6053-68-5

Usage

Chemical Properties

White to light yellow solid

InChI:InChI=1/C9H6O6/c10-6-2-1-3-5(4(2)8(12)14-6)9(13)15-7(3)11/h2-5H,1H2/t2-,3+,4-,5+

Synthetic route

cyclopentane-1,2,3,4-tetracarboxylic acid (3724-52-5) → 1,2,3,4-cyclopentanetetracarboxylic acid dianhydride (6053-68-5)

Conditions	Yield
With acetic anhydride In tetrahydrofuran at 80℃; for 0.5h; Solvent; Temperature; Inert atmosphere;	91.2%

5-norbornene-2,3-dicarboxylic anhydride (826-62-0, 85081-15-8, 85081-16-9) → 1,2,3,4-cyclopentanetetracarboxylic acid dianhydride (6053-68-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: water; acetic acid; ozone / 6 h / 0 °C 2: dihydrogen peroxide / 80 °C 3: acetic anhydride / tetrahydrofuran / 0.5 h / 80 °C / Inert atmosphere View Scheme

1,2,3,4-cyclopentanetetracarboxylic acid dianhydride (6053-68-5) → tetrahydro-cyclopenta[1,2-c;3,4-c']dipyrrole-1,3,4,6-tetraone (22031-22-7, 59121-36-7, 15774-55-7)

Conditions	Yield
With ammonium hydroxide 2.) from 200 to 300 deg C; Multistep reaction;

N1-(4-(9H-carbazol-9-yl)phenyl)-N1-(4-aminophenyl)benzene-1,4-diamine (896452-75-8) + 1,2,3,4-cyclopentanetetracarboxylic acid dianhydride (6053-68-5) → Polymer; Monomer(s): 4,4\-diamino-4\'\-N-carbazolyltriphenylamine; 1,2,3,4-cyclopentanetetracarboxylic dianhydride

Conditions	Yield
In N,N-dimethyl acetamide at 20℃; for 12h;

n-Pent-4-enyl alcohol (821-09-0) + 1,2,3,4-cyclopentanetetracarboxylic acid dianhydride (6053-68-5) → tetra(4-pentenyl)-1,2,3,4-cyclopentanetetracarboxylic acid ester

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 2.5h; Dean-Stark; Reflux;	24 g

n-Pent-4-enyl alcohol (821-09-0) + 1,2,3,4-cyclopentanetetracarboxylic acid dianhydride (6053-68-5) → tetra(4,5-epoxypentyl)-1,2,3,4-cyclopentanetetracarboxylic acid ester

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 2.5 h / Dean-Stark; Reflux 2: 3-chloro-benzenecarboperoxoic acid / chloroform / 20 h / 0 - 20 °C View Scheme

1,2,3,4-cyclopentanetetracarboxylic acid dianhydride (6053-68-5) + 2,2'-bis(trifluoromethyl)benzidine (341-58-2) → 2,5-bis(2,2'-bis(trifluoromethyl)-4'-amino-1,1'-biphenyl-4-yl)hexahydrobenzo[1,2-c:4,5-c']dipyrrole-1,3,5,7(2H,6H)-tetrone

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one at 150 - 180℃; Inert atmosphere;	3 g

Upstream product

• 15102-22-4 (+/-)-cyclopentane-1r,2c,3t,4c-tetracarboxylic acid-1,2-anhydride 
• 3724-52-5 cyclopentane-1,2,3,4-tetracarboxylic acid 
• 826-62-0 5-norbornene-2,3-dicarboxylic anhydride 
• 3724-52-5 (+/-)-cyclopentane-1r,2c,3t,4c-tetracarboxylic acid 
• 3724-52-5 cis,cis,cis,cis-cyclopentane-1,2,3,4-tetracarboxylic acid 

Downstream Products

• 3724-52-5 cis,cis,cis,cis-cyclopentane-1,2,3,4-tetracarboxylic acid 

Relevant academic research and scientific papers

A 1, 2, 3, 4 - cyclopentane tetracarboxylic dianhydride of the preparation method (by machine translation)

The invention discloses a 1, 2, 3, 4 - cyclopentane tetracarboxylic dianhydride of the preparation method, the invention belongs to the field of fine chemicals preparation method. The main technical proposal is to maleic anhydride and the cyclopentadiene as the starting material, the low temperature by 1, 4 - addition reaction intermediate of synthesis of 5 - norbornene - 2, 3 - dicarboxylic acid anhydride; through the ozone oxidation, hydrolysis, hydrogen peroxide oxidation reaction to obtain the cyclopentane tetracarboxylic acid; finally to acetic anhydride as the dehydrating agent, the dehydration ring-closure of the synthesized target product 1, 2, 3, 4 - cyclopentane tetracarboxylic dianhydride. The proposal to the traditional process, mild reaction conditions, the product has high purity, high yield, pollution-free and the like, and is suitable for large-scale industrial production. (by machine translation)

N-cyanoimides

Polyfunctional N-cyanoimides and their precursors and derivatives are disclosed along with methods for their preparation and interconversion. Also disclosed are curable compositions comprising the N-cyanoimides or poly(amide-cyanoamides) and reactive diluents as well as novel dianhydrides, polyimides, and poly(amide-cyanoamides) and methods for making them.