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D178454

Sigma-Aldrich

Dimethyl phosphite

98%

Sinônimo(s):

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

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About This Item

Fórmula linear:
(CH3O)2P(O)H
Número CAS:
868-85-9
Peso molecular:
110.05
Beilstein:
1697490
Número CE:
212-783-8
Número MDL:
MFCD00044633
Código UNSPSC:
12352100
ID de substância PubChem:
24893543
NACRES:
NA.22

Nível de qualidade

200

Ensaio

98%

forma

liquid

Impurezas

≤0.5% trimethyl phosphate
≤1% methyl alcohol

índice de refração

n20/D 1.402 (lit.)

pb

170-171 °C (lit.)

densidade

1.2 g/mL at 25 °C (lit.)

cadeia de caracteres SMILES

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

InChI

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

chave InChI

HZCDANOFLILNSA-UHFFFAOYSA-N

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Aplicação

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.

Pictogramas

Exclamation markHealth hazard
GHS07,GHS08

Palavra indicadora

Warning

Classificações de perigo

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

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

158.0 °F - closed cup

Ponto de fulgor (°C)

70 °C - closed cup

Equipamento de proteção individual

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “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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