Hexamethylphosphoramide

Base Information

• Chemical Name: Hexamethylphosphoramide
• CAS No.: 680-31-9
• Deprecated CAS: 24992-55-0,51557-01-8,51557-01-8
• Molecular Formula: C6H18N3OP
• Molecular Weight: 179.202
• Hs Code.: HOSPHORIC TRIAMIDE PRODUCT IDENTIFICATION
• European Community (EC) Number: 211-653-8
• ICSC Number: 0162
• NSC Number: 113131,7967
• UN Number: 2810,3082
• UNII: M42TU5843Z
• DSSTox Substance ID: DTXSID6020694
• Nikkaji Number: J4.420B
• Wikipedia: Hexamethylphosphoramide
• Wikidata: Q416086
• NCI Thesaurus Code: C44390
• Metabolomics Workbench ID: 53944
• ChEMBL ID: CHEMBL3187047
• Mol file: 680-31-9.mol

Synonyms:Hempa;Hexametapol;Hexamethylphosphoramide;Hexamethylphosphoric Triamide;HMPA;Triamide, Hexamethylphosphoric

Chemical Property of Hexamethylphosphoramide

Chemical Property:

• Appearance/Colour: clear colorless to light amber liquid
• Vapor Pressure: 0.07 mm Hg ( 25 °C)
• Melting Point: 7 °C(lit.)
• Refractive Index: 1.458
• Boiling Point: 233 °C at 760 mmHg
• PKA: 4.69±0.70(Predicted)
• Flash Point: 94.7 °C
• PSA: 36.60000
• Density: 1.03 g/cm³
• LogP: 0.77930
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Soluble), Methanol (Slightly)
• Water Solubility.: Miscible
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 179.11874920
• Heavy Atom Count: 11
• Complexity: 139
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Hexamethyltriamidophosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-46
• Safety Statements: 53-45-99

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: CN(C)P(=O)(N(C)C)N(C)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: Exposure to high concentrations could cause effects on the nervous system, kidneys and respiratory tract.
• Effects of Long Term Exposure: The substance may have effects on the respiratory tract, kidneys and testes. This substance is possibly carcinogenic to humans. May cause genetic damage in humans.
• Uses: 1.?? It can be used as the efficient anti-corrosion agent of PVC and other kinds of chlorine-containing resin products and coatings. 2.?? The product is the weathering solvent of polyvinyl chloride and excellent polar solvent, having a significant effect on the low temperature resistance and aging resistance of the agricultural film; it is a multi-functional high-boiling polar solvent that is aprotic. It can be used as the solvents of polymer synthesis with special effect on the synthesis of polyphenylene sulfide and aromatic polyamide and so on. This product, as the co-catalyst of propylene polymerization catalyst, when supplied to the ethylene propylene rubber, can improve the missile and oil resistance of the latter one. Hexamethylphosphoramide can also be used as a gas chromatographic fixative, ultraviolet inhibitor, rocket fuel additives for lowering the freezing point and chemical sterilizers. 3.?? It is effective non-proton solvent; as fixative of gas chromatography (highest usage temperature: 35°C with methanol as the solvent); used for separation and analysis of hydrocarbons; for separation of alkanes, alkenes and alkynes; accelerator of stereo-specific reaction; Ultraviolet inhibitor of PVC. Aprotic solvent in organic synthesis. Solvent for polymers, gases; polymerization catalyst; thermal stabilizer in polystyrene; protective additive for polyvinyl and polyolefin resins against uv light degradation. De-icing additive for jet fuels. Chemosterilant for a number of insect pests; chemical mutagen. Solvent for polymers; polymerization catalyst; stabilizer against thermal degradation in polystyrene; UV stabilizer in polyvinyl and polyolefin resins Hexamethylphosphoramide is a dipolar co-solvent and an effective additive used in reactions like reduction of halides, deoxygenation of sulfones, halide olefin couplings and cleavage of carbon-sulfur bond.
• Production method: It can be obtained through the reaction between dimethylamine and alkali chlorophosphorus. Put the dimethylamine and phosphorus oxychloride for reaction in triethylene glycol as the solvent; control the temperature at 40-60 °C; upon reaction, add ammonia as acid-binding agent with interaction with the generated hydrogen chloride to become ammonium chloride precipitation. After completion of the reaction, filtration was performed. Recycle the trichlorethylene from the filtration and then perform alkali treatment, and then conduct distillation, collecting the fraction of 113-118 °C (2.0kPa) fractions to derive Hexamethylphosphoramide (HMPA). Tsinghua Unisplendour Group Corporation has cooperated with the production plant to develop a new solvent-free process that can achieve a product purity of 99.2% or more. The industrial hexamethylphosphoramide appears as colorless or light yellow transparent liquid. Catalyst grade content ≥ 99.5%; first-class grade ≥ 99.0%; second-class products ≥ 98.0%. Fixed consumption amount of raw materials: dimethylamine 2410kg/t, phosphorus oxychloride: 1610kg/t, liquid ammonia 430kg/t.

Technology Process of Hexamethylphosphoramide

There total 101 articles about Hexamethylphosphoramide 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: 93.0%

triphenylphosphine (603-35-0) → N,N,N,N,N,N-hexamethylphosphoric triamide (680-31-9)

Guidance literature:

With Oxone; In tetrahydrofuran; methanol; Ambient temperature;

DOI:10.1016/S0040-4039(99)00261-0

Reference yield: 92.0%

Hexamethylphosphorous triamide (1608-26-0) → N,N,N,N,N,N-hexamethylphosphoric triamide (680-31-9)

Guidance literature:

With benzenesulfonyl chloride; In diethyl ether;

DOI:10.1007/BF00954291

Reference yield: 91.0%

carbon dioxide (124-38-9,18923-20-1) + iminotris(dimethylamino)phosphorane (49778-01-0) → N,N,N,N,N,N-hexamethylphosphoric triamide (680-31-9) + N,N,N',N',N'',N''-hexamethylphosphorimidic triamide cyanate

Guidance literature:

In benzene; for 48h;

upstream raw materials:

dimethyl amine

4-Cyanochlorobenzene

diphenyl sulfide

1,1'-sulfinylbisbenzene

Downstream raw materials:

N,N-dimethyl-formamide

schradan

N,N,N',N'-Tetramethylphosphorodiamidic chloride

N,N-dimethyl acetamide

Refernces

• 1、 Romanova,Mironov,Larionova,Morozov,Zverev,Sinyashin. "Formation of the fullerene radical anion in the reaction of C60 with phosphorous triamides". . p. 209 - 211. Retrieved 2008.
• 2、 Preez, J. G. H. du,Vuuren, C. P. J. van. "". . . Retrieved 1975.
• 3、 Pavankumar,Goud, E. Veerashekhar,Selvakumar,Kumar, S. K. Ashok,Sivaramakrishna, Akella,Vijayakrishna, Kari,Rao, C. V. S. Brahmananda,Sabharwal,Jha, Prakash C.. "Function of substituents in coordination behaviour, thermolysis and ligand crossover reactions of phosphine oxides". . p. 4727 - 4736. Retrieved 2015/03/03.
• 4、 Londregan, Allyn T.,Jennings, Sandra,Wei, Liuqing. "General and mild preparation of 2-aminopyridines". scheme or table. p. 5254 - 5257. Retrieved 2011/02/24.