Skip to Content
Merck
All Photos(2)

Documents

489174

Sigma-Aldrich

Benzyloxyacetone

90%

Synonym(s):

1-Benzyloxy-2-propanone

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
C6H5CH2OCH2COCH3
CAS Number:
22539-93-1
Molecular Weight:
164.20
MDL number:
MFCD01863536
UNSPSC Code:
12352100
PubChem Substance ID:
24872460
NACRES:
NA.22

Assay

90%

impurities

3% (benzyloxy)acetic acid
3% benzyl alcohol

refractive index

n20/D 1.512 (lit.)

bp

259 °C (lit.)

density

1.04 g/mL at 25 °C (lit.)

SMILES string

CC(=O)COCc1ccccc1

InChI

1S/C10H12O2/c1-9(11)7-12-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3

InChI key

YHMRKVGUSQWDGZ-UHFFFAOYSA-N

Related Categories

General description

Benzyloxyacetone (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.

Application

Benzyloxyacetone (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 ether
It 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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Stereochemical control of bakers' yeast mediated reduction of a protected 2-hydroxy ketone.
Manzocchi A, et al.
The Journal of Organic Chemistry, 53(18), 4405-4407 (1988)
A stereoselective formation of (Z)-2-methyl-2-alkenol by the wittig reaction: its application to a synthesis of nerylacetone and (Z,Z)-farnesylacetone.
Sato K, et al.
Chemistry Letters (Jpn), 10(12), 1711-1714 (1981)
Cis selective wittig olefination of a-alkoxy ketones and its application to the stereoselective synthesis of plaunotol.
Inoue S, et al.
Bulletin of the Chemical Society of Japan, 63(6), 1629-1635 (1990)
Synthesis and biological evaluation of L-and D-configurations of 2',3'-dideoxy-4'-C-methyl-3'-oxacytidine analogues.
Liu MC, et al.
Bioorganic & Medicinal Chemistry Letters, 11(17), 2301-2304 (2001)
Highly selective direct aldol reaction organocatalyzed by (S)-BINAM-L-prolinamide and benzoic acid using a-chalcogen-substituted ketones as donors.
Guillena G, et al.
ARKIVOC (Gainesville, FL, United States), 4, 260-269 (2007)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service