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696-60-6

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696-60-6 Usage

Description

4-HOBA is an isomer of the isoketal scavenger 2-HOBA that has reduced efficacy as an isoketal scavenger. Unlike 2-HOBA, 4-HOBA has no effect on hypertension induced by angiotensin II in mice. 4-HOBA has been used as a negative control for the activity of 2-HOBA and related compounds in a mouse model of hypertension.

Chemical Properties

4-Hydroxybenzylamine, also known as tyramine and p-hydroxyphenethylamine, is a white or off-white or light green solid. Tyramine, a compound originally isolated from ergot alkaloids and decomposed animal tissues, is an important synthetic drug intermediate.

Uses

4-Hydroxybenzylamine (cas# 696-60-6) is a compound useful in organic synthesis.

Preparation

Synthesis of 4-Hydroxybenzylamine:Ammonia is passed into 500 ml of ethanol at 10° C. until saturation is reached, 122.1 g=1 mole of p-hydroxybenzaldehyde, 20 g of Raney nickel and 0.1 ml of concentrated sulfuric acid are added and the mixture is stirred in an autoclave for 6 hours at room temperature and under a hydrogen pressure of 100 atmospheres. After releasing the pressure, the catalyst is filtered off and the filtrate is boiled up with active charcoal, filtered and concentrated. The residue is recrystallized from a mixture of ethanol and ether. This gives 104 g (85% of theory), melting point: 104° C.Literature source US04391805

Check Digit Verification of cas no

The CAS Registry Mumber 696-60-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,9 and 6 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 696-60:
(5*6)+(4*9)+(3*6)+(2*6)+(1*0)=96
96 % 10 = 6
So 696-60-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H9NO.BrH/c8-5-6-1-3-7(9)4-2-6;/h1-4,9H,5,8H2;1H

696-60-6SDS

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 4-Hydroxybenzylamine

1.2 Other means of identification

Product number -
Other names 4-(aminomethyl)phenol

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:696-60-6 SDS

696-60-6Synthetic route

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
With ammonia; hydrogen; nickel In methanol; water at 20℃; under 760.051 Torr; for 21h;100%
With ammonia; hydrogen; Raney nickel In methanol; water at 20℃; under 760.051 Torr; for 21h;100%
With ammonium hydroxide; hydrogen; sodium hydroxide In water at 50℃; under 6080.41 Torr; Temperature; Pressure; Autoclave; Large scale;88.9%
4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
Stage #1: 4-methoxy-benzylamine With hydrogen bromide In water at 120 - 126℃;
Stage #2: With sodium hydroxide In water Cooling;
92.5%
With hydrogen iodide at 130℃;
With hydrogen iodide at 150℃;
With 2-acetoacetic acid Acidic conditions;
4-(benzyloxy)benzylamine
22171-15-9

4-(benzyloxy)benzylamine

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
palladium-carbon catalyst In tetrahydrofuran; water; hydrogen85%
With ammonium hydroxide; hydrogen; palladium on activated charcoal In ethanol at 0℃; under 760 Torr; for 2h;83%
With ammonium hydroxide; hydrogen; palladium on activated charcoal In ethanol at 0℃; under 760 Torr; for 1h; Yield given;
4-cyanophenol
767-00-0

4-cyanophenol

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
97%
With ammonia; hydrogen; nickel In methanol for 144h;93%
With potassium hydroxide; Raney Ni-Al; water at 90℃;89%
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
With sodium azide; triphenylphosphine In dichloromethane; N,N-dimethyl-formamide at 90℃; for 5h; Substitution; Mitsunobu reaction; Staudinger reaction;95%
4-benzyloxybenzonitrile
52805-36-4

4-benzyloxybenzonitrile

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 97 percent / LiAlH4, AlCl3 / diethyl ether / 2 h / 25 °C
2: 83 percent / H2, NH4OH / 10percent Pd/C / ethanol / 2 h / 0 °C / 760 Torr
View Scheme
Multi-step reaction with 2 steps
1: LiAlH4, AlCl3 / diethyl ether / 2 h / 25 °C
2: H2, aq. NH3 / 10percent Pd-C / ethanol / 1 h / 0 °C / 760 Torr
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

A

4-aminomethylphenol
696-60-6

4-aminomethylphenol

B

tert-butyl (4-hydroxybenzyl)carbamate
149505-94-2

tert-butyl (4-hydroxybenzyl)carbamate

Conditions
ConditionsYield
In tetrahydrofuran; water
(4-hydroxyphenyl)methanol
623-05-2

(4-hydroxyphenyl)methanol

A

(4-aminomethyl)aniline
4403-71-8

(4-aminomethyl)aniline

B

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
With ammonia In water at 100℃; for 24h; Sealed bottle;
4-hydroxybenzaldehyde oxime
699-06-9, 60221-52-5, 60221-53-6

4-hydroxybenzaldehyde oxime

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Raney-Ni
2: aq. HCl
View Scheme
With lithium aluminium tetrahydride
phenol
108-95-2

phenol

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / acetic acid
2: hydrogenchloride / ethanol; water / 2 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: zinc(II) chloride; benzene / 70 - 80 °C
View Scheme
(E)-4-hydroxybenzaldehyde oxime
60221-52-5

(E)-4-hydroxybenzaldehyde oxime

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
With hydrogenchloride; palladium Hydrogenation;
With sodium amalgam; ethanol; acetic acid at 60℃;
N-Chloracetyl-p-hydroxybenzylamin
52447-43-5

N-Chloracetyl-p-hydroxybenzylamin

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water for 2h; Reflux;
N-(chloromethyl)phthalimide
17564-64-6

N-(chloromethyl)phthalimide

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
With zinc(II) chloride; benzene; phenol at 70 - 80℃; und Behandeln des Reaktionsprodukts mit waessrig-alkoholischer Natronlauge in der Kaelte und anschliessend mit verd.Salzsaeure auf dem Wasserbad;
N-[(4-hydroxyphenyl)methyl]formamide
86386-69-8

N-[(4-hydroxyphenyl)methyl]formamide

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
With hydrogenchloride
(4-aminomethyl)aniline
4403-71-8

(4-aminomethyl)aniline

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite
p-nitrobenzylamine
7409-30-5

p-nitrobenzylamine

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tin; hydrochloric acid
2: hydrochloric acid; sodium nitrite
View Scheme
4-nitrobenzyl chloride
100-14-1

4-nitrobenzyl chloride

4-aminomethylphenol
696-60-6

4-aminomethylphenol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: und Spaltung des entstandenen N-<4-Nitro-benzyl>-phthalimids mit rauch.Salzsaeure bei 190-200grad
2: tin; hydrochloric acid
3: hydrochloric acid; sodium nitrite
View Scheme
N5-(4-hydroxybenzyl)glutamine
52026-56-9

N5-(4-hydroxybenzyl)glutamine

A

L-glutamic acid
56-86-0

L-glutamic acid

B

4-aminomethylphenol
696-60-6

4-aminomethylphenol

C

glutamic acid

glutamic acid

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;
hydrogenchloride
7647-01-0

hydrogenchloride

(4-aminomethyl)aniline
4403-71-8

(4-aminomethyl)aniline

NaNO2

NaNO2

4-aminomethylphenol
696-60-6

4-aminomethylphenol

hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

water
7732-18-5

water

2-(4-Hydroxybenzyl)isoindole-1,3-dione
24124-24-1

2-(4-Hydroxybenzyl)isoindole-1,3-dione

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

A

4-aminomethylphenol
696-60-6

4-aminomethylphenol

B

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

4-aminomethylphenol
696-60-6

4-aminomethylphenol

benzyl chloroformate
501-53-1

benzyl chloroformate

(4-hydroxy-benzyl)carbamic acid benzyl ester
75383-60-7

(4-hydroxy-benzyl)carbamic acid benzyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 1.66667h; Product distribution / selectivity;100%
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 19h; Product distribution / selectivity;100%
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 1.5h;97%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-aminomethylphenol
696-60-6

4-aminomethylphenol

tert-butyl (4-hydroxybenzyl)carbamate
149505-94-2

tert-butyl (4-hydroxybenzyl)carbamate

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water100%
With sodium hydrogencarbonate In methanol for 16h; Reflux;99%
With sodium hydrogencarbonate In methanol for 16h; Reflux;99%
(R,S)-N2-(diphenylacetyl)-3-(2-nitrophenyl)-alanine
164648-13-9

(R,S)-N2-(diphenylacetyl)-3-(2-nitrophenyl)-alanine

4-aminomethylphenol
696-60-6

4-aminomethylphenol

(R,S)-N2-(Diphenylacetyl)-N-[(4-hydroxyphenyl)-methyl]-3-(2-nitrophenyl)-alaninamide

(R,S)-N2-(Diphenylacetyl)-N-[(4-hydroxyphenyl)-methyl]-3-(2-nitrophenyl)-alaninamide

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate100%
C10H12Cl3NO6

C10H12Cl3NO6

4-aminomethylphenol
696-60-6

4-aminomethylphenol

C17H19Cl3N2O6

C17H19Cl3N2O6

Conditions
ConditionsYield
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃;100%
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide
(E)-4-ethoxy-4-oxobut-2-enoic acid
2459-05-4

(E)-4-ethoxy-4-oxobut-2-enoic acid

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

4-hydroxy-1-naphthaldehyde
7770-45-8

4-hydroxy-1-naphthaldehyde

4-aminomethylphenol
696-60-6

4-aminomethylphenol

C29H32N2O6

C29H32N2O6

Conditions
ConditionsYield
With lithium chloride; sodium hydroxide In water at 50℃; under 7500.75 Torr; for 1h; pH=7; Inert atmosphere; Microwave irradiation;100%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

4-[tris(4-methoxyphenyl)methyl]benzaldehyde

4-[tris(4-methoxyphenyl)methyl]benzaldehyde

4-({4-[tris(4-methoxyphenyl)methyl]benzylideneamino}methyl)phenol

4-({4-[tris(4-methoxyphenyl)methyl]benzylideneamino}methyl)phenol

Conditions
ConditionsYield
In ethanol for 24h; Reflux;100%
2,6-Pyridinedicarbonyl dichloride
3739-94-4

2,6-Pyridinedicarbonyl dichloride

4-aminomethylphenol
696-60-6

4-aminomethylphenol

2,6-bis(p-hydroxybenzylaminocarbonyl)pyridine
1000591-73-0

2,6-bis(p-hydroxybenzylaminocarbonyl)pyridine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -78 - 20℃; for 12h;99%
With triethylamine In tetrahydrofuran at -78 - 20℃; Inert atmosphere;61%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

formic acid ethyl ester
109-94-4

formic acid ethyl ester

N-[(4-hydroxyphenyl)methyl]formamide
86386-69-8

N-[(4-hydroxyphenyl)methyl]formamide

Conditions
ConditionsYield
for 30h; Reflux;99%
With Novozyme 435 CALB In tetrahydrofuran at 20℃; Green chemistry; Enzymatic reaction; chemoselective reaction;91%
4-tert-butylbenzyl isothiocyanate
31088-81-0

4-tert-butylbenzyl isothiocyanate

4-aminomethylphenol
696-60-6

4-aminomethylphenol

1-(4-tert-butyl-benzyl)-3-(4-hydroxy-benzyl)-thiourea

1-(4-tert-butyl-benzyl)-3-(4-hydroxy-benzyl)-thiourea

Conditions
ConditionsYield
In dichloromethane at 20℃;98%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

C7H7Cl2NO
1158998-90-3

C7H7Cl2NO

Conditions
ConditionsYield
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide at 25℃; for 0.0166667h; grinding; Neat (no solvent);98%
carbon disulfide
75-15-0

carbon disulfide

4-aminomethylphenol
696-60-6

4-aminomethylphenol

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

(Z)-ethyl 2-(3-(4-hydroxybenzyl)-4-oxo-2-thioxothiazolidin-5-ylidene)acetate

(Z)-ethyl 2-(3-(4-hydroxybenzyl)-4-oxo-2-thioxothiazolidin-5-ylidene)acetate

Conditions
ConditionsYield
for 0.0666667h; Sonication; Green chemistry;97%
tert-butyl 2,5-dioxopyrrolidin-1-yl carbonate
13139-12-3

tert-butyl 2,5-dioxopyrrolidin-1-yl carbonate

4-aminomethylphenol
696-60-6

4-aminomethylphenol

tert-butyl (4-hydroxybenzyl)carbamate
149505-94-2

tert-butyl (4-hydroxybenzyl)carbamate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 3h;97%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

1-fluoro-3-isocyanatobenzene
404-71-7

1-fluoro-3-isocyanatobenzene

1-(3-fluorophenyl)-3-(4-hydroxybenzyl)urea

1-(3-fluorophenyl)-3-(4-hydroxybenzyl)urea

Conditions
ConditionsYield
In acetonitrile at 20℃;97%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

5-tert-butylisophthaloyl dichloride
13239-25-3

5-tert-butylisophthaloyl dichloride

5-tert-butyl-N,N'-bis-(4-hydroxy-benzyl)-isophthalamide
381725-21-9

5-tert-butyl-N,N'-bis-(4-hydroxy-benzyl)-isophthalamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 6h;96%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

p-Tolylisocyanate
622-58-2

p-Tolylisocyanate

1-(4-hydroxybenzyl)-3-(p-tolyl)urea

1-(4-hydroxybenzyl)-3-(p-tolyl)urea

Conditions
ConditionsYield
In acetonitrile at 20℃;96%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

2,6-dichloro-9-isopropyl-9H-purine
203436-45-7

2,6-dichloro-9-isopropyl-9H-purine

4-[(2-chloro-9-isopropyl-9H-purin-6-ylamino)-methyl]-phenol
500568-76-3

4-[(2-chloro-9-isopropyl-9H-purin-6-ylamino)-methyl]-phenol

Conditions
ConditionsYield
With triethylamine In butan-1-ol at 115℃; for 2h;95%
With triethylamine In butan-1-ol at 112℃; for 2h;80%
With triethylamine In propan-1-ol at 90℃; for 4h; Inert atmosphere;
4-aminomethylphenol
696-60-6

4-aminomethylphenol

3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

N-(4-hydroxybenzyl)-3,4-dimethoxybenzamide
943518-63-6

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

Conditions
ConditionsYield
With triethylamine In dichloromethane at 15 - 20℃; for 1 - 1.5h;95%
With triethylamine In dichloromethane at 15 - 20℃; for 1 - 1.5h;95%
With pyridine In dichloromethane at 20℃; for 2h; Reflux;95%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine
7306-68-5

6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

6-(4-hydroxybenzylamino)-9-(tetrahydropyran-2-yl)purine
1144854-41-0

6-(4-hydroxybenzylamino)-9-(tetrahydropyran-2-yl)purine

Conditions
ConditionsYield
With triethylamine In propan-1-ol; butan-1-ol at 100℃; for 3h;95%
With triethylamine In propan-1-ol for 3h; Heating / reflux;80%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
2746-19-2

(1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione

(4-hydroxybenzyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

(4-hydroxybenzyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Conditions
ConditionsYield
In N,N-dimethyl-formamide; toluene for 24h; Reflux; Dean-Stark;95%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

m-chlorophenyl isocyanate
2909-38-8

m-chlorophenyl isocyanate

1-(3-chlorophenyl)-3-(4-hydroxybenzyl)urea

1-(3-chlorophenyl)-3-(4-hydroxybenzyl)urea

Conditions
ConditionsYield
In acetonitrile at 20℃;95%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

p-trifluoromethyl-phenylisocyanate
1548-13-6

p-trifluoromethyl-phenylisocyanate

1-(4-hydroxybenzyl)-3-(4-(trifluoromethyl)phenyl)urea

1-(4-hydroxybenzyl)-3-(4-(trifluoromethyl)phenyl)urea

Conditions
ConditionsYield
In acetonitrile at 20℃;94%
2-carboxylic acid-3,5,6-trimethylpyrazine
186534-01-0

2-carboxylic acid-3,5,6-trimethylpyrazine

4-aminomethylphenol
696-60-6

4-aminomethylphenol

N-(4-hydroxybenzyl)-3,5,6-trimethylpyrazine-2-carboxamide

N-(4-hydroxybenzyl)-3,5,6-trimethylpyrazine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;93.5%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;93.5%
tert-Butyl peroxybenzoate
614-45-9

tert-Butyl peroxybenzoate

4-aminomethylphenol
696-60-6

4-aminomethylphenol

N-benzoyl-4-hydroxybenzylamine
41859-85-2

N-benzoyl-4-hydroxybenzylamine

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 14h; chemoselective reaction;93%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

C23H32O4

C23H32O4

C30H39NO4

C30H39NO4

Conditions
ConditionsYield
Stage #1: C23H32O4 With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 20℃; for 1h;
Stage #2: 4-aminomethylphenol In dichloromethane at 20℃; for 4h;
93%
methyl 2-(4-fluorophenyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

methyl 2-(4-fluorophenyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate

4-aminomethylphenol
696-60-6

4-aminomethylphenol

N-(4-hydroxybenzyl)-2-(4-fluorophenyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide

N-(4-hydroxybenzyl)-2-(4-fluorophenyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 90℃; Inert atmosphere;92.4%
4-aminomethylphenol
696-60-6

4-aminomethylphenol

4-cyanophenol
767-00-0

4-cyanophenol

Conditions
ConditionsYield
With trichloroisocyanuric acid; ammonia In water at 20 - 60℃;92%
With N,N,N',N'-tetrachlorobenzene-1,3-disulphonamide; triethylamine In N,N-dimethyl-formamide at 25℃; for 1.5h;90%
With potassium pyrosulfate; potassium aquapentachlororuthenate(III); potassium hydroxide at 20℃; for 0.5h; Catalytic behavior; Sonication;90%
With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; for 12h; Inert atmosphere;86%
With isoquinoline; oxygen; copper; ammonium bromide In toluene at 100℃; under 760.051 Torr; for 24h; Green chemistry;67.2%

696-60-6Relevant articles and documents

Method for synthesizing hydroxybenzylamine

-

Paragraph 0046-0052, (2020/02/27)

The invention discloses a method for synthesizing hydroxybenzylamine, and belongs to the technical field of organic synthesis. The principle of the method comprises that a demethylation reaction is carried out on methoxybenzylamine under the action of hydrobromic acid; the method is characterized in that methoxybenzylamine and hydrobromic acid are distilled in a reflux state to remove redundant water so as to increase the reaction temperature and increase the concentration of the hydrobromic acid in a reaction mixture, so that the demethylation effect of hydrobromic acid on methoxybenzylamineis enhanced, the reaction time is shortened, and the conversion rate is increased; when no bromomethane gas generation is observed, distillation is continued, excessive hydrobromic acid is recovered to further improve the reaction temperature and the conversion rate, meanwhile, the consumption of the raw material hydrobromic acid is reduced, and the treatment capacity of subsequent steps and the consumption of the raw material sodium hydroxide can also be reduced; therefore, the method has the advantages of simple technological process; the reaction time is short; the product is easy to purify; raw material consumption is low; the reaction yield is high.

Metagenomic discovery of a novel transaminase for valorization of monoaromatic compounds

Pawar, Sandip V.,Hallam, Steven J.,Yadav, Vikramaditya G.

, p. 22490 - 22497 (2018/06/29)

The profitability of next-generation biorefineries is acutely contingent on the discovery and utilization of biocatalysts that can valorize lignin. To this end, the metabolic catalogues of diverse microbiota have been mined previously using functional metagenomics in order to identify biocatalysts that can selectively degrade lignin into monoaromatic compounds. Herein, we have further improved the valorization factor of biorefining by deploying functional metagenomics toward the identification of a novel transaminase that can selectively functionalize lignin-derived monoaromatics to produce value-added feedstocks for pharmaceutical synthesis. We implemented a high-throughput colorimetric assay using o-xylylenediamine as the amino donor and successfully identified a transaminase that utilizes the canonical cofactor, pyridoxal 5′-phosphate, to aminate as many as 14 monoaromatic aldehydes and ketones. We subsequently identified the optimal conditions for enzyme activity towards the most favoured amino acceptor, benzaldehyde, including temperature, pH and choice of co-solvent. We also evaluated the specificity of the enzyme towards a variety of amino donors, as well as the optimal concentration of the most favoured amino donor. Significantly, the novel enzyme is markedly smaller than typical transaminases, and it is stably expressed in E. coli without any modifications to its amino acid sequence. Finally, we developed and implemented a computational methodology to assess the activity of the novel transaminase. The methodology is generalizable for assessing any transaminase and facilitates in silico screening of enzyme-substrate combinations in order to develop efficient biocatalytic routes to value-added amines. The computational pipeline is an ideal complement to metagenomics and opens new possibilities for biocatalyst discovery.

MANUFACTURING METHOD OF AROMATIC COMPOUND AND FURAN DERIVATIVE HAVING METHYLAMINO GROUP

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Paragraph 0034; 0035, (2017/10/26)

PROBLEM TO BE SOLVED: To provide a method for manufacturing an aromatic compound or a furan derivative where only aldehyde group is converted to an aminomethyl group while maintaining a structure of aromatic or furan ring from an aromatic compound or a furan derivative having an aldehyde group, capable of being conducted in a water solvent containing no organic solvent and relatively low in by-product. SOLUTION: Amine or ammonia is added in water at first to convert to imine, then a reaction is conducted by using compressive hydrogen with a pressure of 0.1 MPa to 4 MPa in the presence of a metal carried solid catalyst carrying one or more kind of metal selected from rhodium, palladium and platinum or an alloy containing these metal elements. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2017,JPOandINPIT

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