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Hexamethylphosphoramide information


Hexamethylphosphoramide
Chemical structure of HMPA
3D stick model of HMPA
Names
Preferred IUPAC name
Hexamethylphosphoric triamide[3]
Other names
  • Hexamethylphosphoramide
  • Hexametapol
  • HMPA
  • Phosphoric tris(dimethylamide)[1]
  • HMPT[2]
Identifiers
CAS Number
  • 680-31-9 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1099903
ChEBI
  • CHEBI:24565 checkY
ChEMBL
  • ChEMBL3187047
ChemSpider
  • 12158 checkY
ECHA InfoCard 100.010.595 Edit this at Wikidata
EC Number
  • 211-653-8
Gmelin Reference
3259
KEGG
  • C19250 checkY
PubChem CID
  • 12679
RTECS number
  • TD0875000
UNII
  • M42TU5843Z checkY
UN number 2810 3082
CompTox Dashboard (EPA)
  • DTXSID6020694 Edit this at Wikidata
InChI
  • InChI=1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3 checkY
    Key: GNOIPBMMFNIUFM-UHFFFAOYSA-N checkY
  • InChI=1/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3
    Key: GNOIPBMMFNIUFM-UHFFFAOYAP
SMILES
  • O=P(N(C)C)(N(C)C)N(C)C
Properties
Chemical formula
C6H18N3OP
Molar mass 179.20 g/mol
Appearance clear, colorless liquid[4]
Odor aromatic, mild, amine-like[4]
Density 1.03 g/cm3
Melting point 7.20 °C (44.96 °F; 280.35 K)
Boiling point 232.5 °C (450.5 °F; 505.6 K) CRC[5]
Solubility in water
miscible[4]
Vapor pressure 0.03 mmHg (4.0 Pa) at 20 °C[4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Suspected Carcinogen[4]
GHS labelling:
Pictograms
GHS08: Health hazard
Signal word
Danger
Hazard statements
H340, H350
Precautionary statements
P201, P202, P281, P308+P313, P405, P501
Flash point 104.4 °C (219.9 °F; 377.5 K)
NIOSH (US health exposure limits):
PEL (Permissible)
none[4]
REL (Recommended)
Ca[4]
IDLH (Immediate danger)
Ca [N.D.][4]
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula [(CH3)2N]3PO. This colorless liquid is a useful reagent in organic synthesis.

  1. ^ Not recommended: see Blue Book reference.
  2. ^ This name is also used to refer to tris(dimethylamino)phosphine
  3. ^ "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. P001–P004. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  4. ^ a b c d e f g h NIOSH Pocket Guide to Chemical Hazards. "#0321". National Institute for Occupational Safety and Health (NIOSH).
  5. ^ Haynes, William M. (2010). Handbook of Chemistry and Physics (91 ed.). Boca Raton, Florida, USA: CRC Press. p. 3-280. ISBN 978-1-43982077-3.

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Hexamethylphosphoramide

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Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula [(CH3)2N]3PO. This colorless liquid...

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DMPU

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showed that it is possible to replace the suspected carcinogen hexamethylphosphoramide (HMPA) with DMPU. Nomenclature of Organic Chemistry : IUPAC Recommendations...

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Polar aprotic solvent

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C4H8O2 77.11°C 6.02 0.902 g/cm3 1.88 reacts with strong bases hexamethylphosphoramide [(CH3)2N]3PO 232.5 °C 29.6 1.03 g/cm3 5.38 high boiling point,...

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Dimethyl sulfoxide

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dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, and hexamethylphosphoramide (HMPA). DMSO is frequently used as a solvent for chemical reactions...

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Twaron

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DuPont (Fibre B) as Dupont initially used the carcinogenic HMPT (hexamethylphosphoramide). Despite heavy research DuPont now also applies the AKZO patent...

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Kevlar

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mechanical drawing orients the polymer chains in the fiber's direction. Hexamethylphosphoramide (HMPA) was the solvent initially used for the polymerization, but...

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Solvent

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acetate 1.009 Benzonitrile 1.01 1-Methyl-2-pyrrolidinone 1.028 Hexamethylphosphoramide 1.03 1,4-Dioxane 1.033 Acetic acid 1.049 Acetic anhydride 1.08...

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Phosphoramides

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agriculture to enhance the effectiveness of urea-based fertilizers. Hexamethylphosphoramide (HMPA) is a polar solvent. "Phosphoramide". IUPAC GoldBook. Steger...

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IARC group 2B

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Heptachlor Hexachlorobenzene Hexachloroethane Hexachlorocyclohexanes Hexamethylphosphoramide (HMPA) 2,4-Hexadienal Human immunodeficiency virus type 2 (infection...

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Hexamethylphosphorous triamide

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Hexamethylphosphorous triamide (HMPT) could be: Hexamethylphosphoramide Tris(dimethylamino)phosphine This disambiguation page lists articles associated...

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Phosphoramide

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called phosphoramides. An example compound is the polar solvent hexamethylphosphoramide (HMPA). Perrin, D. D., ed. (1982) [1969]. Ionisation Constants...

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Acyloin

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of carbonyls is a system with molybdenum peroxide, pyridine and hexamethylphosphoramide. A family of stereoselective syntheses oxidizes in situ enols with...

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Trisulfur

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water. Another way to make it is with polysulfide dissolved in hexamethylphosphoramide where it gives a blue colour. Other methods of production of S−3...

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Alkali metal

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liquid ammonia or other donor solvents like aliphatic amines or hexamethylphosphoramide to give blue solutions. These solutions are believed to contain...

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Organolithium reagent

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diethyl ether (Et2O), tetramethylethylene diamine (TMEDA) or hexamethylphosphoramide (HMPA). Methyllithium is a special case: its tetrameric structure...

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List of reagents

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common application is for alkylation of aldehydes and ketones: Hexamethylphosphoramide a phosphoramide; useful polar aprotic solvent and additive in organic...

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California Proposition 65 list of chemicals

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Hexachloroethane 67-72-1 2,4-Hexadienal – Hexafluoroacetone 684-16-2 Hexamethylphosphoramide 680-31-9 n-Hexane 110-54-3 2,5-Hexanedione 110-13-4 Hexavalent...

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Solvated electron

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some small primary amines, such as methylamine and ethylamine and hexamethylphosphoramide, forming blue solutions. THF dissolves alkali metal, but a Birch...

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National Emissions Standards for Hazardous Air Pollutants

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Hexachloroethane 822-06-0 Hexamethylene-1,6-diisocyanate 680-31-9 Hexamethylphosphoramide 110-54-3 Hexane 302-01-2 Hydrazine 7647-01-0 Hydrochloric acid...

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Tetramethylurea

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tetramethylurea is often used as a replacement for the carcinogenic hexamethylphosphoramide (HMPT). Tetramethylurea is suitable as a reaction medium for the...

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Germyl

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used as solvents include liquid ammonia, ethyl amine, diglyme, or hexamethylphosphoramide. The choice of solvent depends on the temperature desired, whether...

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Desulfonylation reactions

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used to reductively cleave α-keto sulfones; in the presence of hexamethylphosphoramide (HMPA), SmI2 is able to effect reductive elimination of α-functionalized...

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Uranium pentabromide

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UBr5L are known with such ligands as triphenylphosphine oxide and hexamethylphosphoramide, and are obtained by brominating UBr4 in the presence of the desired...

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