382183

Sigma-Aldrich

Benzyloxyacetaldehyde

97%

Linear Formula:
C6H5CH2OCH2CHO
CAS Number:
Molecular Weight:
150.17
EC Number:
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

Quality Level

assay

97%

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

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.

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-37/39

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

C2-symmetric copper (II) complexes as chiral Lewis acids. Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy) acetaldehyde.
Evans DA, et al.
Journal of the American Chemical Society, 121(4), 669-685 (1999)
Formal total syntheses of Myxothiazols by three different approaches starting from benzyloxyacetaldehyde.
Backhaus D.
Tetrahedron Letters, 41(13), 2087-2090 (2000)
A short enantioselective synthesis of 1-deoxy-L-xylulose by antibody catalysis.
Shabat D, et al.
Tetrahedron Letters, 40(8), 1437-1440 (1999)
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...

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