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32578

Sigma-Aldrich

Diethyl trimethylsilyl phosphite

≥95.0% (GC)

Synonym(s):

Phosphorous acid diethyl trimethylsilylester

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About This Item

Linear Formula:
(CH3)3SiOP(OC2H5)2
CAS Number:
13716-45-5
Molecular Weight:
210.28
Beilstein:
956598
EC Number:
237-268-5
MDL number:
MFCD00464673
UNSPSC Code:
12352100
PubChem Substance ID:
57648689
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Quality Level

100

Assay

≥95.0% (GC)

refractive index

n20/D 1.413 (lit.)
n20/D 1.413

bp

58-59 °C/10 mmHg (lit.)

density

0.921 g/mL at 25 °C (lit.)

SMILES string

CCOP(OCC)O[Si](C)(C)C

InChI

1S/C7H19O3PSi/c1-6-8-11(9-7-2)10-12(3,4)5/h6-7H2,1-5H3

InChI key

ATRMOIYYLVRRBZ-UHFFFAOYSA-N

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Application

Diethyl trimethylsilyl phosphite was used in preparation of:
  • diethyl 1-aryl-1-cyanomethanephosphonates[1]
  • unsymmetrical ketones[2]
  • ketones from aldehydes via α-trimethylsiloxy-phosphonates[3][4]
  • phosphonates[1][5]

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

91.4 °F - closed cup

Flash Point(C)

33 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD9823V
012388/2
038545/1
044942/1
012388/1

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A convenient method of ketone synthesis utilizing the reaction of diethyl trimethylsilyl phosphite with carbonyl compounds.
Hata T, et al.
Tetrahedron Letters, 19(4), 363-366 (1978)
M. Sekine et al.
Bulletin of the Chemical Society of Japan, 55, 224-224 (1982)
D.Y. Kim et al.
Synthetic Communications, 17, 953-953 (1987)
K. Afarinkia et al.
Synlett, 123-123 (1992)
D.A. Evans et al.
Journal of the American Chemical Society, 100, 3467-3467 (1978)

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