10-Bromoanthracene-9-boronic acid

Base Information

• Chemical Name: 10-Bromoanthracene-9-boronic acid
• CAS No.: 641144-16-3
• Molecular Formula: C14H10BBrO2
• Molecular Weight: 300.947
• Hs Code.: 2931900090
• European Community (EC) Number: 663-919-1
• DSSTox Substance ID: DTXSID00584416
• Nikkaji Number: J2.587.056E
• Wikidata: Q72451414
• Mol file: 641144-16-3.mol

Synonyms:10-Bromoanthracene-9-boronic acid;641144-16-3;(10-bromoanthracen-9-yl)boronic acid;10-Bromoanthracen-9-boronic acid;9-Bromoanthracen-10-boronic acid;SCHEMBL971772;DTXSID00584416;FAVOIVPFJSKYBE-UHFFFAOYSA-N;AMY22855;(10-bromoanthracen-9-yl)boronicacid;MFCD06411293;AKOS015835573;AB25204;AS-32774

Chemical Property of 10-Bromoanthracene-9-boronic acid

Chemical Property:

• Vapor Pressure: 7.33E-12mmHg at 25°C
• Melting Point: 165-169 °C(lit.)
• Refractive Index: 1.744
• Boiling Point: 525.3 °C at 760 mmHg
• PKA: 8.29±0.30(Predicted)
• Flash Point: 271.5 °C
• PSA: 40.46000
• Density: 1.6 g/cm³
• LogP: 2.43530
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 299.99572
• Heavy Atom Count: 18
• Complexity: 276

Purity/Quality:

99% ^*data from raw suppliers

10-Bromoanthracene-9-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=C2C=CC=CC2=C(C3=CC=CC=C13)Br)(O)O
• Uses: Reactant for:Suzuki cross-coupling reactionsPalladium-catalyzed 1,4-addition reactions

Technology Process of 10-Bromoanthracene-9-boronic acid

There total 3 articles about 10-Bromoanthracene-9-boronic 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: 69.0%

Trimethyl borate (121-43-7,63156-11-6) + 9,10-Dibromoanthracene (523-27-3) → (10-bromoanthracen-9-yl)boronic acid (641144-16-3)

Guidance literature:

With Li(CH₂)3CH₃; HCl; In tetrahydrofuran; (under Ar, Schlenk); soln. of ligand in THF cooled to -90°C, Li(CH2)3CH3 added, stirred for 45 min at -65°C, treated with B(OCH3)3, warmed to room temp., stirred overnight, H2O added, acidified by HCl pH 3-5; extd. with Et2O, organic layer washed with brine, H2O, dried, solvent removed, residue refluxed in H2O for 2 h, filtered, filtrate cooled to 0°C for 10 min, filtered, silica column chromy. (pentane-EtOAc 4:1),washed with pentane; elem. anal.;

DOI:10.1039/b719282g

Reference yield:

C16H14BBrO2 → (10-bromoanthracen-9-yl)boronic acid (641144-16-3)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; hexane;

DOI:10.1039/b719282g

Reference yield:

→ (10-bromoanthracen-9-yl)boronic acid (641144-16-3)

Guidance literature:

upstream raw materials:

Trimethyl borate

9,10-Dibromoanthracene

Downstream raw materials:

methyl 2-acetamido-3-(10-bromoanthracen-9-yl)propanoate

10,10'-dibromo-9,9'-bianthryl

methyl 2-acetamido-3-(10-bromoanthracen-9-yl)prop-2-enoate

9-bromo-10-(4-(naphthalene-1-yl)phenyl)anthracene

Refernces

• 1、 -. "ASYMMETRIC MONOANTHRACENE DERIVATIVE, MATERIAL FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE UTILIZING THE SAME". Page/Page column 35. . Retrieved 2008/06/13.