%
With Fe3O4-supported (diisopropylamino)acetamide In dichloromethane at 25℃;98%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

benzylamine
100-46-9

benzylamine

N-benzyl-p-toluenesulfonamide
1576-37-0

N-benzyl-p-toluenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 4℃;100%
With pyridine; dmap In dichloromethane at 0 - 20℃; for 16h;99%
With triethylamine at 20℃; for 1h; Inert atmosphere;99%
benzyl isothiocyanate
3173-56-6

benzyl isothiocyanate

benzylamine
100-46-9

benzylamine

1,3-dibenzylurea
1466-67-7

1,3-dibenzylurea

Conditions
ConditionsYield
In tetrahydrofuran at 10 - 35℃; for 16h;100%
In dichloromethane at 5℃; for 0.5h;99%
Multistep reaction;96%
carbon disulfide
75-15-0

carbon disulfide

benzylamine
100-46-9

benzylamine

dibenzyl thiourea
1424-14-2

dibenzyl thiourea

Conditions
ConditionsYield
at 100℃; for 12h; Ionic liquid; Green chemistry;100%
aluminum oxide; zinc(II) oxide at 100℃; for 2h; Condensation;98%
In water at 20℃; for 1.33333h; Solvent; Time; Green chemistry;97%
Benzophenone imine
1013-88-3

Benzophenone imine

benzylamine
100-46-9

benzylamine

benzhydrylidene-benzyl-amine
7699-79-8

benzhydrylidene-benzyl-amine

Conditions
ConditionsYield
In chloroform at 20℃; for 288h;100%
In dichloromethane for 13h; Inert atmosphere; Reflux;98.3%
In dichloromethane for 13h; Reflux; Inert atmosphere;95.3%
formic acid
64-18-6

formic acid

benzylamine
100-46-9

benzylamine

N-benzylformamide
6343-54-0

N-benzylformamide

Conditions
ConditionsYield
With sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; ethyl cyanoglyoxylate-2-oxime In water; N,N-dimethyl-formamide at 20℃; for 3h; Reagent/catalyst; Solvent;100%
With 4-methyl-morpholine; dmap; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane at 35℃; for 0.1h; microwave irradiation;99%
With sulfated tungstate at 70℃; for 0.166667h; Neat (no solvent);99%
diethyl meso-2,5-dibromoadipate
54221-37-3

diethyl meso-2,5-dibromoadipate

benzylamine
100-46-9

benzylamine

diethyl meso-1-benzyl-2,5-pyrrolidinedicarboxylate
17740-40-8

diethyl meso-1-benzyl-2,5-pyrrolidinedicarboxylate

Conditions
ConditionsYield
In toluene for 4h; Reflux;100%
2-methylenesuccinic acid
97-65-4

2-methylenesuccinic acid

benzylamine
100-46-9

benzylamine

1-benzyl-5-oxopyrrolidine-3-carboxylic acid
5733-86-8

1-benzyl-5-oxopyrrolidine-3-carboxylic acid

Conditions
ConditionsYield
at 130℃; Inert atmosphere;100%
86%
at 130℃; for 2.5h; Inert atmosphere;82.9%

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100-46-9Relevant articles and documents

Preparation and characterization of primary amines by potassium borohydride-copper chloride system from nitriles

Jiang, Han,Hu, Jialei,Xu, Xinliang,Zhou, Yifeng

, p. 3564 - 3566 (2015)

Nitriles undergo reduction to primary amines under optimized conditions at 50 °C using 0.25 equiv of copper chloride and 3.0 equiv of potassium borohydride in 80 % isopropanol. The aromatic and aralkyl nitriles could be effectively reduced in yield ranging from 60 to 90 %.

Electronic Effect of Ruthenium Nanoparticles on Efficient Reductive Amination of Carbonyl Compounds

Komanoya, Tasuku,Kinemura, Takashi,Kita, Yusuke,Kamata, Keigo,Hara, Michikazu

, p. 11493 - 11499 (2017)

Highly selective synthesis of primary amines over heterogeneous catalysts is still a challenge for the chemical industry. Ruthenium nanoparticles supported on Nb2O5 act as a highly selective and reusable heterogeneous catalyst for the low-temperature reductive amination of various carbonyl compounds that contain reduction-sensitive functional groups such as heterocycles and halogens with NH3 and H2 and prevent the formation of secondary amines and undesired hydrogenated byproducts. The selective catalysis of these materials is likely attributable to the weak electron-donating capability of Ru particles on the Nb2O5 surface. The combination of this catalyst and homogeneous Ru systems was used to synthesize 2,5-bis(aminomethyl)furan, a monomer for aramid production, from 5-(hydroxymethyl)furfural without a complex mixture of imine byproducts.

A Mild and Base-Free Protocol for the Ruthenium-Catalyzed Hydrogenation of Aliphatic and Aromatic Nitriles with Tridentate Phosphine Ligands

Adam, Rosa,Bheeter, Charles Beromeo,Jackstell, Ralf,Beller, Matthias

, p. 1329 - 1334 (2016)

A novel protocol for the general hydrogenation of nitriles in the absence of basic additives is described. The system is based on the combination of [Ru(cod)(methylallyl)2] (cod=cyclooctadiene) and L2. A variety of aromatic and aliphatic nitriles is hydrogenated under mild conditions (50 °C and 15 bar H2) with this system. Kinetic studies revealed higher activity in the case of aromatic nitriles compared with aliphatic ones.

Total synthesis of capsaicin analogues from lignin-derived compounds by combined heterogeneous metal, organocatalytic and enzymatic cascades in one pot

Anderson, Mattias,Afewerki, Samson,Berglund, Per,Cordova, Armando

, p. 2113 - 2118 (2014)

The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillylamine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using L-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.

Tandem dehydrogenation of ammonia borane and hydrogenation of nitro/nitrile compounds catalyzed by graphene-supported NiPd alloy nanoparticles

Goeksu, Haydar,Ho, Sally Fae,Metin, Oender,Korkmaz, Katip,Mendoza Garcia, Adriana,Gueltekin, Mehmet Serdar,Sun, Shouheng

, p. 1777 - 1782 (2014)

We report a facile synthesis of monodisperse NiPd alloy nanoparticles (NPs) and their assembly on graphene (G) to catalyze the tandem dehydrogenation of ammonia borane (AB) and hydrogenation of R-NO2 and/or R-CN to R-NH2 in aqueous methanol solutions at room temperature. The 3.4 nm NiPd alloy NPs were prepared by coreduction of nickel(II) acetate and palladium(II) acetlyacetonate by borane-tert-butylamine in oleylamine and deposition on G via a solution phase self-assembly process. G-NiPd showed composition-dependent catalysis on the tandem reaction with G-Ni 30Pd70 being the most active. A variety of R-NO 2 and/or R-CN derivatives were reduced selectively into R-NH 2 via G-Ni30Pd70 catalyzed tandem reaction in 5-30 min reaction time with the conversion yields reaching up to 100%. Our study demonstrates a new approach to G-NiPd-catalyzed dehydrogenation of AB and hydrogenation of R-NO2 and R-CN. The G-NiPd NP catalyst is efficient and reusable, and the reaction can be performed in an environment-friendly process with short reaction times and high yields.

A Pd/CeO2 “H2 Pump” for the Direct Amination of Alcohols

Yan, Zhen,Tomer, Ajay,Perrussel, Gaetan,Ousmane, Mohamad,Katryniok, Benjamin,Dumeignil, Franck,Ponchel, Anne,Liebens, Armin,Pera-Titus, Marc

, p. 3347 - 3352 (2016)

A Pd/CeO2 catalyst with a prominent reversible H2 storage capacity revealed a high activity and selectivity in the direct amination of benzyl alcohol with aniline and ammonia via the borrowing hydrogen mechanism.

Synthesis of new Copper Catalyst with Pyrazole Based Tridentate Ligand and Study of Its Activity for Azide Alkyne Coupling

Rajeswari, Panneer Selvam,Nagarajan, Rajendran,P, Sujith K,Emmanuvel, Lourdusamy

, (2021)

Synthesis of new copper catalyst with pyrazole based tridentate ligand and study of its activity for azide alkyne coupling were investigated by researchers. To a solution of acetyl acetone (2.002 g, 20 mmol), 2- nitrophenylhydrazine in ethanol was added five drops of con. HCl and heated at 50° for 1 hour. After confirming the formation of 3, 5-dimethyl-1-(2-nitrophenyl)- 1H-pyrazole by TLC, ice cooled water was added in to the reaction mixture. The precipitate was filtered, washed with water and then hexane. The product formed as yellow precipitate, that precipitate had been filtered by normal filter paper. The product was recrystallized in ethanol. For synthesis, was suspended in 6 mL of deionized and stirred for 4 h until a clear solution was obtained in 50 ml round bottom flask Cu(OAc) 2. The reaction mixture was diluted with water, filtered, washed sequentially with water, methanol and n-hexane. Then dark greenish blue color crystal were formed and used for the reactions. The solid was crystallized in CH2Cl2 to get crystal whose structure was confirmed by single crystal XRD.

The reduction of aromatic oximes to amines with borohydride exchange resin-nickel acetate system

Bandgar,Nikat,Wadgaonkar

, p. 863 - 869 (1995)

Aromatic oximes were reduced to the corresponding amines with borohydride supported on an ion exchange resin (BER)- nickel acetate in methanol in good yields. The isolation of pure products by simple filtration and evaporation is an important feature of this method.

Reduction of Azides to Amines with Sodium Borohydride in Tetrahydrofuran with Dropwise Addition of Methanol

Soai, Kenso,Yokoyama, Shuji,Ookawa, Atsuhiro

, p. 48 - 49 (1987)

Azidoalkanes, azidoarenes, and tosyl azide are reduced to the corresponding amines or p-toluenesulfonamide, respectively, by reaction with sodium borohydride in tetrahydrofuran with dropwise addition of small amounts of methanol.

Platinum-(phosphinito-phosphinous acid) complexes as bi-talented catalysts for oxidative fragmentation of piperidinols: An entry to primary amines

Membrat, Romain,Vasseur, Alexandre,Moraleda, Delphine,Michaud-Chevallier, Sabine,Martinez, Alexandre,Giordano, Laurent,Nuel, Didier

, p. 37825 - 37829 (2019)

Platinum-(phosphinito-phosphinous acid) complex catalyzes the oxidative fragmentation of hindered piperidinols according to a hydrogen transfer induced methodology. This catalyst acts successively as both a hydrogen carrier and soft Lewis acid in a one pot-two steps process. This method can be applied to the synthesis of a wide variety of primary amines in a pure form by a simple acid-base extraction without further purification.

Pyridonate-Supported Titanium(III). Benzylamine as an Easy-To-Use Reductant

Chong, Eugene,Xue, Wei,Storr, Tim,Kennepohl, Pierre,Schafer, Laurel L.

, p. 4941 - 4945 (2015)

The reaction of bis(3-phenyl-2-pyridonate)Ti(NMe2)2 with excess benzylamine leads to an unexpected reduction of the metal center from Ti(IV) to Ti(III). The reduced titanium species was isolated and revealed as tris(3-phenyl-2-pyrido

Mild catalytic deoxygenation of amides promoted by thorium metallocene

Eisen, Moris S.,Saha, Sayantani

, p. 12835 - 12841 (2020)

The organoactinide-catalyzed (Cp*2ThMe2) hydroborated reduction of a wide range of tertiary, secondary, and primary amides to the corresponding amines/amine-borane adductsviadeoxygenation of the amides is reported herein. The catalytic reactions proceed under mild conditions with low catalyst loading and pinacolborane (HBpin) concentration in a selective fashion. Cp*2ThMe2is capable of efficiently catalysing the gram-scale reaction without a drop in efficiency. The amine-borane adducts are successfully converted into free amine products in high conversions, which increases the usefulness of this catalytic system. A plausible mechanism is proposed based on detailed kinetics, stoichiometric, and deuterium labeling studies.

Molecular Addition Compounds. 11. N-Ethyl-N-isopropylaniline-Borane, a Superior Reagent for Hydroborations and Reductions

Brown, Herbert C.,Kanth, J. V. Bhaskar,Zaidlewicz, Marek

, p. 5154 - 5163 (1998)

Hydroboration studies with a new, highly reactive amine-borane adduct, H3B-NPhEtPri, and representative olefins, such as 1-hexene, styrene, β-pinene, cyclopentene, norbornene, cyclohexene, 2-methyl-2-butene, α-pinene, and 2,3-dimethyl-2-butene, in tetrahydrofuran, dioxane, tert-butyl methyl ether, n-pentane, and dichloromethane, at room temperature (22 ± 3°C) were carried out. The reactions are faster in dioxane, requiring 0.5-1 h for the hydroboration of simple, unhindered olefins to the trialkylborane stage. Moderately hindered olefins, such as cyclohexene and 2-methyl-2-butene, give the corresponding dialkylboranes rapidly, with further hydroboration slow. However, the hindered α-pinene and 2,3-dimethyl-2-butene structures give stable monoalkylboranes very rapidly, with further hydroboration proceeding relatively slowly. The hydroborations can also be carried out in other solvents, such as THF, tert-butyl methyl ether, and n-pentane. A significant rate retardation is observed in dichloromethane. Regioselectivity studies in the hydroboration of 1-hexene, styrene, and allyl chloride with H3B-NPhEtPri in selected solvents were made. The selectivities are similar to those reported for BH3-THF with 1-hexene and styrene, whereas some differences were noted for allyl chloride. The alkylboranes obtained after hydroboration were oxidized with hydrogen peroxide/sodium hydroxide, and the product alcohols were obtained in quantitative yields, as established by GC analysis. The rates and stoichiometry of the reaction of H3B-NPhEtPri in tetrahydrofuran with selected organic compounds containing representative functional groups were examined at room temperature. Simple aldehydes, ketones, carboxylic acids, and aliphatic esters were reduced to the alcohol stage. Acid chlorides, anhydrides, and aromatic carboxylic esters were unreactive under similar conditions. Imines, tertiary amides, and nitriles were reduced to the corresponding amines. However, primary and secondary amides and nitro compounds were not reduced under these conditions. The reduction of esters, amides, and nitriles, which exhibit a sluggish reaction at room temperature, proceeds readily under reflux conditions in tetrahydrofuran and dioxane and also without solvent (at 85-90°C). The carrier amine was recovered by simple acid-base manipulations in good yield and can be readily recycled to make the borane adduct.

A Mild and Convenient Reduction of Aromatic and Heteroaromatic Aldoximes with Ammonium Formate/Pd

Kaczmarek, Lukasz,Balicki, Roman

, p. 695 - 697 (1994)

-

The efficient solvent-free reduction of oximes to amines with NaBH3CN catalyzed by ZrCl4/nano Fe3O4 system

Sadighnia, Leila,Zeynizadeh, Behzad

, p. 873 - 878 (2015)

Reduction of various aldoximes and ketoximes to the corresponding amines was carried out easily and efficiently with NaBH3CN in the presence of ZrCl4/nano Fe3O4 system. The reactions were carried out under solvent-free conditions at room temperature or 75-80°C to afford amines in high to excellent yields.

Reductions of aliphatic and aromatic nitriles to primary amines with diisopropylaminoborane

Haddenham, Dustin,Pasumansky, Lubov,DeSoto, Jamie,Eagon, Scott,Singaram, Bakthan

, p. 1964 - 1970 (2009)

Diisopropylaminoborane [BH2Nf)Pr)2] in the presence of a catalytic amount of lithium borohydride (LiBH4) reduces a large variety of aliphatic and aromatic nitriles in excellent yields. BH 2NOPr)2 can be prepared by two methods: first by reacting diisopropylamineborane [(iPr)2N)BH3] with 1.1 equiv of n-butylhthium (n-BuLi) followed by methyl iodide (MeI), or reacting iPrN:BH 3 with 1 equiv of n-BuLi followed by trimethylsilyl chloride (TMSCl). BH2N(ZPr)2 prepared with MeI was found to reduce benzonitriles to the corresponding benzylamines at ambient temperatures, whereas diisopropylaminoborane prepared with TMSCl does not reduce nitriles unless a catalytic amount of a lithium ion source, such as LiBH4 or lithium tetraphenylborate (LiBPh4), is added to the reaction. The reductions of benzonitriles with one or more electron-withdrawing groups on the aromatic ring generally occur much faster with higher yields. For example, 2,4-dichlorobenzonitrile was successfully reduced to 2,4-dichlorobenzylamine in 99% yield after 5 h at 25 °C. On the other hand, benzonitriles containing electron-donating groups on the aromatic ring require refluxing in tetrahydrofuran (THF) for complete reduction. For instance, 4- methoxybenzonitrile was successfully reduced to 4-methoxybenzylamine in 80% yield. Aliphatic nitriles can also be reduced by the BH2N(iPr) 2/cat. LiBH4 reducing system. Benzyl cyanide was reduced to phenethylamine in 83% yield. BH2NOPr)2 can also reduce nitriles in the presence of unconjugated alkenes and alkynes such as the reduction of 2-hexynenitrile to hex-5-yn-l-amine in 80% yield. Unfortunately, selective reduction of a nitrile in the presence of an aldehyde is not possible as aldehydes are reduced along with the nitrile. However, selective reduction of the nitrile group at 25 °C in the presence of an ester is possible as long as the nitrile group is activated by an electron-withdrawing substituent. It should be pointed out that lithium aminoborohydrides (LABs) do not reduce nitriles under ambient conditions and behave as bases with aliphatic nitriles as well as nitriles containing acidic a-protons. Consequently, both LABs and BH2NOPr)2 are complementary to each other and offer methods for the selective reductions of multifunctional compounds.

Reduction of aromatic nitriles into aldehydes using calcium hypophosphite and a nickel precursor

Mouselmani, Rim,Hachem, Ali,Alaaeddine, Ali,Métay, Estelle,Lemaire, Marc

, p. 6600 - 6605 (2018)

Herein we report the reduction of aromatic nitriles into aldehydes with calcium hypophosphite in the presence of base and nickel(ii) complex in a water/ethanol mixture. This catalytic system reduced efficiently a series of aromatic nitriles bearing different functional groups such as -Cl, -CF3, -Br, -CH3, -OCH3, -COOCH2CH3, -OH and -CHO. The corresponding aldehydes were isolated in moderate to excellent yields (30-94%).

Catalytic Activity of Polynuclear Platinum Carbonyl Anions in Homogeneous Hydrogenation Reactions

Bhaduri, Sumit,Sharma, Krishna R.

, p. 727 - 732 (1982)

The homogeneous hydrogenation of benzaldehyde, heptanal, cyclohexanone, cyclohexene, acetonitrile, and benzonitrile has been studied using n4>2 (1) as the catalyst over a range of temperature (40-80 deg C) and pressure (20-64 lbf in-2).Infrared spectroscopic studies suggest the formation of a common intermediate in reactions carried out at >=60 deg C.Benzaldehyde is the most readily hydrogenated; the nature of the products depends on the pressure of hydrogen used and is selective to either benzyl alcohol or a mixture of benzene and methanol.Kinetic studies on the rate of benzyl alcohol formation indicate a first-order dependence of the rate on the concentration of (1).While the rate shows a Michaelis-Menten type of dependence on the PhCHO concentration, it seems to be independent of H2 pressure in the range 20-25 lbf in-2.Under these conditions, a value of 63.81 kJ mol-1 for the activation energy is obtained from the Arrhenius plot.A tentative mechanism for PhCHO hydrogenation is discussed.

A novel, chemoselective and efficient production of amines from azides using ZrCl4/NaBH4

Purushothama Chary,Raja Ram,Salahuddin,Iyengar

, p. 3559 - 3563 (2000)

A practical and cheaper reagent system ZrCl4/NaBH4 is used for the production of amines from azides is described.

Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Cobalt Pincer Complex

Mukherjee, Arup,Srimani, Dipankar,Chakraborty, Subrata,Ben-David, Yehoshoa,Milstein, David

, p. 8888 - 8891 (2015)

The catalytic hydrogenation of nitriles to primary amines represents an atom-efficient and environmentally benign reduction methodology in organic chemistry. This has been accomplished in recent years mainly with precious-metal-based catalysts, with a single exception. Here we report the first homogeneous Co-catalyzed hydrogenation of nitriles to primary amines. Several (hetero)aromatic, benzylic, and aliphatic nitriles undergo hydrogenation to the corresponding primary amines in good to excellent yields under the reaction conditions.

Pd/C(en) catalyzed chemoselective hydrogenation in the presence of aryl nitriles

Maegawa, Tomohiro,Fujita, Yuki,Sakurai, Ai,Akashi, Akira,Sato, Mutsumi,Oono, Keiji,Sajiki, Hironao

, p. 837 - 839 (2007)

Aromatic nitriles are not only important components of natural products, pharmaceuticals, herbicides and agrochemicals but also a synthetic equivalent of various functionalities. The development of synthetic methods of aromatic nitriles have been increasing in terms of its usefulness. Since aromatic nitriles are susceptible to the hydrogenation, it has been desired for the development of chemoselective hydrogenation method with retention of nitrile groups. Pd/C is one of the most popular catalysts for hydrogenation and many of reducible functional groups such as multiple bonds, benzyl ethers, N-Cbzs, nitro groups and so on could be easily reduced under the conditions. Therefore, it is very difficult to achieve the chemoselective hydrogenation of substrates containing two or more reducible functional groups. We have found that a Pd/C catalyst formed an isolable complex with ethylenediamine (en) employed as catalytic poison, and the complex [Pd/C(en)] catalyzed chemoselective hydrogenation of a variety of reducible functionalities distinguishing O-benzyl, N-Cbz and O-TBDMS protective groups, benzyl alcohols and epoxides. In the course of these investigations, we found the aryl nitriles could survive under the Pd/C(en)-catalyzed hydrogenation conditions in THF whose choice is important for the effective suppression. This methodology could be applied to the selective hydrogenation of alkene and alkyne functionalities in the presence of aromatic nitrile.

Schultz,Gmelin

, p. 342,346 (1954)

Dimethylethylamine-Alane and N-Methylpyrrolidine-Alane. A Convenient Synthesis of Alane, a Useful Selective Reducing Agent in Organic Synthesis

Marlett, Everett M.,Park, Won Suh

, p. 2968 - 2969 (1990)

-

An Efficient Ruthenium Catalyst Bearing Tetradentate Ligand for Hydrogenations of Carbon Dioxide

Zhang, Feng-Hua,Liu, Chong,Li, Wei,Tian, Gui-Long,Xie, Jian-Hua,Zhou, Qi-Lin

, p. 1000 - 1002 (2018)

A ruthenium complex with a tetradentate bipyridine ligand was proved to be a highly efficient catalyst for the conversions of CO2. Turnover numbers up to 300 000, 9800, and 2100 were achieved for the hydrogenations of CO2 to formamides, formamides to methanol and amines, and the direct hydrogenation of CO2 to methanol, respectively.

Magnesium-Catalyzed Proficient Reduction of Oximes to Amines Using Ammonium Formate

Abiraj,Gowda, D. Channe

, p. 599 - 605 (2004)

Various aldoximes and ketoximes were selectively reduced to the corresponding amines by catalytic transfer hydrogenation employing low cost magnesium powder and ammonium formate at room temperature. Many other functionalities such as halogens, -OH, -OCH3, -COOH and -CH 3 remained unaffected. The hydrogenation is fast, mild, clean, cost effective and high yielding.

2-(4-Nitrophenyl)-1H-indolyl-3-methyl Chromophore: A Versatile Photocage that Responds to Visible-light One-photon and Near-infrared-light Two-photon Excitations

Abe, Manabu,Guo, Runzhao,Hamao, Kozue,Lin, Qianghua,Takagi, Ryukichi

supporting information, p. 153 - 156 (2022/02/14)

Due to cell damage caused by UV light, photoremovable protecting groups (PPGs) that are removed using visible or near-infrared light are attracting attention. A 2-(4-nitrophenyl)- 1H-indolyl-3-methyl chromophore (NPIM) was synthesized as a novel PPG. Various compounds were caged using this PPG and uncaged using visible or near-infrared light. Low cytotoxicity of NPIM indicates that it may be applied in physiological studies.

Device and production method for continuously generating 2-chloro-5-trifluoromethylpyridine

-

Paragraph 0018, (2021/03/11)

The invention relates to a device for continuously generating 2-chloro-5-trifluoromethylpyridine. The invention also discloses a production method for continuously generating 2-chloro-5-trifluoromethylpyridine. Benzyl chloride is used as a raw material, a

Mechanically Strong Heterogeneous Catalysts via Immobilization of Powderous Catalysts to Porous Plastic Tablets

Li, Tingting,Xu, Bo

supporting information, p. 2673 - 2678 (2021/08/03)

Main observation and conclusion: We describe a practical and general protocol for immobilization of heterogeneous catalysts to mechanically robust porous ultra-high molecular weight polyethylene tablets using inter-facial Lifshitz-van der Waals Interactions. Diverse types of powderous catalysts, including Cu, Pd/C, Pd/Al2O3, Pt/C, and Rh/C have been immobilized successfully. The immobilized catalysts are mechanistically robust towards stirring in solutions, and they worked well in diverse synthetic reactions. The immobilized catalyst tablets are easy to handle and reused. Moreover, the metal leaching of immobilized catalysts was reduced significantly.

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