Hexamethylphosphoramide

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]
  • liquid cancer (colloquial)
Identifiers
3D model (JSmol)
1099903
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.595 Edit this at Wikidata
EC Number
  • 211-653-8
3259
KEGG
RTECS number
  • TD0875000
UNII
UN number 2810 3082
  • 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
  • O=P(N(C)C)(N(C)C)N(C)C
Properties
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]
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:
GHS08: Health hazard
Danger
H340, H350
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 ?)

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.