4271-13-0

Basic information

• Product Name: METHYLPHENYLPHOSPHINIC ACID
• Synonyms: METHYLPHENYLPHOSPHINIC ACID;Methylphenylphosphonic acid
• CAS NO: 4271-13-0
• Molecular Formula: C₇H₉O₂P
• Molecular Weight: 156.12
• Mol File: 4271-13-0.mol

Chemical Properties

• Melting Point: 132-134°C
• Boiling Point: 373.9°C at 760 mmHg
• Flash Point: 179.9°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 2.98E-06mmHg at 25°C
• Refractive Index: 1.522
• PKA: 2.43±0.50(Predicted)
• CAS DataBase Reference: METHYLPHENYLPHOSPHINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLPHENYLPHOSPHINIC ACID(4271-13-0)
• EPA Substance Registry System: METHYLPHENYLPHOSPHINIC ACID(4271-13-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 4271-13-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methylphenylphosphinic acid is used as a reagent for various pharmaceutical applications, contributing to the synthesis of different drugs and medications. Its chemical properties make it a valuable component in the development of new therapeutic agents.
Used in Chemical Industry:
Methylphenylphosphinic acid is used as a catalyst in the production of certain macrocyclic complexes. Its ability to facilitate chemical reactions enhances the efficiency and yield of these complex molecules, which are essential in various chemical processes.
Used in Organic Reactions:
Methylphenylphosphinic acid is employed as a reagent in organic reactions, where it aids in the formation of new compounds and molecules. Its participation in these reactions is crucial for the synthesis of various organic compounds used in different industries.
However, it is important to note that Methylphenylphosphinic acid, like other chemicals, may have potential health repercussions if not handled properly. Exposure to this compound can cause skin or eye irritation, and more serious consequences to human health due to its toxic nature. Therefore, it is essential to handle this chemical with care and proper protection.

InChI:InChI=1/C7H9O2P/c1-10(8,9)7-5-3-2-4-6-7/h2-6H,1H3,(H,8,9)

Upstream product

• 110-89-4 piperidine 
• 644-97-3 Dichlorophenylphosphine 
• 14365-34-5 phenyl methylphenylphosphinate 
• 3676-96-8 1,2-dimethyl-1,2-diphenyldiphosphine 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 6172-81-2 butyl phenylphosphinate 
• 74-88-4 methyl iodide 
• 74-87-3 methylene chloride 
• 71-43-2 benzene 
• 2946-61-4 phenylphosphonous acid dimethyl ester 
• 540-49-8 cis+trans-dibromoethylene 
• 6389-79-3 methyl methylphenylphosphinate 
• 14337-83-8 Methyl-phenyl-phosphinsaeure-anhydrid 
• 69737-69-5 Acetylmethylphenylphosphanoxid 

Downstream Products

• 5761-97-7 methyl(phenyl)phosphinic chloride 
• 94933-73-0 C₁₄H₁₆O₂P₂S 
• 115692-95-0 (Sp)-myrtenyl methyl(phenyl)phosphinate 
• 115692-94-9 (Rp)-myrtenyl methyl(phenyl)phosphinate 
• 16934-92-2 L-Menthyl-methylphenylphosphinat 
• 16934-92-2 (R_p)-menthyl methylphenylphosphinate 
• 16934-93-3 (S_p)-Menthylmethylphenylphosphinate 
• 14365-34-5 phenyl methylphenylphosphinate 
• 35691-25-9 Methyl-phenyl-phosphinsaeure-(p)-nitrophenylester 
• 118201-59-5 4-methylphenyl methyl(phenyl)phosphinate 
• 80751-37-7 4-chlorophenylmethylphenylphosphinate 
• 118201-61-9 4-acetylphenyl methyl(phenyl)phosphinate 
• 118201-62-0 3-nitrophenyl methylphenylphosphinate 
• 4583-37-3 methylphenylphosphinic azide 

Relevant articles and documents

Evaluation and development of methodologies for the synthesis of thiophosphinic acids

Thiophosphorus acids R1R2P(S)OH constitute an important class of organophosphorus compounds, in which the phosphorus atom is intrinsically chiral if R1 ≠ R2. In connection with a project aimed at the preparation of chiral thiophosphorus acids, various available literature methods were considered, but few fit the requirement of odorless reagents. Herein, the results of our studies on the synthesis of thiophosphinic acids are reported. Ultimately, two major approaches were selected: (1) the Stec reaction of phosphorus amides with carbon disulfide; and (2) the one-pot synthesis of thiophosphorus acids from H-phosphinates, an organometallic nucleophile, and quenching with elemental sulfur. An application to the preparation of a potential chiral phosphorus organocatalyst is also reported.

Desymmetrization of Phosphinic Acids via Pd-Catalyzed Asymmetric Allylic Alkylation: Rapid Access to P-Chiral Phosphinates

The synthesis of P-chiral compounds is challenging, especially since useful catalytic methods for preparing such molecules are scarce. Herein we disclose a desymmetrization that employs phosphinic acids as prochiral nucleophiles in a Pd-catalyzed asymmetr

Resolution of chiral phosphate, phosphonate, and phosphinate esters by an enantioselective enzyme library

An array of 16 enantiomeric pairs of chiral phosphate, phosphonate, and phosphinate esters was used to establish the breadth of the stereoselective discrimination inherent within the bacterial phosphotriesterase and 15 mutant enzymes. For each substrate,

Catalysis of the ethanolysis of aryl methyl phenyl phosphinate esters by alkali metal ions: Transition state structures for uncatalyzed and metal ion-catalyzed reactions

This paper reports on a spectrophotometric kinetic study of the effects of the alkali metal ions Li+ and K+ on the ethanolysis of the aryl methyl phenyl phosphinate esters 3a-f in anhydrous ethanol at 25°C. Rate data obtained in the absence and presence of complexing agents afford the second-order rate constants for the reaction of free ethoxide (kEtO-) and metal ion-ethoxide ion pairs (kMOEt). The sequence k EtO- MOEt is established for all the substrates, contrary to the generally observed reactivity order in nucleophilic substitution processes. The quantities δGip, δGts and ΔGcat, which quantify the observed alkali metal ion effect in terms of transition state stabilization through chelation of the metal ion, give the order δGts > δGip for Li+ and K+. Hammett plots show significantly better correlation of rates with σ and σo substituent constants than with σ-, yielding moderately large Ρ(Ρo) values that are consistent with a stepwise mechanism in which formation of a pentacoordinate (phosphorane) intermediate is the rate-limiting step. The range of the values of the selectivity parameter, Ρn (= Ρ/Ρeq), 1.3 1.6, obtained for the uncatalyzed and alkali metal ion catalyzed reactions indicates that there is no significant perturbation of the transition state (TS) structure upon chelation of the metal ions. This finding is relevant to the mechanism of enzymatic phosphoryl transfer involving metal ion co-factors. The present results enable one to compare structural effects for nucleophilic reactions of several series of organophosphorus substrates. It is shown that the order of reactivity of the substrates: 4-nitrophenyl dimethyl phosphinate (2) > 3a > 4-nitrophenyl diphenyl phosphinate (1) is determined mainly by the steric effects of the alkyl/aryl substituents around the central P atom in the TS of the reaction. The Royal Society of Chemistry 2005.

Photolysis of the cycloadduct of a 1,2-dihydrophosphinine oxide with N-phenylmaleimide in the presence of protic species: New aspects on the mechanism of the fragmentation of a 2-phosphabicyclo[2.2.2]octene

Phosphabicyclo[2.2.2]octene 2 is useful in the UV light mediated phosphorylation of protic species. Experiments suggest that the fragmentation takes place according to concurrent EA and AE mechanisms.

OPTICALLY ACTIVE PHOSPHINE OXIDES. 8. SYNTHESIS OF NONSYMMETRICAL 1,2-DIPHOSPHINYLETHENES AND RELATED SYSTEMS

The synthesis of the nonsymmetrical and the optically active trans-1,2-diphosphinylethenes has been accomplished.The employed addition-elimination route is potentially general and utilizes readily accessible secondary phosphine oxides and tertiary 1-halog

PHOSPHINYLALKANOYL PROLINES

New phosphinylalkanoyl prolines which have the general formula STR1 wherein R 1 is lower alkyl, phenyl or phenyl-lower alkyl; R 2 is hydrogen, phenyl-lower alkyl or a metal ion; R 3 is hydrogen or lower alkyl;R. sub. 4 is hydrogen, lower alkyl, phenyl-lower alkyl or a metal ion; andN IS 0 OR 1,ARE USEFUL AS HYPOTENSIVE AGENTS.