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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)
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)
A J Gutierrez et al.
Nucleosides, nucleotides & nucleic acids, 20(4-7), 1299-1302 (2001-09-21)
Chlorotrimethylsilane completely dealkylates phosphonate esters at elevated temperature in a sealed reaction vessel. These conditions are tolerated by a variety of functional groups and lead to high conversions of dimethyl, diethyl and diisopropyl phosphonates to their corresponding phosphonic acids.
Igor Pastirk et al.
Applied optics, 46(19), 4041-4045 (2007-06-16)
Phase-shaped femtosecond laser pulses and mass spectrometry were implemented as a tool for improving molecular identification. We demonstrate that the specific lines in the mass spectra of several chemical warfare simulants are sensitive to the phase characteristics of the incident
Yeonju Kim et al.
Nanotechnology, 21(49), 495501-495501 (2010-11-17)
Single-walled carbon nanotube (SWNT) networks were used to detect hazardous dimethyl-methyl-phosphonate (DMMP) gas in real time, employing two different metals as electrodes. Random networks of SWNTs were simply obtained by drop-casting a SWNT-containing solution onto a surface-oxidized Si substrate. Although
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