4-Hydroxybenzylamine
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Basic information
- CAS
696-60-6- Standard SMILES
NCc1ccc(O)cc1- InChIKey
RQJDUEKERVZLLU-UHFFFAOYSA-N- Molecular formula
- C7H9NO
- Average molar mass
- 123.15 g/mol
- Monoisotopic mass
- 123.06841391
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 propertiesFilling in
- XLogP
- 0
- Topological polar surface area
- 46.3 Ų
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
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
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
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
64 records
Compound notes
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