Methyl oct-2-enoate

Base Information

• Chemical Name: Methyl oct-2-enoate
• CAS No.: 7367-81-9
• Molecular Formula: C9H16O2
• Molecular Weight: 156.225
• European Community (EC) Number: 219-259-8,230-912-6
• NSC Number: 617617
• UNII: 9EN9V40J78
• DSSTox Substance ID: DTXSID00223919
• Nikkaji Number: J126.498B,J45.116I
• Wikidata: Q27272448
• RXCUI: 2585678
• Metabolomics Workbench ID: 45503
• ChEMBL ID: CHEMBL4076957
• Mol file: 7367-81-9.mol

Synonyms:Methyl trans-2-octenoate;Methyl oct-2-enoate;7367-81-9;Methyl (E)-oct-2-enoate;METHYL 2-OCTENOATE;2396-85-2;2-Octenoic acid, methyl ester;2-Octenoic acid, methyl ester, (2E)-;Methyl (E)-2-octenoate;trans-2-Octenoic Acid Methyl Ester;Methyl 2-octenoate, (E)-;2-Octenoic acid methyl ester;(E)-2-Methyl oct-2-enoate;2-Octenoic acid, methyl ester, (E)-;FEMA No. 3712;(E)-methyl oct-2-enoate;UNII-9EN9V40J78;methyl 2-octenoate (High Trans);9EN9V40J78;EINECS 219-259-8;EINECS 230-912-6;2-Octenoic acid, methyl ester, (Z)-;Methyl trans-2-octenoate, 90+%, remainder mainly cis-isomer;Methyloctenoat;(E)-methyl 2-octenoate;trans-Methyl-2-octenoate;METHYLTRANS-2-OCTENOATE;SCHEMBL1404267;CHEMBL4076957;DTXSID00223919;CHEBI:171779;CJBQSBZJDJHMLF-BQYQJAHWSA-N;(E)-2-Octenoic acid methyl ester;METHYL 2-OCTENOATE, TRANS-;LMFA07010944;MFCD00036620;NSC617617;METHYL 2-OCTENOATE, (2E)-;AKOS015836245;2-Octenoic acid, methylester, (2E)-;HY-W039379;NSC-617617;METHYL TRANS-2-OCTENOATE [FHFI];Methyl trans-2-octenoate, >=96%, FG;BS-49141;CS-0097187;M2014;Q27272448

Chemical Property of Methyl oct-2-enoate

Chemical Property:

• Appearance/Colour: COLORLESS LIQUID
• Refractive Index: n20/D 1.442(lit.)
• Boiling Point: 194.6 °C at 760 mmHg
• Flash Point: 82.8 °C
• PSA: 26.30000
• Density: 0.896 g/cm³
• LogP: 2.29590
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 156.115029749
• Heavy Atom Count: 11
• Complexity: 128

Purity/Quality:

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

Methyl trans-2-Octenoate >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/38:Irritating to eyes and skin.
• Hazard Codes: R36/38:Irritating to eyes and skin.
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CC(=O)OC
• Isomeric SMILES: CCCCC/C=C/C(=O)OC
• Description: Methyl trans-2-octenoate has a fruity green odor.

Technology Process of Methyl oct-2-enoate

There total 69 articles about Methyl oct-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: 93.0%

methyl 2-octynoate (111-12-6,53073-28-2) → methyl (E)-oct-2-enoate (7367-81-9)

Guidance literature:

methyl 2-octynoate; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,4-di(diphenylphosphino)-butane; In 1,4-dioxane; water; at 20 ℃; for 0.25h; Inert atmosphere;

With formic acid; In 1,4-dioxane; at 80 ℃; for 10h; optical yield given as %ee; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja2069246

Reference yield: 92.0%

methyl (2Z)-3-iodooct-2-enoate (160729-74-8) → methyl (E)-oct-2-enoate (7367-81-9)

Guidance literature:

methyl (2Z)-3-iodooct-2-enoate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; at -78 ℃; for 0.5h;

With water; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; at 20 ℃; for 0.5h; Further stages.;

DOI:10.1016/j.enconman.2005.12.005

Reference yield: 86.0%

((1R,2S)-1-Methoxy-2-pentyl-cyclopropoxy)-trimethyl-silane → methyl (E)-oct-2-enoate (7367-81-9) + (E)-methyl oct-3-enoate (35234-16-3) + 2,3-dichloro-5,6-dicyanohydroquinone (4640-41-9) + methyl (Z)-oct-3-enoate (69668-85-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In acetonitrile; at 60 ℃; for 20h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)73235-7

upstream raw materials:

diazomethane

(E)-oct-2-enoic acid

1,1-dimethoxyethylene

hexanal

Downstream raw materials:

Methyl 3-phthalimidooctanoate

(E)-1-bromo-oct-2-ene

(7E)-tetradec-7-en-1-ol

E-7-tetradecen-1-yl acetate

Refernces

• 1、 Davies, Huw M. L.,Hatridge, Taylor A.,Jones, Christopher W.,Liu, Wenbin,Yoo, Chun-Jae. "Optimized Immobilization Strategy for Dirhodium(II) Carboxylate Catalysts for C?H Functionalization and Their Implementation in a Packed Bed Flow Reactor". supporting information. p. 19525 - 19531. Retrieved 2020/07/13.
• 2、 Hernán-Gómez, Alberto,Rodríguez, Mònica,Parella, Teodor,Costas, Miquel. "Electrophilic Iron Catalyst Paired with a Lithium Cation Enables Selective Functionalization of Non-Activated Aliphatic C?H Bonds via Metallocarbene Intermediates". supporting information. p. 13904 - 13911. Retrieved 2019/08/30.