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449458

(tert-Butyldimethylsilyloxy)acetaldehyde

90%

Synonym(s):

(tert-Butyldimethylsiloxy)acetaldehyde, 2-(tert-Butyldimethylsilyloxy)acetaldehyde, 2-[(tert-Butyl)dimethylsiloxy]acetaldehyde, 2-[(tert-Butyldimethylsilanyl)oxy]acetaldehyde, 2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]acetaldehyde, Dimethyl-tert-butylsilyloxyacetaldehyde

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About This Item

Linear Formula:
(CH3)3CSi(CH3)2OCH2CHO
CAS Number:
102191-92-4
Molecular Weight:
174.31
NACRES:
NA.22
PubChem Substance ID:
24868481
UNSPSC Code:
12352100
MDL number:
MFCD01321229
Assay:
90%

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Quality Segment

200

assay

90%

refractive index

n20/D 1.432 (lit.)

bp

165-167 °C (lit.)

density

0.915 g/mL at 25 °C (lit.)

functional group

aldehyde

storage temp.

2-8°C

SMILES string

CC(C)(C)[Si](C)(C)OCC=O

InChI

1S/C8H18O2Si/c1-8(2,3)11(4,5)10-7-6-9/h6H,7H2,1-5H3

InChI key

MEBFFOKESLAUSJ-UHFFFAOYSA-N

Application

Employed in the construction of the key tetrahydropyran subunit in a recent synthesis of the marine natural product (–)-dactylodide.[1]
(tert-Butyldimethylsilyloxy)acetaldehyde is a versatile reagent commonly used in synthetic glycobiology.[2] It can act both as an aldol donor and an aldol acceptor in the stereocontrolled production of erythrose.[2] It is used as an important reagent in the total synthesis of (+)-ambruticin, (−)-laulimalide, (−)-salinosporamide A, and (+)-leucascandrolide A.

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(tert-Butyldimethylsilyloxy)acetaldehyde 90%

Sigma-Aldrich

449458

(tert-Butyldimethylsilyloxy)acetaldehyde

trans-3-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-1,3-butadien-1-amine 90%

Sigma-Aldrich

495956

trans-3-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-1,3-butadien-1-amine

5-(tert-Butyldimethylsilyloxy)-1-pentanol 90%

Sigma-Aldrich

435732

5-(tert-Butyldimethylsilyloxy)-1-pentanol

N,N-Dimethylformamide di-tert-butyl acetal technical, ≥90% (GC)

Sigma-Aldrich

40263

N,N-Dimethylformamide di-tert-butyl acetal

assay

90%

assay

90%

assay

90%

assay

≥90% (GC)

Quality Level

200

Quality Level

100

Quality Level

100

Quality Level

100

bp

165-167 °C (lit.)

bp

234 °C (lit.)

bp

140 °C/6 mmHg (lit.)

bp

56-57 °C/8 mmHg (lit.)

refractive index

n20/D 1.432 (lit.)

refractive index

n20/D 1.493 (lit.)

refractive index

n20/D 1.442 (lit.)

refractive index

-

density

0.915 g/mL at 25 °C (lit.)

density

0.878 g/mL at 25 °C (lit.)

density

0.885 g/mL at 25 °C (lit.)

density

0.848 g/mL at 25 °C (lit.)

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

140.0 °F - closed cup

flash_point_c

60 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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