4-Hydroxybenzylamine (HCID 97472)

Overview

4-Hydroxybenzylamine is an aromatic amine.

Names & identifiers

Preferred name: 4-Hydroxybenzylamine
IUPAC: 4-(aminomethyl)phenol
English name: 4-Hydroxybenzylamine
Molecular formula: C7H9NO
Molecular weight: 123.15

Names & synonyms

4-Hydroxybenzylamine4-(aminomethyl)phenol696-60-6para-HydroxybenzylaminePhenol, 4-(aminomethyl)-NSC-1257207J7F85B7BIDTXSID00219872RefChem:99287DTXCID50142363671-027-94-Aminomethyl-phenol

Show more names

AI320348AI3 20348AI3-20348NSC 125720RARECHEM AL BW 0048Bisoprolol Impurity 26

4-hydroxybenzyl amineMFCD008704994-(Aminomethyl)-Phenol4-HOBAp-hydroxybenzylamineP-(AMINOMETHYL)PHENOSCHEMBL63123CHEMBL202519

Database identifiers

CAS: 696-60-6
PubChem CID: 97472
DTXSID: DTXSID00219872
ChEMBL: CHEMBL202519
ChEBI: CHEBI:173335
UNII: 7J7F85B7BI
EC Number: 671-027-9
Nikkaji: J765.581I

Properties

Computed structural properties

XLogP: 0
Topological polar surface area: 46.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 9
Formal charge: 0
Complexity: 77

Experimental & physicochemical properties

Melting Point114 - 115 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 123 · 123-128 °C
Boiling point: 262.4 · 262.4±15.0 °C(Predicted)
Density: 1.141 · 1.141±0.06 g/cm3(Predicted)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2–8 °C
solubility: DMSO (Slightly), Water (Slightly, Heated)
pka: 8.93 · 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: 0.35 · 0.350 (est)
CAS DataBase Reference: 696 · 696-60-6(CAS DataBase Reference)
FDA UNII: 7 J7F85B7BI · 7J7F85B7BI
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 302 · P302+P352-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xi
Risk Statements: 34 · 34-36/37/38
Safety Statements: 26 · 26-36/37/39-24/25
RIDADR: 2735 · 2735
WGK Germany: 3 · 3
Hazard Note: Irritant
HazardClass: IRRITANT, CORROSIVE
HS Code: 29214990 · 29214990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk: 3
ridadr: 2735
hs_code: 29214990
risk_code: 34-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-36/37/39-24/25
hazard_class: IRRITANT, CORROSIVE
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Applications · 2 items

Description4-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.

Uses4-Hydroxybenzylamine (cas# 696-60-6) is a compound useful in organic synthesis.

Preparation methods · 1 item

PreparationSynthesis 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