Cubane-1-carboxylic Acid

Base Information

• Chemical Name: Cubane-1-carboxylic Acid
• CAS No.: 53578-15-7
• Molecular Formula: C9H8O2
• Molecular Weight: 148.161
• Hs Code.: 2915900090
• European Community (EC) Number: 818-350-5
• DSSTox Substance ID: DTXSID80451172
• Nikkaji Number: J9.716K
• Wikidata: Q82271058
• Mol file: 53578-15-7.mol

Synonyms:Cubane-1-carboxylic Acid;53578-15-7;1-cubanecarboxylic acid;carboxycubane;Cubanecarboxylic acid;Pentacyclo[4.2.0.02,5.03,8.04,7]octanecarboxylic acid (7CI,9CI);cubanecarboxylic;cubane carboxylic;Cubane-1-carboxylicAcid;SCHEMBL4732666;DTXSID80451172;NVBIDTXRBMYRGD-UHFFFAOYSA-N;MFCD10568733;AKOS006375829;SB13675;AS-79163;CS-0052586;EN300-93169;P18358;A934674;Z1205493725

Chemical Property of Cubane-1-carboxylic Acid

Chemical Property:

• Melting Point: 124-125 °C
• Boiling Point: 274.5±8.0 °C(Predicted)
• PKA: 4.65±0.20(Predicted)
• PSA: 37.30000
• Density: 2.029±0.06 g/cm3(Predicted)
• LogP: 0.43880
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 148.052429494
• Heavy Atom Count: 11
• Complexity: 276

Purity/Quality:

98% ^*data from raw suppliers

(2R,3R,5R,6R,7R,8R)-Cubane-1-carboxylic acid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C12C3C4C1C5C2C3C45C(=O)O

Technology Process of Cubane-1-carboxylic Acid

There total 2 articles about Cubane-1-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: 10.8%

4-methoxycarbonylcubane-1-carbonyl chloride (60462-18-2) → cubane-1-carboxylic acid (53578-15-7) + cubane-1,4-dicarboxylic acid (32846-66-5)

Guidance literature:

With dmap; 2-mercaptopyridine-1-oxide sodium salt; 2-methylpropan-2-thiol; In benzene; Heating; Irradiation;

Reference yield:

cubane-1,4-dicarboxylic acid dimethyl ester (29412-62-2) → cubane-1-carboxylic acid (53578-15-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / NaOH / methanol; tetrahydrofuran

2.1: iodobenzene diacetate; I₂ / benzene / 7 h / Heating

3.1: 4.76 g / aq. NaOH / methanol; tetrahydrofuran / 20 °C

4.1: BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

4.2: 88 percent / MeOH / tetrahydrofuran; hexane / -78 - 20 °C

With sodium hydroxide; n-butyllithium; [bis(acetoxy)iodo]benzene; iodine; In tetrahydrofuran; methanol; hexane; benzene; 2.1: Moriarty reaction;

DOI:10.1055/s-2002-35981

Reference yield: 94.0%

cubane-1-carboxylic acid (53578-15-7) → Cubancarbonsaeurechlorid (60462-14-8)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 1h; Inert atmosphere;

DOI:10.1002/chem.201805124

upstream raw materials:

4-methoxycarbonylcubane-1-carbonyl chloride

cubane-1,4-dicarboxylic acid dimethyl ester

Downstream raw materials:

(cubyl)(methyl)methanone

Cubancarbonsaeurechlorid

Iodocubane

pentacyclo[4.2.0.0(2,5).0(3,8).0(4,7)]octane-1-methanol

Refernces

• 1、 Della, Ernest W.,Tsanaktsidis, John. "Decarboxylation of Bridgehead Carboxylic Acids by the Barton Procedure". . p. 2061 - 2066. Retrieved 2007/10/02.