6630-13-3

Basic information

• Product Name: 1-[chloro-(2-methylphenoxy)phosphoryl]oxy-2-methyl-benzene
• Synonyms: 1-[chloro-(2-methylphenoxy)phosphoryl]oxy-2-methyl-benzene;o-Tolyl Phosphorochloridate
• CAS NO: 6630-13-3
• Molecular Formula: C₁₄H₁₄ClO₃P
• Molecular Weight: 296.69
• Product Categories: Aromatics, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 6630-13-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 396.2°C at 760 mmHg
• Flash Point: 298.5°C
• Appearance: /
• Density: 1.271g/cm³
• Vapor Pressure: 3.98E-06mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: 1-[chloro-(2-methylphenoxy)phosphoryl]oxy-2-methyl-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[chloro-(2-methylphenoxy)phosphoryl]oxy-2-methyl-benzene(6630-13-3)
• EPA Substance Registry System: 1-[chloro-(2-methylphenoxy)phosphoryl]oxy-2-methyl-benzene(6630-13-3)

Safety Data

• Hazardous Substances Data: 6630-13-3(Hazardous Substances Data)

Usage

Description

1-[chloro-(2-methylphenoxy)phosphoryl]oxy-2-methyl-benzene, also known as o-Tolyl Phosphorochloridate, is an organic compound that serves as an intermediate in the synthesis of various metabolites. It is characterized by its chloro-(2-methylphenoxy)phosphoryl group attached to a 2-methyl-benzene core. 1-[chloro-(2-methylphenoxy)phosphoryl]oxy-2-methyl-benzene plays a significant role in the production of certain chemicals and materials due to its unique structural properties.

Uses

1. Used in Flame Retardant Plasticizers:
o-Tolyl Phosphorochloridate is used as an intermediate in the synthesis of tri-o-cresyl phosphate (TOCP), which is a flame retardant plasticizer. It is added to plastics to improve their resistance to fire and reduce the risk of ignition, making them safer for various applications.
2. Used in Neurotoxin Production:
In addition to its application in the plastics industry, o-Tolyl Phosphorochloridate is also involved in the synthesis of TOCP, which is known to be a neurotoxin. This makes it an important compound in the study and understanding of neurotoxic effects and potential applications in the field of neuroscience.

InChI:InChI=1/C14H14ClO3P/c1-11-7-3-5-9-13(11)17-19(15,16)18-14-10-6-4-8-12(14)2/h3-10H,1-2H3

Upstream product

• 95-48-7 ortho-cresol 

Downstream Products

• 35294-41-8 O,O-Di-o-kresyl-N-(β-bromethyl)-phosphorsaeureamid 
• 35787-74-7 bis(2-methylphenyl)phosphoric acid 
• 1236286-20-6 C₁₆H₁₆NO₃P 
• 1207716-80-0 C₂₄H₂₄N₃O₃P 
• 116992-79-1 C₁₄H₁₄Cl₃NO₃P₂ 
• 10359-39-4 Di-(2-methylphenyl)-4-nitrophenylphosphat 
• 78370-06-6 Phosphoramidic acid di-o-tolyl ester 
• 91785-87-4 Bis(2-methylphenyl) 2-methoxy-4-(2,3-dichloropropyl)phenyl phosphate 
• 139301-34-1 (S)-3-(Bis-o-tolyloxy-phosphoryloxy)-2-tert-butoxycarbonylamino-propionic acid benzyl ester 
• 91809-70-0 Bis(2-methylphenyl) 2-methoxy-4-n-propylphenyl phosphate 
• 91785-86-3 Bis(2-methylphenyl) 4-chloro-3-methylphenyl phosphate 
• 139301-38-5 (S)-3-(Bis-o-tolyloxy-phosphoryloxy)-2-tert-butoxycarbonylamino-propionic acid 

Relevant articles and documents

Neodymium tris-diarylphosphates: Systematic study of the structure-reactivity relationship in butadiene and isoprene polymerisation

The catalytic properties of neodymium tris-phosphates with various diarylphosphate ligands in the stereoregular 1,4-cis-polymerisation of butadiene and isoprene were studied. The considerable variability of the diaryl phosphate structure allowed for the systematic investigation of the dependence of the catalytic properties of neodymium tris-diarylphosphates on the electronic and steric properties of the ligand. Electron-withdrawing substituents (F, Cl, Br) in the aryl moiety increased the catalyst activity of tris-diarylphosphate. Neodymium aryl phosphates containing lipophilic bulky ligands provided the synthesis of polydienes with a monomodal molecular-weight distribution. The optimal catalytic properties demonstrated that the neodymium aryl phosphate prepared from bis(2,6-dimethyl-4-tert-butylphenyl)-phosphoric acid showed high activity and ensured a monomodal MWD of polydienes (Mw/Mn ～ 2 for polybutadiene and Mw/Mn ～ 3 for polyisoprene) in various conditions.

Highly Z-selective synthesis of a,b-unsaturated nitriles using the Horner-Wadsworth-Emmons reaction

A new HWE reagent, (o-tBuC6H4O)2P(O)CH2CN (2e), reacts with various types of aldehydes to give Z-a,bunsaturated nitriles with 86% to >99% Z-selectivity. Especially, the reaction of 2e with bulkier aldehydes, both aromatic and aliphatic, gave the Z-olefins with extremely high selectivity. The combination of t-BuOK and 18-crown-6 (1 equiv) is the base of choice for aromatic aldehydes and t-BuOK is generally the base of choice for aliphatic aldehydes.

Synthesis of Some New Aryl Phosphates

Eight new triaryl phosphates (1-8) were synthesized by phosphorylation of the corresponding phenol with phosphorus oxychloride for evaluation as stationary phases in gas chromatography.They were duly characterized by infrared, proton magnetic resonance, and mass spectral techniques after their purity was established by HPLC.