57443-18-2

Basic information

• Product Name: BENZYL DIMETHYL PHOSPHONOACETATE
• Synonyms: BENZYL DIMETHYL PHOSPHONOACETATE;DIMETHYL (CBZ-METHYL)PHOSPHONATE;DIMETHYL(BENZYLOXYCARBONYL)METHYL PHOSPHONATE;DIMETHYLPHOSPHONOACETIC ACID BENZYL ESTER;Dimethyl (benzyloxycarbonyl)methylphosphonate 98%;Dimethyl-(benzyloxycarbonyl)methyl phosphonate, 98 %;Benzyl dimethyl phosphonoacetate,98%;Dimethyl (Benzyloxycarbonylmethyl)phosphonate Dimethyl (Cbz-methyl)phosphonate Dimethylphosphonoacetic Acid Benzyl Ester
• CAS NO: 57443-18-2
• Molecular Formula: C₁₁H₁₅O₅P
• Molecular Weight: 258.21
• Mol File: 57443-18-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 148-150 °C (0.1 mmHg)
• Flash Point: 184.8 °C
• Appearance: Clear colorless to light brown/Liquid
• Density: 1.23
• Vapor Pressure: 2.38E-05mmHg at 25°C
• Refractive Index: 1.505-1.507
• CAS DataBase Reference: BENZYL DIMETHYL PHOSPHONOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL DIMETHYL PHOSPHONOACETATE(57443-18-2)
• EPA Substance Registry System: BENZYL DIMETHYL PHOSPHONOACETATE(57443-18-2)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• Hazardous Substances Data: 57443-18-2(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light brown liquid

InChI:InChI=1/C11H15O5P/c1-14-17(13,15-2)9-11(12)16-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3

Upstream product

• 140-18-1 Benzyl chloroacetate 
• 121-45-9 phosphorous acid trimethyl ester 
• 5437-45-6 Benzyl bromoacetate 
• 100-51-6 benzyl alcohol 
• 5927-18-4 trimethyl phosphonoacetate 

Downstream Products

• 194613-69-9 (E)-3-Methyl-4-phenylselanyl-but-2-enoic acid benzyl ester 
• 219310-71-1 benzyl (E)-3-(imidazo<1,2-a>pyridin-3-yl)acrylate 
• 756491-93-7 benzyl 4,4-dimethyl-5-(1-naphthyl)-5-oxo-pent-2-enoate 
• 516493-75-7 benzyl 4-[1-(1,3-dithian-2-yl)-cyclohexyl]-but-2-enoate 
• 756491-91-5 benzyl 4,4-dimethyl-5-(2-furyl)-5-oxo-pent-2-enoate 
• 756491-92-6 benzyl 4,4-dimethyl-5-oxo-5-(2-thienyl)-pent-2-enoate 
• 756491-96-0 benzyl 3-[1-(2-furoyl)cyclohexyl]-prop-2-enoate 
• 122297-88-5 3-(4-tert-Butoxycarbonylamino-3-oxo-pyrazolidin-1-yl)-2-(dimethoxy-phosphoryl)-propionic acid benzyl ester 
• 106892-52-8 Allyl-<7-(R,S)-(tert-Butoxycarbonylamino)-3-benzyloxycarbonyl>-8-oxo-1,5-diazabicyclo<3.3.0>oct-2-ene-2-carboxylate 
• 106892-55-1 3-Benzyloxycarbonyl-7-(R,S)-<2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetamido>-8-oxo-1,5-diazabicyclo<3.3.0>oct-2-ene-2-carboxylic acid 
• 106892-54-0 6-{2-(2-Allyloxycarbonylamino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-7-oxo-6,7-dihydro-3H,5H-pyrazolo[1,2-a]pyrazole-1,2-dicarboxylic acid 1-allyl ester 2-benzyl ester 
• 1186680-40-9 4-((E)-1-benzyloxycarbonylmethylpropenyl)benzoic acid methyl ester 
• 1352741-10-6 C₁₅H₁₉BrO₂ 
• 1380291-59-7 3-[2-(benzyloxy)-2-oxoethylidene]cyclobutane-1-carboxylic acid 

Relevant articles and documents

Studies of the Electronic Effects of Zinc Cluster Catalysts and Their Application to the Transesterification of β-Keto Esters

The electronic effects of tetranuclear zinc cluster catalysts on transesterification were investigated by changing the carboxylate ligands in the clusters. High catalyst activity crucially depended on the balance between Lewis acidity and Br?nsted basicity of the catalyst; this was consistent with the dual activation of both the electrophile and nucleophile by the cooperative zinc centers. In addition, tetranuclear zinc cluster catalysts achieved the transesterification of β-keto esters with unprecedented levels of broad substrate generality, in which a newly developed pentafluoropropionate-bridged zinc cluster and 4-dimethylaminopyridine additive greatly improved the reactivity of sterically congested α- and α,α-disubstituted β-keto esters. Lewis versus Br?nsted: High catalyst activity of zinc clusters on transesterification crucially depend on a balance between Lewis acidity and Br?nsted basicity of the catalyst. Zinc clusters, including a newly developed pentafluoropropionate-bridged zinc cluster, achieved the transesterification of β-keto esters with unprecedented levels of broad substrate generality (see figure).

Intramolecular cyclopropanation reactions en route to novel P- heterocycles

The first examples of intramolecular cyclopropanation reactions on a phosphonate template catalyzed by Rh2(OAc)4 are described. These reactions proceed in excellent yield and give mixtures of the P-heterocycles cis-2a-d and trans-2a-d with moderate levels of diastereoselectivity. The diastereoselectivity of this transformation is dependent upon the size of the alkyl group R contained in the alkyl α-diazodiallylphosphonoacetate starting materials 1a-d.

EFFICIENT ESTER EXCHANGE REACTION OF PHOSPHONOACETATES

A novel method for the preparation of differentially substituted phosphonoacetates and phosphonoacetamides using 4-DMAP catalyzed ester exchange reaction has been developed.