2,4-Decadienoic acid, methyl ester, (2E,4E)-

Base Information

• Chemical Name: 2,4-Decadienoic acid, methyl ester, (2E,4E)-
• CAS No.: 4493-42-9
• Molecular Formula: C11H18 O2
• Molecular Weight: 182.263
• Hs Code.: 2916190090
• European Community (EC) Number: 224-787-7,230-815-9
• UNII: OX7820P9JJ
• DSSTox Substance ID: DTXSID30884370
• Nikkaji Number: J81.367B,J114.260G,J80.846F
• Wikidata: Q27285901
• Metabolomics Workbench ID: 4123
• Mol file: 4493-42-9.mol

Synonyms:2,4-Decadienoic acid methyl ester;4493-42-9;7328-33-8;2,4-Decadienoic acid, methyl ester, (2E,4E)-;Methyl (2E,4E)-2,4-decadienoate;methyl (2E,4E)-deca-2,4-dienoate;Methyl 2,4-decadienoate, (2E,4E)-;2,4-Decadienoic acid, methyl ester, (E,E)-;UNII-OX7820P9JJ;Methyl 2,4-decadienoate;OX7820P9JJ;(2E,4E)-2,4-Decadienoic acid methyl ester;Methyl E, 4-2,4-Decadienoate;EINECS 230-815-9;2,4-Decadienoic acid,methyl ester, (2E,4E)-;2,4-Decadienoic acid,methyl ester, (2E,4Z)-;WE(1:0/10:2(2E,4E));formyl 2E,4E-decadienoate;methyl (2E,4Z)-deca-2,4-dienoate;methyl decadienoate;METHYL(E)-2-(Z)-4-DECADIENOATE;2,4-DECADIENOICACIDMETHYLESTER;(2E,4Z)-2,4-Decadienoic Acid Methyl Ester;2,4-Decadienoic acid, methyl ester, (E,Z )-;Methyl 2E,4E-decadienoate;SCHEMBL1532447;DTXSID30884370;SFHSEXGIVSBRRK-XBLVEGMJSA-N;(2E,4E)-methyl 2,4-decadienoate;LMFA07010478;(2E,4E)-methyl deca-2,4-dienoate;Methyl 2,4-Decadienoate CAS 4493-42-9;Q27285901;53172-59-1

Chemical Property of 2,4-Decadienoic acid, methyl ester, (2E,4E)-

Chemical Property:

• Vapor Pressure: 0.0278mmHg at 25°C
• Refractive Index: 1.459
• Boiling Point: 246 °C at 760 mmHg
• Flash Point: 108.1 °C
• PSA: 26.30000
• Density: 0.907 g/cm³
• LogP: 2.85210
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 182.130679813
• Heavy Atom Count: 13
• Complexity: 181

Purity/Quality:

99%, ^*data from raw suppliers

(2E,4Z)-2,4-DecadienoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CC=CC(=O)OC
• Isomeric SMILES: CCCCC/C=C/C=C/C(=O)OC
• Uses: (2E,4Z)-2,4-Decadienoic Acid Methyl Ester is used in the syntheses of Methyl (R,E)-2,4,5-tetradecatrienoate and Methyl (2E,4Z)-2,4-decadienoate, the pheromone components of the male dried bean beetle, Acanthoscelides obtectus (Say).

Technology Process of 2,4-Decadienoic acid, methyl ester, (2E,4E)-

There total 26 articles about 2,4-Decadienoic acid, methyl ester, (2E,4E)- 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: 78.0%

n-pentylmagnesium bromide (693-25-4) + methyl (2E,4Z)-5-chloropenta-2,4-dienoate (38666-08-9) → methyl (2E,4Z)-deca-2,4-dienoate (4493-42-9)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1134/S1070363217070325

Reference yield: 69.0%

1-Heptyne (628-71-7) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl (2E,4Z)-deca-2,4-dienoate (4493-42-9)

Guidance literature:

With carbonylchlorohydridotris(triphenylphosphine)ruthenium (II); In N,N-dimethyl-formamide; at 100 ℃; for 24h; optical yield given as %de; regioselective reaction; Inert atmosphere;

Reference yield:

methyl (E)-dec-2-en-4-ynoate (118793-68-3,94133-53-6) → methyl (2E,4Z)-deca-2,4-dienoate (4493-42-9) + methyl (2E,4E)-decadienoate (7328-33-8)

Guidance literature:

methyl (E)-dec-2-en-4-ynoate; With dimethylsulfide borane complex; cyclohexene; In tetrahydrofuran; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; at 50 ℃; for 2.33333h; Inert atmosphere;

DOI:10.1016/j.tet.2011.12.064

upstream raw materials:

methyl (E)-dec-2-en-4-ynoate

methyl (2E,4E)-decadienoate

methyl deca-(2Z)-en-4-ynoate

methyl 4-(diethylphosphono)crotonate

Downstream raw materials:

(2E,4Z)-decadienoic acid

deca-2E,4Z-dienoic acid isobutylamide

Refernces

• 1、 Wen, Zhen-Kang,Xu, Yun-He,Loh, Teck-Peng. "Palladium(ii)-catalyzed cross-coupling of simple alkenes with acrylates: A direct approach to 1,3-dienes through C-H activation". . p. 4520 - 4524. Retrieved 2013/11/19.
• 2、 Neisius, N. Matthias,Plietker, Bernd. "The ruthenium-catalyzed hydrovinylation of internal alkynes by acrylates: An atom economic approach to highly substituted 1,3-dienes". supporting information; experimental part. p. 5752 - 5755. Retrieved 2009/12/06.