7071-12-7

Basic information

• Product Name: Triethyl 2-chloro-2-phosphonoacetate
• Synonyms: 2-CHLORO-2-PHOSPHONOACETIC ACID TRIETHYL ESTER;ACETIC ACID, CHLOROPHOSPHONO-, TRIETHYL ESTER;TRIETHYL 2-CHLORO-2-PHOSPHONOACETATE, 97 %;Triethyl 2-Chloro-2-phosphoacetate;Diethyl chloro ethoxycarbonylmethyl phosphonate, 98 %;Ethyl 2-chloro-2-(diethoxyphosphoryl)acetate;Chloro(diethoxyphosphinyl)acetic acid ethyl ester;Triethyl 2-chloro-2-phosphonoacetate 97%
• CAS NO: 7071-12-7
• Molecular Formula: C₈H₁₆ClO₅P
• Molecular Weight: 258.64
• Product Categories: C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination
• Mol File: 7071-12-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 93-95 °C0.01 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.21 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00073mmHg at 25°C
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: Store at R.T.
• CAS DataBase Reference: Triethyl 2-chloro-2-phosphonoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Triethyl 2-chloro-2-phosphonoacetate(7071-12-7)
• EPA Substance Registry System: Triethyl 2-chloro-2-phosphonoacetate(7071-12-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 7071-12-7(Hazardous Substances Data)

Usage

Uses

Triethyl 2-chloro-2-phosphonoacetate is a reagent that is used in the synthesis of isotope labelled Mutagen X (MX), which is a chlorinated furanone that accounts for more of the mutagenic activity of drinking water than any other disinfection byproduct. DNA damages provoked by the six mutagens (furylframide, MX, 4-nitroquinoline N-oxide, sodium azide, 1-nitropyrene, and captan) used in the present study have been known to subject to the nucleotide excision repair system.

InChI:InChI=1/C8H16ClO5P/c1-4-12-8(10)7(9)15(11,13-5-2)14-6-3/h7H,4-6H2,1-3H3

Upstream product

• 5823-12-1 ethyl 2,2-dichloro-2-diethoxyphosphorylacetate 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 51507-22-3 (Z)-ethyl 3-(4-methoxyphenyl)acrylate 
• 66051-39-6 (Z)-methoxyphenyl-3 chloro-2 propenoate d'ethyle 
• 66051-40-9 (E)-methoxyphenyl-3 chloro-2 propenoate d'ethyle 
• 849701-73-1 ethyl 2-(1-benzhydrylazetidin-3-ylidene)-2-chloroacetate 
• 1424388-06-6 C₂₁H₂₂ClF₂N₅O₄ 
• 1424388-05-5 C₂₁H₂₃ClFN₅O₄ 
• 872551-02-5 (E)-2-chloro-3-[4-(6-methoxy-3-methyl-2-phenyl-naphthalen-1-yloxy)-phenyl]-acrylic acid ethyl ester 
• 872551-03-6 (Z)-2-chloro-3-[4-(6-methoxy-3-methyl-2-phenyl-naphthalen-1-yloxy)-phenyl]-acrylic acid ethyl ester 
• 501334-17-4 ethyl-(Z)-2-chloro-3-[4-(methoxymethoxy)phenyl]-2-butenoate 
• 3699-66-9 ethyl 2-diethoxyphosphorylpropionate 
• 277307-93-4 2-(diethoxy-phosphoryl)-4-ethoxythiocarbonylsulfanyl-5-(1-methyl-2-oxo-cyclohexyl)-pentanoic acid ethyl ester 
• 277307-99-0 2-(diethoxy-phosphoryl)-5-(1-methyl-2-oxo-cyclohexyl)-pentanoic acid ethyl ester 

Relevant articles and documents

Carbanions phosphonate prepares par voie electrochimique: formation et reactivite vis-a-vis d'un aldehyde

Reactivity towards p-methoxybenzaldehyde (ArCHO) of electrochemically generated phosphonate carbanions has been investigated.Electrolyses were carried out at a mercury cathode in DMF and two routes to the desired carbanion have been compared: (i) Deprotonation of phosphonates of general formula (EtO)2P(O)CHYW (Y = W = Cl; Y = H, W = Cl; Y = Cl, W = CO2Et; Y = H, W = CO2Et; Y = CH3, W = CO2Et; Y = Cl, W = CH3), by the bases resulting from the electroreduction of azobenzene; addition of the carbanion formed onto the carbonyl group takes place and leads to the adduct (EtO)2P(O)CYW(Ar)O-. (ii) Two-electron reduction of halophosphonates (EtO)2P(O)CXYW (X = Cl, Y and W as above; X = Br, W = CO2Et, Y = Cl, Br, or CH3); when no H atom is present on the carbon bearing the phosphonate group (Y and W no = H), the same evolution leading to the above adduct is observed, on the contrary, when Y = H, the electrogenerated carbanion deprotonates the substrate and the resulting carbanion (EtO)2P(O)CXW reacts with the aldehyde; giving the adduct (EtO)2P(O)CXW(Ar)O-.Evolution of the intermediate adduct depends on the substituents Y (or X) and W: when W = CO2Et, whatever the nature of Y (or X), diethyl phosphate is eliminated with formation of the ethylenic ArCH=CWY (or X) (Wittig-Horner reaction); the same evolution is observed when Y = W = Cl.When W = Cl and Y = H or CH3, the final product is the phosphonate epoxyde resulting from chloride elimination (Darzens reaction).Chemo- and stereoselectivity depend only on the nature of Y and W but are independent of the mode of generation of the carbanion.Yields are limited by side-protonation reactions, which are related to the basicity of the phosphonate carbanions.Analysis of the results permits selection of the optimal electrolysis conditions for purposes of synthesis.Key words: electrosynthesis, electrogenerated bases, phosphonates, Wittig-Horner.