(E)-alpha-Butylcinnamic acid

Base Information

• Chemical Name: (E)-alpha-Butylcinnamic acid
• CAS No.: 4134-20-7
• Molecular Formula: C₁₃H₁₆O₂
• Molecular Weight: 204.269
• NSC Number: 8486
• DSSTox Substance ID: DTXSID90417789
• Nikkaji Number: J978.587F,J2.411.695F
• Wikidata: Q82227965
• Mol file: 4134-20-7.mol

Synonyms:NSC8486;4134-20-7;alpha-Butylbenzeneacrylic acid;(E)-alpha-Butylcinnamic acid;(e)-2-benzylidenehexanoic acid;SCHEMBL1786246;DTXSID90417789;NSC-8486

Chemical Property of (E)-alpha-Butylcinnamic acid

Chemical Property:

• Vapor Pressure: 6E-05mmHg at 25°C
• Boiling Point: 332°Cat760mmHg
• Flash Point: 235.5°C
• Density: 1.07g/cm³
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 204.115029749
• Heavy Atom Count: 15
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC(=CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CCCC/C(=C\C1=CC=CC=C1)/C(=O)O

Technology Process of (E)-alpha-Butylcinnamic acid

There total 21 articles about (E)-alpha-Butylcinnamic acid 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: 76.0%

carbon dioxide (124-38-9,18923-20-1) + (hex-1-yn-1-yl)benzene (1129-65-3) → acide 2-butyl-3(E)-phenyl-but-3-en-2-one (77136-32-4,4134-20-7) + (E)-2-Phenyl-hept-2-enoic acid (78427-52-8)

Guidance literature:

carbon dioxide; (hex-1-yn-1-yl)benzene; With Triethoxysilane; C₂₁H₂₂Cl₂CuFN₂; In hexane; at 70 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; In hexane; dichloromethane; water; at 20 ℃; for 0.25h; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201006292

Reference yield: 43.0%

tributyl borane (122-56-5) + carbon dioxide (124-38-9,18923-20-1) + phenylacetylene (536-74-3) → acide 2-butyl-3(E)-phenyl-but-3-en-2-one (77136-32-4,4134-20-7)

Guidance literature:

With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate; In tetrahydrofuran; 1,4-dioxane; at 20 ℃; for 24h; under 760.051 Torr; stereoselective reaction;

DOI:10.1021/acs.orglett.6b03860

Reference yield:

carbon monoxide (201230-82-2) + (hex-1-yn-1-yl)benzene (1129-65-3) → C13H16O2 (4134-20-7) + C13H16O2

Guidance literature:

With water; palladium diacetate; 4,5-bis(diphenylphosphanyl)-9,9-dimethyl-9H-xanthene-2,7-disulfonic acid; at 100 ℃; for 24h; under 2250.23 Torr; Overall yield = 93 percent; regioselective reaction;

DOI:10.1039/d1cy00699a

upstream raw materials:

(E)-3-butyl-4-phenyl-3-buten-2-one

methyl hexanoate

benzaldehyde

2-bromohexanoic acid

Refernces

• 1、 Chen, Pengquan,Cheng, Ruixiang,Jiang, Huanfeng,Lei, Ming,Lou, Hongming,Qi, Chaorong,Shi, Fuxing,Wang, Lu,Wu, Wanqing,Xiong, Wenfang,Zhu, Baiyao. "Palladium-Catalyzed Highly Regioselective Hydrocarboxylation of Alkynes with Carbon Dioxide". . p. 7968 - 7978. Retrieved 2020/08/21.
• 2、 Rzymkowski, Jan,Pi?tek, Anna. "The Development of a Stereoselective Method for the Synthesis of Tetrasubstituted Derivatives of α,β-Unsaturated Carboxylic Acids". . p. 665 - 673. Retrieved 2016/09/21.