1,2-DICARBADODECABORANE(12)-1-CARBOXYLIC ACID

Base Information

• Chemical Name: 1,2-DICARBADODECABORANE(12)-1-CARBOXYLIC ACID
• CAS No.: 18178-04-6
• Molecular Formula: C3B10O2
• Molecular Weight: 188.237
• Mol file: 18178-04-6.mol

Synonyms:o-carborane-1-carboxylic acid;1-CO2H-2-H-1,2-closo-C2B10H10;1-carboxy-1,2-dicarba-closo-dodecaborane(12);1,2-dicarba-closo-dodecarborane -1-carboxylic acid;1,2-dicarba-closo-dodecaboranyl-1-carboxylic acid;

Chemical Property of 1,2-DICARBADODECABORANE(12)-1-CARBOXYLIC ACID

Chemical Property:

• PSA: 40.13000
• LogP: -5.40230

Purity/Quality:

98.5% ^*data from raw suppliers

o-Carborane-1-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: o-Carborane-1-carboxylic Acid is a versatile reactant used in the iridium catalyzed regioselective cage boron alkenylation via direct cage B-H activation. It is also used in the preparation of o-Carbaborane indomethacin pharmacophores as selective COX-2 inhibitors.

Technology Process of 1,2-DICARBADODECABORANE(12)-1-CARBOXYLIC ACID

There total 5 articles about 1,2-DICARBADODECABORANE(12)-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: 97.0%

ethyl (1,2-dicarba-closo-dodecaborane)-1-carboxylate (15527-72-7) → 1,2-dicarba-closo-dodecaborane-1-carboxylic acid (18178-04-6)

Guidance literature:

With sodium hydroxide; In methanol; water; stirred for 3 d; evapd., the residue is acidified with HCl, extd., the extract is dried,the solvent is evapd.;

Reference yield: 95.0%

hydrogenchloride (7647-01-0,15364-23-5) + 1,2-dicarba-closo-dodecaborane(12) (16872-09-6) + carbon dioxide (124-38-9,18923-20-1) → 1,2-dicarba-closo-dodecaborane-1-carboxylic acid (18178-04-6)

Guidance literature:

With n-butyllithium; In diethyl ether; Ar-atmosphere; addn. of BuLi (in hexanes) to carborane (in ether) at -78°C, stirring at -78°C for 20 min, addn. of excess crushed dry ice, stirring for 1 h, evapn., water addn., extn. with hexanes, acidification of aq. layer (3 M HCl); extn. into hexanes, drying (MgSO4), concn.;

Reference yield: 70.0%

1,2-dicarba-closo-dodecaborane(12) (16872-09-6) + carbon dioxide (124-38-9,18923-20-1) → 1,2-dicarba-closo-dodecaborane-1-carboxylic acid (18178-04-6)

Guidance literature:

1,2-dicarba-closo-dodecaborane⁽¹²⁾; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; Inert atmosphere;

carbon dioxide; In diethyl ether; hexane; at -78 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmcl.2015.09.062

upstream raw materials:

1,2-dicarba-closo-dodecaborane⁽¹²⁾

hydrogenchloride

carbon dioxide

ethyl (1,2-dicarba-closo-dodecaborane)-1-carboxylate

Downstream raw materials:

1,2-dicarba-closo-dodecaborane⁽¹²⁾

3-(N-benzoylamino)-1,2-dicarba-closo-dodecaborane