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Merck
CN

382183

Benzyloxyacetaldehyde

97%

Synonym(s):

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:
60656-87-3
Molecular Weight:
150.17
NACRES:
NA.22
PubChem Substance ID:
24863874
UNSPSC Code:
12352100
EC Number:
262-349-7
MDL number:
MFCD00191779
Assay:
97%
Form:
liquid

Key Documents

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InChI key

NFNOAHXEQXMCGT-UHFFFAOYSA-N

InChI

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

SMILES string

O=CCOCc1ccccc1

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.)

functional group

aldehyde, ether, phenyl

Quality Level

100

Related Categories

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

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ7162
MKCG4110
MKBT6833V
MKBQ8586V
MKBK4292V

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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)
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
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)

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