4009-39-6

Basic information

• Product Name: methyl phenyl hydrogen phosphate
• CAS NO: 4009-39-6
• Molecular Formula: C₇H₉O₄P
• Molecular Weight: 188.1177
• Mol File: 4009-39-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 280.2°C at 760 mmHg
• Flash Point: 123.3°C
• Density: 1.329g/cm³
• Vapor Pressure: 0.00183mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: methyl phenyl hydrogen phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl phenyl hydrogen phosphate(4009-39-6)
• EPA Substance Registry System: methyl phenyl hydrogen phosphate(4009-39-6)

Safety Data

• Hazardous Substances Data: 4009-39-6(Hazardous Substances Data)

Usage

General Description

Methyl phenyl hydrogen phosphate is a chemical compound with the molecular formula C7H8O4P. It is a colorless liquid with a faint odor and is commonly used as a flame retardant and plasticizer in various applications. Methyl phenyl hydrogen phosphate is also utilized in the production of organic intermediates, agricultural chemicals, and pharmaceuticals. It can act as a solvent or reagent in organic synthesis and is considered to be relatively stable under normal conditions. However, it should be handled with care as it may cause irritation to the skin, eyes, and respiratory system upon exposure.

Upstream product

• 10113-28-7 dimethyl phenyl phosphate 
• 67-56-1 methanol 
• 4281-48-5 2-hydroxypropyl phenyl phosphate 
• 108-95-2 phenol 
• 6719-79-5 methyl phenyl phosphorochloridate 
• 918660-72-7 4-acetylphenyl methyl phenyl phosphate 
• 846-02-6 methyl phenyl 4-nitrophenyl phosphate 
• 41255-51-0 Phosphorsaeure-(8-chinolyl)-phenylester 
• 32599-82-9 diammonium salt of phenyl phosphatosulfate 
• 97598-57-7 Imidazol-1-yl-phosphonic acid monophenyl ester; compound with cyclohexylamine 
• 701-64-4 phosphoric acid monophenyl ester 
• 770-12-7 O-phenyl phosphorodichloridate 

Downstream Products

• 813-78-5 dimethylphosphoric acid 
• 108-95-2 phenol 
• 1432474-88-8 (E)-ethyl 3-(2-((dimethoxyphosphoryl)oxy)phenyl)acrylate 

Relevant articles and documents

Palladium-catalyzed ortho-alkenylation of aryl hydrogen phosphates using a new mono-phosphoric acid directing group

A highly efficient Pd-catalyzed ortho-alkenylation is reported using a mono-phosphoric acid-directing group for the first time. This phosphoric acid-directing group is successfully utilized for the synthesis of various alkenylated products and offers a new approach to transition-metal-catalyzed C-H activation. The Royal Society of Chemistry 2013.

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,

ZrIV-tetraphenylporphyrinates as nuclease mimics: structural, kinetic and mechanistic studies on phosphate diester transesterification.

The Zr(IV)-tetraphenylpor-phyrinates Zr(TPP)(X,X'), (X,X' = -OAc, -OMe, Cl ) 4-6, 8 were prepared and their complexing properties as well as catalytic properties towards solvolysis of the phosphate diesters hpp (2), dmp (3) and pmp (16) characterised. The diesters 2 and 16, representing model phosphates for RNA and DNA, were substrates for the catalyst Zr(TPP)Cl2 (4), and rate accelerations over background by 6-9 orders of magnitude were measured. These accelerations are comparable to those of dinuclear transition metal catalysts and lanthanide ions. Catalytic turnover was observed. Kinetic studies revealed that the catalytically active species of 4 in the solvolysis of 2 and 16 in methanol-containing solvents are dinuclear complexes containing either one or two phosphate esters depending upon the phosphate concentration. Besides the usual solvolysis pathway of the RNA model hpp (2), which proceeds via the cyclophosphate 20, a second, unusual pathway via direct substitution of the hydroxypropyl substituent was found. X-ray analysis of the Zr(TPP)(dmp) complex 19 revealed a dinuclear structure with two bridging dmp ligands and one monomethyl phosphate unit. In 19 one of the two dmp residues occurs in a very unusual high energy ac,ap conformation. Based on this structure and on the kinetic data, mechanistic models for the two solvolysis reaction pathways were developed. From an extensive CSD search on phosphodiester structures no correlation between P-O ester bond lengths and diester conformations could be found. However, P-O ester bonds decrease in length with increasing formal charge of the complexing metal ions. This underlines the higher importance of electrostatic activation relative to stereoelectronic effects in phosphodiester hydrolysis.