1-CYCLOPENTENE-1,2-DICARBOXYLIC ANHYDRIDE

Base Information

• Chemical Name: 1-CYCLOPENTENE-1,2-DICARBOXYLIC ANHYDRIDE
• CAS No.: 3205-94-5
• Molecular Formula: C7H6 O3
• Molecular Weight: 138.123
• Hs Code.: 2932999099
• Mol file: 3205-94-5.mol

Synonyms:1-Cyclopentene-1,2-dicarboxylicanhydride (7CI,8CI); 5,6-Dihydro-4H-cyclopenta[c]furan-1,3-dione;Cyclopentene-1,2-dicarboxylic acid anhydride; NSC 291644

Chemical Property of 1-CYCLOPENTENE-1,2-DICARBOXYLIC ANHYDRIDE

Chemical Property:

• Vapor Pressure: 0.00758mmHg at 25°C
• Melting Point: 42-45 °C(lit.)
• Refractive Index: n20/D 1.4978(lit.)
• Boiling Point: 133-135 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 43.37000
• Density: 1.37g/cm³
• LogP: 0.55030
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

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

1-Cyclopentene-1,2-dicarboxylic anhydride 96% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Valuable Diels-Alder dienophile, for example, in approach to the bicycloundecane system in taxanes.

Technology Process of 1-CYCLOPENTENE-1,2-DICARBOXYLIC ANHYDRIDE

There total 8 articles about 1-CYCLOPENTENE-1,2-DICARBOXYLIC ANHYDRIDE 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: 47.0%

methyl 2-(trifluoromethylsulfonyloxy)cyclopent-1-enecarboxylate (65832-21-5) + sodium formate (141-53-7) → 1-cyclopentene-1,2-dicarboxylic anhydride (3205-94-5)

Guidance literature:

With palladium diacetate; acetic anhydride; diisopropylamine; lithium chloride; In N,N-dimethyl-formamide; at 5 - 20 ℃; for 24h; Molecular sieve; Inert atmosphere; Cooling with ice;

Reference yield:

methyl 2-(trifluoromethylsulfonyloxy)cyclopent-1-enecarboxylate (65832-21-5) + acetic anhydride (108-24-7) → 1-cyclopentene-1,2-dicarboxylic anhydride (3205-94-5)

Guidance literature:

With lithium chloride; sodium formate; palladium diacetate; diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h; Inert atmosphere; Molecular sieve;

DOI:10.1002/anie.201410115

Reference yield:

methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0) → 1-cyclopentene-1,2-dicarboxylic anhydride (3205-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dichloromethane / 0.25 h / -78 °C

1.2: 0.5 h / -78 - 20 °C

2.1: lithium chloride; diisopropylamine; acetic anhydride; palladium diacetate / N,N-dimethyl-formamide / 24 h / 5 - 20 °C / Molecular sieve; Inert atmosphere; Cooling with ice

With palladium diacetate; acetic anhydride; diisopropylamine; lithium chloride; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

cyclopent-1-ene-1,2-dicarboxylic acid

heptanedioic acid

diethyl pimelate

diethyl 2,6-dibromoheptanedioate

Downstream raw materials:

4,7-dimethyl-8-oxo-5,6-diphenyl-4,7-dihydro-4,7-methano-indane-3ar,7ac-dicarboxylic acid-anhydride

4,7-diethyl-8-oxo-5,6-diphenyl-4,7-dihydro-4,7-methano-indane-3ar,7ac-dicarboxylic acid-anhydride

5,6-bis-(4-methoxy-phenyl)-8-oxo-4,7-diphenyl-4,7-dihydro-4,7-methano-indane-3a,7a-dicarboxylic acid-anhydride

5,6-bis-benzo[1,3]dioxol-5-yl-4,7-diphenyl-indan-3a,7a-dicarboxylic acid-anhydride

Refernces

• 1、 Ralph, Michael J.,Harrowven, David C.,Gaulier, Steven,Ng, Sean,Booker-Milburn, Kevin I.. "The profound effect of the ring size in the electrocyclic opening of cyclobutene-fused bicyclic systems". supporting information. p. 1527 - 1531. Retrieved 2015/01/30.