(5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid

Base Information

• Chemical Name: (5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid
• CAS No.: 475102-13-7
• Molecular Formula: C13H15BBrNO4
• Molecular Weight: 339.981
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40383344
• Nikkaji Number: J1.814.448D
• Wikidata: Q72452182
• Mol file: 475102-13-7.mol

Synonyms:475102-13-7;(5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid;5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-ylboronic acid;1-BOC-5-bromoindole-2-boronic acid;[5-bromo-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic Acid;MFCD03701683;1-BOC-5-BROMO-1H-INDOLE-2-BORONIC ACID;(N-Boc-5-bromo-2-indolyl)boronic acid;[5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl]boronic acid;N-Boc-5-bromo-2-indoleboronic Acid;5-BROMO-N-(BOC)INDOLE-2-BORONIC ACID;SCHEMBL7921587;DTXSID40383344;AKOS004116257;AB15799;AM86990;PS-9690;AC-33449;SY022306;CS-0002263;FT-0644717;N-(BOC-5-BROMO-2-INDOLYL)BORONIC ACID;N11949;5-bromo-1-tert-butoxycarbonylindole-2-boronic acid;5-Bromo-1H-indole-2-boronic acid, N-BOC protected;J-517175;5-BROMO-1-T-BUTOXYCARBONYLINDOLE-2-BORONIC ACID;[5-Bromo-1-(tert-butoxycarbonyl)-1H-indole-2-yl]boronic acid;{5-bromo-1-[(tert-butoxy)carbonyl]-1H-indol-2-yl}boronic acid;1-(TERT-BUTOXYCARBONYL)-5-BROMO-1H-INDOL-2-YL-2-BORONIC ACID

Chemical Property of (5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.39E-10mmHg at 25°C
• Melting Point: 93 °C
• Refractive Index: 1.576
• Boiling Point: 488.3 °C at 760 mmHg
• Flash Point: 249.1 °C
• PSA: 71.69000
• Density: 1.45 g/cm³
• LogP: 1.86680
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 339.02775
• Heavy Atom Count: 20
• Complexity: 374

Purity/Quality:

97% ^*data from raw suppliers

1-BOC-5-bromoindole-2-boronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; Xi
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(N1C(=O)OC(C)(C)C)C=CC(=C2)Br)(O)O

Technology Process of (5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid

There total 5 articles about (5-Bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)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: 52.0%

Triisopropyl borate (5419-55-6) + water (7732-18-5) + 5-bromo-indole-1-carboxylic acid tert-butyl ester (182344-70-3) → 2-borono-5-bromo-1H-indole-1-carboxylic acid-1-(1,1-dimethylethyl) ester (475102-13-7)

Guidance literature:

Triisopropyl borate; 5-bromo-indole-1-carboxylic acid tert-butyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -5 - 0 ℃; for 1h;

water; In tetrahydrofuran;

Reference yield:

5-bromo-indole-1-carboxylic acid tert-butyl ester (182344-70-3) → 2-borono-5-bromo-1H-indole-1-carboxylic acid-1-(1,1-dimethylethyl) ester (475102-13-7)

Guidance literature:

5-bromo-indole-1-carboxylic acid tert-butyl ester; With Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; at 0 - 5 ℃; for 0.5h;

With hydrogenchloride; In tetrahydrofuran; Further stages.;

DOI:10.1021/jo026087j

Reference yield:

5-bromo-1H-indole (10075-50-0) → 2-borono-5-bromo-1H-indole-1-carboxylic acid-1-(1,1-dimethylethyl) ester (475102-13-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMAP / CH₂Cl₂ / 0.75 h / 20 °C

2.1: (iPrO)3B; LDA / tetrahydrofuran / 0.5 h / 0 - 5 °C

2.2: 92 percent Chromat_. / 2N HCl / tetrahydrofuran

With dmap; Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo026087j

upstream raw materials:

5-bromo-indole-1-carboxylic acid tert-butyl ester

5-bromo-1H-indole

di-tert-butyl dicarbonate

Triisopropyl borate

Downstream raw materials:

dimethyl 2-(2-((5-bromo-1-(tert-butoxycarbonyl)-1H-indol-2-yl)methyl)benzylidene)malonate

5-bromo-2-(4-fluoro-3-methyl-phenyl)-indole-1-carboxylic acid tert-butyl ester

potassium N-Boc-5-bromo-2-indolyltrifluoroborate