Butyl (2E)-2-methylbut-2-enoate

Base Information

• Chemical Name: Butyl (2E)-2-methylbut-2-enoate
• CAS No.: 7785-66-2
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.225
• European Community (EC) Number: 232-084-1,232-086-2
• UNII: 7VD4CT8NDW
• Nikkaji Number: J107.436I,J3.397.304G
• Wikidata: Q67879749
• Mol file: 7785-66-2.mol

Synonyms:Butyl tiglate;n-Butyl tiglate;7785-66-2;butyl (E)-2-methylbut-2-enoate;butyl (2E)-2-methylbut-2-enoate;2-Butenoic acid,2-methyl-, butyl ester, (2E)-;7VD4CT8NDW;Tiglic acid n-butyl ester;N-BUTYLTIGLATE;2-Butenoic acid, 2-methyl-, butyl ester, (E)-;Butyl .alpha.-methylcrotonate;BUTYL 2-METHYLCROTONATE;TIGLIC ACID, BUTYL ESTER;2-Butenoic acid, 2-methyl-, butyl ester, (2E)-;EINECS 232-086-2;AI3-33792;butyl 2 - methylcrotonate;7785-64-0;Butyl 2-methylcrotonate (Z);2-Butenoic acid, 2-methyl-, butyl ester, (2Z)-;UNII-7VD4CT8NDW;Butyl 2-methyl-2-butenoate;Butyl 2-methylcrotonate (E);SCHEMBL262657;Butyl 2-methylcrotonate (E)-;BUTYL alpha-METHYLCROTONATE;(E)-butyl 2-methylbut-2-enoate;RBGFLIOXJWFKKX-VMPITWQZSA-N;AKOS006274556;AS-66500;Q67879749

Chemical Property of Butyl (2E)-2-methylbut-2-enoate

Chemical Property:

• PSA: 26.30000
• LogP: 2.29590
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 156.115029749
• Heavy Atom Count: 11
• Complexity: 148

Purity/Quality:

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

N-BUTYL TIGLATE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Butyl (2E)-2-methylbut-2-enoate

There total 2 articles about Butyl (2E)-2-methylbut-2-enoate 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: 52.0%

Tiglic acid (80-59-1) + butan-1-ol (71-36-3) → (E)-butyl 2-methylbut-2-enoate (7785-64-0,66917-60-0,7785-66-2)

Guidance literature:

With sulfuric acid; Reflux; Inert atmosphere;

DOI:10.1002/asia.201101018

Reference yield: 43.0%

2,3-dimethylbutene (590-19-2) + carbon monoxide (201230-82-2) + butan-1-ol (71-36-3) → (E)-butyl 2-methylbut-2-enoate (7785-64-0,66917-60-0,7785-66-2)

Guidance literature:

With 2-(diphenylphosphino)pyridine; palladium diacetate; trifluoroacetic acid; In toluene; at 110 ℃; for 20h; under 30003 Torr; regioselective reaction; Autoclave; Inert atmosphere;

DOI:10.1021/jacs.5b04052

Reference yield: 46.0%

1-bromo-3-chlorobenzene (108-37-2) + (E)-butyl 2-methylbut-2-enoate (7785-64-0,66917-60-0,7785-66-2) → (Z)-butyl 3-(3-bromo-5-chlorophenyl)-2-methylbut-2-enoate (1380708-62-2)

Guidance literature:

With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; cesium pivalate; Trimethylacetic acid; at 160 ℃; for 21h; regioselective reaction; Inert atmosphere;

DOI:10.1002/asia.201101018

upstream raw materials:

Tiglic acid

butan-1-ol

2,3-dimethylbutene

carbon monoxide

Downstream raw materials:

(Z)-butyl 3-(3-bromophenyl)-2-methylbut-2-enoate

(Z)-butyl 3-(4-bromophenyl)-2-methylbut-2-enoate

(Z)-butyl 3-(3-bromo-5-chlorophenyl)-2-methylbut-2-enoate

(Z)-butyl 3-(3-bromo-5-(trifluoromethyl)phenyl)-2-methylbut-2-enoate

Refernces

• 1、 Wencel-Delord, Joanna,Nimphius, Corinna,Patureau, Frederic W.,Glorius, Frank. "Undirected arene and chelate-assisted olefin C-H bond activation: [Rh IIICp*]-catalyzed dehydrogenative alkene-arene coupling as a new pathway for the selective synthesis of highly substituted Z olefins". supporting information; experimental part. p. 1208 - 1212. Retrieved 2012/07/28.