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D178454 Sigma-Aldrich

Dimethyl phosphite

98%

  • CAS Number 868-85-9

  • Linear Formula (CH3O)2P(O)H

  • Molecular Weight 110.05

  •  Beilstein/REAXYS Number 1697490

  •  EC Number 212-783-8

  •  MDL number MFCD00044633

  •  PubChem Substance ID 24893543

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Chemical Synthesis, Organic Building Blocks, Organic Phosphates/Phosphites, Phosphorus Compounds More...
Quality Level   200
assay   98%
impurities   ≤0.5% trimethyl phosphate
  ≤1% methyl alcohol
refractive index   n20/D 1.402 (lit.)
bp   170-171 °C (lit.)
density   1.2 g/mL at 25 °C (lit.)
SMILES string   [H]P(=O)(OC)OC
InChI   1S/C2H7O3P/c1-4-6(3)5-2/h6H,1-2H3
InChI key   HZCDANOFLILNSA-UHFFFAOYSA-N

Description

Application

Dimethyl phosphite is used in the synthesis of α-aminophosphonates, which are medicinally important phosphorus analogs of amino acids, by treating with an amine and an aldehyde or a ketone. It can also be employed in asymmetric hydrophosphonylation of aldehydes to synthesize optically active α-hydroxy phosphonates.

Dimethyl phosphite may be used as an effective alternative to organic tin hydrides as radical reducing agents for organic halides, thionoesters, and isocyanides to form the corresponding hydrocarbons. Radical translocation/cyclization reactions of terminal alkynes to form cyclic phosphonates can also be effectively carried using dimethyl phosphite as a reagent under tin-free condition.

Packaging

25, 500 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
RIDADR 
UN 3278 6.1 / PGIII
WGK Germany 
WGK 1
RTECS 
SZ7710000
Flash Point(F) 
158.0 °F - closed cup
Flash Point(C) 
70 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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