Hexamethylphosphoramide
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| Hexamethylphosphoramide | |
|---|---|
| Image:HMPA-2D-skeletal.png | |
| Chemical name | Hexamethylphosphoramide |
| Other names | Hexametapol HMPA HMPT |
| Chemical formula | C6H18N3OP |
| Molecular mass | 179.20 g/mol |
| CAS number | [680-31-9] |
| Density | 1.03 g/cm³ |
| Melting point | 7.20 °C |
| Boiling point | 235 °C |
| SMILES | CN(C)P(=O)(N(C)C)N(C)C |
| Disclaimer and references | |
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Overview
Hexamethylphosphoramide (abbreviated HMPA) is a colorless organic liquid with the formula [(CH3)2N]3PO. It is used as a polymer solvent, as a selective solvent for gases, stabilizer in polystyrene against thermal degradation, as a laboratory solvent for organometallic and organic reactions. It has been tested as a fire retardant and as an insect chemosterilant, but there is no known current use of HMPA for these applications. It is useful for improving the selectivity of certain organic reactions. For instance in some deprotonation reactions HMPA breaks up the oligomers of lithium bases such as butyl lithium. Also because HMPA solvates cations so well, while not solvating anions, it has been used as a solvent for some difficult SN2 reactions. The basic oxygen atom in HMPA coordinates strongly to lithium cation.[1] A molybdenum peroxide complex of HMPA is used in synthetic chemistry as an oxidant.
HMPA is the oxide of the highly basic tertiary phosphine P(NMe2)3. Like other phosphine oxides, e.g. Triphenylphosphine oxide, the molecule has tetrahedral core and the P-O bond is highly polarlized, with significant negative charge residing on oxygen.
Alternative reagents
Dimethyl sulfoxide can often be used in place of HMPA as a solvent. Both are strong hydrogen bond acceptors, and their oxygen atoms are able to bind to metal cations. Other alternatives to HMPA include the tetraalkylureas.[1]
Toxicity
HMPA is only mildly toxic but has been shown to cause nasal cancers in rats.[1]
HMPA can be degraded to less toxic compounds by the action of hydrochloric acid. In phosphorus chemistry it is the case in general that the treatment of a compound containing a nitrogen phosphorus single bond with hydrogen chloride will form a protonated amine and a P-chloro compound. For example if P-dimethylamino-P, P-diphenyl phosphine is treated with hydrogen chloride then P-chloro-P, P-diphenyl phosphine and dimethylamine HCl salt will be obtained.
References
- Merck Index, 12th Edition, 4761.
External links
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
