358819
Dimethyl trimethylsilyl phosphite
95%
Synonym(s):
Trimethylsilyl dimethyl phosphite
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About This Item
Linear Formula:
(CH3)3SiOP(OCH3)2
CAS Number:
Molecular Weight:
182.23
Beilstein:
1849308
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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
- phosphoenolpyruvate (PEP) via trimethylsilylation, bromination and Perkow reaction
- sialyl phosphonate
- sulfonamide phosphonates
Signal Word
Danger
Hazard Statements
Precautionary Statements
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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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)
Amberlyst-15-Catalyzed Facile Synthesis of a-Amino Phosphonates.
Sudhakar D, et al.
Synthetic Communications, 41(7), 976-980 (2011)
Synthesis of novel CMP-NeuNAc analogues having a glycosyl phosphonate structure.
Imamura M and Hashimoto H.
Tetrahedron Letters, 37(9), 1451-1454 (1996)
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
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