All Photos(1)

Documents

382183

Benzyloxyacetaldehyde

Name: Benzyloxyacetaldehyde
Brand: ALDRICH

97%

Synonym(s):

α-(Benzyloxy)acetaldehyde, (Benzyloxy)acetaldehyde, (Benzyloxy)ethanal, (Phenylmethoxy)acetaldehyde, 2-(Benzyloxy)acetaldehyde, 2-(Benzyloxy)ethanal, 2-(Phenylmethoxy)acetaldehyde

Sign Into View Organizational & Contract Pricing

All Photos(1)

About This Item

Linear Formula:

C₆H₅CH₂OCH₂CHO

CAS Number:

60656-87-3

Molecular Weight:

150.17

EC Number:

262-349-7

MDL number:

MFCD00191779

UNSPSC Code:

12352100

PubChem Substance ID:

24863874

NACRES:

NA.22

Quality Level

100

Assay

97%

form

liquid

contains

0.5% hydroquinone as stabilizer

refractive index

n20/D 1.518 (lit.)

bp

118-120 °C/13 mmHg (lit.)

density

1.069 g/mL at 25 °C (lit.)

SMILES string

O=CCOCc1ccccc1

InChI

1S/C9H10O2/c10-6-7-11-8-9-4-2-1-3-5-9/h1-6H,7-8H2

InChI key

NFNOAHXEQXMCGT-UHFFFAOYSA-N

Related Categories

Aldehydes

Organic Building Blocks

General description

Benzyloxyacetaldehyde is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).

Application

Benzyloxyacetaldehyde may be used in the following syntheses:

(3S,5S)-methyl 6-benzyloxy-3,5-dihydroxyhexanoate
(S)-5-benzyloxy-4-hydroxypentan-2-one
myxothiazols

Benzyloxyacetaldehyde may be used in the synthesis of 1-deoxy-L-xylulose, via antibody catalysis.

Pictograms

GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315,H319,H335,H411

Precautionary Statements

P261 - P264 - P271 - P273 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(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

A short enantioselective synthesis of 1-deoxy-L-xylulose by antibody catalysis.

Shabat D, et al.

Tetrahedron Letters, 40(8), 1437-1440 (1999)

Recombinant production of serine hydroxymethyl transferase from Streptococcus thermophilus and its preliminary evaluation as a biocatalyst.

L Vidal et al.

Applied microbiology and biotechnology, 68(4), 489-497 (2005-02-24)

The glyA gene encoding a serine hydroxymethyl transferase (SHMT) with threonine aldolase activity was isolated from Streptococcus thermophilus YKA-184 chromosomal DNA. This aldolase is a pyridoxal 5'-phosphate-dependent enzyme that stereospecifically catalyzes the interconversion of L-threonine to glycine and acetaldehyde. The

Evans DA, et al.

Journal of the American Chemical Society, 121, 669-685 (1999)

Formal total syntheses of Myxothiazols by three different approaches starting from benzyloxyacetaldehyde.

Backhaus D.

Tetrahedron Letters, 41(13), 2087-2090 (2000)

C2-symmetric copper (II) complexes as chiral Lewis acids. Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy) acetaldehyde.