682-34-8

Basic information

• Product Name: DIETHYL 2-BUTENYLPHOSPHONATE 95
• Synonyms: DIETHYL 2-BUTENYLPHOSPHONATE 95;diethyl 2-butenylphosphonate, predominantly trans
• CAS NO: 682-34-8
• Molecular Formula: C₈H₁₇O₃P
• Molecular Weight: 192.19
• Mol File: 682-34-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 245.385°C at 760 mmHg
• Flash Point: 219 °F
• Appearance: /
• Density: 1.014 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.045mmHg at 25°C
• Refractive Index: n20/D 1.4400(lit.)
• CAS DataBase Reference: DIETHYL 2-BUTENYLPHOSPHONATE 95(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 2-BUTENYLPHOSPHONATE 95(682-34-8)
• EPA Substance Registry System: DIETHYL 2-BUTENYLPHOSPHONATE 95(682-34-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 682-34-8(Hazardous Substances Data)

Usage

Uses

Olefinic partner for Pauson-Khand reaction with alkyne cobalt complexReactant for: Synthesis of di-Et 1-substituted vinylphosphonates via decarboxylative condensationSequential lithiation and silylationPalladium catalyzed allylic acetoxylationPreparation of building blocks of retinoid chemistry

InChI:InChI=1/C8H17O3P/c1-4-7-8-12(9,10-5-2)11-6-3/h4,7H,5-6,8H2,1-3H3/b7-4+

Upstream product

• 563-52-0 2-chloro-3-butene 
• 2303-76-6 sodium diethyl phosphite 
• 4784-77-4 (E/Z)-crotyl bromide 
• 122-52-1 triethyl phosphite 
• 762-04-9 Diethyl phosphonate 
• 591-97-9 1-chloro-2-butene 

Downstream Products

• 1067-90-9 diethyl 3-oxobutylphosphonate 
• 51795-80-3 1-Benzyl-2-butenphosphonsaeurediethylester 

Relevant articles and documents

New Synthetic Routes to β-Olefinic Trialkoxyphosphonium Salts and Phosphonates: Organometallic Variants of the Michaelis-Arbuzov Reaction

The low-temperature addition of tertiary phosphites to +X- complexes proceeds regio- and stereospecifically and produces metal-coordinated β-olefinic trialkoxyphosphonium ions.These can be converted by various routes

Aprotic Conjugate Addition of Allyllithium Reagents Bearing Polar Groups to Cyclic Enones. 1. 3-Alkylallyl Systems

The conjugate addition of lithiated (E)- and (Z)-oct-2-enyl sulfoxides and phosphine oxides, but-2-enyl sulfoxides, phosphine oxides and phosphonates, and 3,3-dimethylallyl and allyl sulfoxides to cyclic enones has been examined.The E and Z carbanions react in highly diastereoselective fashion with five-membered cyclic enones to deliver respectively syn and anti vinylic sulfoxides, phosphine oxides, and phosphonates.Hexamethylphosphoric triamide has no regiochemical influence on these reactions.The regiochemical and stereochemical outcomes of these reactions are rationalized in terms of planar lithiated reagents in which Li+ is bound to oxygen attached to sulfur or phosphorus of the polar group and a 10-membered "trans-decalyl"- or "trans-fused chair-chair"-like transition-state model in which the lithiated reagent adopts an endo orientation over one face of the enone such that for the reagent, the 3-alkyl group is pseudoequatorial, and for the Z, pseudoaxial.