N-Methylindole-5-boronic acid

Base Information

• Chemical Name: N-Methylindole-5-boronic acid
• CAS No.: 192182-55-1
• Molecular Formula: C₉H₁₀BNO₂
• Molecular Weight: 174.995
• Hs Code.: 2933990090
• European Community (EC) Number: 675-110-0
• DSSTox Substance ID: DTXSID40374954
• Nikkaji Number: J852.957D
• Wikidata: Q72491872
• Mol file: 192182-55-1.mol

Synonyms:192182-55-1;1-Methylindole-5-boronic acid;N-Methylindole-5-boronic acid;1-Methyl-1H-indole-5-boronic acid;(1-methyl-1H-indol-5-yl)boronic acid;n-methylindol-5-boronic acid;(1-methylindol-5-yl)boronic Acid;1-methyl-1H-indol-5-ylboronic acid;Boronic acid, (1-methyl-1H-indol-5-yl)-;MFCD03412070;1-methyl-5-indoleboronic acid;1-Methyl-5-indolylboronic acid;1-Methylindole-5-boronicacid;Boronic acid,B-(1-methyl-1H-indol-5-yl)-;Boronic acid, B-(1-methyl-1H-indol-5-yl)-;N-Methylndole-5-boronc acd;SCHEMBL310439;1-methyl-1h-indole-5-boronic;1-methylindol-2-ylboronic acid;N-methyl indole-5-boronic acid;N-methyl-indole-5-boronic acid;1-methyl-5-indole boronic acid;1-methyl-5-indolyl boronic acid;DTXSID40374954;SYWDZJWBRYIJJB-UHFFFAOYSA-N;AKOS004116177;AB14362;PS-9492;AM803439;BP-11447;SY024632;N-Methylindole-5-boronic acid, AldrichCPR;CS-0035643;FT-0604518;EN300-212563;J-523684

Chemical Property of N-Methylindole-5-boronic acid

Chemical Property:

• Vapor Pressure: 3.33E-07mmHg at 25°C
• Refractive Index: 1.57
• Boiling Point: 402.6 °C at 760 mmHg
• PKA: 8.99±0.30(Predicted)
• Flash Point: 197.3 °C
• PSA: 45.39000
• Density: 1.16 g/cm³
• LogP: -0.14190
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 175.0804587
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

97% ^*data from raw suppliers

N-Methylindole-5-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-41-37/38
• Safety Statements: 26-36/37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)N(C=C2)C)(O)O

Technology Process of N-Methylindole-5-boronic acid

There total 3 articles about N-Methylindole-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: 87.3%

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (837392-62-8) → (1-methyl-1H-indol-5-yl)boronic acid (192182-55-1)

Guidance literature:

With hydrogenchloride; at 25 ℃; for 6h;

Reference yield: 75.0%

5-bromo-1-methyl-H-indole (10075-52-2) → (1-methyl-1H-indol-5-yl)boronic acid (192182-55-1)

Guidance literature:

5-bromo-1-methyl-H-indole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/jm101388d

Reference yield:

5-bromo-1H-indole (10075-50-0) → (1-methyl-1H-indol-5-yl)boronic acid (192182-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C

1.2: 0.75 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

2.2: 0.5 h / 0 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran;

upstream raw materials:

5-bromo-1-methyl-H-indole

5-bromo-1H-indole

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Downstream raw materials:

potassium trifluoro(1-methyl-1H-indol-5-yl)boranuide

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole