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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:
Peso molecular:
110.05
Beilstein:
1697490
Número CE:
Número MDL:
Código UNSPSC:
12352100
ID de substância PubChem:
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

Nível de qualidade

Ensaio

98%

Formulário

liquid

Impurezas

≤0.5% trimethyl phosphate
≤1% methyl alcohol

índice de refração

n20/D 1.402 (lit.)

p.e.

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.[1][2] It can also be employed in asymmetric hydrophosphonylation of aldehydes to synthesize optically active α-hydroxy phosphonates.[3]
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.[4] 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.[5]

Pictogramas

Health hazardExclamation mark

Palavra indicadora

Warning

Frases de perigo

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


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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)
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)
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)
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)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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