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6935-27-9 Usage

Chemical Properties

white to off-white powder

Uses

2-(Benzylamino)pyridine is used as a reactant in the amination of aryl chlorides, bromides, and triflates catalyzed by palladium complexes.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 91, 1963The Journal of Organic Chemistry, 67, p. 4965, 2002 DOI: 10.1021/jo020057z

General Description

2-Benzylaminopyridine on reaction with BBr3 yields the corresponding amino or hydroxy substituted compounds. It forms 5- and 6-coordinated organometallic complexes of gallium(III) and indium(III).

Check Digit Verification of cas no

The CAS Registry Mumber 6935-27-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,9,3 and 5 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 6935-27:
(6*6)+(5*9)+(4*3)+(3*5)+(2*2)+(1*7)=119
119 % 10 = 9
So 6935-27-9 is a valid CAS Registry Number.
InChI:InChI=1/C12H12N2/c1-2-6-11(7-3-1)10-14-12-8-4-5-9-13-12/h1-9H,10H2,(H,13,14)

6935-27-9 Well-known Company Product Price

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  • Alfa Aesar

  • (B22441)  2-Benzylaminopyridine, 98%   

  • 6935-27-9

  • 50g

  • 256.0CNY

  • Detail
  • Alfa Aesar

  • (B22441)  2-Benzylaminopyridine, 98%   

  • 6935-27-9

  • 250g

  • 995.0CNY

  • Detail
  • Alfa Aesar

  • (B22441)  2-Benzylaminopyridine, 98%   

  • 6935-27-9

  • 1000g

  • 2988.0CNY

  • Detail
  • Aldrich

  • (195057)  2-Benzylaminopyridine  98%

  • 6935-27-9

  • 195057-50G

  • 267.93CNY

  • Detail

6935-27-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Benzylaminopyridine

1.2 Other means of identification

Product number -
Other names 2-Pyridinamine, N-(phenylmethyl)-

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:6935-27-9 SDS

6935-27-9Synthetic route

2-aminopyridine
504-29-0

2-aminopyridine

benzyl alcohol
100-51-6

benzyl alcohol

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With dichloro-[1,3-bis(4-tert-butylbenzyl)perhydrobenzimidazol-2-ylidene](p-cymene)ruthenium(II); potassium tert-butylate at 120℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube;100%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 24h;99%
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;99%
2-chloropyridine
109-09-1

2-chloropyridine

benzylamine
100-46-9

benzylamine

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With sodium t-butanolate In toluene at 100 - 110℃; for 24h; Buchwald-Hartwig amination; Inert atmosphere; Sealed vial;99%
With potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation;95%
With copper(l) iodide; C14H16N2O; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere; Sealed tube;93%
2-iodopyridine
5029-67-4

2-iodopyridine

benzylamine
100-46-9

benzylamine

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With cesium acetate; copper In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;99%
With copper(l) iodide; 1-tetralone oxime; potassium hydroxide In water at 25℃; for 18h; Sealed tube; Inert atmosphere; Green chemistry;93%
With tetra(n-butyl)ammonium hydroxide; copper(II) sulfate In water at 80℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere;80%
With tetramethyl ammoniumhydroxide; ethyl 2-oxocyclohexane carboxylate; copper(l) chloride In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;72%
N-benzylidenepyridin-2-amine
1883-96-1, 82299-15-8, 88785-73-3

N-benzylidenepyridin-2-amine

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With Triethoxysilane; [bis(2,6-diisopropylaniline)acenaphthene]Fe(η6-toluene) at 70℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox; Sealed tube;98%
With (4-Ph)Triaz(NHPiPr2)2Mn(CO)2Br; potassium tert-butylate; hydrogen In tetrahydrofuran at 50℃; under 15001.5 Torr; for 4h; Glovebox; Autoclave; Sealed tube; chemoselective reaction;92%
With sodium tetrahydroborate In tetrahydrofuran at 25℃; for 4h;40%
With sodium tetrahydroborate In methanol for 5h; Cooling;19.09 g
With [MnBr(CO)3(2-(diphenylphosphinoamino)pyridine)]; potassium tert-butylate; hydrogen In ethanol at 80℃; for 48h; Autoclave;50.7 mg
methyl benzylpyridin-2-ylcarbamate
1444866-70-9

methyl benzylpyridin-2-ylcarbamate

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With water; sodium hydroxide In methanol for 3h; Reflux;98%
benzyl-pyridin-2-yl-carbamic acid tert-butyl ester
442513-39-5

benzyl-pyridin-2-yl-carbamic acid tert-butyl ester

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane; water97%
With trifluoroacetic acid In dichloromethane; water at 25℃;
2-bromo-pyridine
109-04-6

2-bromo-pyridine

benzylamine
100-46-9

benzylamine

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With dibenzylphosphoramidous acid 1,1'-binaphthyl-2,2'-diyl ester; caesium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 90℃; for 36h;97%
With copper(l) iodide; 1-tetralone oxime; potassium hydroxide In water at 65℃; for 18h; Sealed tube; Inert atmosphere; Green chemistry;95%
With cesium acetate; copper In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;92%
N-benzyl-N-(pyridin-2-yl)hydroxylamine
1335111-43-7

N-benzyl-N-(pyridin-2-yl)hydroxylamine

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 0.5h; Inert atmosphere;97%
2-nitropyridine
15009-91-3

2-nitropyridine

benzyl alcohol
100-51-6

benzyl alcohol

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With [RuCl(CO)(PPh3)(PNS-Me)]; potassium hydroxide In toluene at 100℃; for 12h;96%
With bis(5-chlorosalicylidene)hydrazone binuclear copper(I) complex; potassium hydroxide In toluene at 100℃; for 18h;80%
With aluminum (III) chloride; water In acetonitrile at 20℃; Irradiation;50%
2-aminopyridine
504-29-0

2-aminopyridine

benzaldehyde
100-52-7

benzaldehyde

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 2h;93%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In neat (no solvent) at 150℃; for 0.25h;92%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; thiourea In toluene at 70℃; for 24h;91%
2-aminopyridine
504-29-0

2-aminopyridine

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

A

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

B

N-[(4-chlorophenyl)methyl]pyridin-2-amine
22881-33-0

N-[(4-chlorophenyl)methyl]pyridin-2-amine

Conditions
ConditionsYield
With potassium tert-butylate; copper diacetate In 1,4-dioxane at 130℃; for 24h;A 8%
B 90%
With cesium hydroxide; palladium diacetate In toluene at 150℃; for 12h;A 19%
B 74%
N-(pyridin-2-yl)benzimidamide
4931-08-2

N-(pyridin-2-yl)benzimidamide

benzyl alcohol
100-51-6

benzyl alcohol

A

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

B

benzamide
55-21-0

benzamide

Conditions
ConditionsYield
With potassium hydroxide In toluene at 120℃; for 15h; Schlenk technique; Glovebox; Inert atmosphere; Sealed tube;A 82%
B 94 %Chromat.
N-benzyl-2,2-difluoro-2-(pyridin-2-ylsulfonyl)acetamide

N-benzyl-2,2-difluoro-2-(pyridin-2-ylsulfonyl)acetamide

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 60℃; for 3h; Julia-Kocienski Olefination;80%
2-<α-(p-tolylthio)benzylamino>pyridine
78508-26-6

2-<α-(p-tolylthio)benzylamino>pyridine

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,2-dimethoxyethane for 1h; Heating;75%
1-[benzyl(pyridin-2-yl)amino]pyridinium bromide

1-[benzyl(pyridin-2-yl)amino]pyridinium bromide

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With acetic acid; zinc at 20℃; for 29h; Reduction;75%
2-aminopyridine
504-29-0

2-aminopyridine

N-butylamine
109-73-9

N-butylamine

benzyl alcohol
100-51-6

benzyl alcohol

A

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

B

N-benzylidenebutan-1-amine
1077-18-5

N-benzylidenebutan-1-amine

Conditions
ConditionsYield
With iron(II,III) oxide; potassium tert-butylate In 1,4-dioxane at 90℃; for 168h; Inert atmosphere;A 74%
B 26%
pyridine N-oxide
694-59-7

pyridine N-oxide

benzylamine
100-46-9

benzylamine

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 25℃; for 15h;70%
2-aminopyridine
504-29-0

2-aminopyridine

benzyl bromide
100-39-0

benzyl bromide

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With oxygen; lithium carbonate; copper(II) bis(trifluoromethanesulfonate) In toluene at 100℃; under 760.051 Torr; for 12h; Schlenk technique;62%
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; Inert atmosphere;56%
benzylamine
100-46-9

benzylamine

pyridin-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
202923-80-6

pyridin-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
In dimethyl sulfoxide at 100℃; for 24h;60%
2-aminopyridine
504-29-0

2-aminopyridine

benzylamine
100-46-9

benzylamine

A

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

B

tribenzylamine
620-40-6

tribenzylamine

C

dibenzylamine
103-49-1

dibenzylamine

Conditions
ConditionsYield
With C4F9SO3H at 200℃; for 42h; Yields of byproduct given;A 54%
B n/a
C n/a
2-aminopyridine
504-29-0

2-aminopyridine

toluene
108-88-3

toluene

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With di-tert-butyl peroxide; copper In neat (no solvent) at 120℃; for 12h; Inert atmosphere; Schlenk technique;51%
2-fluoropyridine
372-48-5

2-fluoropyridine

benzylamine
100-46-9

benzylamine

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

Conditions
ConditionsYield
With cesium acetate; copper In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere;50%
In 1-methyl-pyrrolidin-2-one at 150℃; for 0.25h; Flow reactor;
2-aminopyridine
504-29-0

2-aminopyridine

benzyl chloride
100-44-7

benzyl chloride

A

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

B

2-Benzylamino-5-benzylpyridine
137002-80-3

2-Benzylamino-5-benzylpyridine

Conditions
ConditionsYield
1) 180 to 250 deg C, 3 h, 2) 250 deg C, 0.5 h;A 20%
B 41%
2-(Dimethylamino)pyridine
5683-33-0

2-(Dimethylamino)pyridine

benzyl chloride
100-44-7

benzyl chloride

A

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

B

N-benzyl-N-methyl-N-(2-pyridyl)amine
20173-75-5

N-benzyl-N-methyl-N-(2-pyridyl)amine

C

2-Benzylamino-5-benzylpyridine
137002-80-3

2-Benzylamino-5-benzylpyridine

D

2-(N,N-dibenzylamino)pyridine
154424-43-8

2-(N,N-dibenzylamino)pyridine

Conditions
ConditionsYield
at 250℃; for 4h;A 15%
B 21%
C 4.7%
D 19%
benzyl chloride
100-44-7

benzyl chloride

dimethylamino-pyridine hydrochloride

dimethylamino-pyridine hydrochloride

A

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

B

2-amino-5-benzylpyridine
98477-40-8

2-amino-5-benzylpyridine

C

N-benzyl-N-methyl-N-(2-pyridyl)amine
20173-75-5

N-benzyl-N-methyl-N-(2-pyridyl)amine

D

2-(N,N-dibenzylamino)pyridine
154424-43-8

2-(N,N-dibenzylamino)pyridine

Conditions
ConditionsYield
at 250℃; for 4h; Further byproducts given;A 17%
B 4.3%
C 20%
D 14%
benzyl chloride
100-44-7

benzyl chloride

dimethylamino-pyridine hydrochloride

dimethylamino-pyridine hydrochloride

A

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

B

N-benzyl-N-methyl-N-(2-pyridyl)amine
20173-75-5

N-benzyl-N-methyl-N-(2-pyridyl)amine

C

2-Benzylamino-5-benzylpyridine
137002-80-3

2-Benzylamino-5-benzylpyridine

D

2-(N,N-dibenzylamino)pyridine
154424-43-8

2-(N,N-dibenzylamino)pyridine

Conditions
ConditionsYield
at 250℃; for 4h; Further byproducts given;A 17%
B 20%
C 14%
D 12%
2-aminopyridine
504-29-0

2-aminopyridine

benzyl formate
104-57-4

benzyl formate

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

2-aminopyridine
504-29-0

2-aminopyridine

benzoic acid benzyl ester
120-51-4

benzoic acid benzyl ester

A

N-benzyl-2-pyridone
1753-62-4

N-benzyl-2-pyridone

B

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

C

benzamide
55-21-0

benzamide

D

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
at 190 - 200℃; anschliessend Behandeln mit wss. Salzsaeure;
2-aminopyridine
504-29-0

2-aminopyridine

formic acid
64-18-6

formic acid

benzaldehyde
100-52-7

benzaldehyde

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

bis(1,5-cyclooctadiene)diiridium(I) dichloride
12112-67-3

bis(1,5-cyclooctadiene)diiridium(I) dichloride

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

(2-benzylaminopyridine)chloro(1,5-cyclooctadiene)iridium(I)

(2-benzylaminopyridine)chloro(1,5-cyclooctadiene)iridium(I)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 7h;100%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

tetraacetatodiruthenium chloride

tetraacetatodiruthenium chloride

Ru(2+)*Ru(3+)*Cl(1-)*4C6H5CH2NC5H4N(1-)=Ru2(C6H5CH2NC5H4N)4Cl

Ru(2+)*Ru(3+)*Cl(1-)*4C6H5CH2NC5H4N(1-)=Ru2(C6H5CH2NC5H4N)4Cl

Conditions
ConditionsYield
In neat (no solvent) stirring at 120°C, 16h; sublimating excess ligand; repeating heating with fresh benzylaminopyridine; collecting; washing (acetone, methanol, diethyl ether); drying (vac., 80°C); elem. anal.;97%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

benzo[4,5]imidazo[1,2-a]pyridine
245-47-6

benzo[4,5]imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; bis(tertbutylcarbonyloxy)iodobenzene at 25℃; for 7h; Reagent/catalyst; Solvent;97%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

acetyl chloride
75-36-5

acetyl chloride

N-benzyl-N-(pyridin-2-yl)acetamide

N-benzyl-N-(pyridin-2-yl)acetamide

Conditions
ConditionsYield
Stage #1: N-benzylpyridin-2-amine With methylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: acetyl chloride In tetrahydrofuran at 20℃; for 1h;
94%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

S,S-diethyl 2-phenylpropanebis(thioate)

S,S-diethyl 2-phenylpropanebis(thioate)

1-benzyl-3-phenyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate

1-benzyl-3-phenyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate

Conditions
ConditionsYield
In chlorobenzene for 3h; Reflux;93%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

(butane-1-sulfenyl)-dipropyl-borane
2938-91-2

(butane-1-sulfenyl)-dipropyl-borane

(C3H7)2BN(CH2C6H5)(2-C5H4N)
64738-97-2

(C3H7)2BN(CH2C6H5)(2-C5H4N)

Conditions
ConditionsYield
In dichloromethane byproducts: C4H9SH;92%
In dichloromethane byproducts: C4H9SH;92%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

benzyl(5-bromopyridin-2-yl)amine
280116-83-8

benzyl(5-bromopyridin-2-yl)amine

Conditions
ConditionsYield
With dihydrogen peroxide; 1-butylpyridinium bromide; toluene-4-sulfonic acid In 1,2-dimethoxyethane at 80℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Green chemistry; regioselective reaction;91%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

bis(2,4,6-trichlorophenyl) ethylmalonate
15781-72-3

bis(2,4,6-trichlorophenyl) ethylmalonate

anhydro-(1-benzyl-3-ethyl-4-oxo-2-hydroxypyrido[1,2-a]pyrimidinium hydroxide)

anhydro-(1-benzyl-3-ethyl-4-oxo-2-hydroxypyrido[1,2-a]pyrimidinium hydroxide)

Conditions
ConditionsYield
at 180℃; for 0.0833333h; Cyclization;86%
at 160℃; for 0.0666667h; Condensation;70%
formaldehyd
50-00-0

formaldehyd

N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

diphenylphosphane
829-85-6

diphenylphosphane

2-(N-diphenylphosphinomethyl-N-benzyl)aminopyridine
562108-07-0

2-(N-diphenylphosphinomethyl-N-benzyl)aminopyridine

Conditions
ConditionsYield
With acetic acid In toluene at 70 - 80℃; for 6h;86%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

2-aminopyridine
504-29-0

2-aminopyridine

Conditions
ConditionsYield
With sulfuric acid for 24h; Ambient temperature;85%
With 9,10-Dicyanoanthracene In water; acetonitrile Irradiation;75%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

benzyl chloride
100-44-7

benzyl chloride

2-(N,N-dibenzylamino)pyridine
154424-43-8

2-(N,N-dibenzylamino)pyridine

Conditions
ConditionsYield
With sodium amide In toluene83%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

chlorocarbonyl-diazo-acetic acid ethyl ester
57072-87-4

chlorocarbonyl-diazo-acetic acid ethyl ester

N-benzyl-N-(2-pyridinyl)-α-(ethoxycarbonyl)-α-diazoacetamide

N-benzyl-N-(2-pyridinyl)-α-(ethoxycarbonyl)-α-diazoacetamide

Conditions
ConditionsYield
83%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

N-(4-chlorobenzyl)-3-methylpyridin-2-amine

N-(4-chlorobenzyl)-3-methylpyridin-2-amine

A

benzo[4,5]imidazo[1,2-a]pyridine
245-47-6

benzo[4,5]imidazo[1,2-a]pyridine

B

8-methyl-4-chloropyrido[1,2-a]benzimidazole
1445436-82-7

8-methyl-4-chloropyrido[1,2-a]benzimidazole

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; bis(tertbutylcarbonyloxy)iodobenzene at 25℃; for 7h;A 83%
B 79%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

(6R,8R)-(-)-2-chloro-5,6,7,8,-tetrahydro-7,7-dimethyl-[6,8-methanoquinoline]
304857-39-4

(6R,8R)-(-)-2-chloro-5,6,7,8,-tetrahydro-7,7-dimethyl-[6,8-methanoquinoline]

(6R,8R)-(+)-benzyl-(5,6,7,8-tetrahydro-7,7-dimethyl-6,8-methanoquinolin-2-yl)-pyridin-2-yl-amine

(6R,8R)-(+)-benzyl-(5,6,7,8-tetrahydro-7,7-dimethyl-6,8-methanoquinolin-2-yl)-pyridin-2-yl-amine

Conditions
ConditionsYield
With 1,3-bis-(diphenylphosphino)propane; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; tetrabutylammomium bromide In toluene at 100℃; Buchwald-Hartwig amination reaction;81%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

phenylacetylene
536-74-3

phenylacetylene

phenyl-(2-phenylimidazo[1,2-a]pyridin-3-yl)methanone
61122-85-8

phenyl-(2-phenylimidazo[1,2-a]pyridin-3-yl)methanone

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; lithium carbonate; copper(II) bis(trifluoromethanesulfonate) In toluene at 100℃; under 760.051 Torr; for 12h; Schlenk technique;81%
N-benzylpyridin-2-amine
6935-27-9

N-benzylpyridin-2-amine

pivaloyl chloride
3282-30-2

pivaloyl chloride

N-benzyl-N-(pyridin-2-yl)pivalamide
521300-02-7

N-benzyl-N-(pyridin-2-yl)pivalamide

Conditions
ConditionsYield
Stage #1: N-benzylpyridin-2-amine With methylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: pivaloyl chloride In tetrahydrofuran at 20℃; for 1h;
79%

6935-27-9Relevant articles and documents

Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction

-

Paragraph 0086-0091; 0095, (2021/05/29)

The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.

Nickel?Copper bimetallic mesoporous nanoparticles: As an efficient heterogeneous catalyst for N-alkylation of amines with alcohols

Nasresfahani, Zahra,Kassaee, Mohamad Z.

, (2020/10/30)

A bimetallic catalyst (Ni/Cu-MCM-41) is prepared via co-condensation method. The latter is characterized by Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), diffuse reflectance spectroscopy (DRS), and nitrogen adsorption–desorption analysis. Catalytic performance of Ni/Cu-MCM-41 is probed in N-alkylation of amines with alcohols through a hydrogen autotransfer process. Noteworthy, this catalytic system appears very efficient for synthesis of a range of secondary and tertiary amines in good to excellent isolated yields. Moreover, the catalyst is successfully recovered and reused four times without notable decrease in its activity.

Synthesis of an Fe-Pd bimetallic catalyst for: N -alkylation of amines with alcohols via a hydrogen auto-transfer methodology

Wu, Peng-Yu,Lu, Guo-Ping,Cai, Chun

, p. 396 - 404 (2021/01/28)

Hydrogen auto-transfer (HAT) or borrowing hydrogen (BH) methodology which combines dehydrogenation, intermediate reaction and hydrogenation, is recognized as an excellent strategy for one-pot synthesis from an economic and environmental point of view. Although much effort has been made on the development of catalysts for HAT reactions, harsh conditions, external base or large amounts of noble metals are still required in most reported catalysis systems, and thus the exploration of a highly efficient and recyclable heterogeneous catalyst remains meaningful. In this work, a novel bimetallic catalyst, Fe10Pd1/NC500 derived from bimetallic MOF NH2-MIL-101(Fe10Pd1), has been prepared, and the catalyst exhibits superior catalytic performance for the N-alkylation of amines with alcohols via a hydrogen auto-transfer methodology. High yields of the desired products were achieved at 120 °C with an alcohol/amine molar ratio of 2?:?1 and required no external additive or solvent. A distinct enhancement in catalytic performance is observed when compared with monometallic catalysts, which can be ascribed to the "synergistic effects"inside the bimetallic alloys. The N-doped carbon support has been revealed to provide the necessary basicity which avoids the requirement of an external base. Moreover, a wide substrate range and remarkable reusability have been shown by Fe10Pd1/NC500, and this work highlights new possibilities for bimetallic catalysts applied in sustainable chemistry.

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