Diethyl butyl(prop-2-en-1-yl)propanedioate

Base Information

• Chemical Name: Diethyl butyl(prop-2-en-1-yl)propanedioate
• CAS No.: 1575-76-4
• Molecular Formula: C14H24 O4
• Molecular Weight: 256.342
• NSC Number: 128928
• DSSTox Substance ID: DTXSID20935683
• Nikkaji Number: J2.281.837F
• Wikidata: Q82911755
• Mol file: 1575-76-4.mol

Synonyms:1575-76-4;diethyl butyl(prop-2-en-1-yl)propanedioate;NSC128928;SCHEMBL9478485;DTXSID20935683;NSC-128928

Chemical Property of Diethyl butyl(prop-2-en-1-yl)propanedioate

Chemical Property:

• Vapor Pressure: 0.00363mmHg at 25°C
• Boiling Point: 281.1°C at 760 mmHg
• Flash Point: 123.4°C
• Density: 0.979g/cm³
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 256.16745924
• Heavy Atom Count: 18
• Complexity: 266

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(CC=C)(C(=O)OCC)C(=O)OCC

Technology Process of Diethyl butyl(prop-2-en-1-yl)propanedioate

There total 4 articles about Diethyl butyl(prop-2-en-1-yl)propanedioate 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%

1-bromo-butane (109-65-9) + (2-propenyl)propanedioic acid diethyl ester (2049-80-1) → 2-butyl-2-ethoxycarbonylpenten-4-oic acid ethyl ester (1575-76-4)

Guidance literature:

With sodium ethanolate; In ethanol; for 1h; Heating;

DOI:10.1021/ja047320t

Reference yield:

diallylmalonic acid diethyl ester (3195-24-2) → 2-butyl-2-ethoxycarbonylpenten-4-oic acid ethyl ester (1575-76-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent Spectr_. / Et₃Al; RuCl₂(PPh₃)3 / toluene / 36 h / 20 °C

2: 69 percent / NaOEt / ethanol / 1 h / Heating

With tris(triphenylphosphine)ruthenium(II) chloride; triethylaluminum; sodium ethanolate; In ethanol; toluene;

DOI:10.1021/ja047320t

Reference yield:

(2-propenyl)propanedioic acid diethyl ester (2049-80-1) → 2-butyl-2-ethoxycarbonylpenten-4-oic acid ethyl ester (1575-76-4)

Guidance literature:

With sodium ethanolate; Diethyl carbonate; Abdestillieren des Alkohols und Erhitzen mit Butylbromid auf 100-105grad;

upstream raw materials:

(2-propenyl)propanedioic acid diethyl ester

1-bromo-butane

diallylmalonic acid diethyl ester

diethyl malonate

Downstream raw materials:

diethyl butylmalonate

5-n-Butyl-5-allylbarbitursaeure

Refernces

• 1、 Kurata,Tanaka,Takahashi. "Synthesis of δ lactone derivatives. V. 3 Alkyl derivatives". . p. 538 - 540. Retrieved 2007/10/05.