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Merck
CN

D178454

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24893543
EC Number:
212-783-8
Beilstein/REAXYS Number:
1697490
MDL number:
MFCD00044633
Assay:
98%
Form:
liquid

Key Documents

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InChI key

HZCDANOFLILNSA-UHFFFAOYSA-N

InChI

1S/C2H7O3P/c1-4-6(3)5-2/h6H,1-2H3

SMILES string

[H]P(=O)(OC)OC

assay

98%

form

liquid

impurities

≤0.5% trimethyl phosphate, ≤1% methyl alcohol

Quality Level

200

bp

170-171 °C (lit.)

density

1.2 g/mL at 25 °C (lit.)

Related Categories

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

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

10 - Combustible liquids

wgk

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

Regulatory Information

监管及禁止进口产品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7574
BCCF9422
BCCB1541
BCBW0928
BCBQ7496V

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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)
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)
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 hydrogen phosphite.
IARC monographs on the evaluation of carcinogenic risks to humans, 48, 85-93 (1990-01-01)
Ming Xie et al.
Journal of hazardous materials, 181(1-3), 975-980 (2010-06-18)
Nanofiltration (NF) was investigated for the removal of glyphosate in the neutralization liquor produced by the glycine-dimethylphosphit process. The Desal-5 DK membrane was chosen as the most suitable membrane for the NF process when compared to the DL and NTR7450
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