20412-07-1

Basic information

• Product Name: C₆H₅⁽²⁾H₂N*Cl⁽²⁾H
• CAS NO: 20412-07-1
• Molecular Weight: 132.565
• Mol File: 20412-07-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₆H₅⁽²⁾H₂N*Cl⁽²⁾H(CAS DataBase Reference)
• NIST Chemistry Reference: C₆H₅⁽²⁾H₂N*Cl⁽²⁾H(20412-07-1)
• EPA Substance Registry System: C₆H₅⁽²⁾H₂N*Cl⁽²⁾H(20412-07-1)

Safety Data

• Hazardous Substances Data: 20412-07-1(Hazardous Substances Data)

Upstream product

• 1122-59-4 aniline-N,N-d2 
• 15873-72-0 dicyclohexylphosphinoyl chloride 
• 1111-92-8 dimethylphosphinic acid chloride 
• 5761-97-7 methyl(phenyl)phosphinic chloride 

Relevant articles and documents

Kinetics and mechanism of the anilinolysis of dicyclohexyl phosphinic chloride in acetonitrile

The nucleophilic substitution reactions of dicyclohexyl phosphinic chloride [3; cHex2P(=O)Cl] with substituted anilines (XC6H 4NH2) and deuterated anilines (XC6H 4ND2) are investigated kinetically in acetonitrile at 60.0 °C. The anilinolysis rate is too slow to be rationalized by the stereoelectronic effects. The rate is contrary to expectations for the electronic influence of the two ligands and exhibits exceptionally great negative deviation from the Taft's eq. The deuterium kinetic isotope effects (DKIEs) involving deuterated anilines invariably change from primary normal (kH/kD > 1; max kH/kDt = 1.10 with X = 4-MeO) with the strongly basic anilines (X = 4-MeO, 4-Me, 3-Me) to secondary inverse (kH/kDt H/k Dt = 0.673 with X = 3-Cl) with the weakly basic anilines (X = H, 4-F, 4-Cl, 3-Cl). A concerted SN2 mechanism is proposed on the basis of both secondary inverse and primary normal DKIEs. The obtained DKIEs imply that the fraction of a frontside attack increases as the aniline becomes more basic. A hydrogen-bonded, four-center-type transition state is suggested for a frontside attack, while the trigonal bipyramidal pentacoordinate transition state is suggested for a backside attack.