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D178454

Sigma-Aldrich

Dimethyl phosphite

98%

Synonym(s):

Dimethoxyphosphine oxide, Dimethyl hydrogen phosphite, Dimethyl hydrogen phosphonate, Dimethyl phosphonate, Hydrogen dimethyl phosphite

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About This Item

Linear Formula:
(CH3O)2P(O)H
CAS Number:
868-85-9
Molecular Weight:
110.05
Beilstein/REAXYS Number:
1697490
EC Number:
212-783-8
MDL number:
MFCD00044633
UNSPSC Code:
12352100
PubChem Substance ID:
24893543
NACRES:
NA.22

Quality Level

200

assay

98%

form

liquid

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

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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.

pictograms

Exclamation markHealth hazard
GHS07,GHS08

signalword

Warning

Hazard Classifications

Aquatic Chronic 3 - Carc. 2 - Muta. 2 - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 1

flash_point_f

158.0 °F - closed cup

flash_point_c

70 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Zirconium (IV) compounds as efficient catalysts for synthesis of α-aminophosphonates.
Bhagat S and Chakraborti A K
The Journal of Organic Chemistry, 73(15), 6029-6032 (2008)
Dimethyl Phosphite Mediated Hydrogen Atom Abstraction: A Tin?Free Procedure for the Preparation of Cyclopentane Derivatives.
Beaufils F, et al.
Angewandte Chemie (International Edition in English), 44(33), 5273-5275 (2005)
Synthesis of an Optically Active C1?Symmetric Al (salalen) Complex and Its Application to the Catalytic Hydrophosphonylation of Aldehydes.
Saito B and Katsuki T
Angewandte Chemie (International Edition in English), 117(29), 4676-4678 (2005)
The invention of radical reactions. Part 32. Radical deoxygenations, dehalogenations, and deaminations with dialkyl phosphites and hypophosphorous acid as hydrogen sources.
Barton DH, et al.
The Journal of Organic Chemistry, 58(24), 6838-6842 (1993)
Microwave-assisted solvent-free and catalyst-free Kabachnik?Fields reactions for α-amino phosphonates.
Mu X J, et al.
Tetrahedron Letters, 47(7), 1125-1127 (2006)
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