100281-31-0

Basic information

• Product Name: (E/Z)-(Bromomethylene)(2,4,6-tri-tert-butylphenyl)phosphane
• CAS NO: 100281-31-0
• Molecular Weight: 369.325
• Mol File: 100281-31-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (E/Z)-(Bromomethylene)(2,4,6-tri-tert-butylphenyl)phosphane(CAS DataBase Reference)
• NIST Chemistry Reference: (E/Z)-(Bromomethylene)(2,4,6-tri-tert-butylphenyl)phosphane(100281-31-0)
• EPA Substance Registry System: (E/Z)-(Bromomethylene)(2,4,6-tri-tert-butylphenyl)phosphane(100281-31-0)

Safety Data

• Hazardous Substances Data: 100281-31-0(Hazardous Substances Data)

Upstream product

• 100281-23-0 [(dibromomethylene)(2,4,6-tri-tertbutylphenyl)phosphine] 
• 92957-41-0 Dibromomethyl-(2,4,6-tri-tert-butyl-phenyl)-phosphane 
• 93746-68-0 2,4,6-tri-tert-butylphenyl-P=C(Br)SiMe₃ 
• 177902-37-3 (E)-1-Bromo-2-(2,4,6-tri-tert-butylphenyl)-2-phosphaethenyllithium 
• 75-25-2 Bromoform 
• 79074-00-3 2,4,6-tri-t-butylphenylphosphonous dichloride 
• 83115-12-2 (2,4,6-tri-tert-butylphenyl)phosphine 
• 118281-77-9 (Diiodomethylene)(2,4,6-tri-tert-butylphenyl)phosphine 
• 84751-28-0 2-(2,4,6-tri-tert-butylphenyl)-1,1-bis(trimethylsilyl)phosphaethene 

Downstream Products

• 123542-40-5 Eth-(Z)-ylidene-(2,4,6-tri-tert-butyl-phenyl)-phosphane 
• 84114-18-1 1-(2,4,6-tri-tert-butylphenyl)-1-phosphaethene 
• 99364-92-8 (E)-benzylidene(2,4,6-tri-tert-butylphenyl)phosphane 
• 156696-16-1 Bromo(dibromomethyl)(2,4,6-tri-tert-butylphenyl)phosphane 
• 112150-07-9 Dimethyl-[4-(2,4,6-tri-tert-butyl-phenylphosphanylidenemethyl)-phenyl]-amine 

Relevant articles and documents

Formation of 6,8-di-tert-butyl-3,4-dihydro-4,4-dimethyl-1-phosphanaphthalene by the reaction of 2,2-dibromo-1-(2,4,6-tri-tert-butylphenyl)-1-phosphaethene with butyllithium

Sterically crowded 1-bromo-2-(2,4,6-tri-tert-butylphenyl)-2-phosphaethenyllithium gave 6,8-di-tert-butyl-3,4-dihydro-4,4-dimethyl-1-phosphanaphthalene by intramolecular insertion of an intermediary phosphinidene carbene species into one of the C-H bonds of the two o-tert-butyl groups.

C-Halophosphaalkenes: probing the range of stability and reactivity towards bromine

The importance of steric protection for the stability of phosphaalkenes RP=CI2 (6) was investigated by varying the size of group R.The phosphaalkene IsP=CI2 (6b) (Is = 2,4,6-triisopropylphenyl) could be prepared in 15percent isolated yield by reaction of IsPCl2 and HCI3 with two equivalents of lithium diisopropylamide, in analogy to the synthesis of the stable, sterically more protected, Mes*P=CI2 (6a) (Mes* = 2,4,6-tri-tert-butylphenyl).If the steric protection on the phosphorus eas decreased further (R = Es = 2,4,6-triethylphenyl, R = Mes = 2,4,6-trimethylphenyl), the substitution products RP(Cl)N(i-Pr)2 (R = Es (9c) or Mes (9d)) were formed as main products, in addition to thermally unstable phosphaalkenes EsP=CI2 (6c) and MesP=CI2 (6d).The structures of 9c-d were corroborated by independent synthesis from RPCl2 and two equivalents of diisopropylamine.The reaction of 6a with bromine gave an E/Z mixture of the C-bromo-C-iodophoaphaalkene (EZ)-Mes*P=CBrI (E/Z-10).Further reaction with bromine proceeded via Mes*P=CBr2 (5a) and finally led to Mes*P(Br)(CHBr2) (12).

SYNTHESE UND REAKTIONEN DER 2,4,6-TRI-TERT-BUTYLPHENYLDIHALOGENMETHYLENPHOSPHANE1

The synthesis of dihalogenated phosphaalkanes 2a,b is reported.After metallation with n-BuLi they could be substituted by halogenated compounds.