Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS No.: 934-30-5
• Deprecated CAS: 193277-13-3,1404083-86-8
• Molecular Formula: C8H10O2
• Molecular Weight: 138.166
• Hs Code.: 2916209090
• European Community (EC) Number: 204-422-8,624-387-6
• NSC Number: 155661,152348
• DSSTox Substance ID: DTXSID80883313
• Nikkaji Number: J297.767B
• ChEMBL ID: CHEMBL276474
• Mol file: 934-30-5.mol

Synonyms:120-74-1;5-Norbornene-2-carboxylic acid;Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid;Norbornenecarboxylic acid;exo-5-Norbornene-2-carboxylic acid;5-Norbornene-2-carboxylic acid, exo-;NSC 155661;5-Norbornene-2-carboxylic acid (8CI);BRN 3196451;Bicyclo(2.2.1)hept-2-ene-5-carboxylic acid;Bicyclo[2.2.1]-5-heptene-2-carboxylic acid;Bicyclo[2.2.1]hept-2-ene-5-carboxylic acid;norborn-5-ene-2-carboxylic acid;EINECS 204-422-8;NSC 152348;AI3-51329;Bicyclo(2.2.1)hept-5-ene-2-carboxylic acid;4-09-00-00224 (Beilstein Handbook Reference);Bicyclo(2.2.1)hept-5-ene-2-carboxylic acid, exo-;Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, exo-;934-30-5;exo-Bicyclo(2.2.1)hept-5-ene-2-carboxylic acid;67999-53-5;exo-Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid;5-norbornene-carboxylic acid;SCHEMBL75505;5-norbomene-2-carboxylic acid;5-norbornen-2-carboxylic acid;2-norbornene-5-carboxylic acid;5-norbornene 2-carboxylic acid;CHEMBL276474;WLN: L55 A CUTJ FVQ;2-norborn-5-ene carboxylic acid;DTXSID80883313;MFCD00085356;NSC152348;NSC155661;5-Norbornene-2-carboxylic acid 97%;AKOS000120886;AKOS016311792;AKOS025243184;AC-4854;CS-W016495;NSC-152348;NSC-155661;SB45385;SB45624;BP-24389;LS-97175;5-bicyclo[2,2,1]heptene-2-carboxylic acid;AM20080145;BB 0216344;BB 0301297;Bicyclo[2.2.1]hept-5-ene-2-carboxylicacid;FT-0622951;FT-0678039;N0667;bicyclo[2,2,1]hept-5-ene-2-carboxylic acid;bicyclo[2.2.1]hept-2-ene-6-carboxylic acid;bicyclo[2.2.1]hept-5-ene-3-carboxylic acid;EN300-21280;A804582;J-802156;(1S,4S,5S)-bicyclo[2.2.1]hept-2-ene-5-carboxylate;F3095-4888;Z104495016

Chemical Property of Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Chemical Property:

• Melting Point: 40-44 °C
• Boiling Point: 266.7±19.0 °C(Predicted)
• PKA: 4.63±0.20(Predicted)
• Flash Point: >110°C
• PSA: 37.30000
• Density: 1.247±0.06 g/cm3(Predicted)
• LogP: 1.28320
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 138.068079557
• Heavy Atom Count: 10
• Complexity: 195

Purity/Quality:

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

exo-5-Norbornenecarboxylic acid 97% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC(C1C=C2)C(=O)O

Technology Process of Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

There total 183 articles about Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 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%

→ 5-norbornene-endo-2-carboxylic acid (934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7,120-74-1)

Guidance literature:

Reference yield: 97.9%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + acrylic acid (79-10-7) → 5-norbornene-endo-2-carboxylic acid (934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7,120-74-1)

Guidance literature:

In benzene;

Reference yield: 95.0%

(1S,2S,4S)-2-(2-hydroxy-2-methylpropanoyl)bicyclo[2.2.1]hept-5-ene (637033-13-7) → (1S,2S,4S)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) + acetone (67-64-1)

Guidance literature:

With ammonium cerium (IV) nitrate; In water; acetonitrile; at 0 ℃; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/jo9023039

upstream raw materials:

endo-norbornenecarboxylic acid

(R)-pantolactone (1S,2S,4S)-bicyclo<2.2.1>hept-5-ene-2-carboxylate

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

(1R,2R,3R,6R,7S)-2-Bromo-4-oxa-tricyclo[4.2.1.0^3,7]nonan-5-one

Downstream raw materials:

bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

(3S,3aR,5S,6S,6aS)-6-iodohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

(-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol

(-)-(1S,2S)-5-norbornene-2-carboxylic acid chloride