Dimalone

Base Information

• Chemical Name: Dimalone
• CAS No.: 39589-98-5
• Molecular Formula: C11H14O4
• Molecular Weight: 210.23
• Hs Code.: 2917209090
• NSC Number: 196235,46419
• Nikkaji Number: J3.373.817J
• Mol file: 39589-98-5.mol

Synonyms:DIMALONE;NISY;Compound 3916;Dimethyl-5-norbornene-2,3-dicarboxylate;Dimelone;Compound 3,916;5-Norbornene-2, dimethyl ester, cis-endo-;Dimethyl bicyclo[2.2.1]-5-heptene-2,3-dicarboxylate;Bicyclo[2.2.1]hept-5-ene-2, dimethyl ester, (endo,endo)-;NSC-46419;NSC-196235;Dimethyl 5-bicyclo(2.2.1)hepten-2,3-dicarboxylate;SCHEMBL7197213;VGQLNJWOULYVFV-WZENYGAOSA-N;NSC46419;NSC196235;5-Norbornene-2,3-dicarboxylic acid dimethyl ester;5-Norbornene-2,3-dicarboxylic acid, dimethyl ester;Dimethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate #;Bicyclo(2.2.1)hept-5-ene-2,3-dicarboxylic acid dimethyl ester;3,6-Endomethylene-.DELTA.4-tetrahydrophthalic acid dimethylester;Bicyclo(2,2,1)hept-5-ene-2,3-dicarboxylic acid, dimethyl ester;Bicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid, dimethyl ester

Chemical Property of Dimalone

Chemical Property:

• Vapor Pressure: 0.00295mmHg at 25°C
• Melting Point: 38° when very pure
• Refractive Index: nD20 1.4852
• Boiling Point: 284.6°Cat760mmHg
• Flash Point: 137.5°C
• PSA: 52.60000
• Density: 1.21g/cm³
• LogP: 0.77070
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 210.08920892
• Heavy Atom Count: 15
• Complexity: 291

Purity/Quality:

99% ^*data from raw suppliers

DIMETHYL CARBATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C2CC(C1C(=O)OC)C=C2
• Isomeric SMILES: COC(=O)[C@@H]1[C@@H](C2CC1C=C2)C(=O)OC

Technology Process of Dimalone

There total 44 articles about Dimalone 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: 99.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + dimethylfumarate (624-49-7) → dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1)

Guidance literature:

Reference yield: 98.0%

bi(cyclopentadiene) (77-73-6,933-60-8,1755-01-7,25038-78-2) + dimethylfumarate (624-49-7) → dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1)

Guidance literature:

With hydroquinone; at 150 ℃; for 2h; Microwave irradiation;

DOI:10.1039/c5ob00621j

Reference yield: 94.0%

methanol (67-56-1) + 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → dimethyl 5-cis-norbornene-2,3-dicarboxylate (3014-58-2,5826-73-3,7184-07-8,39589-98-5,116404-47-8,117604-28-1,135357-64-1)

Guidance literature:

With hydrogenchloride; In water; at 65 ℃; for 4h; Inert atmosphere;

upstream raw materials:

cyclopenta-1,3-diene

dimethylfumarate

dimethyl cis-but-2-ene-1,4-dioate

methanol

Downstream raw materials:

(2R,3R)-dimethyl bicyclo[2.2.1]heptane-2,3-dicarboxylate

dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol

3-phenyl-(3at,7at)-3a,4,5,6,7,7a-hexahydro-4r,7c-methano-benzo[d]isothiazole-5t,6t-dicarboxylic acid dimethyl ester

Refernces

• 1、 Rajsfus, David E.,Alter-Zilberfarb, Sari,Frimer, Aryeh A.. "The synthesis of fluorinated endcaps: Part 1. the effect of C-7 fluorination on the base-catalyzed monohydrolysis of 5-norbornenyl-2,3-diesters". . p. 49 - 58. Retrieved 2013.
• 2、 Boobalan, Ramalingam,Chein, Rong-Jie. "Oxathiaborolium-Catalyzed Enantioselective [4 + 2] Cycloaddition and Its Application in Lewis Acid Coordinated and Chiral Lewis Acid Catalyzed [4 + 2] Cycloaddition". . p. 6760 - 6764. Retrieved 2021/09/11.
• 3、 Wang, Yaxin,Hu, Xiafei,Morales-Rivera, Cristian A.,Li, Guo-Xing,Huang, Xin,He, Gang,Liu, Peng,Chen, Gong. "Epimerization of Tertiary Carbon Centers via Reversible Radical Cleavage of Unactivated C(sp3)-H Bonds". supporting information. p. 9678 - 9684. Retrieved 2018/07/21.