149443-46-9

Basic information

• Product Name: 3-Methyl-1-phenyl-4,5-dihydrophosphol
• CAS NO: 149443-46-9
• Molecular Weight: 176.198
• Mol File: 149443-46-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3-Methyl-1-phenyl-4,5-dihydrophosphol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-1-phenyl-4,5-dihydrophosphol(149443-46-9)
• EPA Substance Registry System: 3-Methyl-1-phenyl-4,5-dihydrophosphol(149443-46-9)

Safety Data

• Hazardous Substances Data: 149443-46-9(Hazardous Substances Data)

Upstream product

• 78-79-5 isoprene 
• 1445-83-6 4-methyl-1-phenyl-2,3-dihydro-1H-phosphole 
• 644-97-3 Dichlorophenylphosphine 
• 569680-54-2 (R)-4-Methyl-1-phenyl-2,3-dihydro-phosphole 1-oxide 
• 707-61-9 3-Methyl-1-phenyl-2-phospholene 1-oxide 
• 17786-49-1 1-chloro-4-methyl-1-phenyl-2,3-dihydro-1H-phosphol-1-ium chloride 

Downstream Products

• 569680-53-1 (S)-4-Methyl-1-phenyl-2,3-dihydro-phosphole 1-oxide 
• 569680-54-2 (R)-4-Methyl-1-phenyl-2,3-dihydro-phosphole 1-oxide 
• 149443-46-9 3-Methyl-1-phenyl-4,5-dihydrophosphol 
• 62726-70-9 1r-benzyl-3c-methoxy-3t-methyl-1-phenyl-phospholanium; bromide 
• 62726-70-9 1r-benzyl-3t-methoxy-3c-methyl-1-phenyl-phospholanium; bromide 
• 62726-87-8 3r-methoxy-3-methyl-1-phenyl-phospholane 1t-oxide 
• 62726-87-8 3r-methoxy-3-methyl-1-phenyl-phospholane 1c-oxide 
• 62726-73-2 1-benzyl-3-tert-butoxy-3-methyl-1-phenyl-phospholanium; bromide 
• 62726-72-1 1-benzyl-3-isopropoxy-3-methyl-1-phenyl-phospholanium; bromide 
• 52561-63-4 3-methylene-1-phenyl-phospholane 
• 52561-70-3 3r-tert-butoxy-3-methyl-1t-phenyl-phospholane 
• 52561-70-3 3r-tert-butoxy-3-methyl-1c-phenyl-phospholane 
• 52561-70-3 3-tert-butoxy-3-methyl-1-phenyl-phospholane 
• 52561-69-0 3-isopropoxy-3-methyl-1-phenyl-phospholane 

Relevant articles and documents

Novel Base-Free Catalytic Wittig Reaction for the Synthesis of Highly Functionalized Alkenes

A highly efficient catalyst system for base-free catalytic Wittig reactions has been developed and optimized. Initially, several potential (pre)catalysts as well as different silanes as reducing agents were screened. A system based on a readily available

Poly(methylhydrosiloxane) as a green reducing agent in organophosphorus-catalysed amide bond formation

Development of catalytic amide bond formation reactions has been the subject of the intensive investigations in the past decade. Herein we report an efficient organophosphorus-catalysed amidation reaction between unactivated carboxylic acids and amines. Poly(methylhydrosiloxane), a waste product of the silicon industry, is used as an inexpensive and green reducing agent for in situ reduction of phosphine oxide to phosphine. The reported method enables the synthesis of a wide range of secondary and tertiary amides in very good to excellent yields.

Reactivity of Cyclopentenyl-Anion-Analogous Heterocycles: Homophospholes - Synthesis, 1,5-Electrocyclization, and Inversion at the Phosphorus Atom

The key step of a novel homophosphole synthesis is the reaction of phospholes 3a-d with diazomethane in the presence of water leading to the oxidized 1,3-dipolar cycloadducts anti-7a-d.The 1,5-electrocyclization of homophosphole was observed by the temperature-dependent rate of racemization of optically active anti-8b (ΔH(excit.) = (31.24 +/- 0.59) kcal/mol; ΔS(excit.) = -(2.32 +/- 1.47) cal/mol K).In order to determine the activation parameters for the inversion at the phosphorus atom a (60:40) mixture of syn- and anti-homophosphole syn- and anti-8b was prepared by H2O2 oxidation of anti-8b complexed by CuCl and subsequent reduction with Cl3SiH.The enantiomerization (-)-anti-8b> proceeds at 169.5 deg C 22 times faster than the inversion at the phosphorus atom (anti-8b -> syn-8b).This shows unambiguously that the electrocyclic ring opening does not require a planar configuration at the phosphorus atom and can start from the nonplanar anti configuration due to a dihedral angle of ca. 0 deg between the orbital of the lone pair at the phosphorus atom and the cyclopropane Walsh orbitals favourable for a strong electronic interaction in this configuration.From the comparison of the activation parameters for the inversion at the phosphorus atom in the homophosphole (syn-8b anti-8b) and the dihydrophosphole (+)-23> one can extrapolate, that the homoaromatic resonance stabilization in the planar homophosphole is small (ca. -2 kcal/mol) contrary to the surprisingly large aromatic stabilization in the planar phosphole (ca. -20 kcal/mol). Key Words: Homophospholes / Phospholes, 4,5-dihydro, optically active / 1,5-Electrocyclization / Phosphomethine ylides / Inversion at the phosphorus atom