7564-51-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-1-phenyl-3-phospholene 1-oxide is used as a reagent in the Graf reaction for the synthesis of alpha-amino acids, which are essential building blocks for proteins and have significant applications in drug development and therapeutics.
Used in Chemical Industry:
3-METHYL-1-PHENYL-3-PHOSPHOLENE 1-OXIDE serves as an important chemical substance in the chemical industry, where it may be utilized in the synthesis of various chemical products or as an intermediate in the production of other complex molecules.
Used in Agrochemical Industry:
3-Methyl-1-phenyl-3-phospholene 1-oxide may also find applications in the agrochemical industry, potentially as a component in the development of new pesticides, herbicides, or other agricultural chemicals that can improve crop yield and protect against pests.
Used in Research Contexts:
In research settings, 3-Methyl-1-phenyl-3-phospholene 1-oxide is valuable for studying the properties and reactions of phosphorus-containing compounds, contributing to the advancement of organic chemistry and related fields.

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 
• 104629-24-5 1-chloro-3-methyl-1-phenylphosphol-3-enium chloride 
• 104629-22-3 3-Methyl-1-phenyl-1H-phosphole; hydrochloride 
• 104629-25-6 3-Methyl-1-phenyl-1H-phosphole; compound with trifluoro-methanesulfonic acid 
• 30540-42-2 3-methyl-1-phenylphosphole 

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 
• 7162-15-4 methyl phenylphosphinate 
• 109011-51-0 6,6-dichloro-1-methyl-3-phenyl-3-phosphabicyclo<3.1.0>hexane 3-oxide 
• 127412-94-6 4,5-dichloro-3-methyl-1-phenylphosphepine 1-oxide 
• 109891-12-5 3-methyl-4-chloro-1,2-dihydro-1-phenylphosphorin 1-oxide 
• 109891-15-8 5-methyl-4-chloro-1-phenyl-1,2-dihydrophosphinine 1-oxide 
• 96659-19-7 [(2-Oxo-propyl)-phenyl-phosphinoyl]-acetaldehyde 
• 72812-05-6 3,4-epoxy-3-methyl-1-phenylphospholane 1-oxide 
• 72812-00-1 (1S,3S)-4-Chloro-4-methyl-1-oxo-1-phenyl-1λ⁵-phospholan-3-ol 
• 72812-00-1 (1S,3R)-4-Chloro-4-methyl-1-oxo-1-phenyl-1λ⁵-phospholan-3-ol 
• 5958-61-2 1-phenyl-3-methyl-3-phospholene 1-sulfide 

Relevant academic research and scientific papers

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.

General Approaches to Phosphinidenes via Retroadditions

The retroaddition strategy for the generation of phosphinidenes involves thermal and photochemical decomposition of 1-arylphosphiranes and photolysis of 1-aryl-3-phospholenes.Evidence that free phosphinidenes are produced as reactive intermediates includes a lack of dependence of the conversion rate on precursor and substrate concentrations and the nature of the reaction products.These are best rationalized by the addition of phosphinidenes to carbon-carbon ?-bonds forming three-membered rings and the dimerization of phosphinidenes to diphosphenes.

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.