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D178454

Sigma-Aldrich

Dimethyl phosphite

98%

Sinonimo/i:

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

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About This Item

Formula condensata:
(CH3O)2P(O)H
Numero CAS:
Peso molecolare:
110.05
Beilstein:
1697490
Numero CE:
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22

Livello qualitativo

Saggio

98%

Stato

liquid

Impurezze

≤0.5% trimethyl phosphate
≤1% methyl alcohol

Indice di rifrazione

n20/D 1.402 (lit.)

P. ebollizione

170-171 °C (lit.)

Densità

1.2 g/mL at 25 °C (lit.)

Stringa SMILE

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

InChI

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

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Applicazioni

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.

Pittogrammi

Health hazardExclamation mark

Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

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

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

158.0 °F - closed cup

Punto d’infiammabilità (°C)

70 °C - closed cup

Dispositivi di protezione individuale

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


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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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