Indole-5-boronic acid

Base Information

• Chemical Name: Indole-5-boronic acid
• CAS No.: 144104-59-6
• Molecular Formula: C8H8BNO2
• Molecular Weight: 160.968
• Hs Code.: 29339900
• European Community (EC) Number: 627-180-9
• DSSTox Substance ID: DTXSID60370251
• Nikkaji Number: J979.444A
• Wikidata: Q72483141
• ChEMBL ID: CHEMBL342460
• Mol file: 144104-59-6.mol

Synonyms:5-Indolylboronic acid;144104-59-6;Indole-5-boronic acid;(1H-indol-5-yl)boronic acid;1H-indol-5-ylboronic Acid;1h-indole-5-boronic acid;5-indolboronic acid;Boronic acid, 1H-indol-5-yl-;MFCD01319013;5-1H-indole boronic acid;CHEMBL342460;1~{H}-indol-5-ylboronic acid;1H-INDOL-5-YL-5-BORONIC ACID;5-indolyl boronic acid;5-Indoleboric Acid;5-Indoleboronic acid;indol-5-boronic acid;indole 5-boronic acid;indole-5 boronic acid;5-Indole boronic acid;5-indolyl-boronic acid;indol-5-ylboronic acid;SCHEMBL5940;1H-Indole-5-ylboronic acid;(1H-indol-5-yl)boronicacid;1H-indol-5-yl boronic acid;1H-indol-5-yl-boronic acid;DTXSID60370251;VHADYSUJZAPXOW-UHFFFAOYSA-N;BCP00079;BBL100901;BDBM50067908;STL554695;AKOS002670086;CS-W020721;PB26056;PS-9518;SB10006;NCGC00249466-01;BORONIC ACID, B-1H-INDOL-5-YL-;SY013664;5-Indoleboronic acid, Indole-5-boronic acid;AM20020493;FT-0607903;EN300-212500;5-Indole Boric Acid;(1H-Indol-5-yl)boronic acid;J-500194;Z1255403238;JDN

Chemical Property of Indole-5-boronic acid

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 2.83E-08mmHg at 25°C
• Melting Point: 170-175 °C
• Refractive Index: 1.662
• Boiling Point: 433.2 °C at 760 mmHg
• PKA: 8.91±0.30(Predicted)
• Flash Point: 215.8 °C
• PSA: 56.25000
• Density: 1.33 g/cm³
• LogP: -0.15230
• Storage Temp.: 0-6°C
• Sensitive.: Air Sensitive
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 161.0648087
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

Indole-5-boronicacid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)NC=C2)(O)O
• Uses: Indole-5-boronic acid is a useful reagent for palladium and copper catalyzed oxidative cross-coupling of mercaptoacetylenes and arylboronic acids. A reagent used in the synthesis of other biologically active molecules. Reactant involved in the synthesis of biologically active molecules including:Indole inhibitors of MMP-13 for arthritic disease treatmentSubstituted pyrimidines acting as tubulin polymerization inhibitorsReactant involved in Suzuki coupling reactions for synthesis of Aryl- hetarylfurocoumarinsAryl-substituted oxabenzindoles and methanobenzindolesReactant involved in: Oxidative cross-coupling with mercaptoacetylenesTrifluoromethylation

Technology Process of Indole-5-boronic acid

There total 24 articles about Indole-5-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: 91.0%

→ 2-(1H-indol-5-yl)-5-[[(4S)-4-methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl]carbonyl]benzoate + 1H-indole-5-boronic acid (144104-59-6)

Guidance literature:

Reference yield: 87.5%

→ N-[2-(1H-indol-5-yl)-5-[[(4S)-4-methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl]carbonyl]phenyl]-N-methylacetamide + 1H-indole-5-boronic acid (144104-59-6)

Guidance literature:

Reference yield: 85.5%

→ 1-[4-(1H-indol-5-yl)-3-methoxybenzoyl]-4,4-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine + 1H-indole-5-boronic acid (144104-59-6)

Guidance literature:

upstream raw materials:

5-bromo-1H-indole

boric acid tributyl ester

Triisopropyl borate

tetrahydroxydiboron

Downstream raw materials:

5-(furan-3-yl)-1H-indole

5-(thiophen-3-yl)-1H-indole

5-phenyl-1H-indole

C₁₄H₁₅NO

Refernces

• 1、 Munteanu, Charissa,Spiller, Taylor E.,Qiu, Jun,Delmonte, Albert J.,Wisniewski, Steven R.,Simmons, Eric M.,Frantz, Doug E.. "Pd- And Ni-Based Systems for the Catalytic Borylation of Aryl (Pseudo)halides with B2(OH)4". . p. 10334 - 10349. Retrieved 2020/09/18.
• 2、 Molander, Gary A.,Cavalcanti, Livia N.,Garcia-Garcia, Carolina. "Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4]". . p. 6427 - 6439. Retrieved 2013/07/26.