Hexaethylphosphoramide

Base Information

• Chemical Name: Hexaethylphosphoramide
• CAS No.: 2622-07-3
• Molecular Formula: C12H30 N3 O P
• Molecular Weight: 263.363
• DSSTox Substance ID: DTXSID60180857
• Nikkaji Number: J934.465I
• Wikidata: Q83051473
• Mol file: 2622-07-3.mol

Synonyms:Hexaethylphosphoramide;2622-07-3;Hexaethylphosphoric triamide;HEPA;Tris(diethylamino)phosphine oxide;Hexaethylphosphorylamide;Hexaethylphosphorotriamide;Phosphoric triamide, hexaethyl-;((C2H5)2N)3P=O;BRN 1073869;AI3-50917;Phosphoric triamide, N,N,N',N',N'',N''-hexaethyl-;hexaethyltriamidophosphate;N-[bis(diethylamino)phosphoryl]-N-ethylethanamine;SCHEMBL1276852;DTXSID60180857;OP(N(C2H5)2)3;[bis(diethylamino)phosphoryl]diethylamine;LS-107916;FT-0748664

Chemical Property of Hexaethylphosphoramide

Chemical Property:

• Boiling Point: 338.7°Cat760mmHg
• PKA: 6.89±0.70(Predicted)
• Flash Point: 158.6°C
• PSA: 36.60000
• Density: 0.966g/cm³
• LogP: 3.11990
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 263.21264959
• Heavy Atom Count: 17
• Complexity: 198

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)P(=O)(N(CC)CC)N(CC)CC
• Recent ClinicalTrials: Evaluation of Safety and Immunogenicity of Combined Immunization of sIPV, DTaP and HepA

Technology Process of Hexaethylphosphoramide

There total 10 articles about Hexaethylphosphoramide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

1-(4-methylphenyl)-5-phenyl-2,3-dihydro-1H-pyrrole-2,3-dione + hexaethylphosphoric triamide (2283-11-6) → hexaethylphosphorous triamide (2622-07-3) + 1,1′-bis(4-methylphenyl)-5,5′-diphenyl-1H,1′H-3,3′-bipyrrolylidene-2,2′-dione

Guidance literature:

In dichloromethane; at 20 ℃; Cooling;

DOI:10.1134/S1070428014070227

Reference yield: 70.0%

tetrakis(diethylamino)phosphonium bromide (81175-49-7) → hexaethylphosphorous triamide (2622-07-3) + ethanol (64-17-5) + diethylamine (109-89-7) + hydrochloride of heptaethylphosphorimidic triamide

Guidance literature:

With sodium hydroxide; at 200 ℃; under 0.02 Torr; Product distribution; Mechanism;

Reference yield: 69.4%

4-nitrobenzaldehdye (555-16-8) + C19H36N3P (76502-51-7) → hexaethylphosphorous triamide (2622-07-3) + 4-nitrostilbene (1694-20-8,4003-94-5,6624-53-9,101977-34-8)

Guidance literature:

In ethanol; at 50 - 60 ℃; for 1h;

upstream raw materials:

diphenyl diethylphosphoramidate

4-nitrobenzaldehdye

tris(diethylamino)<(diethylcarbamoyl)methyl>phosphonium chloride

C₁₉H₃₆N₃P

Downstream raw materials:

diethylacetamide

N,N-diethyl-2-oxo-2-phenylacetamide

4-chloro-N,N-diethyl-α-oxo-benzeneacetamide

N,N-diethyl-4-methyl-α-oxo-benzeneacetamide

Refernces

• 1、 Pudovik,Kibardina,Pudovik. "Reaction of Bis(chloromethyl)phosphinoyl Chloride and Phenyl (Chloromethyl)phosphonochloridate with Diethyl Bis(trimethylsilyl) phosphoramidite [1]". . p. 151 - 152. Retrieved 2007/10/03.
• 2、 Marchenko, A. P.,Koidan, G. N.,Pinchuk, A. M.. "REACTIONS OF TETRAKIS(DIALKYLAMINO)PHOSPHONIUM BROMIDES WITH BASES". . p. 2405 - 2409. Retrieved 2007/10/02.