18178-04-6

Basic information

• Product Name: 1,2-DICARBADODECABORANE(12)-1-CARBOXYLIC ACID
• 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
• CAS NO: 18178-04-6
• Molecular Formula: C3B10O2
• Molecular Weight: 188.237
• Mol File: 18178-04-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,2-DICARBADODECABORANE(12)-1-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DICARBADODECABORANE(12)-1-CARBOXYLIC ACID(18178-04-6)
• EPA Substance Registry System: 1,2-DICARBADODECABORANE(12)-1-CARBOXYLIC ACID(18178-04-6)

Safety Data

• Hazardous Substances Data: 18178-04-6(Hazardous Substances Data)

Usage

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.

Upstream product

• 15527-72-7 ethyl (1,2-dicarba-closo-dodecaborane)-1-carboxylate 
• 16872-09-6 1,2-dicarba-closo-dodecaborane⁽¹²⁾ 
• 124-38-9 carbon dioxide 
• 20394-07-4 1-formyl-o-carborane 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 877076-40-9 (o-carborane-1-carboxylic acid)*(NH₂C₆H₄OH-o) 
• 855119-99-2 (o-carborane-1-carboxylic acid)*(Me₂NC₆H₄CHO-p) 
• 855120-05-7 triphenylphosphonium o-carborane-1-carboxylate 
• 16872-09-6 1,2-dicarba-closo-dodecaborane⁽¹²⁾ 
• 22043-75-0 3-(N-benzoylamino)-1,2-dicarba-closo-dodecaborane 

Relevant articles and documents

Carborane-containing urea-based inhibitors of glutamate carboxypeptidase II: Synthesis and structural characterization

Glutamate carboxypeptidase II (GCPII) is a zinc metalloprotease on the surface of astrocytes which cleaves N-acetylaspartylglutamate to release N-acetylaspartate and glutamate. GCPII inhibitors can decrease glutamate concentration and play a protective role against apoptosis or degradation of brain neurons. Herein, we report the synthesis and structural analysis of novel carborane-based GCPII inhibitors. We determined the X-ray crystal structure of GCPII in complex with a carborane-containing inhibitor at 1.79 ? resolution. The X-ray analysis revealed that the bulky closo-carborane cluster is located in the spacious entrance funnel region of GCPII, indicating that the carborane cluster can be further structurally modified to identify promising lead structures of novel GCPII inhibitors.

Reduction of hydroxy-functionalised carbaboranyl carboxylic acids to tertiary alcohols by organolithium reagents

Reduction of hydroxy-functionalised carbaboranyl carboxylic acids by organolithium reagents yields the corresponding tertiary alcohols. This is in contrast to exo-polyhedral C-C bond cleavage of unsubstituted carbaboranyl carboxylic acids upon reaction with lithium organyls. The proposed dimeric contact ion pairs may also explain the formation of tertiary alcohols instead of the expected ketones.

Tumour-targetted Boranes. Part 3. Synthesis of Carbamate-linked Nitroimidazolyl Carboranes Designed for Boron Neutron Capture Therapy of Cancer

Carboranes targetted to specific tumour tissues are important for boron neutron capture therapy of cancer (BNCT).Carbamoylation of 2-ethoxy>ethanol 5 and 1-(chloromethyl-2-(nitroimidazol-1-yl)ethanol 6 with carboran-1-yl isocyanate (generated in situ by a Curtius rearrangement of carborane-1-carbonyl azide) gave the corresponding carbamate-linked nitroimidazolylcarboranes 16 and 17.A similar reaction of 4-carboranylphenyl isocyanate with 6 afforded the corresponding carbamate 24.