29074-98-4

Basic information

• Product Name: Diethyl 2-chlorobenzylphosphonate
• Synonyms: Diethyl 2-chlorobenzylphosphonate;1-Diethoxyphosphonomethyl-2-chlorobenzene;2-(Chlorobenzyl)phosphonic acid diethyl ester
• CAS NO: 29074-98-4
• Molecular Formula: C₁₁H₁₆ClO₃P
• Molecular Weight: 262.669701
• Mol File: 29074-98-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 146°C/0.4mmHg(lit.)
• Appearance: /
• Refractive Index: 1.5060 to 1.5140
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Diethyl 2-chlorobenzylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl 2-chlorobenzylphosphonate(29074-98-4)
• EPA Substance Registry System: Diethyl 2-chlorobenzylphosphonate(29074-98-4)

Safety Data

• Hazardous Substances Data: 29074-98-4(Hazardous Substances Data)

Usage

General Description

Diethyl 2-chlorobenzylphosphonate is a chemical compound with the molecular formula C12H16ClO3P. It belongs to the phosphonate ester group of chemicals, which are typically used in industry as flame retardants, antioxidants, and plasticizers. Due to its phosphonic ester structure, it has the potential to have a high reactivity with hydroxyl ions, making it potentially useful in a broad spectrum of chemical reactions. However, detailed information on its specific uses, safety measures and hazards in handling, are scarce in open scientific literature, indicating that it's likely a specialized reagent rather than a common laboratory chemical.

Upstream product

• 122-52-1 triethyl phosphite 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 

Downstream Products

• 130948-86-6 [1-(2-Chloro-phenyl)-cyclopentyl]-phosphonic acid diethyl ester 
• 1395054-33-7 (E)-1-chloro-2-(hept-1-en-6-yn-1-yl)benzene 
• 85650-56-2 trans-5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenz<2,3:6,7>oxepino<4,5-c>pyrrolidine maleate 
• 65576-45-6 asenapine 
• 1370255-96-1 trans-2,5'-dichloro-2'-hydroxystilbene 
• 112704-51-5 E-2-(4-fluorophenyl)-3-(2-chlorophenyl)-propenal 
• 72398-88-0 2-[(Z)-2-(2-Chloro-phenyl)-vinyl]-phenol 
• 130948-85-5 [1-(2-Chloro-phenyl)-cyclobutyl]-phosphonic acid diethyl ester 

Relevant articles and documents

Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution

A novel and transition metal-free synthesis of 3,4-dihydro-1,2-oxaphosphinine 2-oxides was developed. LiHMDS-mediated tandem Michael addition and nucleophilic substitution of readily available phosphonochloridates and chalcones afforded a variety of valuable 3,4-dihydro-1,2-oxaphosphinine 2-oxides bearing diverse functionalities in excellent yields and satisfactory to good diastereoselectivity (up to 99% yield and up to 99?:?1 dr).

Synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds

The invention discloses a synthetic method for alkyl group phosphorous acid diester compounds or alkyl group phosphinic acid ester compounds. According to the synthetic method, alcohols which are cheap, easy to get, wide in source, stable and low in toxicity serve as alkylating reagents, iodine salt which is cheap and easy to get serves as catalysts, no solvent is needed, and the alkyl group phosphorous acid diester compounds can be selectively directly obtained after a reaction. The reaction method is simple, the condition is mild, no organic solvent is needed and operation is simple. According to the method, the requirements for reaction conditions are low, various types of alcohols such as a benzyl group type, an allyl type and a fat type can be utilized as the alkylate reagents to implement the synthesis of different types of substituted alkyl group phosphorous acid diester, and the method can be further expanded to the synthesis of the alkyl group phosphinic acid ester compounds through the reaction between the substituted phosphonous acid diester and the alcohols.

Steric effects of the initiator substituent position on the externally initiated polymerization of 2-bromo-5-iodo-3-hexylthiophene

Externally initiated polymerization of 2-bromo-3-hexyl-5-iodothiophene was attempted from four aryl and thiophene based small molecule initiators functionalized with a phosphonate moiety. Initiated poly(3-hexylthiophene) product was obtained in various yields depending on the nature of the initiating molecule. Reaction intermediates for the oxidative addition and the ligand exchange steps were analyzed utilizing both experimental and theoretical methods. It was observed that an ortho substituent plays a crucial role in the outcome of the polymerization mechanism and that aryl based initiators are generally more stable than thiophene based initiators. Density functional theory (DFT) calculations revealed the importance of the steric effects on the success of the externally initiated chain growth polymerization mechanism.