1-(Benzyloxy)propan-2-one

HCID 3691284CAS 22539-93-1

Substructure search Find similar structures

Basic information

Standard SMILES: CC(=O)COCc1ccccc1
InChIKey: YHMRKVGUSQWDGZ-UHFFFAOYSA-N
Molecular formula: C10H12O2
Average molar mass: 164.2 g/mol
Monoisotopic mass: 164.08372962

Names & identifiers

Preferred name: 1-(Benzyloxy)propan-2-one
IUPAC: 1-phenylmethoxypropan-2-one
English name: Benzyloxyacetone
Molecular formula: C10H12O2
Molecular weight: 164.2

Names & synonyms

1-(Benzyloxy)propan-2-oneRefChem:427122828-028-6Benzyloxyacetone22539-93-11-phenylmethoxypropan-2-one1-Benzyloxy-2-propanone1-(benzyloxy)acetoneMFCD018635361-Benzyloxypropan-2-one2-Propanone, 1-(phenylmethoxy)-SCHEMBL712779

Show more names

3-benzyloxypropanoneBenzyloxyacetone 90%1-(Benzyloxy)propane-2-one1-phenylmethoxy-2-propanone

1-[(phenylmethyl)oxy]-2-propanoneAKOS009157009SY107427EN300-108880Z9061954141-(Benzyloxy)-2-propanone1-BenzyloBenzyloxyacetone, 90%

Database identifiers

CAS: 22539-93-1
PubChem CID: 3691284
DTXSID: DTXSID10395111
EC Number: 828-028-6
Nikkaji: J325.157H

Properties

Computed structural properties

XLogP: 1.3
Topological polar surface area: 26.3 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 4
Heavy atoms: 12
Formal charge: 0
Complexity: 137

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift

Physicochemical properties

Boiling point: 259 °C · 259 °C (lit.)
Density: 1.04 g/mL · 1.04 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.512(lit.)
Flash point: 230 °F · >230 °F
storage temp.: Inert atmosphere,Room Temperature
Appearance: Colorless to light yellow Liquid
InChI: InChI=1S/C10H12O2/c1-9(11)7-12-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
InChIKey: YHMRKVGUSQWDGZ-UHFFFAOYSA-N
SMILES: C(OCC1=CC=CC=C1)C(=O)C
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 335 · H335-H315-H319
Precautionary statements: 264 · P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
WGK Germany: 3 · 3
Storage Class: 10 · 10 - Combustible liquids

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 2 reports by companies from 1 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

PPE: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
wgk: 3
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 10 - Combustible liquids
Hazard statements: H335-H315-H319
Precautionary statements: P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Applications · 2 items

UsesBenzyloxyacetone (1-Benzyloxy-2-propanone) may be used in the synthesis of:7-benzyloxy-6-methyl-5-hepten-1-yne(Z)-2-methylhept-2-en-6-yn-1-o1(S)-(+)-1,2-propanediol, 1-benzyl etherIt may be used as a starting material in synthesizing (2S,4RS)-4-acetoxy-2-[(benzyloxy)methyl]-2-methyldioxolane and (2R,4RS)-4-acetoxy-2-[(benzyloxy)methyl]-2-methyldioxolane.

General DescriptionBenzyloxyacetone (α-Benzyloxyacetone) is an α-substituted acetone. It undergoes direct aldol reaction with 4-nitrobenzaldehyde in the presence of (S)-BINAM-L-prolinamide/benzoic acid to form predominantly the syn-diasteroisomer.