1-PHENYL-2 3-NAPHTHALENEDICARBOXYLIC

Base Information

• Chemical Name: 1-PHENYL-2 3-NAPHTHALENEDICARBOXYLIC
• CAS No.: 1985-37-1
• Molecular Formula: C18H10 O3
• Molecular Weight: 274.276
• Mol file: 1985-37-1.mol

Synonyms:2,3-Naphthalenedicarboxylicanhydride, 1-phenyl- (6CI,7CI,8CI);1-Phenyl-2,3-naphthalenedicarboxylicanhydride;NSC 17350;

Chemical Property of 1-PHENYL-2 3-NAPHTHALENEDICARBOXYLIC

Chemical Property:

• Vapor Pressure: 9.64E-10mmHg at 25°C
• Melting Point: 259-262 °C(lit.)
• Refractive Index: 1.7
• Boiling Point: 489.8°Cat760mmHg
• Flash Point: 246.7°C
• PSA: 43.37000
• Density: 1.358g/cm³
• LogP: 3.81740

Purity/Quality:

98/% ^*data from raw suppliers

1-Phenyl-2,3-naphthalenedicarboxylic anhydride ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-Phenyl-2,3-naphthalenedicarboxylic anhydride is a polyaromatic small molecule dye. Dyes and metabolites.

Technology Process of 1-PHENYL-2 3-NAPHTHALENEDICARBOXYLIC

There total 15 articles about 1-PHENYL-2 3-NAPHTHALENEDICARBOXYLIC 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: 100.0%

phenylpropyolic acid (637-44-5) → 4-phenylnaphtho[2,3-c]furan-1,3-dione (1985-37-1)

Guidance literature:

phenylpropyolic acid; With triethylamine; In dichloromethane; at 20 ℃; for 1.5h; Schlenk technique; Inert atmosphere;

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In dichloromethane; 1,2-dichloro-ethane; at 0 - 20 ℃; Temperature; Time; Reagent/catalyst; Schlenk technique; Inert atmosphere;

DOI:10.3762/bjoc.13.231

Reference yield: 73.0%

phenylpropiolic acid sodium salt (7063-23-2) + phenyl chloroformate (1885-14-9) → bis(phenyl) carbonate (102-09-0) + phenyl 3-phenylprop-2-ynoate (100954-03-8) + 4-phenylnaphtho[2,3-c]furan-1,3-dione (1985-37-1)

Guidance literature:

In tetrahydrofuran; at 40 - 67 ℃;

DOI:10.1002/1522-2675(20011219)84:12<3548::AID-HLCA3548>3.0.CO;2-2

Reference yield: 61.0%

(3E, 4E)-3,4-dibenzylidenedihydrofuran-2,5-dione (16269-23-1,53243-99-5,53244-00-1,53244-01-2) → 4-phenylnaphtho[2,3-c]furan-1,3-dione (1985-37-1)

Guidance literature:

With methanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; for 50h; Inert atmosphere; Reflux;

DOI:10.1002/adsc.201301169

upstream raw materials:

phenylpropiolyl chloride

phenylpropyolic acid

benzene

N-hydroxy-1-phenylnaphthalene-2,3-dicarboximide

Downstream raw materials:

4-phenyl-1H-benzo[f]isoindole-1,3(2H)-dione

ethyl 3-(1,3-dioxo-4-phenyl-1,3-dihydro-benzo[f]isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate

tetra-1-phenylnaphthalocyanine vanadyl complex

2,3-bis(hydroxymethyl)-1-phenylnaphthalene

Refernces

• 1、 Park, Jaerim,Kim, Ji Dang,Raja, Gabriel Charles Edwin,Choi, Hyun Chul,Lee, Sunwoo. "Room temperature cyclization of arylpropiolic acid anhydride: Synthesis of naphtho[2,3-c]furan-1,3-dione derivatives". supporting information. p. 1973 - 1979. Retrieved 2017/10/17.
• 2、 Kim, Ko Hoon,Lim, Cheol Hee,Lim, Jin Woo,Kim, Jae Nyoung. "2,3-Dichloro-5,6-dicyano-para-benzoquinone (DDQ)/methanesulfonic acid (MsOH)-mediated intramolecular arene-alkene oxidative coupling". supporting information. p. 697 - 704. Retrieved 2014/04/03.