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D178454

Sigma-Aldrich

Dimethyl phosphite

98%

Sinónimos:

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

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About This Item

Fórmula lineal:
(CH3O)2P(O)H
Número de CAS:
868-85-9
Peso molecular:
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

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_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

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Certificados de análisis (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)
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
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.
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