Bicyclo[2.2.1]heptane-1,4-dicarboxylic acid

Base Information

• Chemical Name: Bicyclo[2.2.1]heptane-1,4-dicarboxylic acid
• CAS No.: 15544-51-1
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.192
• European Community (EC) Number: 873-894-0
• Nikkaji Number: J1.402.046B
• Mol file: 15544-51-1.mol

Synonyms:Bicyclo[2.2.1]heptane-1,4-dicarboxylic acid;15544-51-1;MFCD20639579;bicyclo[2.2.1]heptane-1,4-dicarboxylicacid;SCHEMBL478303;XTHLMMQPSUSPPS-UHFFFAOYSA-N;AMY35733;AKOS027322291;SB13278;AS-51501;SY036384;CS-0049786;EN300-119040;P12808;Z1262515050

Chemical Property of Bicyclo[2.2.1]heptane-1,4-dicarboxylic acid

Chemical Property:

• Melting Point: 248 °C (acetone)
• PSA: 74.60000
• LogP: 1.10610
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 184.07355886
• Heavy Atom Count: 13
• Complexity: 245

Purity/Quality:

97% ^*data from raw suppliers

Bicyclo[2.2.1]heptane-1,4-dicarboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC2(CCC1(C2)C(=O)O)C(=O)O

Technology Process of Bicyclo[2.2.1]heptane-1,4-dicarboxylic acid

There total 6 articles about Bicyclo[2.2.1]heptane-1,4-dicarboxylic 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: 88.7%

dimethyl bicyclo<2.2.1>heptane-1,4-dicarboxylate (15448-76-7) → bicyclo<2.2.1>heptane-1,4-dicarboxylic acid (15544-51-1) + 4-carbomethoxybicyclo<2.2.1>heptane-1-carboxylic acid (15448-77-8)

Guidance literature:

With Novozym 435 from Candida antarctica; In aq. phosphate buffer; for 24h; pH=4.81; Concentration; pH-value; Solvent; Enzymatic reaction;

DOI:10.1021/op400254c

Reference yield: 80.0%

dimethyl bicyclo<2.2.1>heptane-1,4-dicarboxylate (15448-76-7) → bicyclo<2.2.1>heptane-1,4-dicarboxylic acid (15544-51-1)

Guidance literature:

With lipaze PS-30 from Burkholderia cepacia; In aq. phosphate buffer; at 40 ℃; for 65h; pH=7; Concentration; pH-value; Reagent/catalyst; Temperature; Time; Enzymatic reaction;

DOI:10.1021/op400254c

Reference yield:

cyclopentane-1,3-dicarboxylic acid (4056-78-4,826-02-8) → bicyclo<2.2.1>heptane-1,4-dicarboxylic acid (15544-51-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride / 20 °C / Inert atmosphere; Cooling with ice

2.1: lithium diisopropyl amide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere

2.2: 17 h / -78 - 20 °C

3.1: lithium hydroxide; water / methanol / 48 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; water; lithium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol;

upstream raw materials:

dimethyl bicyclo<2.2.1>heptane-1,4-dicarboxylate

cyclopentane-1,3-dicarboxylic acid

3-(methoxycarbonyl)-cyclopentane-1-carboxylic acid

cyclopentane?1,3?dimethyl formate

Downstream raw materials:

bicyclo[2.2.1]heptane-1,4-diamine dihydrochloride