acenaphthene-5,6-dicarboxic acid

Base Information

• Chemical Name: acenaphthene-5,6-dicarboxic acid
• CAS No.: 5698-99-7
• Molecular Formula: C14H10 O4
• Molecular Weight: 242.231
• European Community (EC) Number: 227-178-4
• NSC Number: 109931
• UNII: P379ZHZ4LC
• DSSTox Substance ID: DTXSID70205585
• Nikkaji Number: J225.100K
• Wikidata: Q83079197
• Mol file: 5698-99-7.mol

Synonyms:5,6-Acenaphthenedicarboxylicacid (6CI,8CI); Acenaphthalic acid; NSC 109931

Chemical Property of acenaphthene-5,6-dicarboxic acid

Chemical Property:

• Vapor Pressure: 3.75E-12mmHg at 25°C
• Boiling Point: 532.1°C at 760 mmHg
• Flash Point: 289.7°C
• PSA: 74.60000
• Density: 1.514g/cm³
• LogP: 2.33480
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 242.05790880
• Heavy Atom Count: 18
• Complexity: 344

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=CC=C(C3=C(C=CC1=C23)C(=O)O)C(=O)O

Technology Process of acenaphthene-5,6-dicarboxic acid

There total 9 articles about acenaphthene-5,6-dicarboxic acid 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:

acenaphthene (83-32-9) → 5,6-acenaphthenedicarboxylic acid (5698-99-7)

Guidance literature:

Multi-step reaction with 2 steps

1: AlCl₃ / chlorobenzene

2: aq. HCl

With hydrogenchloride; aluminium trichloride; In chlorobenzene;

DOI:10.1021/ja00732a031

Reference yield:

carbon monoxide (201230-82-2) + 5,6-dichloroacenaphthene (4208-97-3) → 5,6-acenaphthenedicarboxylic acid (5698-99-7) + 6-Chlor-acenaphthen-carbonsaeure-(5) (6756-43-0)

Guidance literature:

With dicobalt octacarbonyl; potassium carbonate; methyloxirane; In methanol; at 60 ℃; for 4h; under 760 Torr; Title compound not separated from byproducts;

DOI:10.1007/s11167-005-0619-y

Reference yield:

carbon dioxide (124-38-9,18923-20-1) + 5,6-dibromoacenaphthene (19190-91-1) → 5,6-acenaphthenedicarboxylic acid (5698-99-7)

Guidance literature:

5,6-dibromoacenaphthene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; at -78 - 20 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1007/s11426-014-5282-9

upstream raw materials:

carbon dioxide

N⁵,N⁵,N⁶,N⁶-tetramethyl-1,2-dihydroacenaphthylene-5,6-dicarboxamide

acenaphthene

carbon monoxide

Downstream raw materials:

1,2-dihydro-6-oxacyclopentaphenalene-5,7-dione

naphthalene-1,4,5,8-tetracarboxylic acid

Acenaphthen-5,6-dicarbonsaeure-dimethylester

Refernces

• 1、 Barattin, Regis,Gourdon, Andre. "Synthesis of two complementary molecular moulds". supporting information; experimental part. p. 1022 - 1026. Retrieved 2009/07/19.
• 2、 Tanaka, Norio,Kasai, Toshiyasu. "Reactions of 5,6-Dilithioacenaphthene-N,N,N',N'-Tetramethyl-1,2-ethanediamine Complex with α-Diketones. I. cis-Directing 1:1 Cyclic Additions with Acyclic and Cyclic α-Diketones and Related Compounds". . p. 3020 - 3025. Retrieved 2007/10/02.