Methyl tiglate

Base Information

• Chemical Name: Methyl tiglate
• CAS No.: 6622-76-0
• Molecular Formula: C6H10 O2
• Molecular Weight: 114.144
• European Community (EC) Number: 255-518-1,229-575-8
• DSSTox Substance ID: DTXSID30878830
• Nikkaji Number: J278.257J,J45.087A
• Wikidata: Q10382439
• ChEMBL ID: CHEMBL55121
• Mol file: 6622-76-0.mol

Synonyms:Methyl tiglate;6622-76-0;Tiglic acid methyl ester;Methyl 2-methyl-2-butenoate;Methyl 2-methylcrotonate;methyl (E)-2-methylbut-2-enoate;METHYLTIGLATE;Methyl (E)-2-methylcrotonate;41725-90-0;methyl 2-methylbut-2-enoate;Methyl alpha-methylcrotonate;Methyl trans-2-methylcrotonate;2-Butenoic acid, 2-methyl-, methyl ester, (E)-;2-Carbomethoxy-2-butene, (E)-;Methyl trans-2-methyl-2-butenoate;EINECS 229-575-8;EINECS 255-518-1;NSC 55277;BRN 1720455;AI3-35988;Crotonic acid, 2-methyl-, methyl ester, (E)-;2-Butenoic acid, 2-methyl-, methyl ester;2-Butenoic acid, 2-methyl-, methyl ester, (2E)-;Methyl (2E)-2-methyl-2-butenoate;Tiglic acid methyl;Tiglic acid, methyl ester;methyl 2 - methylcrotonate;Methyl tiglate, AldrichCPR;CHEMBL55121;SCHEMBL306388;DTXSID30878830;CHEBI:185318;methyl (2Z)-2-methylbut-2-enoate;MFCD00016654;Tiglic acid, methyl ester (6CI,7CI);AS-76802;LS-47182;METHYL (2E)-2-METHYLBUT-2-ENOATE;T0248;EN300-98186;EN300-658913;Q63396422;InChI=1/C6H10O2/c1-4-5(2)6(7)8-3/h4H,1-3H3/b5-4

Chemical Property of Methyl tiglate

Chemical Property:

• Appearance/Colour: colourless liquid
• Melting Point: 37.22°C (estimate)
• Refractive Index: n20/D 1.436(lit.)
• Boiling Point: 137-138 ºC (758 mmHg)
• Flash Point: 35 ºC
• PSA: 26.30000
• Density: 0.95
• LogP: 1.12560
• Storage Temp.: Flammables area
• Water Solubility.: Soluble in alcohol, water 3813 mg/L @ 25°C (est).
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 114.068079557
• Heavy Atom Count: 8
• Complexity: 114

Purity/Quality:

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

Methyl tiglate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(=O)OC
• Isomeric SMILES: C/C=C(\C)/C(=O)OC
• Uses: Methyl Tiglate is a useful reactant in elaboration of conjugagted alkenes initiated by insertion into a vinylic C-H bond.

Technology Process of Methyl tiglate

There total 33 articles about Methyl tiglate 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: 100.0%

methanol (67-56-1) + Tiglic acid (80-59-1) → methyl (E)-2-methyl-2-butenoate (6622-76-0)

Guidance literature:

With toluene-4-sulfonic acid; for 3h; Heating;

DOI:10.1039/b316899a

Reference yield: 95.0%

acetaldehyde (75-07-0,9002-91-9) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → methyl (E)-2-methyl-2-butenoate (6622-76-0)

Guidance literature:

In dichloromethane; Ambient temperature;

DOI:10.1021/ja00132a006

Reference yield: 85.0%

methyl 2-(bromomethyl)-2-butenoate (33935-64-7) → methyl (E)-2-methyl-2-butenoate (6622-76-0)

Guidance literature:

With acetic acid; zinc; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2004.08.018

upstream raw materials:

diazomethane

methacrylic acid methyl ester

quinoline

3-chloro-2-methyl-butyric acid methyl ester

Downstream raw materials:

4--2-methylbut-2-en-4-olide

methyl boninenalate

trans-1-chloro-2-methylbut-2-ene

methyl 2-hydroxy-2-methyl-3-oxobutanoate

Refernces

• 1、 Lindel, Thomas,Franck, Burchard. "Synthesis and Biomimetic Rearrangement of a Chiral Diterpene Dioxide". . p. 9465 - 9468. Retrieved 1995.
• 2、 Kassi, Eleni,Patrickios, Costas S.. "Well-defined polymers from biosourced monomers: The case of 2-(methacryloyloxy)ethyl tiglate". . p. 1411 - 1415. Retrieved 2010.
• 3、 -. "The acylated piperazine compound and use thereof". Paragraph 0167; 0262-0267. . Retrieved 2019/05/16.
• 4、 Granchi, Carlotta,Fortunato, Serena,Meini, Serena,Rizzolio, Flavio,Caligiuri, Isabella,Tuccinardi, Tiziano,Lee, Hyang Yeon,Hergenrother, Paul J.,Minutolo, Filippo. "Characterization of the Saffron Derivative Crocetin as an Inhibitor of Human Lactate Dehydrogenase 5 in the Antiglycolytic Approach against Cancer". . p. 5639 - 5649. Retrieved 2017/07/26.