4-Hydroxybenzylamine Chemical Properties

Melting point:

123-128 °C

Boiling point:

262.4±15.0 °C(Predicted)

Density 

1.141±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMSO (Slightly), Water (Slightly, Heated)

pka

8.93±0.26(Predicted)

form 

Powder

color 

Off-white to pale yellow

InChI

InChI=1S/C7H9NO/c8-5-6-1-3-7(9)4-2-6/h1-4,9H,5,8H2

InChIKey

RQJDUEKERVZLLU-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(CN)C=C1

LogP

0.350 (est)

CAS DataBase Reference

696-60-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

34-36/37/38

Safety Statements 

26-36/37/39-24/25

RIDADR 

2735

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, CORROSIVE

HS Code 

29214990

4-Hydroxybenzylamine Usage And Synthesis

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

Definition

ChEBI: 4-Hydroxybenzylamine is an aromatic amine.

Synthesis

Preparative Example A: Synthesis of sodium 4-((2-aminopyridine-3-carbonyl)amino)methyl)phenol. To a solution of 4-hydroxybenzaldehyde (10 g, 81.9 mmol) in methanol (45 mL) was added nickel ryenne (3 g) and 7N aqueous ammonia solution (45 mL). The reaction mixture was stirred for 21 hours at room temperature under hydrogen atmosphere (1 atm). Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated to afford 4-aminomethylphenol (10 g, quantitatively) as a light green solid. Subsequently, 2-aminonicotinic acid (3.0 g, 21.7 mmol) was dissolved in N,N-dimethylformamide (30 mL), 1-hydroxybenzotriazole (3.51 g, 26 mmol) and (3-dimethylaminopropyl)-ethylcarbodiimide (4.04 g, 26 mmol) were added, and the solution was cooled to 0°C. To this solution, 4-aminomethylphenol (3.0 g , 21.7 mmol) to a solution of N,N-dimethylformamide (20 mL) and the reaction mixture was stirred for 18 hours at room temperature. Upon completion of the reaction, the reaction solution was partitioned into brine and the organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was dissolved in ethyl acetate, filtered through silica gel and the filtrate was concentrated. The residue was dissolved in methanol (90 mL), 1N sodium hydroxide solution (17.8 mL, 17.8 mmol) was added and stirred at room temperature for 1.5 hours. The reaction solution was concentrated in vacuum to give 4-hydroxybenzylamine (5.66 g) as a light yellow solid.

target

GABA Receptor

References

[1] Patent: EP1782811, 2007, A1. Location in patent: Page/Page column 46-47
[2] Patent: EP1669348, 2006, A1. Location in patent: Page/Page column 55
[3] Patent: CN105481701, 2016, A. Location in patent: Paragraph 0016
[4] Patent: WO2007/74386, 2007, A2. Location in patent: Page/Page column 8
[5] Patent: US2009/177008, 2009, A1. Location in patent: Page/Page column 2-3

4-Hydroxybenzylamine(696-60-6)Related Product Information

• Itopride Impurity C
• Itopride Impurity A
• Itopride N-Oxide
• ETHYL 3,4-DIMETHOXYBENZOATE
• NA
• 4-[2-(DIMETHYLAMINO)ETHOXY]BENZYLAMINE
• 3,4-DIMETHOXYBENZOYL CHLORIDE
• Itopride Impurity 1
• 2-(p-tolyloxy)-N,N-dimethylethanamine hydrochloride
• Benzaldehyde, 4-[2-(diMethylaMino)ethoxy]-, oxiMe
• Benzoic acid, 3,4-dimethoxy-, 4-formylphenyl ester
• Itopride Impurity B
• DL-LAUDANOSINE
• 3,4-Dichlorobenzylamine
• Veratrylamine
• 4-Ethoxybenzamide
• 4-Methoxybenzamide
• 1-Benzylpiperazine