5625-99-0

Basic information

• Product Name: N,N'-diphenylphosphorodiamidic chloride
• Synonyms: N,N'-diphenylphosphorodiamidic chloride;N,N'-Diphenyldiamidophosphoric chloride;Phosphorodiamidic chloride, N,N-diphenyl-;Bis(phenylamino)chlorophosphine oxide;Bis(phenylamino)phosphinyl chloride;Brn 2215936;Diamidophosphoryl chloride, N,N'-diphenyl-;Dianilidophosphochloridate
• CAS NO: 5625-99-0
• Molecular Formula: C₁₂H₁₂ClN₂OP
• Molecular Weight: 266.663241
• EINECS: 227-063-9
• Mol File: 5625-99-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 167 °C
• Boiling Point: 382.5°Cat760mmHg
• Flash Point: 185.1°C
• Appearance: /
• Density: 1.39g/cm³
• PKA: -1.07±0.38(Predicted)
• CAS DataBase Reference: N,N'-diphenylphosphorodiamidic chloride(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-diphenylphosphorodiamidic chloride(5625-99-0)
• EPA Substance Registry System: N,N'-diphenylphosphorodiamidic chloride(5625-99-0)

Safety Data

• Hazardous Substances Data: 5625-99-0(Hazardous Substances Data)

Usage

General Description

N,N'-diphenylphosphorodiamidic chloride is a chemical compound with the molecular formula C12H12ClN2P. It is an organophosphorus compound that is used as a powerful tool in the synthesis of a variety of organic compounds. It is a white to pale yellow solid that is soluble in organic solvents such as dichloromethane and benzene. N,N'-diphenylphosphorodiamidic chloride is commonly used as a reagent in the synthesis of amides, phosphoramidates, and ureas. It is also used as a catalyst in organic reactions and as a building block for the production of various chemicals and pharmaceuticals. It is important to handle N,N'-diphenylphosphorodiamidic chloride with care as it is a highly reactive compound that can cause skin and eye irritation.

Upstream product

• 142-04-1 aniline hydrochloride 
• 62-53-3 aniline 
• 10025-87-3 trichlorophosphate 
• 71-43-2 benzene 
• 56-23-5 tetrachloromethane 

Downstream Products

• 5586-09-4 N,N'-diphenyl-diamidophosphoric acid ethyl ester 
• 36218-06-1 3-dianilinophosphoryloxy-cholest-5-ene 
• 30546-53-3 diphosphoric acid tetraanilide 
• 91958-92-8 methyl NN'diphenylphosphorodiamidate 
• 101275-87-0 N,N'-diphenyl-diamidophosphoric acid-(2-dimethylamino-ethyl ester) 
• 4707-91-9 bis(phenylamino)phenylphosphine oxide 
• 4743-42-4 N,N'-diphenylphosphoric acid diamide 
• 13824-04-9 2,4-dianilino-1,3-diphenyl-cyclodiphosphazane-2,4-dioxide 
• 330-08-5 N,N'-diphenyl-diamidophosphoryl fluoride 
• 54529-81-6 C₁₃H₁₇N₄OP 
• 1445-36-9 N-phenylamidophosphoric acid 
• 78162-22-8 [2]naphthyloxy-acetic acid anilide 
• 214784-90-4 8-bromo-2',3'-O-isopropylideneinosine-5'-O-phosphorodianilidate 
• 7647-01-0 hydrogenchloride 

Relevant articles and documents

New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions

Ten novel hydrogen-bonding catalysts based on open-chain PV-amides of BINOL and chinchona alkaloids as well as three catalysts based on rigid cis-PV-cyclodiphosphazane amides of N1,N1-dimethylcyclohexane-1,2-diamine have been developed. Employed in the asymmetric Michael addition of 2-hydroxynaphthoquinone to β-nitrostyrene, the open-chain 9-epi-aminochinchona-based phosphorus amides show a high catalytic activity with almost quantitative yields of up to 98% and enantiomeric excesses of up to 51%. The cyclodiphosphazane catalysts show the same high activity and give improved enantiomeric excesses of up to 75%, thus representing the first successful application of a cyclodiphosphazane in enantioselective organocatalysis. DFT computations reveal high hydrogen-bonding strengths of cyclodiphosphazane PV-amides compared to urea-based catalysts. Experimental results and computations on the enantiodetermining step with cis-cyclodiphosphazane 14a suggest a strong bidentate H-bond activation of the nitrostyrene substrate by the catalyst.

N,N'-Diphenylphosphorodiamido Chloridate, a Novel Reagent for the Synthesis of Anilides

N,N'-Diphenylphosphorodiamido chloridate (I) is found to be a suitable reagent for the synthesis of anilides (II) of carboxylic acids.A plausible reaction mechanism has been proposed.