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104-86-9 Usage

Chemical Properties

clear slightly yellow liquid

Uses

4-Chlorobenzylamine is used as pharmaceutical intermediate.

Check Digit Verification of cas no

The CAS Registry Mumber 104-86-9 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 4 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 104-86:
(5*1)+(4*0)+(3*4)+(2*8)+(1*6)=39
39 % 10 = 9
So 104-86-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H8ClN/c8-7-3-1-6(5-9)2-4-7/h1-4H,5,9H2/p+1

104-86-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A13984)  4-Chlorobenzylamine, 97+%   

  • 104-86-9

  • 5g

  • 229.0CNY

  • Detail
  • Alfa Aesar

  • (A13984)  4-Chlorobenzylamine, 97+%   

  • 104-86-9

  • 25g

  • 762.0CNY

  • Detail
  • Alfa Aesar

  • (A13984)  4-Chlorobenzylamine, 97+%   

  • 104-86-9

  • 100g

  • 2447.0CNY

  • Detail

104-86-9SDS

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 4-Chlorobenzylamine

1.2 Other means of identification

Product number -
Other names Benzenemethanamine, 4-chloro-

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:104-86-9 SDS

104-86-9Synthetic route

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen In ethanol at 130℃; under 7500.75 Torr; for 12h; Autoclave;100%
With ammonia; hydrogen In methanol at 89.84℃; under 30003 Torr; for 3h;98%
With [pentamethylcyclopentadienyl*Ir(N-phenyl-2-pyridinecarboxamidate)Cl]; ammonium formate In methanol at 37℃; for 15h; chemoselective reaction;98%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With [Ru(H)(BH4)(CO)(PPh3)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2 yl)methyl)propylamine)]; hydrogen In isopropyl alcohol at 70℃; for 3h; Inert atmosphere; Autoclave;99%
With ammonia; hydrogen In water; isopropyl alcohol at 80℃; under 15001.5 Torr; for 24h; Autoclave;98%
With C19H34Cl2CoN2P; hydrogen; sodium ethanolate; sodium triethylborohydride In benzene at 135℃; under 22502.3 Torr; for 36h; Autoclave;93%
4-chlorobenzaldoxime
3848-36-0

4-chlorobenzaldoxime

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With (pyridine)(tetrahydroborato)zinc In tetrahydrofuran for 2.8h; Heating;96%
With sodium hydrogensulfate monohydrate; molybdenum(V) chloride; sodium cyanoborohydride In ethanol for 2.2h; Reflux;96%
With sodium tetrahydroborate at 20℃; for 0.0333333h; neat (no solvent, solid phase);95%
4-chlorobenzyl azide
27032-10-6

4-chlorobenzyl azide

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With Amberlite IRA-400; borohydride form; copper(II) sulfate In methanol at 20℃; for 6h; Reduction;94%
With ammonium chloride; zinc In ethanol; water
With hydrogen; palladium In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; under 6080.41 Torr; for 22h; Inert atmosphere;
With formic acid; 2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 40h; Irradiation;84 %Chromat.
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

A

N,N-bis(4-chlorobenzyl)amine
21913-13-3

N,N-bis(4-chlorobenzyl)amine

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In ethanol at 20℃; for 0.0833333h;A 7%
B 85%
With methanol; cobalt(II) chloride; diborane at -10℃; for 0.5h;A 9.4%
B 71.1%
With methanol; cobalt(II) chloride; diborane for 0.5h; Ambient temperature;A 52%
B 27%
1-Chloro-4-(chloromethyl)benzene
104-83-6

1-Chloro-4-(chloromethyl)benzene

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With ammonium hydroxide; potassium dihydrogenphosphate In tert-butyl methyl ether at 20℃; for 0.5h; Reagent/catalyst; Solvent; Autoclave;85%
With hexamethylenetetramine
With hydrogenchloride; potassium hydride; 1,1,3,3-tetramethyldisilazane 1.) THF, 1 h, 0 deg C; 1 h, r.t.; Yield given. Multistep reaction;
With ammonia at 25℃; Kinetics; Activation energy; Temperature;
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

A

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

B

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With potassium hydroxide; samarium diiodide In tetrahydrofuran for 0.0666667h; Ambient temperature;A 6%
B 77%
para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With ammonium hydroxide; C19H37IrN4(2+)*2I(1-) at 170℃; for 100h; Sealed tube;77%
With ammonia In toluene at 110℃; under 5250.53 Torr; for 20h;72%
Multi-step reaction with 2 steps
1: acetic acid; hydrogen bromide / 0.5 h / 0 °C
2: ammonia / ethanol; water / 4 h / 20 °C
View Scheme
2-(4-chloro-benzyl)-1H-isoindole-1,3(2H)-dione
131523-32-5

2-(4-chloro-benzyl)-1H-isoindole-1,3(2H)-dione

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane at 110℃; Gabriel Amine Synthesis; Inert atmosphere;74%
With hydrazine hydrate In ethanol for 3h; Inert atmosphere; Reflux;42%
With hydrazine hydrate In methanol for 1h; Heating;
4-chlorobenzamide
619-56-7

4-chlorobenzamide

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With titanium tetrachloride; magnesium In tetrahydrofuran at 0 - 20℃; Inert atmosphere;72%
With sulfuric acid at 35 - 40℃; Electrolysis.an einer Bleikathode;
With 1,10-Phenanthroline; diethoxymethylane; iron(II) acetate In toluene at 100℃; for 28h; Inert atmosphere; chemoselective reaction;60 %Chromat.
methanol
67-56-1

methanol

4-chlorobenzyl azide
27032-10-6

4-chlorobenzyl azide

A

N,N-dimethyl-4-chlorobenzylamine
15184-98-2

N,N-dimethyl-4-chlorobenzylamine

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

C

N-methyl-4-chlorobenzylamine
104-11-0

N-methyl-4-chlorobenzylamine

Conditions
ConditionsYield
With trans-RuCl(phenpyra-Me)(PPh3)2PF6; sodium hydroxide at 125℃; for 2.5h; Sealed tube; Inert atmosphere; Glovebox;A 5 %Chromat.
B 7 %Chromat.
C 69%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

A

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

B

benzylamine
100-46-9

benzylamine

Conditions
ConditionsYield
With potassium hydroxide; samarium diiodide In tetrahydrofuran for 0.05h; Ambient temperature;A 12%
B 56%
4-vinylbenzyl chloride
1073-67-2

4-vinylbenzyl chloride

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With D-glucose; E. coli LZ220; ammonia; oxygen; ammonium chloride In aq. phosphate buffer at 30℃; for 24h; pH=8; Green chemistry; Enzymatic reaction;47%
N,N-bis(p-chlorobenzylamino)ethane dihydrobromide

N,N-bis(p-chlorobenzylamino)ethane dihydrobromide

A

6‐chloro‐1,2,3,4‐tetrahydroisoquinoline
33537-99-4

6‐chloro‐1,2,3,4‐tetrahydroisoquinoline

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With aluminium trichloride In decalin at 180℃; for 2h;A 45%
B n/a
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

A

N,N-bis(4-chlorobenzyl)amine
21913-13-3

N,N-bis(4-chlorobenzyl)amine

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

C

para-Chlorobenzyl alcohol
873-76-7

para-Chlorobenzyl alcohol

Conditions
ConditionsYield
With nickel dichloride; zinc In methanol for 4h; Heating;A 5%
B 37.4%
C 39.2%
With nickel dichloride; zinc In methanol for 4h; Heating;A 5%
B 37.4%
C 39.2%
(1E, 2E)-1,2-bis (4-chlorobenzylidene) hydrazine
41097-37-4

(1E, 2E)-1,2-bis (4-chlorobenzylidene) hydrazine

A

(1R,2S)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine
86212-34-2, 91044-20-1, 98674-96-5, 74641-30-8

(1R,2S)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

(1R,2R)-1,2-Bis-(4-chloro-phenyl)-ethane-1,2-diamine

(1R,2R)-1,2-Bis-(4-chloro-phenyl)-ethane-1,2-diamine

Conditions
ConditionsYield
With methanesulfonic acid; zinc In tetrahydrofuran at 25℃; for 8h; reduction;A n/a
B 35%
C n/a
With titanium tetrachloride; zinc In tetrahydrofuran at 25℃; for 8h; reduction;A n/a
B 13%
C n/a
4-chlorobenzaldoxime
3848-36-0

4-chlorobenzaldoxime

A

(1R,2S)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine
86212-34-2, 91044-20-1, 98674-96-5, 74641-30-8

(1R,2S)-1,2-bis(4-chlorophenyl)ethane-1,2-diamine

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

(1R,2R)-1,2-Bis-(4-chloro-phenyl)-ethane-1,2-diamine

(1R,2R)-1,2-Bis-(4-chloro-phenyl)-ethane-1,2-diamine

Conditions
ConditionsYield
With methanesulfonic acid; zinc In acetonitrile at 25℃; reduction;A n/a
B 32%
C n/a
With titanium tetrachloride; zinc In tetrahydrofuran at 25℃; reduction;A n/a
B 3%
C n/a
N-(4-chloro-benzyl)-phthalamic acid
17332-59-1

N-(4-chloro-benzyl)-phthalamic acid

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With hydrogenchloride
(4-chloro-benzyl)-hexamethylenetetraminium; chloride
96634-13-8

(4-chloro-benzyl)-hexamethylenetetraminium; chloride

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With hydrogenchloride; methanol
ammonium formate
540-69-2

ammonium formate

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
anschliessenden Behandeln mit wss.HCl;
4-chlorobenzaldehyde-O-methyl oxime
33499-37-5, 54615-09-7, 87861-05-0

4-chlorobenzaldehyde-O-methyl oxime

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
(i) B2H6, THF, (ii) aq. KOH; Multistep reaction;
(E)-N′-(4′-chlorobenzylidene)isonicotinohydrazide
6342-46-7

(E)-N′-(4′-chlorobenzylidene)isonicotinohydrazide

A

pyridine-4-methanol
586-95-8

pyridine-4-methanol

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide Mechanism; polarographic reduction,;
(Z)-p-chlorobenzaldehyde oxime
3717-23-5

(Z)-p-chlorobenzaldehyde oxime

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With tetramethylammonium bromide Mechanism; polarographic reduction at pH=3, other supporting electrolytes; values of diffusion current constant;
4-chlorobenzaldehyde oxime
3717-24-6

4-chlorobenzaldehyde oxime

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With tetramethylammonium bromide Mechanism; polarographic reduction at pH=3, other supporting electrolytes; values of diffusion current constant;
N-(4-chlorobenzyl)acetamide
57058-33-0

N-(4-chlorobenzyl)acetamide

A

acetic acid
64-19-7

acetic acid

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

C

5-(Acetylamino-methyl)-2-chloro-benzenesulfonic acid

5-(Acetylamino-methyl)-2-chloro-benzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid In water at 60 - 92℃; Kinetics; Mechanism; Thermodynamic data; ΔH(excit.), ΔS(excit.);
C7H8ClN*H(1+)

C7H8ClN*H(1+)

C14H13NO
114444-46-1

C14H13NO

A

1-methyl-4-(phenylacetyl)pyridinium cation
124225-44-1

1-methyl-4-(phenylacetyl)pyridinium cation

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
In water at 25℃; Equilibrium constant; Rate constant;
3-amino-4-chlorobenzylamine dihydrochloride
102677-74-7

3-amino-4-chlorobenzylamine dihydrochloride

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With hydrogenchloride; hypophosphorous acid; sodium nitrite 2.) 15 min; Multistep reaction;
C9H12ClNS*ClH
97732-00-8

C9H12ClNS*ClH

A

dimethylsulfide
75-18-3

dimethylsulfide

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With iodide; hydrogen cation In water at 25℃; Rate constant; pH dependence (pH = 0.5-3.0), μ = 1.0 with KCl;
N-(4-chlorobenzyl)-S,S-dimethylsulfilimmonium chloride
97732-00-8

N-(4-chlorobenzyl)-S,S-dimethylsulfilimmonium chloride

A

dimethylsulfide
75-18-3

dimethylsulfide

B

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Conditions
ConditionsYield
With 3-nitro-5-thiobenzoic acid; hydrogen cation In water at 25℃; Rate constant; var. reductant thiol anions, ionic strength: μ = 1.0 with KCl, catalytic constants for buffer, leaving group effects;
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

4-Ethoxy-2,3,5,6,7,8-hexahydro-chinazolin-2-on
98077-17-9

4-Ethoxy-2,3,5,6,7,8-hexahydro-chinazolin-2-on

4-(4-Chlor-benzylamino)-2,3,5,6,7,8-hexahydrochinazolin-2-on

4-(4-Chlor-benzylamino)-2,3,5,6,7,8-hexahydrochinazolin-2-on

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 20.5h; Heating;100%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-(4-chlorobenzylidene)-4-chlorobenzylamine
31264-06-9

N-(4-chlorobenzylidene)-4-chlorobenzylamine

Conditions
ConditionsYield
With oxygen; methylene blue; potassium carbonate In acetonitrile at 20℃; for 10h; Irradiation; Green chemistry;100%
With oxygen at 100℃; for 8h; Time; Schlenk technique;99%
With oxygen; 2Co(2+)*2C12H6O4(2-)*C34H12Cl4N4O4*4C3H7NO In N,N-dimethyl-formamide at 40℃; for 6h; Irradiation;99%
1-(3-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

1-(3-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-(4-chlorobenzyl)-1-(3-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide
694479-04-4

N-(4-chlorobenzyl)-1-(3-methylphenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V); diisopropylamine In dichloromethane at 20℃; for 1h;100%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-[(tert-butoxy)carbonyl]-N-(2-oxo-3-phenylpropyl)glycine
305324-43-0

N-[(tert-butoxy)carbonyl]-N-(2-oxo-3-phenylpropyl)glycine

4-[(tert-butoxy)carbonyl]-1-[(4-chlorophenyl)methyl]-6-(phenylmethyl)piperazin-2-one
305324-50-9

4-[(tert-butoxy)carbonyl]-1-[(4-chlorophenyl)methyl]-6-(phenylmethyl)piperazin-2-one

Conditions
ConditionsYield
Stage #1: 4-chlorobenzylamine; N-[(tert-butoxy)carbonyl]-N-(2-oxo-3-phenylpropyl)glycine With sodium tris(acetoxy)borohydride; acetic acid at 25℃; Condensation;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; Cyclization;
100%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-[(tert-butoxy)carbonyl]-N-(2-oxo-4-phenylbutyl)glycine
305324-44-1

N-[(tert-butoxy)carbonyl]-N-(2-oxo-4-phenylbutyl)glycine

4-[(tert-butoxy)carbonyl]-1-[(4-chlorophenyl)methyl]-6-(2-phenylethyl)piperazin-2-one
305324-55-4

4-[(tert-butoxy)carbonyl]-1-[(4-chlorophenyl)methyl]-6-(2-phenylethyl)piperazin-2-one

Conditions
ConditionsYield
Stage #1: 4-chlorobenzylamine; N-[(tert-butoxy)carbonyl]-N-(2-oxo-4-phenylbutyl)glycine With sodium tris(acetoxy)borohydride; acetic acid at 25℃; Condensation;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; Cyclization;
100%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

1,1'-Thiocarbonyldiimidazole
6160-65-2

1,1'-Thiocarbonyldiimidazole

methyl iodide
74-88-4

methyl iodide

3-(4-chloro-benzylthiocarbamoyl)-1-methyl-3H-imidazol-1-ium; iodide

3-(4-chloro-benzylthiocarbamoyl)-1-methyl-3H-imidazol-1-ium; iodide

Conditions
ConditionsYield
Stage #1: 4-chlorobenzylamine; 1,1'-Thiocarbonyldiimidazole In acetonitrile at 20℃; for 1h;
Stage #2: methyl iodide In acetonitrile at 20℃;
100%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

propionaldehyde
123-38-6

propionaldehyde

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

2-hydroxynitrobenzene
88-75-5

2-hydroxynitrobenzene

2-[(4-chlorobenzyl)-(2-nitrophenyl)amino]-N-cyclohexylbutyramide

2-[(4-chlorobenzyl)-(2-nitrophenyl)amino]-N-cyclohexylbutyramide

Conditions
ConditionsYield
In methanol microwave irradiation;100%
In toluene at 60℃; for 20h; Ugi-Smiles coupling;90%
In methanol at 40℃; for 20h; Ugi reaction;74%
phosgene
75-44-5

phosgene

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

4-chlorobenzyl isocyanate
30280-44-5

4-chlorobenzyl isocyanate

Conditions
ConditionsYield
In toluene100%
In toluene at 20℃; for 2.25h; Heating / reflux;100%
In toluene at 20℃; for 2.25h; Heating / reflux;100%
With triethylamine In dichloromethane; toluene at -20 - 25℃; for 4.08333h; Inert atmosphere;
2,6-Dibromopyridine
626-05-1

2,6-Dibromopyridine

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

(6-bromopyridin-2-yl)(4-chlorobenzyl)amine
866546-12-5

(6-bromopyridin-2-yl)(4-chlorobenzyl)amine

Conditions
ConditionsYield
at 150℃; for 0.5h; Neat (no solvent); Microwave irradiation;100%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid
84358-13-4

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

tert-butyl 4-(4-chlorobenzylcarbamoyl)piperidine-1-carboxylate
881833-22-3

tert-butyl 4-(4-chlorobenzylcarbamoyl)piperidine-1-carboxylate

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 16h;100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 15h;88%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 18h;72%
Pyruvic aldehyde dimethyl acetal
6342-56-9

Pyruvic aldehyde dimethyl acetal

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

(4-chloro-benzyl)-[2,2-dimethoxy-1-methyl-eth-(Z)-ylidene]-amine
919994-55-1

(4-chloro-benzyl)-[2,2-dimethoxy-1-methyl-eth-(Z)-ylidene]-amine

Conditions
ConditionsYield
In toluene for 3h; Heating / reflux;100%
N-tert-butyloxycarbonylpiperidin-4-one
79099-07-3

N-tert-butyloxycarbonylpiperidin-4-one

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

4-(4-chloro-benzylamino)-piperidine-1-carboxylic acid tert-butyl ester
849106-37-2

4-(4-chloro-benzylamino)-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane100%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 2h; Inert atmosphere;
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

C13H14ClNO4
1012859-65-2

C13H14ClNO4

Conditions
ConditionsYield
In water at 20℃; for 2h; Michael-type addition;100%
In dichloromethane at 20℃; for 0.166667h;
In methanol for 0.5h; Reflux;
In dichloromethane at 20℃; Inert atmosphere;
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Benzoyl isothiocyanate
532-55-8

Benzoyl isothiocyanate

N-((4-chlorobenzyl)carbamothioyl)benzamide
145383-00-2

N-((4-chlorobenzyl)carbamothioyl)benzamide

Conditions
ConditionsYield
100%
In diethyl ether at 0 - 20℃; for 2h;
In acetone at 20℃;
(Z)-3-ethoxy-3-[(2-nitrophenyl)hydrazono]propanoic acid ethyl ester
100032-83-5

(Z)-3-ethoxy-3-[(2-nitrophenyl)hydrazono]propanoic acid ethyl ester

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

(Z)-N-(4-chlorobenzyl)-3-ethoxy-3-[(2-nitrophenyl)hydrazono]propanamide

(Z)-N-(4-chlorobenzyl)-3-ethoxy-3-[(2-nitrophenyl)hydrazono]propanamide

Conditions
ConditionsYield
at 50℃; for 1h; Inert atmosphere; Microwave irradiation;100%
2-chloro-6,7-dimethoxy-3H-quinazolin-4-one
27631-29-4

2-chloro-6,7-dimethoxy-3H-quinazolin-4-one

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

2-chloro-N-(4-chlorobenzyl)-6,7-dimethoxyquinazolin-4-amine
864291-36-1

2-chloro-N-(4-chlorobenzyl)-6,7-dimethoxyquinazolin-4-amine

Conditions
ConditionsYield
Stage #1: 2-chloro-6,7-dimethoxy-3H-quinazolin-4-one; 4-chlorobenzylamine In N,N-dimethyl-formamide at 20℃; for 29h;
Stage #2: With sodium hydroxide In water
100%
4-fluoro-3-nitro-benzoic acid methyl ester
329-59-9

4-fluoro-3-nitro-benzoic acid methyl ester

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

methyl 4-(4-chlorobenzylamine)-3-nitrobenzoic acid ester
174422-22-1

methyl 4-(4-chlorobenzylamine)-3-nitrobenzoic acid ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 5h;100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 5h;100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 17h; Reflux;
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 50℃; for 16h;
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 150℃; for 0.0833333h; Inert atmosphere;
carbon disulfide
75-15-0

carbon disulfide

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

4-chlorobenzylisothiocyanate
3694-45-9

4-chlorobenzylisothiocyanate

Conditions
ConditionsYield
Stage #1: carbon disulfide; 4-chlorobenzylamine In diethyl ether for 0.25h; Cooling with ice;
Stage #2: With dicyclohexyl-carbodiimide In diethyl ether at 20℃; for 24h;
100%
Stage #1: carbon disulfide; 4-chlorobenzylamine With triethylamine In tetrahydrofuran at 0 - 20℃; for 1.75h;
Stage #2: With p-toluenesulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 1h;
85%
With dmap; di-tert-butyl dicarbonate; triethylamine In ethanol at 0 - 20℃; for 1h;71%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

Veratric acid
93-07-2

Veratric acid

N-(4-chlorobenzyl)-3,4-dimethoxybenzamide

N-(4-chlorobenzyl)-3,4-dimethoxybenzamide

Conditions
ConditionsYield
Stage #1: Veratric acid With 1-hydroxy-pyrrolidine-2,5-dione In dichloromethane at -10 - 0℃; for 0.166667h;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane for 2h; Reflux;
Stage #3: 4-chlorobenzylamine With triethylamine In methanol; dichloromethane for 2h; Reflux;
99.5%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

Conditions
ConditionsYield
With oxygen In acetone at 20℃; for 3.2h; Electrochemical reaction;99%
With potassium hydroxide; nickel copper formate; (Bu4N)2S2O8 In 1,2-dichloro-ethane at 20℃; for 13h; Oxidation;95%
With [hydroxy(tosyloxy)iodo]benzene; ammonium acetate In water; acetonitrile at 80℃; for 3h;92%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-(4-chlorobenzylidene)-4-chlorobenzylamine
31264-06-9

N-(4-chlorobenzylidene)-4-chlorobenzylamine

Conditions
ConditionsYield
In dichloromethane at 40℃; under 760.051 Torr; for 1.5h; Molecular sieve;99%
With magnesium sulfate In dichloromethane for 3h; Reflux;95%
In toluene for 24h; Condensation; Heating;56%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-[(2-methoxycarbonylbenzene)sulfenyl]-1,2-benzisothiazolin-3-one
54856-20-1

N-[(2-methoxycarbonylbenzene)sulfenyl]-1,2-benzisothiazolin-3-one

2-(4-chlorobenzyl)benzo[d]isothiazol-2(3H)-one
4322-81-0

2-(4-chlorobenzyl)benzo[d]isothiazol-2(3H)-one

Conditions
ConditionsYield
In toluene at 100℃; for 3h;99%
(R)-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid
1201482-15-6

(R)-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

(R)-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide
1201482-18-9

(R)-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

Conditions
ConditionsYield
Stage #1: (R)-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h;
Stage #2: 4-chlorobenzylamine With dmap In dichloromethane
99%
methyl 2-chloro-2-cyclopropylideneacetate
82979-45-1

methyl 2-chloro-2-cyclopropylideneacetate

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

methyl 2-(4-chlorobenzylamino)cyclobut-1-enecarboxylate
1239987-62-2

methyl 2-(4-chlorobenzylamino)cyclobut-1-enecarboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; lithium iodide In N,N-dimethyl-formamide at 0 - 20℃; for 72h; Michael condensation; Inert atmosphere;99%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

ethyl 4,4,4-trifluoroacetoacetate
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

ethyl 3-(4-chlorobenzyl)amino-4,4,4-trifluorobut-2-enoate
1384849-55-1

ethyl 3-(4-chlorobenzyl)amino-4,4,4-trifluorobut-2-enoate

Conditions
ConditionsYield
Stage #1: 4-chlorobenzylamine With acetic acid In chloroform at 20℃; for 0.0833333h;
Stage #2: ethyl 4,4,4-trifluoroacetoacetate In chloroform for 5h; Reflux;
99%
ethanol
64-17-5

ethanol

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

C9H10ClN
1538636-70-2

C9H10ClN

Conditions
ConditionsYield
With potassium hydroxide at 30℃; for 3h; Green chemistry;99%
S-methylthiouronium iodide
4338-95-8

S-methylthiouronium iodide

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

4-chlorobenzylguanidine hydroiodide

4-chlorobenzylguanidine hydroiodide

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; for 12h;99%
carbon dioxide
124-38-9

carbon dioxide

4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

N-(4-chlorobenzyl)formamide
86386-67-6

N-(4-chlorobenzyl)formamide

Conditions
ConditionsYield
With phenylsilane; C14H24N4Si*HI In benzene-d6 at 40℃; Inert atmosphere; Schlenk technique;99%
With Au-TiO2; hydrogen In N,N-dimethyl acetamide at 120℃; for 5h;94%
With tris(2-diphenylphosphinoethyl)phosphine; hydrogen; potassium carbonate; cobalt(II) perchlorate hexahydrate In ethanol at 140℃; under 45004.5 Torr; for 24h; Autoclave; Green chemistry;90%

104-86-9Relevant articles and documents

Polarographic and Cyclic Voltametric Reduction of p-Chlorobenzaldehyde Isonicotinoylhydrazone

Reddy, Papammagari Raveendra,Rao, Sukuru Brahmaji

, p. 1397 - 1398 (1988)

p-Chlorobenzaldehyde isonicotinoylhydrazone (p-Cl-BAINH) exhibits a single wave in acid buffered solutions (pH 2-6) and two waves in alkaline buffered solutions (pH 7- 9).However, the compound exhibits three cathodic peaks in acid solution and two cathodic peaks in alkaline solutions.The electrode reactions are attributed to the reductive cleavage of =N-N- linkage and the reduction of the amide formed in the cleavage.

Stable and Inert Cobalt Catalysts for Highly Selective and Practical Hydrogenation of C≡N and C=O Bonds

Chen, Feng,Topf, Christoph,Radnik, J?rg,Kreyenschulte, Carsten,Lund, Henrik,Schneider, Matthias,Surkus, Annette-Enrica,He, Lin,Junge, Kathrin,Beller, Matthias

, p. 8781 - 8788 (2016)

Novel heterogeneous cobalt-based catalysts have been prepared by pyrolysis of cobalt complexes with nitrogen ligands on different inorganic supports. The activity and selectivity of the resulting materials in the hydrogenation of nitriles and carbonyl compounds is strongly influenced by the modification of the support and the nitrogen-containing ligand. The optimal catalyst system ([Co(OAc)2/Phenα-Al2O3]-800 = Cat. E) allows for efficient reduction of both aromatic and aliphatic nitriles including industrially relevant dinitriles to primary amines under mild conditions. The generality and practicability of this system is further demonstrated in the hydrogenation of diverse aliphatic, aromatic, and heterocyclic ketones as well as aldehydes, which are readily reduced to the corresponding alcohols.

Generation of Oxidoreductases with Dual Alcohol Dehydrogenase and Amine Dehydrogenase Activity

Tseliou, Vasilis,Schilder, Don,Masman, Marcelo F.,Knaus, Tanja,Mutti, Francesco G.

supporting information, p. 3315 - 3325 (2020/12/11)

The l-lysine-?-dehydrogenase (LysEDH) from Geobacillus stearothermophilus naturally catalyzes the oxidative deamination of the ?-amino group of l-lysine. We previously engineered this enzyme to create amine dehydrogenase (AmDH) variants that possess a new hydrophobic cavity in their active site such that aromatic ketones can bind and be converted into α-chiral amines with excellent enantioselectivity. We also recently observed that LysEDH was capable of reducing aromatic aldehydes into primary alcohols. Herein, we harnessed the promiscuous alcohol dehydrogenase (ADH) activity of LysEDH to create new variants that exhibited enhanced catalytic activity for the reduction of substituted benzaldehydes and arylaliphatic aldehydes to primary alcohols. Notably, these novel engineered dehydrogenases also catalyzed the reductive amination of a variety of aldehydes and ketones with excellent enantioselectivity, thus exhibiting a dual AmDH/ADH activity. We envisioned that the catalytic bi-functionality of these enzymes could be applied for the direct conversion of alcohols into amines. As a proof-of-principle, we performed an unprecedented one-pot “hydrogen-borrowing” cascade to convert benzyl alcohol to benzylamine using a single enzyme. Conducting the same biocatalytic cascade in the presence of cofactor recycling enzymes (i.e., NADH-oxidase and formate dehydrogenase) increased the reaction yields. In summary, this work provides the first examples of enzymes showing “alcohol aminase” activity.

Simplified preparation of a graphene-co-shelled Ni/NiO@C nano-catalyst and its application in theN-dimethylation synthesis of amines under mild conditions

Liu, Jianguo,Ma, Longlong,Song, Yanpei,Zhang, Mingyue,Zhuang, Xiuzheng

supporting information, p. 4604 - 4617 (2021/06/30)

The development of Earth-abundant, reusable and non-toxic heterogeneous catalysts to be applied in the pharmaceutical industry for bio-active relevant compound synthesis remains an important goal of general chemical research.N-methylated compounds, as one of the most essential bioactive compounds, have been widely used in the fine and bulk chemical industries for the production of high-value chemicals. Herein, an environmentally friendly and simplified method for the preparation of graphene encapsulated Ni/NiO nanoalloy catalysts (Ni/NiO@C) was developed for the first time, for the highly selective synthesis ofN-methylated compounds using various functional amines and aldehydes under easy to handle, and industrially applicable conditions. A large number of primary and secondary amines (more than 70 examples) could be converted to the correspondingN,N-dimethylamines with the participation of different functional aldehydes, with an average yield of over 95%. A gram-scale synthesis also demonstrated a similar yield when compared with the benchmark test. In addition, it was further proved that the catalyst could easily be recycled because of its intrinsic magnetism and reused up to 10 times without losing its activity and selectivity. Also, for the first time, the tandem synthesis ofN,N-dimethylamine products in a one-pot process, using only a single earth-abundant metal catalyst, whose activity and selectivity were more than 99% and 94%, respectively, for all tested substrates, was developed. Overall, the advantages of this newly developed method include operational simplicity, high stability, easy recyclability, cost-effectiveness of the catalyst, and good functional group compatibility for the synthesis ofN-methylation products as well as the industrially applicable tandem synthesis process.

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

Amberchan, Gabriella,Snelling, Rachel A.,Moya, Enrique,Landi, Madison,Lutz, Kyle,Gatihi, Roxanne,Singaram, Bakthan

supporting information, p. 6207 - 6227 (2021/05/06)

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

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