9-(2,4,6-Trimethyl-phenyl)-9,10-dihydro-9-bora-anthracene

Base Information

• Chemical Name: 9-(2,4,6-Trimethyl-phenyl)-9,10-dihydro-9-bora-anthracene
• CAS No.: 33586-37-7
• Molecular Formula: C₂₂H₂₁B
• Molecular Weight: 296.22
• European Community (EC) Number: 685-960-4
• Nikkaji Number: J3.511.572B
• Mol file: 33586-37-7.mol

Synonyms:5-Mesityl-5,10-dihydrodibenzo[b,e]borinine;33586-37-7;9-(2,4,6-TRIMETHYL-PHENYL)-9,10-DIHYDRO-9-BORA-ANTHRACENE;AKOS024322905;J3.511.572B;9-(2,4,6-Trimethylphenyl)-9,10-dihydro-9-boraanthracene

Chemical Property of 9-(2,4,6-Trimethyl-phenyl)-9,10-dihydro-9-bora-anthracene

Chemical Property:

• Melting Point: 130-132 °C
• Boiling Point: 418.6±45.0 °C(Predicted)
• Density: 1.07±0.1 g/cm3(Predicted)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 296.1736308
• Heavy Atom Count: 23
• Complexity: 371

Purity/Quality:

98%,99%, ^*data from raw suppliers

9-(2,4,6-TRIMETHYL-PHENYL)-9,10-DIHYDRO-9-BORA-ANTHRACENE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(C2=CC=CC=C2CC3=CC=CC=C31)C4=C(C=C(C=C4C)C)C

Technology Process of 9-(2,4,6-Trimethyl-phenyl)-9,10-dihydro-9-bora-anthracene

There total 17 articles about 9-(2,4,6-Trimethyl-phenyl)-9,10-dihydro-9-bora-anthracene 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: 67.0%

bis(9,10-dihydro-9-boraanthryl) oxide (28830-35-5) + 2-mesitylmagnesium bromide (2633-66-1) → 9-mesityl-9,10-dihydro-9-boraanthracene (33586-37-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; soln. of mesityl-MgBr was added to boraanthryl oxide soln. and mixt. was refluxed for 3 h, cooled and quenched with water and aq. HCl; soln. was extd. with ether, dried (Na2SO4) and concd. exts. were chromd. (alumina; hexane);

DOI:10.1021/ja00319a032

Reference yield: 65.0%

2,2’-dibromodiphenylmethane (61592-89-0) + dimethoxy(mesityl)borane (34907-53-4) → 9-mesityl-9,10-dihydro-9-boraanthracene (33586-37-7) + C26H29B

Guidance literature:

2,2’-dibromodiphenylmethane; With n-butyllithium; In diethyl ether; hexane; at -94 ℃; for 1h; Inert atmosphere;

dimethoxy(mesityl)borane; In diethyl ether; hexane; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.202003319

Reference yield: 26.0%

2,4,6-trimethylphenyl bromide (576-83-0) + C15H16BNO → 9-mesityl-9,10-dihydro-9-boraanthracene (33586-37-7) + (CH(C6H4)2BC6H2(CH3)3)2 (88916-30-7)

Guidance literature:

2,4,6-trimethylphenyl bromide; With iodine; magnesium; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

C₁₅H₁₆BNO; In tetrahydrofuran; at -94 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/chem.202003319

upstream raw materials:

bis(9,10-dihydro-9-boraanthryl) oxide

2-mesitylmagnesium bromide

9-bora-9-chloro-9,10-dihydroanthracene

10-diazo-9-mesityl-9,10-dihydro-9-boraanthracene

Downstream raw materials:

10-methylene-5-(2,4,6-trimethyl-phenyl)-5,10-dihydro-dibenzo[b,e]borinine

[5-(2,4,6-trimethyl-phenyl)-5,10-dihydro-dibenzo[b,e]borinin-10-yl]-methanol

5-(2,4,6-trimethyl-phenyl)-10-trimethylsilanyl-5,10-dihydro-dibenzo[b,e]borinine

5-(2,4,6-trimethyl-phenyl)-5,10-dihydro-dibenzo[b,e]borinine-10-carboxylic acid

Refernces

• 1、 Lapin, Stephen C.,Brauer, Beth-Ellen,Schuster, Gary B.. "9-Mesityl-9,10-dihydro-9-boraanthrylidene: A Probe of Structure and Reactivity for Aromatic Carbenes". . p. 2092 - 2100. Retrieved 2007/10/02.