Ethyl tiglate

Base Information

• Chemical Name: Ethyl tiglate
• CAS No.: 5837-78-5
• Molecular Formula: C7H12O2
• Molecular Weight: 128.171
• Hs Code.: 29161900
• European Community (EC) Number: 227-425-6,259-688-8
• UNII: 0MQ7E9082G
• ChEMBL ID: CHEMBL299599
• DSSTox Substance ID: DTXSID8047688
• Metabolomics Workbench ID: 48392
• Nikkaji Number: J267.017H,J107.434B
• NSC Number: 55278
• Wikidata: Q27106534
• Mol file: 5837-78-5.mol

Synonyms:Ethyl tiglate;5837-78-5;Tiglic acid, ethyl ester;Ethyl 2-methylcrotonate;ethyl (E)-2-methylbut-2-enoate;Ethyl trans-2-methyl-2-butenoate;Ethyl alpha-methylcrotonate;Ethyl 2-methylbut-2-enoate;(E)-2-Methyl-2-butenoic acid ethyl ester;2-Butenoic acid, 2-methyl-, ethyl ester, (2E)-;Ethyl (E)-2-methylcrotonate;Ethyl trans-2-methylcrotonate;FEMA No. 2460;Tiglic acid ethyl ester;Ethyl (E)-2-methyl-2-butenoate;ETHYLTIGLATE;2-Butenoic acid, 2-methyl-, ethyl ester, (E)-;2-Butenoic acid, 2-methyl-, ethyl ester;(E)-ethyl 2-methylbut-2-enoate;ethyl (2E)-2-methylbut-2-enoate;Crotonic acid, 2-methyl-, ethyl ester, (E)-;CHEBI:4892;0MQ7E9082G;Ethyl (2E)-2-methyl-2-butenoate;NSC-55278;Ethyl 2-methyl-2-butenoate;2-Butenoic acid, 2-methyl-, ethyl ester, (2Z)-;Ethyl 2-methylcrotonate, (E)-;EINECS 227-425-6;Ethyl 2-methyl-2-butenoate, (E)-;NSC 55278;BRN 1720895;UNII-0MQ7E9082G;Tiglic acid, ethyl ester (6CI,7CI);Ethyl tiglate, >=98%;Ethyl alpha -methylcrotonate;Ethyl-2-methylbut-2-enoate;ETHYL TIGLATE [FHFI];(E)-Ethyl 2-methylcrotonate;SCHEMBL111293;CHEMBL299599;Ethyl tiglate, >=98%, FG;(E)-ethyl2-methylbut-2-enoate;DTXSID8047688;FEMA 2460;(E)-Ethyl 2-methyl-2-butenoate;NSC55278;LMFA07010884;MFCD00015183;AKOS015903267;2-Methyl-ethyl ester(E)-Crotonic acid;2-Methyl-ethyl ester(E)-2-Butenoic acid;LS-13312;2-Methyl-ethyl ester(2E)-2-Butenoic acid;2-methyl-trans-but-2-enoic acid ethyl ester;CS-0186102;NS00012464;T0247;Ethyl tiglate stabilized with alpha-tocopherol;(E)-2-butenoic acid, 2-methyl-, ethyl ester;C08487;D94746;Q27106534

Chemical Property of Ethyl tiglate

Chemical Property:

• Appearance/Colour: liquid
• Vapor Pressure: 4.27mmHg at 25°C
• Melting Point: -62.68°C (estimate)
• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 148.2 °C at 760 mmHg
• Flash Point: 44.4 °C
• PSA: 26.30000
• Density: 0.909 g/cm³
• LogP: 1.51570
• Storage Temp.: Flammables area
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 128.083729621
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl Tiglate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• Statements: 10
• Safety Statements: 16-27-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=CC)C
• Isomeric SMILES: CCOC(=O)/C(=C/C)/C
• Uses: Ethyl Tiglate is an aroma compound present in fruits. Also used in the synthesis of grandisol and fraganol.

Technology Process of Ethyl tiglate

There total 43 articles about Ethyl 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: 94.0%

Tiglic acid (80-59-1) + ethanol (64-17-5) → Ethyl tiglate (5837-78-5,55514-48-2)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; Heating;

DOI:10.1016/j.tetasy.2004.04.002

Reference yield: 86.6%

α-methylene-γ-butyrolactone (547-65-9) + ethanol (64-17-5) → 3-methyl-5H-furan-2-one (22122-36-7) + Ethyl tiglate (5837-78-5,55514-48-2)

Guidance literature:

With rhodium(III) chloride; at 100 ℃; for 3h;

DOI:10.1021/np0400860

Reference yield: 11.0%

ethyl 2-methylenebutyrate (3070-65-3) + carbon monoxide (201230-82-2) → Ethyl tiglate (5837-78-5,55514-48-2) + (R)-ethyl 2-ethyl-4-oxobutanoate (1345836-55-6) + (S)-ethyl 2-ethyl-4-oxobutanoate

Guidance literature:

With (R,R)-(-)-2,3-bis(tert-butylmethylphosphino)benzene; (acetylacetonato)dicarbonylrhodium (l); hydrogen; In dodecane; at 100 ℃; under 7500.75 Torr; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ja2092689

upstream raw materials:

quinoline

2-bromo-2-ethyl-2-methyl acetic acid ethyl ester

Tiglic acid

ethanol

Downstream raw materials:

4-(2-Isocyano-phenyl)-2,3-dimethyl-butyric acid ethyl ester

ethyl 2-methylbutyrate

ethyl (Z)-2-methyl-2-butenoate

ethyl 2-methylenebutyrate