5-Norbornene-2,3-dicarboxylic anhydride

Base Information

• Chemical Name: 5-Norbornene-2,3-dicarboxylic anhydride
• CAS No.: 129-64-6
• Deprecated CAS: 66075-60-3
• Molecular Formula: C9H8O3
• Molecular Weight: 164.161
• Hs Code.: 29172090
• 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: 129-64-6.mol

Synonyms:himic anhydride

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

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 165-167 °C(lit.)
• Refractive Index: 1.4365
• Boiling Point: 331.1 °C at 760 mmHg
• Flash Point: 163.8 °C
• PSA: 43.37000
• Density: 1.405 g/cm³
• LogP: 0.50810
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: DECOMPOSES
• 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:

≧98% ^*data from raw suppliers

CarbicAnhydride ^*data from reagent suppliers

Safty Information:

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

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: Carbic Anhydride is an intermediate used to prepare Endo-2,3-Norbornanedicarboximide (N661225) which is used to prepare piperidinylbenzisoxazole antipsychotic drugs.

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

There total 33 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%

maleic anhydride (108-31-6) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6)

Guidance literature:

With 3-(n-butoxycarbonyl)-1-methylpyridinium bis(trifluoromethanesulfonyl)imide; at 20 ℃; for 0.166667h; diastereoselective reaction;

DOI:10.1039/b811814k

Reference yield: 87.0%

bicyclo<2.2.1>-5-hepten-2endo,3endo-dicarboxylic anhydride (129-64-6,826-62-0,2746-19-2,85081-15-8,85081-16-9) → 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:

With sodium hydroxide; In water; at 70 ℃; for 0.166667h; Product distribution / selectivity;

Reference yield: 85.0%

cis-5-norbornene-endo-2,3-carboxycylic acid disodium salt → 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:

cis-5-norbornene-endo-2,3-carboxycylic acid disodium salt; With hydrogenchloride; In water; at 5 - 70 ℃; for 3.16667h;

With acetic anhydride; at 5 - 70 ℃; for 3.16667h; Product distribution / selectivity;

upstream raw materials:

2-chloromaleic anhydride

endo-Dicyclopentadien

dichloromaleic acid anhydride

norbornene-5,6-dicarboxylic acid

Downstream raw materials:

2-(3-morpholino-propyl)-(3ac,7ac)-3a,4,7,7a-tetrahydro-4r,7c-methano-isoindole-1,3-dione

endo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic dimethyl ester

endo-3-methoxycarbonyl-2,6-norbornanecarbolactone

(+/-)-2-(2-ethyl-hexyl)-(3ac,7ac)-3a,4,7,7a-tetrahydro-4r,7c-methano-isoindole-1,3-dione

Refernces

• 1、 Grieger,Eckert. "". . p. 7149,7150, 7151. Retrieved 1970.
• 2、 Pavlovi?, Radoslav Z.,Border, Sarah E.,Gallucci, Judith,Badji?, Jovica D.. "Stereo- and regioselective halogenation of norbornenes directed by neighboring group participation". . p. 5584 - 5587. Retrieved 2016.
• 3、 Border, Sarah E.,Pavlovi?, Radoslav Z.,Zhiquan, Lei,Badji?, Jovica D.. "Removal of Nerve Agent Simulants from Water Using Light-Responsive Molecular Baskets". . p. 18496 - 18499. Retrieved 2017.
• 4、 Kocyigit, Umit M.,Aslan, Osman Nuri,Gulcin, Ilhami,Temel, Yusuf,Ceylan, Mustafa. "Synthesis and Carbonic Anhydrase Inhibition of Novel 2-(4-(Aryl)thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione Derivatives". . p. 955 - 963. Retrieved 2016.
• 5、 Tahir Gunkara, Omer. "Modification of polyhedral oligomeric silsesquioxane derivatives with heck reaction as possible new bio-hybrid materials". . p. 909 - 916. Retrieved 2019.
• 6、 Houk. "". . p. 361. Retrieved 1975.
• 7、 Hara,M. et al.. "-". . p. 95 - 100. Retrieved 1966.
• 8、 Lowe, Adam J.,Pfeffer, Frederick M.. "Size matters - Strong binding of the terephthalate dianion by thiourea functionalised fused [n]polynorbornane hosts". . p. 1871 - 1873. Retrieved 2008.
• 9、 Robson, Ryan N.,Pfeffer, Frederick M.. "Using steric bulk for selective recognition; Blocking the binding site to differentiate guests". . p. 8719 - 8721. Retrieved 2016.
• 10、 Berson,Mueller. "-". . p. 4940. Retrieved 1961.