17806-44-9

Upstream product

• 766-97-2 4-n-methylphenylacetylene 
• 16872-09-6 1,2-dicarba-closo-dodecaborane⁽¹²⁾ 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 17702-41-9 nido-decaborane 
• 106-43-4 para-chlorotoluene 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 133385-93-0 4-[1''-(1'',2''-o-dicarba-closo-dodecacarboranyl)]benzaldehyde 
• 150174-85-9 1-{p-(alpha-bromo)tolyl}-1,2-dicarba-closo-dodecaborane 

Relevant academic research and scientific papers

Light-promoted copper-catalyzed cage C-Arylation of: O-carboranes: facile synthesis of 1-Aryl-o-carboranes and o-carborane-fused cyclics

Light-promoted, copper catalyzed cage C-H arylation of o-carboranes with aryl halides has been achieved, leading to the facile synthesis of a variety of 1-Aryl-o-carboranes and o-carborane-fused cyclics. This method has the following features: (1) using o

Phosphine oxide-directed palladium-catalyzed B(3)–H arylation of o-carboranes

The selective functionalization of carboranes has received increasing research interests due to their wild applications in chemistry, life, and material sciences. Among various structurally diverse carboranes, the development of selective functionalization of the commercially available o-carborane (1,2-C2B10H12) has largely focused on the two acidic C[sbnd]H bonds. By contrast, research on the activation of the other ten hydridic cage B–H vertices is relatively less explored. Of particularly challenging, the most electron-deficient nature of B(3,6)-H bonds render very few synthetic methods available for their functionalization. Herein, we develop a phosphine oxide-directed palladium-catalyzed highly B(3)–H selective arylation of o-carboranes under very mild reaction conditions in short reaction time.

Monosubstituted carborane aromatic acid derivative as well as preparation method and application of monosubstituted carborane aromatic acid derivative

The invention relates to the technical field of carborane preparation and relates to a monosubstituted carborane aromatic acid derivative as well as a preparation method and an application of the monosubstituted carborane aromatic acid derivative. The pre

Palladium-Catalyzed Direct Cross-Coupling of Carboranyllithium with (Hetero)Aryl Halides

A palladium-catalyzed direct C-arylation reaction of readily available cage carboranyllithium reagents with aryl halides has been developed for the first time. This method is applicable to a wide range of aryl halide substrates including aryl iodides, aryl bromides, and heteroaromatic halides.

Nickel-catalyzed cross-coupling reactions of o-carboranyl with aryl iodides: Facile synthesis of 1-aryl-o-carboranes and 1,2-diaryl-o-carboranes

A nickel-catalyzed arylation at the carbon center of o-carborane cages has been developed, thus leading to the preparation of a series of 1-aryl-o-carboranes and 1,2-diaryl-o-carboranes in high yields upon isolation. This method represents the first examp

Straightforward synthesis of radioiodinated Cc-substituted o-carboranes: Towards a versatile platform to enable the in vivo assessment of BNCT drug candidates

Due to their high boron content and rich chemistry, dicarba-closo-dodecaboranes (carboranes) are promising building blocks for the development of drug candidates with application in Boron Neutron Capture Therapy. However, the non-invasive determination of their pharmacokinetic properties to predict therapeutic efficacy is still a challenge. Herein, we have reported the unprecedented preparation of mono-[125I] iodinated decaborane via a catalyst-assisted isotopic exchange. Subsequent reactions of the radiolabelled species with acetylenes in acetonitrile under microwave heating yield the corresponding 125I-labelled, Cc-substituted o-carboranes with good overall radiochemical yields in short reaction times. The same synthetic strategy was successfully applied to the preparation of 131I-labelled analogues, and further extension to other radioisotopes of iodine such as 124I (positron emitter) or 123I (gamma emitter) can be envisaged. Hence, the general strategy reported here is suitable for the preparation of a wide range of radiolabelled Cc-substituted o-carborane derivatives. The labelled compounds might be subsequently investigated in vivo by using nuclear imaging techniques such as Single Photon Emission Computerized Tomography or Positron Emission Tomography.

Synthesis of Carboranyl Amino Acids, Hydantoins, and Barbiturates

The syntheses of three novel boronated hydantoins, 5-(o-carboran-1-ylmethyl)hydantoin, 14, the tetraphenylphosphonium salt of 7-(hydantoin-5-ylmethyl)dodecahydro-7,8-dicarba-nido-undecaborate, 15, 5-(o-carboran-1-ylmethyl)-2-thiohydantoin, 16, and two new barbiturates, 5,5-bis(but-2-ynyl)barbiturate, 18, and 5,5-bis[(2-methyl-o-carboran-1-yl)methyl]barbiturate, 20, are described. Hydantoins 14-16 were synthesized from o-carboranylalanine (Car, 13). The detailed syntheses of Car and two other carborane-containing amino acids, O-(o-carboran-1-ylmethyl)tyrosine (CBT, 5a) and p-(o-carboran-1-yl)phenylalanine (CBPA, 5b), presented earlier as a communication,16 are also described. Hydantoin 14 and barbiturates 18 and 20 were tested for their potential anticonvulsant activity. Initial qualitative screening showed moderate activities for hydantoin 14 and barbiturate 18. Barbiturate 20 had no activity. Compound 14 appeared to be nontoxic at doses of 300 mg/kg (mice, ip) and 50 mg/kg (rats, oral). However, 18 was very toxic under similar conditions.