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Key Documents

382183

Sigma-Aldrich

Benzyloxyacetaldehyde

97%

동의어(들):

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

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About This Item

Linear Formula:
C6H5CH2OCH2CHO
CAS Number:
Molecular Weight:
150.17
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

분석

97%

형태

liquid

포함

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

일반 설명

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).

애플리케이션

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.

픽토그램

Exclamation markEnvironment

신호어

Warning

유해 및 위험 성명서

Hazard Classifications

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

표적 기관

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point (°F)

235.4 °F - closed cup

Flash Point (°C)

113 °C - closed cup

개인 보호 장비

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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문서 라이브러리 방문

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
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)

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