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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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25 G
47,50 €
500 G
83,90 €

47,50 €

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25 G
47,50 €
500 G
83,90 €

About This Item

Formula condensata:
(CH3O)2P(O)H
Numero CAS:
868-85-9
Peso molecolare:
110.05
Beilstein:
1697490
Numero CE:
212-783-8
Numero MDL:
MFCD00044633
Codice UNSPSC:
12352100
ID PubChem:
24893543
NACRES:
NA.22

47,50 €

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Livello qualitativo

200

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.[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]

Pittogrammi

Health hazardExclamation mark
GHS08,GHS07

Avvertenze

Warning

Indicazioni di pericolo

H317,H341,H351,H412

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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Certificati d'analisi (COA)

Lot/Batch Number
BCCL7574
BCCF9422
BCCB1541
BCBW0928
BCBQ7496V

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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)
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)
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Domande

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

    1 risposta

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

    1 risposta

    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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