tert-Butyl crotonate

Base Information

• Chemical Name: tert-Butyl crotonate
• CAS No.: 79218-15-8
• Molecular Formula: C8H14 O2
• Molecular Weight: 142.198
• Hs Code.: 29161900
• European Community (EC) Number: 221-821-2,628-481-8
• UNII: SMM9GBT5XV
• DSSTox Substance ID: DTXSID401033020
• Nikkaji Number: J262.352H,J208.285C
• Wikidata: Q76306603
• Mol file: 79218-15-8.mol

Synonyms:tert-Butyl crotonate;79218-15-8;3246-27-3;Crotonic Acid tert-Butyl Ester;(E)-tert-butyl but-2-enoate;t-butyl crotonate;tert-butyl (E)-but-2-enoate;tert-butyl but-2-enoate;tert-Butyl 2-butenoate;tert-Butyl (E)-2-butenoate;2-Butenoic acid, 1,1-dimethylethyl ester, (2E)-;SMM9GBT5XV;trans-tert-Butyl crotonate;tert-butyl (2E)-2-butenoate;EINECS 221-821-2;1,1-Dimethylethyl (2E)-2-butenoate;(2E)-2-Butenoic acid 1,1-dimethylethyl ester;2-Butenoic acid, 1,1-dimethylethyl ester, (E)-;starbld0009558;UNII-SMM9GBT5XV;SCHEMBL391777;SCHEMBL391778;QHSPZGZEUDEIQM-AATRIKPKSA-N;DTXSID401033020;tert-Butyl crotonate, >=97.0%;MFCD00059055;AKOS006222290;(E)-2-Butenoic acid tert-butyl ester;(2E)but-2-enoic acid tert-butyl ester;(E)-but-2-enoic acid tert-butyl ester;2-Methyl-2-propanyl (2E)-2-butenoate;D89365;A839622;J-500778

Chemical Property of tert-Butyl crotonate

Chemical Property:

• Refractive Index: n20/D 1.425
• Boiling Point: 82 °C / 97mmHg
• Flash Point: 23 °C
• PSA: 26.30000
• Density: 0,89 g/cm3
• LogP: 1.90420
• Storage Temp.: Refrigerator
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

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

tert-Butyl Crotonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-41
• Safety Statements: 16-39-26

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of tert-Butyl crotonate

There total 3 articles about tert-Butyl crotonate 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:

carbon monoxide (201230-82-2) + 3-chloroprop-1-ene (107-05-1) + tert-butyl alcohol (75-65-0) → t-butyl vinylacetate (14036-55-6) + tert-butyl (E)-crotonate (79218-15-8)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 100 ℃; for 10h; under 20686.5 Torr; Autoclave;

DOI:10.1055/s-0031-1289659

Reference yield:

carbon monoxide (201230-82-2) + 3-chloroprop-1-ene (107-05-1) + tert-butyl alcohol (75-65-0) → t-butyl vinylacetate (14036-55-6) + tert-butyl (E)-crotonate (79218-15-8) + crotonic acid tert-butyl ester (73981-49-4)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 100 ℃; for 20h; under 20686.5 Torr; optical yield given as %de; Autoclave;

DOI:10.1055/s-0031-1289659

Reference yield:

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + tert-butyl alcohol (75-65-0) → t-butyl vinylacetate (14036-55-6) + tert-butyl (E)-crotonate (79218-15-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.5h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(01)80823-6

upstream raw materials:

trans-chrotonyl chloride

tert-butyl alcohol

carbon monoxide

3-chloroprop-1-ene

Downstream raw materials:

(1S,3R)-2-Chloro-3-methyl-2-trichlorovinyl-cyclopropanecarboxylic acid

isobutene

3-Methyl-2-phenyl-pentanedioic acid 5-tert-butyl ester 1-methyl ester

(2S,3R)-2-Dibenzylamino-2,3-dimethyl-pentanedioic acid 5-tert-butyl ester 1-methyl ester

Refernces

• 1、 Lombardo, Luciano. "A VERSATILE ROUTE TO MIXED VINYLKETENE ACETALS : USE OF 1-t-BUTYLDIMETHYLSILOXY-1-ETHOXY BUTADIENE IN CYCLOHEXENONE SYNTHESIS". . p. 381 - 384. Retrieved 2007/10/02.