7564-51-4

Basic information

• Product Name: 3-METHYL-1-PHENYL-3-PHOSPHOLENE 1-OXIDE
• Synonyms: 1H-Phosphole,2,5-dihydro-3-methyl-1-phenyl-1-oxide;2,5-dihydro-3-methyl-1-phenyl-1h-phosphol1-oxide;2,5-Dihydro-3-methyl-1-phenyl-1H-phosphole,1-oxide;3-METHYL-1-PHENYL-3-PHOSPHOLENE 1-OXIDE;2,5-DIHYDRO-3-METHYL-1-PHENYLPHOSPHOLE 1-OXIDE;2,5-Hydro-3-Methyl-1-Phenyl-Oxo-Pentylidene Phosphine;3-Methyl-1-phenyl-1-phospha-3-cyclopentene-1-oxide;3-METHYL-1-PHENYL-3-PHOSPHOLENE 1-OXIDE (=3-METHYL-1-PHENYL-1-PHOSPHA-3-CYCLOPENTENE 1-OXIDE) 95+%
• CAS NO: 7564-51-4
• Molecular Formula: C₁₁H₁₃OP
• Molecular Weight: 192.19
• EINECS: 231-463-9
• Mol File: 7564-51-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 61-65 °C
• Boiling Point: 174 °C0.7 mm Hg(lit.)
• Flash Point: 175.4 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: 3-METHYL-1-PHENYL-3-PHOSPHOLENE 1-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-1-PHENYL-3-PHOSPHOLENE 1-OXIDE(7564-51-4)
• EPA Substance Registry System: 3-METHYL-1-PHENYL-3-PHOSPHOLENE 1-OXIDE(7564-51-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-9
• Hazardous Substances Data: 7564-51-4(Hazardous Substances Data)

Usage

General Description

3-Methyl-1-phenyl-3-phospholene 1-oxide is a complex organic compound that is recognized for its application in various sectors such as pharmaceuticals, chemical industry, agrochemicals and others. It is used as a reagent in the Graf reaction for the synthesis of alpha-amino acids. This chemical falls under the category of phospholene oxides and it’s composed of a five-membered ring that includes one phosphorus atom and one oxygen atom. Its chemical formula is C11H11O1P. Like many chemical compounds, it needs to be handled with care due to its potentially reactive nature. Its properties and uses make it an important chemical substance in industrial and research contexts.

InChI:InChI=1/C11H13OP/c1-10-7-8-13(12,9-10)11-5-3-2-4-6-11/h2-7H,8-9H2,1H3/t13-/m0/s1

Upstream product

• 644-97-3 Dichlorophenylphosphine 
• 78-79-5 isoprene 
• 39834-66-7 1-bromo-3-methyl-3-phospholene 
• 30540-42-2 3-methyl-1-phenylphosphole 
• 104629-25-6 3-Methyl-1-phenyl-1H-phosphole; compound with trifluoro-methanesulfonic acid 
• 104629-22-3 3-Methyl-1-phenyl-1H-phosphole; hydrochloride 
• 104629-24-5 1-chloro-3-methyl-1-phenylphosphol-3-enium chloride 

Downstream Products

• 21904-70-1 (3-methyl-1-phenyl-2,5-dihydro-1H-1λ⁵-phosphol-1-ylidene)-phenyl-sulfamide 
• 15450-93-8 3-methyl-1-phenyl-3-phospholene 
• 92412-56-1 3,4-dibromo-3-methyl-1-phenyl-phospholane 1-oxide 
• 5958-61-2 1-phenyl-3-methyl-3-phospholene 1-sulfide 
• 179989-97-0 1-phenyl-2,5-dihydro-3-methyl-1H-phosphole-1-borane 
• 104629-24-5 1-chloro-3-methyl-1-phenylphosphol-3-enium chloride 
• 707-61-9 3-Methyl-1-phenyl-2-phospholene 1-oxide 
• 179989-93-6 4-methyl-1-phenyl-2,3-dihydro-1H-phosphol-1-ane borane 

Relevant articles and documents

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Dynamic kinetic resolution of 1-substituted-3-methyl-3-phospholene oxides via the formation of diastereomeric alkoxyphospholenium salts

A dynamic kinetic resolution method based on the formation of covalent diastereomeric intermediates was elaborated for the preparation of enantiomerically enriched 1-substituted-3-methyl-3-phospholene oxides. The 3-phospholene oxides were first converted to the corresponding chloro-3-phospholenium chlorides. The dynamic interconversion between the enantiomers of the chlorophospholenium salts was verified experimentally, as it is the key step for a dynamic resolution. The cyclic chlorophospholenium salts were reacted with a chiral auxiliary bearing a hydroxy function to form the corresponding diastereomeric alkoxyphospholenium salts in unequal amounts. The diastereomeric species then rearranged into the corresponding optically active 3-phospholene oxides upon heating. After a screening of chiral auxiliaries and the optimization of the reaction conditions, several scalemic 1-aryl- or 1-alkyl-3-methyl-3-phospholene oxides were prepared in excellent yields and with ee-s up to 35%. The key steps of this resolution were investigated by quantum chemical calculations to get some insights into the factors responsible for the stereoselection.

REACTION OF PHOSPHOLES WITH ACIDS; PROTON SHIFTS IN 1H-λ5-PHOSPHOLES

Addition to phospholes of gaseous HCl at -90 deg C or of an excess of trifluoromethanesulphonic acid at -70 deg C, results in P-protonation.The triflate solutions are stable up to room temperature, but the 1H-phospholium chlorides form PV adducts at -70 deg C, which rapidly rearrange by a sigmatropic H-shift.The observed product is a 1-chloro-2,5-dihydrophospholium chloride.Addition of a chloride ion source to the triflates produces the same result.Unprotonated 3,4-dimethyl-1-phenyl phosphole was found to react at a double bond of its 1H-phospholium ion, forming a crystalline 1,3'-biphospholium dimer.