Dimethyl trans,trans-muconate

Base Information

• Chemical Name: Dimethyl trans,trans-muconate
• CAS No.: 1119-43-3
• Molecular Formula: C8H10 O4
• Molecular Weight: 170.165
• Hs Code.: 2917190090
• European Community (EC) Number: 651-442-1,825-707-9
• NSC Number: 167514
• UNII: E2B8XTM21E
• Nikkaji Number: J123.472B,J123.503F,J125.857E,J47.049J
• Wikidata: Q27276777
• Mol file: 1119-43-3.mol

Synonyms:1119-43-3;Dimethyl trans,trans-muconate;dimethyl (2E,4E)-hexa-2,4-dienedioate;Dimethyl muconate, (E,E)-;Dimethyl (E,E)-2,4-hexadienoate;trans,trans-Dimethyl muconate;NSC-167514;(1E,3E)-1,3-Butadiene-1,4-dicarboxylic acid dimethyl ester;(2E,4E)-muconic acid dimethyl ester;UNII-E2B8XTM21E;E2B8XTM21E;Muconic acid (E,E)-form dimethyl ester [MI];2,4-Hexadienedioic acid, dimethyl ester,;1,6-DIMETHYL (2E,4E)-HEXA-2,4-DIENEDIOATE;2,4-Hexadienedioic acid, 1,6-dimethyl ester, (2E,4E)-;Dimethyl (E,Z)-muconate;2,4-Hexadienedioic acid, dimethyl ester, (E,Z)-;dimethyl trans-muconate;starbld0008151;(E,E)-dimethyl muconate;dimethyl trans-transmuconate;trans,trans dimethyl muconate;(E,E)-Muconic acid dimethyl;(Z,Z)-Muconic acid dimethyl;SCHEMBL821014;2, dimethyl ester, (E,E)-;2,4-Hexadienedioic acid dimethyl;BAA11943;1,6-dimethyl hexa-2,4-dienedioate;NSC167514;Dimethyl (E,Z)-2,4-hexadienedioate;trans,trans-muconic acid dimethyl ester;DIMETHYL 2,4-HEXADIENE-1,6-DIOATE;2,4-HEXADIENEDIOIC ACID DIMETHYL ESTER;EN300-1700269;EN300-2010616;(2E,4Z)-2,4-Hexadienedioic acid dimethyl ester;Q27276777

Chemical Property of Dimethyl trans,trans-muconate

Chemical Property:

• Vapor Pressure: 0.0212mmHg at 25°C
• Melting Point: 157-158℃
• Boiling Point: 251℃
• Flash Point: 122℃
• PSA: 52.60000
• Density: 1.099
• LogP: 0.44480
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 170.05790880
• Heavy Atom Count: 12
• Complexity: 191

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Dimethyl trans,trans-muconate

There total 11 articles about Dimethyl trans,trans-muconate 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: 91.0%

(E)-methyl 3-iodoacrylate (6213-88-3) + (3aR,4S,5S,6aS)-5-[(1E,6S)-6-{[tert-butyl(diphenyl)silyl]oxy}hept-1-en-1-yl]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxole-4-carbaldehyde (1272414-21-7) → (E,E)-hexa-2,4-dienedioic acid dimethyl ester (1119-43-3) + methyl (2E)-4-{(3aR,4R,5S,6aS)-5-[(1E,6S)-6-{[tert-butyl(diphenyl)silyl]oxy}hept-1-en-1-yl]-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}-4-hydroxybut-2-enoate (1272414-22-8)

Guidance literature:

With chromium dichloride; nickel dichloride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1002/ejoc.201001297

Reference yield: 3.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + acetylene (74-86-2,25067-58-7) → cis,cis-dimethyl muconate (692-91-1,692-92-2,1119-43-3,1733-37-5) + dimethyl cis-but-2-ene-1,4-dioate (624-48-6) + dimethylfumarate (624-49-7)

Guidance literature:

PdI₂-KI; at 60 ℃; for 15h; under 19000 Torr;

Reference yield:

dimethyl galactarate (24808-45-5,911479-56-6) → hexanedioic acid dimethyl ester (627-93-0) + (E,E)-hexa-2,4-dienedioic acid dimethyl ester (1119-43-3)

Guidance literature:

With hydrogen; methyltrioxorhenium(VII); at 120 ℃; for 72h; under 3750.38 Torr; Autoclave;

DOI:10.1002/anie.202010035

upstream raw materials:

methanol

carbon monoxide

acetylene

methyl (2Z)-3-iodoprop-2-enoate

Downstream raw materials:

tetramethyl 5-cyclohexene-1,2,3,4-tetracarboxylate

Methyl-N-cyclohexyl-4-keto-adipamat

N,N'-Dicyclohexyl-3-keto-adipamid

1,4-benzenedicarboxylic acid dimethyl ester

Refernces

• 1、 She, Xiaoyan,Brown, Heather M.,Zhang, Xiao,Ahring, Birgitte K.,Wang, Yong. "Selective hydrogenation of trans,trans-muconic acid to adipic acid over a titania-supported rhenium catalyst". . p. 1071 - 1073. Retrieved 2011.
• 2、 Batsanov, Andrei S.,Knowles, Jonathan P.,Samsam, Benedict,Whiting, Andrew. "A stereoselective palladium-mediated reductive coupling of electron-deficient terminal iodoalkenes". supporting information; experimental part. p. 227 - 233. Retrieved 2009/04/11.