Isobutyl 2-butenoate

Base Information

• Chemical Name: Isobutyl 2-butenoate
• CAS No.: 73545-15-0
• Molecular Formula: C8H14O2
• Molecular Weight: 142.198
• European Community (EC) Number: 209-658-5,687-874-2
• UNII: 6H6IW50K3Z
• DSSTox Substance ID: DTXSID2047690
• Nikkaji Number: J188.461A,J94.999J
• Wikidata: Q18464456
• Mol file: 73545-15-0.mol

Synonyms:Isobutyl 2-butenoate;Isobutyl crotonate;Crotonic Acid Isobutyl Ester;73545-15-0;589-66-2;Isobutyl trans-2-butenoate;2-methylpropyl (E)-but-2-enoate;Isobutyl but-2-enoate;(E)-isobutyl but-2-enoate;UNII-6H6IW50K3Z;6H6IW50K3Z;2-Butenoic acid, 2-methylpropyl ester, (E)-;2-Butenoic acid, 2-methylpropyl ester, (2E)-;2-BUTENOIC ACID, 2-METHYLPROPYL ESTER;(E)-2-Butenoic acid isobutyl ester;Crotonic acid, isobutyl ester, (trans)-;FEMA No. 3432;DTXSID7047691;crotonicacidisobutylester;ISOBUTYL-2-BUTENOATE;SCHEMBL182261;SCHEMBL182262;2-Butenoic acid isobutyl ester;2-Butenoic Acid Isobuyl Ester;TRANS-ISOBUTYL CROTONATE;DTXCID5027691;DTXSID2047690;XDOWKOALJBOBBL-SNAWJCMRSA-;XDOWKOALJBOBBL-SNAWJCMRSA-N;ISOBUTYL-2-BUTENOATE [FCC];2-Methylpropyl (2E)-but-2-enoate;ISOBUTYL 2-BUTENOATE [FHFI];Tox21_303966;MFCD00036651;AKOS015915512;NCGC00357274-01;CAS-589-66-2;Isobutyl trans-2-butenoate, >=98%, FCC, FG;Q18464456;InChI=1/C8H14O2/c1-4-5-8(9)10-6-7(2)3/h4-5,7H,6H2,1-3H3/b5-4+

Chemical Property of Isobutyl 2-butenoate

Chemical Property:

• Refractive Index: n20/D1.428(lit.)
• Boiling Point: 166.4°Cat760mmHg
• Flash Point: 55°C
• PSA: 26.30000
• Density: 0.899g/cm³
• LogP: 1.76170
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 125

Purity/Quality:

99%min ^*data from raw suppliers

Isobutyl trans-2-butenoate ≥98%,FCC,FG ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=CC(=O)OCC(C)C
• Isomeric SMILES: C/C=C/C(=O)OCC(C)C

Technology Process of Isobutyl 2-butenoate

There total 6 articles about Isobutyl 2-butenoate 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: 18.0%

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + benzyl iso-butyl ether (940-49-8) → isobutyl trans-crotonate (73545-15-0) + (2E,6E)-octa-2,6-diene-4,5-dione (55409-19-3) + benzyl chloride (100-44-7)

Guidance literature:

CoCl₂; In acetonitrile; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4020(01)96041-7

Reference yield:

isobutyl n-butyrate (539-90-2) → isobutyl trans-crotonate (73545-15-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: i-Pr₂NH; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 65 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 93 percent / Et₃N; mesyl azide / acetonitrile / 15 h / 20 °C

3.1: Cu(acac)2 / CH₂Cl₂ / 2 h / Heating

With n-butyllithium; triethylamine; diisopropylamine; Methanesulfonyl azide; copper acetylacetonate; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 1.1: Metallation / 1.2: Acylation / 2.1: diazo transfer / 3.1: Elimination;

DOI:10.1016/S0040-4020(00)00893-0

Reference yield:

2-ethyl-4,4,4-trifluoro-3-oxo-butyric acid isobutyl ester → isobutyl trans-crotonate (73545-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Et₃N; mesyl azide / acetonitrile / 15 h / 20 °C

2: Cu(acac)2 / CH₂Cl₂ / 2 h / Heating

With triethylamine; Methanesulfonyl azide; copper acetylacetonate; In dichloromethane; acetonitrile; 1: diazo transfer / 2: Elimination;

DOI:10.1016/S0040-4020(00)00893-0

upstream raw materials:

2-butenoic acid

2-methyl-propan-1-ol

2-bromo-butyric acid isobutyl ester

N,N-diethylaniline

Downstream raw materials:

3,4,4-trimethylcyclopent-2-en-1-one

isobutyl 3-<2-(3,5-dihydroxyphenyl)-2-hydroxy-ethylamino>-butyrate, sulfate

isobutyl (3S)-3-{methyl[(1S)-1-phenylethyl]amino}butanoate

isobutyl 3-(4-methylphenyl)crotonate

Refernces

• 1、 Iqbal,Srivastava. "Cobalt(II)chloride catalysed cleavage of ethers with acyl halides: Scope and mechanism". . p. 3155 - 3170. Retrieved 2007/10/02.