4-(Diethylphosphono)-3-methyl-2-butenenitrile, E/Z mixture

Base Information

• Chemical Name: 4-(Diethylphosphono)-3-methyl-2-butenenitrile, E/Z mixture
• CAS No.: 87549-50-6
• Molecular Formula: C9H16NO3P
• Molecular Weight: 217.205
• Mol file: 87549-50-6.mol

Synonyms:Diethyl 3-methyl-4-phosphonocrotononitrile;diethyl 3-cyano-2-methylprop-2-enyl-phosphonate;diethyl o-methoxybenzylidenemalonate;2-Methoxy-benzalmalonsaeure-diaethylester;

Chemical Property of 4-(Diethylphosphono)-3-methyl-2-butenenitrile, E/Z mixture

Chemical Property:

• Boiling Point: 118-120°C@0.2mmHg
• PSA: 69.13000
• LogP: 2.72238
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(Diethylphosphono)-3-methyl-2-butenenitrile,E/Zmixture ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(Diethylphosphono)-3-methyl-2-butenenitrile, E/Z mixture (cas# 87549-50-6) is a compound useful in organic synthesis.

Technology Process of 4-(Diethylphosphono)-3-methyl-2-butenenitrile, E/Z mixture

There total 2 articles about 4-(Diethylphosphono)-3-methyl-2-butenenitrile, E/Z mixture which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

4-chloro-3-methyl-2-butenenitrile (4450-34-4) + triethyl phosphite (122-52-1) → diethyl (2-methyl-3-cyano-2-propenyl)phosphonate (87549-50-6)

Guidance literature:

at 180 ℃; for 8h; Inert atmosphere;

DOI:10.1021/ja3007929

Reference yield:

→ diethyl (2-methyl-3-cyano-2-propenyl)phosphonate (87549-50-6)

Guidance literature:

/BRN= 902171/, Triethyl-phosphit / Δ;

Reference yield: 100.0%

diethyl (2-methyl-3-cyano-2-propenyl)phosphonate (87549-50-6) + (2E,4E)-5-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-3-methyl-penta-2,4-dienal → (4R)-4-<(tert-Butyldimethylsilyl)oxy>retinonitrile

Guidance literature:

With sodium hydride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)75995-8

upstream raw materials:

4-chloro-3-methyl-2-butenenitrile

triethyl phosphite

Downstream raw materials:

(2E,4E,6E)-3-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienenitrile

Dehydroretinsaeurenitril

9,10-Didehydro-19-norretinsaeurenitril

19-Nor-7,8-dehydroretinaldehyd

Refernces

• 1、 Trehan,Mirzadegan,Liu. "The doubly hindered 7,11-dicis, 7,9,11-tricis, 7,11,13-tricis and all-cis isomers of retinonitrile and retinal". . p. 3769 - 3780. Retrieved 2007/10/02.