Dimethyl 2,3-naphthalenedicarboxylate

Base Information

• Chemical Name: Dimethyl 2,3-naphthalenedicarboxylate
• CAS No.: 13728-34-2
• Molecular Formula: C14H12O4
• Molecular Weight: 244.247
• Hs Code.: 29173990
• DSSTox Substance ID: DTXSID20350791
• Nikkaji Number: J534.138H
• Wikidata: Q82126895
• Mol file: 13728-34-2.mol

Synonyms:dimethyl 2,3-naphthalenedicarboxylate

Chemical Property of Dimethyl 2,3-naphthalenedicarboxylate

Chemical Property:

• Vapor Pressure: 5.98E-05mmHg at 25°C
• Melting Point: 52-54 °C(lit.)
• Refractive Index: 1.594
• Boiling Point: 345.9 °C at 760 mmHg
• Flash Point: 170.8 °C
• PSA: 52.60000
• Density: 1.225 g/cm³
• LogP: 2.41300
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 244.07355886
• Heavy Atom Count: 18
• Complexity: 294

Purity/Quality:

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

Dimethyl2,3-Naphthalenedicarboxylate,97% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=CC=CC=C2C=C1C(=O)OC

Technology Process of Dimethyl 2,3-naphthalenedicarboxylate

There total 17 articles about Dimethyl 2,3-naphthalenedicarboxylate 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%

1,4-Dihydro-1,4-etheno-naphthalin-2,3-dicarbonsaeure (19981-73-8) → dimethyl 2,3-naphthalenedicarboxylate (13728-34-2)

Guidance literature:

With 1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester; In toluene; at 110 ℃; for 1h; Sealed tube; Inert atmosphere;

DOI:10.1016/j.tet.2017.07.058

Reference yield: 93.0%

1,2,4,5-tetrazine-3,6-dicarboxylic acid dimethyl ester (2166-14-5) + 1,4-Dihydro-1,4-etheno-naphthalin-2,3-dicarbonsaeure (19981-73-8) → dimethyl 2,3-naphthalenedicarboxylate (13728-34-2) + pyridazine-3,6-dicarboxylic acid dimethyl ester (2166-24-7)

Guidance literature:

In toluene; at 110 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2017.07.058

Reference yield: 91.0%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) + o-phthalic dicarboxaldehyde (643-79-8) → dimethyl 2,3-naphthalenedicarboxylate (13728-34-2)

Guidance literature:

dimethyl cis-but-2-ene-1,4-dioate; With tributylphosphine; In dichloromethane; at 0 - 20 ℃;

o-phthalic dicarboxaldehyde; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 3h; Cooling with ice;

upstream raw materials:

methanol

naphthalene-2,3-dicarboxylic acid

1,4-Dihydro-naphthalene-2,3-dicarboxylic acid dimethyl ester

dimethyl 1-hydroxy-1,4-dihydronaphthalene-2,3-dicarboxylate

Downstream raw materials:

1H-cyclopenta[b]naphthalene-1,3(2H)-dione

Naphthalin-2,3-dicarbonsaeure-di-N-benzyl-amid

2-Phenylbenz<5,6>indan-1,3-dion

naphthalene-2,3-dicarboxylic acid

Refernces

• 1、 Butler,D.N.,Snow,R.A.. "-". . p. 256 - 262. Retrieved 1975.
• 2、 Craig, Donald,Robson, Michael J.,Shaw, Simon J.. "Traceless linkers for solid-phase synthesis. Homo- and hetero-Diels-Alder reactions of o-quinodimethanes". . p. 1381 - 1383. Retrieved 1998.
• 3、 -. "A 3 - amino -2 - naphthalene armor acid compound preparation process (by machine translation)". Paragraph 0030; 0031. . Retrieved 2019/06/27.
• 4、 Luo, Kui,Cao, Tongxiang,Jiang, Huanfeng,Chen, Lianfen,Zhu, Shifa. "Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium". supporting information. p. 5856 - 5859. Retrieved 2017/11/10.