Bis(dimethylamino)phosphoryl chloride

Base Information

• Chemical Name: Bis(dimethylamino)phosphoryl chloride
• CAS No.: 1605-65-8
• Molecular Formula: C4H12ClN2OP
• Molecular Weight: 170.579
• Hs Code.: 29299090
• European Community (EC) Number: 216-517-1
• NSC Number: 30697
• DSSTox Substance ID: DTXSID3075096
• Nikkaji Number: J195.223D
• Wikidata: Q72445168
• Mol file: 1605-65-8.mol

Synonyms:Phosphorodiamidicchloride, tetramethyl- (6CI,7CI,8CI,9CI);Bis(N,N-dimethylamino)phosphinicchloride;Bis(dimethylamino)chlorophosphine oxide;Bis(dimethylamino)phosphinicchloride;Bis(dimethylamino)phosphinyl chloride;Bis(dimethylamino)phosphorylchloride;Chlorobis(dimethylamino)phosphine oxide;N,N,N',N'-Tetramethyldiamidophosphorochloridate;N,N,N',N'-Tetramethylphosphorodiamidicchloride;NSC 30697;Tetramethyldiamidophosphoryl chloride;Tetramethylphosphorochloridic diamide;Tetramethylphosphorodiamidic chloride;Tetramethylphosphorodiamidoyl chloride;

Chemical Property of Bis(dimethylamino)phosphoryl chloride

Chemical Property:

• Appearance/Colour: Clear colourless to slightly yellow liquid
• Vapor Pressure: 0.644mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Boiling Point: 187 °C at 760 mmHg
• PKA: -0.04±0.70(Predicted)
• Flash Point: 66.9 °C
• PSA: 33.36000
• Density: 1.179 g/cm³
• LogP: 1.45650
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 170.0375777
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

98%, ^*data from raw suppliers

Bis(dimethylamino)phosphoryl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-37-20/21/22
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)P(=O)(N(C)C)Cl
• Uses: N,N,N′,N′-Tetramethylphosphorodiamidic chloride was used in the synthesis of (-)-allohedycaryol and C2-symmetric binaphthyl phosphortriamide. It was also used in total synthesis of neohedycaryol.

Technology Process of Bis(dimethylamino)phosphoryl chloride

There total 15 articles about Bis(dimethylamino)phosphoryl chloride 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: 95.0%

bis(N,N-dimethylamino)chlorophosphine (3348-44-5) → N,N,N',N'-Tetramethylphosphorodiamidic chloride (1605-65-8)

Guidance literature:

With ozone; In dichloromethane; at -80 ℃;

Reference yield: 90.0%

N,N-dibenzyl-O-diphenylphosphinylhydroxylamine (102269-11-4) → N-benzylidene benzylamine (780-25-6) + N,N,N',N'-Tetramethylphosphorodiamidic chloride (1605-65-8)

Guidance literature:

In chloroform; for 3h; Heating;

DOI:10.1055/s-1988-27750

Reference yield: 88.0%

dimethyl amine (124-40-3) → N,N,N',N'-Tetramethylphosphorodiamidic chloride (1605-65-8)

Guidance literature:

With trichlorophosphate;

upstream raw materials:

N,N,N,N,N,N-hexamethylphosphoric triamide

dimethyl amine

N,N-dimethylphosphoroamidic dichloride

tetrachloro-cyclopent-4-ene-1,3-dione

Downstream raw materials:

Bis-(dimethylamino)-α-phenylcyanomethylphosphonat

Phosphorsaeure-pentachlorphenylester-bis-dimethylamid

ethyl-μ-imido-diphosphoric acid-1,1-diethyl ester-2,2-bis-dimethylamide

meso-tetratolylporphyrinatocobalt(II)

Refernces

• 1、 Doucet Ladeveze, G.,Rodehueser, L.,Rubini, P.,Selve, C.,Delpuech, J-J.. "SYNTHESE DE COMPOSES BIPHOSPHPORYLES UTILISES COMME AGENTS COMPLEXANTS". . p. 643 - 646. Retrieved 1982.
• 2、 Olszewski, Tomasz K.,Bomont, Catherine,Coutrot, Philippe,Grison, Claude. "Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera". supporting information; experimental part. p. 2354 - 2358. Retrieved 2010/10/19.
• 3、 Nuretdinova, O. N.,Guseva, F. F.,Troitskaya, L. B.. "REACTIONS OF P(IV)-ACID DIMETHYLAMIDES WITH ACETYL CHLORIDE". . p. 2493 - 2495. Retrieved 2007/10/02.