5-Norbornene-2,3-dicarboxylic anhydride

Base Information

• Chemical Name: 5-Norbornene-2,3-dicarboxylic anhydride
• CAS No.: 2746-19-2
• Deprecated CAS: 66075-60-3
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• Hs Code.: 29189900
• European Community (EC) Number: 212-557-9,204-957-7
• NSC Number: 110659,102277,3999
• DSSTox Substance ID: DTXSID0047456
• Nikkaji Number: J41.836F
• Wikipedia: Nadic_anhydride
• Metabolomics Workbench ID: 129944
• ChEMBL ID: CHEMBL268522
• Mol file: 2746-19-2.mol

Synonyms:himic anhydride

Chemical Property of 5-Norbornene-2,3-dicarboxylic anhydride

Chemical Property:

• Appearance/Colour: Off-white to tan solid
• Vapor Pressure: 0.00016mmHg at 25°C
• Melting Point: 140-145 °C(lit.)
• Refractive Index: 1.583
• Boiling Point: 331.056 °C at 760 mmHg
• Flash Point: 163.801 °C
• PSA: 43.37000
• Density: 1.406 g/cm³
• LogP: 0.50810
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 164.047344113
• Heavy Atom Count: 12
• Complexity: 277

Purity/Quality:

99% ^*data from raw suppliers

cis-Norbornene-exo-2,3-dicarboxylicAnhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 37/38-41-42/43
• Safety Statements: 26-36-37/39-24-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Acid Anhydrides, Cyclic
• Canonical SMILES: C1C2C=CC1C3C2C(=O)OC3=O
• Uses: cis-5-Norbornene-exo-2,3-dicarboxylic anhydride is used as an organic chemical synthesis intermediate.

Technology Process of 5-Norbornene-2,3-dicarboxylic anhydride

There total 20 articles about 5-Norbornene-2,3-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: 100.0%

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (2746-19-2)

Guidance literature:

at 180 ℃; for 24h;

DOI:10.1021/acs.orglett.6b00537

Reference yield: 93.0%

maleic anhydride (108-31-6) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (2746-19-2)

Guidance literature:

With C₂₇H₃₁ClCuF₆N₂O₈S₂; In dichloromethane; at -5 - 20 ℃; for 2h; stereoselective reaction; Inert atmosphere;

Reference yield: 92.0%

hepta-1,6-dien-3-yl 2,2,2-trichloroacetate (873296-28-7) + maleic anhydride (108-31-6) → (1R,2R,6S,7S)-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (2746-19-2)

Guidance literature:

hepta-1,6-dien-3-yl 2,2,2-trichloroacetate; With copper(l) chloride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In chloroform-d1; at 20 ℃; for 2h;

maleic anhydride; In chloroform-d1; for 3h; Heating;

DOI:10.1016/j.tetlet.2005.12.018

upstream raw materials:

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

5,6-dibromobicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

maleic anhydride

cyclopenta-1,3-diene

Downstream raw materials:

bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid monomethyl ester

(+/-)-5exo-p-tolylmercapto-norbornane-2exo,3exo-dicarboxylic acid-anhydride

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

exo-bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride

Refernces

• 1、 Welch, Christopher J.,Gong, Xiaoyi,Cuff, James,Dolman, Sarah,Nyrop, Jason,Lin, Fiona,Rogers, Hallena. "Online analysis of flowing streams using microflow HPLC". . p. 1022 - 1025. Retrieved 2009.
• 2、 -. "Preparation method of exo-Dickson anhydride". Paragraph 0017-0018; 0038-0041; 0044-0045. . Retrieved 2021/10/16.
• 3、 Li, Fanfan,Wang, Xuan,Zhang, Yanwu,Zhao, Huanhuan. "ROMP polymer supported manganese porphyrins: Influence of C[dbnd]C bonds along polymer chains on catalytic behavior in oxidation of low concentration Fe2+". . . Retrieved 2020/02/22.