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358819

Sigma-Aldrich

Dimethyl trimethylsilyl phosphite

95%

Synonym(s):

Trimethylsilyl dimethyl phosphite

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About This Item

Linear Formula:
(CH3)3SiOP(OCH3)2
CAS Number:
36198-87-5
Molecular Weight:
182.23
Beilstein:
1849308
EC Number:
252-908-3
MDL number:
MFCD00075439
UNSPSC Code:
12352100
PubChem Substance ID:
24862029
NACRES:
NA.22
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Assay

95%

form

liquid

refractive index

n20/D 1.410 (lit.)

bp

36-37 °C/11 mmHg (lit.)

density

0.954 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

COP(OC)O[Si](C)(C)C

InChI

1S/C5H15O3PSi/c1-6-9(7-2)8-10(3,4)5/h1-5H3

InChI key

HWMXPTIFAGBDIK-UHFFFAOYSA-N

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Application

Dimethyl trimethylsilyl phosphite may be used in the preparation of:
  • protected phosphoamino acid, Fmoc-Abu(PO3Me2)-OH, used in Fmoc/solid-phase peptide synthesis[1]
  • phosphoenolpyruvate (PEP) via trimethylsilylation, bromination and Perkow reaction[2]
  • sialyl phosphonate[3]
  • sulfonamide phosphonates[4]

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

89.6 °F - closed cup

Flash Point(C)

32 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000135109
0000089133
0000074260
0000065823
0000041148

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Tris(dimethylamino)phosphine 97%

Sigma-Aldrich

393290

Tris(dimethylamino)phosphine

Diethyl phosphite 98%

Sigma-Aldrich

D99234

Diethyl phosphite

J W Perich
International journal of peptide and protein research, 44(3), 288-294 (1994-09-01)
The synthesis of the two 4-phosphono-2-aminobutanoyl-containing peptides, Leu-Arg-Arg-Val-Abu(P)-Leu-Gly-OH.CF3CO2H and Ile-Val-Pro-Asn-Abu(P)-Val-Glu-Glu-OH.CF3CO2H was accomplished by the use of Fmoc-Abu(PO3Me2)-OH in Fmoc/solid-phase peptide synthesis. The protected phosphoamino acid, Fmoc-Abu(PO3Me2)-OH, was prepared from Boc-Asp-OtBu in seven steps, the formation of the C-P linkage being
Silyl phosphites. Part 20. A facile synthesis of phosphoenolpyruvate and its analogue utilizing in situ generated trimethylsilyl bromide.
Sekine M, et al.
Journal of the Chemical Society. Perkin Transactions 1, 2509-2513 (1982)
Synthesis of novel CMP-NeuNAc analogues having a glycosyl phosphonate structure.
Imamura M and Hashimoto H.
Tetrahedron Letters, 37(9), 1451-1454 (1996)
Amberlyst-15-Catalyzed Facile Synthesis of a-Amino Phosphonates.
Sudhakar D, et al.
Synthetic Communications, 41(7), 976-980 (2011)

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