[bis(dimethylamino)phosphanyl]dimethylamine

• ChemBase ID: 74081
• Molecular Formular: C6H18N3P
• Molecular Mass: 163.200981
• Monoisotopic Mass: 163.12383422
• SMILES: P(N(C)C)(N(C)C)N(C)C
• Canonical SMILES: CN(P(N(C)C)N(C)C)C
• InChI: InChI=1S/C6H18N3P/c1-7(2)10(8(3)4)9(5)6/h1-6H3
• InChIKey: XVDBWWRIXBMVJV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [bis(dimethylamino)phosphanyl]dimethylamine
• IUPAC Traditional name: [bis(dimethylamino)phosphanyl]dimethylamine
• Synonyms: HMPT; Tris(dimethylamino)phosphine; (Me2N)3P; Hexamethyltriamidophosphite; Hexamethyltriaminophosphine; Hexamethylphosphorous triamide; Tris(dimethylamino)phosphine; Hexamethylphosphorous triamide; Hexamethyl-phosphorous Triamide; N,N,N',N',N'',N''-Hexamethyl-phosphorous Triamide; NSC 102707; Tris(dimethylamino)phosphine; Trisdimethylaminophosphorus; Hexamethylphosphorous Triamide; 六甲基亚磷酰三胺; 三(二甲胺基)膦; 三(二甲氨基)膦

Database IDs

• CAS Number: 1608-26-0
• EC Number: 216-534-4
• MDL Number: MFCD00008301
• Beilstein Number: 906778
• PubChem SID: 24864511; 162039000; 24848595; 24889847
• PubChem CID: 15355

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -1.8339126
• LogD (pH = 7.4): -1.3347348
• Log P: -0.3046
• Molar Refractivity: 48.5162 cm^3
• Polarizability: 19.082659 Å^3
• Polar Surface Area: 9.72 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -44°C; -44°C
• Boiling Point: 162-164°C; 48-50 °C/12 mmHg(lit.); 49-51°C/12mm
• Flash Point: 22 °C; 27 °C; 27°C; 37°C(98°F); 71.6 °F; 80.6 °F
• Density: 0.890; 0.898; 0.898 g/mL at 25 °C(lit.)
• Refractive Index: 1.4650; n20/D 1.463(lit.); n20/D 1.466
• Ligand For: Reductions; Suzuki-Miyaura Coupling; Wittig Reaction

Safety Information

• Storage Warning: Air Sensitive; Flammable/Store under inert gas
• RTECS: TH3390000
• European Hazard Symbols: Toxic (T)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10; 45-46-10
• Safety Statements: 53-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H225-H340-H350; H226-H340-H350; H340-H350-H226
• GHS Precautionary statements: P201-P210-P308 + P313; P201-P308 + P313; P210; P210-P241-P280-P303+P361+P353-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: ≥97.0% (GC); 85%; 97%
• Grade: purum; technical grade
• Impurities: ≤0.1% hexamethylphosphoric acid triamide
• Linear Formula: P[N(CH3)2]3

DETAILS

Sigma Aldrich - 143553

Packaging
10, 50 g in glass bottle

Sigma Aldrich - 393290

Application
Reagent combination with CCl4 for the conversion of hydroxyl groups to the corresponding chlorides; hydroxyl group activation; dehydrations.
Packaging
5, 25 mL in glass bottle

Sigma Aldrich - 93338

Caution
may contain precipitate

Toronto Research Chemicals - H294225

A compound widely used in industry, with applications such as being a flame retardant for building materials to a phosphorylating agent in synthetic chemistry. It is a classified carcinogen.

REFERENCES

• Ryu, H., et al.: J. Mat. Sci., 41, 8265 (2006)
• Benaniba, M., et al.: Eur. J. Lip. Sci. Technol., 109, 1186 (2006)
• Reduces aromatic aldehydes to symmetrical epoxides in good yield: J. Am. Chem. Soc., 85, 1884 (1963). Both cis- and trans-isomers are formed. For list of examples, see: Org. Synth. Coll., 5, 358 (1973). Under suitable conditions, reaction of the intermediate with a second aldehyde can lead to mixed deoxybenzoins or diaryl enamines: Synthesis, 225 (1991).
• Has also been used for a variety of other reductions including that of ozonolysis intermediates: Helv. Chim. Acta, 50, 2387 (1967), and of primary alkyl nitro compounds to nitriles: Synthesis, 36 (1979). Bromohydrins can be converted to alkenes, by reductive elimination from their triflate esters: J. Am. Chem. Soc., 102, 1433 (1980):
  
• Reacts with BrCCl₃ to give dichloromethylenephosphorane Cl₂C=PPh₃, which undergoes Wittig reaction with aldehydes to give 1,1-dichloroalkenes, giving better results than the CCl₄/PPh₃ combination: Tetrahedron Lett., 1237, 1239 (1977);Synthesis, 554 (1980). Similarly, with Br₂CF₂, the CF₂ group can be transferred to both aldehydes and ketones: J. Fluorine Chem., 1, 123 (1971); Synth. Commun., 3, 197 (1973).