o-Carborane

Base Information

• Chemical Name: o-Carborane
• CAS No.: 16872-09-6
• Molecular Formula: C2H12 B10
• Molecular Weight: 144.227
• Hs Code.: 29319090
• Mol file: 16872-09-6.mol

Synonyms:1,2-Dicarba-closo-dodecaborane(12);1,2-Dicarba-o-carborane;1,2-Dicarbadodecaborane;Barene;Decaborinene;Dekene;closo-1,2-Dicarbadodecaborane;closo-1,2-Dicarbadodecaborane(12);closo-Ortho-carborane;o-Barene;o-Carborane;o-Carborane(12);o-Dicarbadodecaborane(12);

Chemical Property of o-Carborane

Chemical Property:

• Appearance/Colour: White Powder
• Melting Point: 285-287°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: g/cm³
• LogP: -3.39940
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.

Purity/Quality:

98% ^*data from raw suppliers

o-Carborane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic by ingestion and inhalation.
• Hazard Codes: Xn
• Statements: 22-20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: o-Carborane is used in a wide range of applications such as heat-resistant polymers and medical applications. In coordination chemistry, it is used as unique bulky ligand scaffolds.

Technology Process of o-Carborane

There total 106 articles about o-Carborane 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: 100.0%

3-iodo-1,2-dicarba-closo-dodecaborane (137495-63-7) → 1,2-dicarba-closo-dodecaborane(12) (16872-09-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In N,N-dimethyl-formamide; (Pd(PPh3)4), PPh3, and DMF were heated at 50°C for 1 h, soln. 3-I-o-carborane in DMF was added and stirred under N2 at 50°C for 24h;

DOI:10.1016/S0022-328X(01)01108-1

Reference yield: 95.0%

3-iodo-1,2-dicarba-closo-dodecaborane (137495-63-7) → 1,2-dicarba-closo-dodecaborane(12) (16872-09-6) + dodecahydro-7,8-dicarba-nido-undecaborate (1-)

Guidance literature:

With triphenylphosphine; zinc; In N,N-dimethyl-formamide; (NiCl2(PPh3)2), PPh3, Zn, and DMF were heated at 50°C for 1 h, soln. 3-I-o-carborane in DMF was added and stirred under N2 at 50°Cfor 24 h;

DOI:10.1016/S0022-328X(01)01108-1

Reference yield: 80.9%

bis(1,2-dicarba-closo-dodecaboran(12)-yl-1)mercury (64114-80-3) → 1,2-dicarba-closo-dodecaborane(12) (16872-09-6) + 9,9'-bis(1,2-dicarbaclosododecaboranyl(12)) (68183-96-0)

Guidance literature:

With sodium chloride; tris(triphenylphosphine)rhodium(l) chloride; In N,N,N,N,N,N-hexamethylphosphoric triamide; byproducts: Hg; stirring mixture of 9,9'-bis(o-carboranyl)mercury and catalytic amt. of(PPh3)3RhCl in HMPA for 20 h at 100°C; decanting from metallic Hg, pouring into concd. aq. NaCl, extg. with ether, washing ext. with NaCl soln. and water, drying over Na2SO4, distg. off solvent;

upstream raw materials:

diborane

nido-decaborane

acetylene

1,2-bis(hydroxymethyl)-ortho-carborane

Downstream raw materials:

boric acid

palladium

9-ethyl-1,2-dicarba-closo-dodecaborane

2-ethylanisole

Refernces

• 1、 Brattsev, V. A.,Stanko, V. I.. "". . p. 205 - 207. Retrieved 1973.
• 2、 Boone,Brotherton,Petterson. "O-Carboranyl derivatives of boron compounds". . p. 910 - 912. Retrieved 1965.
• 3、 Feng, Chen,Zhang, Haicheng,Yang, Jiping,Chen, Gong. "A novel approach to ortho-carborane by decarboranylation of 1-(isopropyl benzoate)-1,2-dicarba-closo-dodecaborane". . p. 2027 - 2029. Retrieved 2015.
• 4、 Fein, Marvin M.,Bobinski, Jack,Mayes, Nathan,Schwartz, Nelson,Cohen, Murray S.. "Carboranes. I. The preparation and chemistry of 1-isopropenylcarborane and its derivatives (a new family of stable clovoboranes)". . p. 1111 - 1115. Retrieved 1963.
• 5、 Laromaine, Anna,Teixidor, Francesc,Vinas, Clara. "Carbon extrusion in 1,2-dicarba-closo-dodecaboranes: Regioselective boron substitution in ten-vertex closo-monocarbaborane anions". . p. 2220 - 2222. Retrieved 2005.
• 6、 Heying,Ager Jr.,Clark,Mangold,Goldstein,Hillman,Polak,Szymanski. "A new series of organoboranes. I. Carboranes from the reaction of decaborane with acetylenic compounds". . p. 1089 - 1092. Retrieved 1963.
• 7、 Stanko, V. I.,Klimova, T. V.,Beletskaya, I. P.. "". . p. 191 - 195. Retrieved 1973.
• 8、 Vi?as, Clara,Barberà, Gemma,Teixidor, Francesc. "The BI activation in o-carborane clusters: their fate towards BH. Easy synthesis of [7,10-C2B10H13]-". . p. 16 - 19. Retrieved 2002.
• 9、 Han, Gi Uk,Shin, Seohyun,Baek, Yonghyeon,Kim, Dongwook,Lee, Kooyeon,Kim, Jeung Gon,Lee, Phil Ho. "Mechanochemical Iridium(III)-Catalyzed B-Amidation of o-Carboranes with Dioxazolones". supporting information. p. 8622 - 8627. Retrieved 2021/11/13.
• 10、 Kahlert, Jan,B?hling, Lena,Brockhinke, Andreas,Stammler, Hans-Georg,Neumann, Beate,Rendina, Louis M.,Low, Paul J.,Weber, Lothar,Fox, Mark A.. "Syntheses and reductions of C-dimesitylboryl-1,2-dicarba-closo-dodecaboranes". . p. 9766 - 9781. Retrieved 2015/06/08.