Structure via PubChem · Public domain (PubChem)
hexamethylphosphoramide triamide
Sign in to saveAlso known as Hexamethyl phosphoramide, Hexamethylphosphoric triamide, Hexamethylphosphorotriamide, HMPA, Tris(dimethylamino)phosphine oxide, hexamethylorthophosphoric triamide, phosphoric acid hexamethyltriamide, HEMPA
Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula This colorless liquid is used as a solvent in organic synthesis.
Chemical data
- Formula
- C6H18N3OP
- Molecular weight
- 179.2 g/mol
- IUPAC name
- N-[bis(dimethylamino)phosphoryl]-N-methylmethanamine
- SMILES
- CN(C)P(=O)(N(C)C)N(C)C
- InChIKey
- GNOIPBMMFNIUFM-UHFFFAOYSA-N
- XLogP
- 0.3
- Polar surface area
- 26.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
143 papers- Juvenile Idiopathic Arthritis.Balkan medical journal · 2017
- Hexamethylphosphoramide.IARC monographs on the evaluation of carcinogenic risks to humans · 1999
- Hexamethylphosphoramide.Report on carcinogens : carcinogen profiles · 2002
- Hexamethylphosphoramide.Report on carcinogens : carcinogen profiles · 2004
- Hexamethylphosphoramide.Report on carcinogens : carcinogen profiles · 2011
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- phosphorus
- Mass
- 179.119
Show 11 more facts
- chemical formula
- C₆H₁₈N₃OP
- subject has role
- carcinogen
- NIOSH Pocket Guide ID
- 0321
- density
- 1.03
- melting point
- 43
- boiling point
- 451
- vapor pressure
- 0.03
- flash point
- 220
- ceiling exposure limit
- 0
- canonical SMILES
- CN(C)P(=O)(N(C)C)N(C)C
- Commons category
- Hexamethylphosphoramide
via Wikidata · CC0
~2 min read
Encyclopedic overview
6 sectionsContents
- Structure and reactivity
- Applications
- Alternative reagents
- Toxicity
- References
- External links
Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula This colorless liquid is used as a solvent in organic synthesis.
==Structure and reactivity== HMPA is the oxide of tris(dimethylamino)phosphine, P(NMe2)3. Like other phosphine oxides (such as triphenylphosphine oxide), the molecule has a tetrahedral core and a P=O bond that is highly polarized, with significant negative charge residing on the oxygen atom.
Excerpted from Wikipedia’s “hexamethylphosphoramide triamide” article, available under the CC BY-SA 4.0 licence.