10419-78-0

Basic information

• Product Name: (1-Chloroethyl)phosphonic acid diethyl ester
• Synonyms: (1-Chloroethyl)phosphonic acid diethyl ester
• CAS NO: 10419-78-0
• Molecular Formula: C₆H₁₄ClO₃P
• Molecular Weight: 0
• Mol File: 10419-78-0.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1-Chloroethyl)phosphonic acid diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1-Chloroethyl)phosphonic acid diethyl ester(10419-78-0)
• EPA Substance Registry System: (1-Chloroethyl)phosphonic acid diethyl ester(10419-78-0)

Safety Data

• Hazardous Substances Data: 10419-78-0(Hazardous Substances Data)

Usage

General Description

"(1-Chloroethyl)phosphonic acid diethyl ester" is a chemical compound that is commonly used as a plant growth regulator. It is a colorless, odorless liquid that is soluble in organic solvents. (1-Chloroethyl)phosphonic acid diethyl ester is known for its ability to stimulate plant growth and increase productivity by inhibiting the enzyme responsible for producing gibberellins, a plant hormone that regulates various aspects of plant growth and development. It is also used as a chemical intermediate in the synthesis of other organic compounds. However, it is important to note that (1-Chloroethyl)phosphonic acid diethyl ester is highly toxic and requires careful handling to avoid any adverse effects on human health or the environment.

Upstream product

• 51346-81-7 (1,1-dichloro-ethyl)-phosphonic acid diethyl ester 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 123098-27-1 (E)-p-methoxyphenyl-2 methyl-1 epoxy-1,2 ethanephosphonate 
• 123098-27-1 (Z)-p-methoxyphenyl-2 methyl-1 epoxy-1,2 ethanephosphonate 
• 78-38-6 ethylphosphonic acid diethyl ester 
• 249571-90-2 diethyl (2R,3R)-2-methyl-3-phenyl-aziridine-2-phosphonate 
• 249571-89-9 diethyl (S_S,2R,3R)-2-methyl-3-phenyl-1-(p-toluenesulfinyl)-aziridine-2-phosphonate 
• 742101-86-6 1-chloroethyl-phosphonochloridic acid, ethyl ester 
• 1498-51-7 ethyl phosphodichloridite 

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.