(1-(tert-Butoxycarbonyl)-5-methyl-1H-indol-2-yl)boronic acid

Base Information

• Chemical Name: (1-(tert-Butoxycarbonyl)-5-methyl-1H-indol-2-yl)boronic acid
• CAS No.: 475102-14-8
• Molecular Formula: C₁₄H₁₈BNO₄
• Molecular Weight: 275.112
• Hs Code.: 2933990090
• European Community (EC) Number: 691-667-2
• DSSTox Substance ID: DTXSID50397538
• Nikkaji Number: J1.814.450F
• Wikidata: Q82198976
• Mol file: 475102-14-8.mol

Synonyms:475102-14-8;(1-(tert-Butoxycarbonyl)-5-methyl-1H-indol-2-yl)boronic acid;1-BOC-5-methylindole-2-boronic acid;1-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID;[5-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic Acid;1-(tert-Butoxycarbonyl)-5-methyl-1H-indol-2-yl-2-boronic acid;N-BOC-5-METHYL-1H-INDOLE-2-BORONIC ACID;[1-(tert-butoxycarbonyl)-5-methyl-1h-indol-2-yl]boronic acid;5-Methyl-1H-indole-2-boronic acid, BOC protected;SCHEMBL593975;DTXSID50397538;AMY41906;MFCD04114580;AKOS015836476;AB18597;BS-2073;CS-0002262;FT-0644718;N-BOC-5-METHYLINDOLE-2-BORONIC ACID;W17385;A827254;J-503652;1-Boc-5-methyl-1H-indole-2-boronic acid, AldrichCPR;1-(tert-butoxycarbonyl)-5-methyl-1H-indol-2-ylboronic acid;5-METHYL-1H-INDOLE-2-BORONIC ACID, N-BOC PROTECTED;(1-(tert-Butoxycarbonyl)-5-methyl-1H-indol-2-yl)boronicacid;[5-Methyl-1-(tert-butoxycarbonyl)-1H-indole-2-yl]boronic acid;{1-[(tert-butoxy)carbonyl]-5-methyl-1H-indol-2-yl}boronic acid;[5-methyl-1-[(2-methylpropan-2-yl)oxy-oxomethyl]-2-indolyl]boronic acid

Chemical Property of (1-(tert-Butoxycarbonyl)-5-methyl-1H-indol-2-yl)boronic acid

Chemical Property:

• Vapor Pressure: 3.87E-09mmHg at 25°C
• Melting Point: 112-116 °C
• Refractive Index: 1.541
• Boiling Point: 456.8 °C at 760 mmHg
• Flash Point: 230.1 °C
• PSA: 71.69000
• Density: 1.16 g/cm³
• LogP: 1.41270
• Storage Temp.: Keep Cold
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 275.1328882
• Heavy Atom Count: 20
• Complexity: 369

Purity/Quality:

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

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

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (1-(tert-Butoxycarbonyl)-5-methyl-1H-indol-2-yl)boronic acid

There total 3 articles about (1-(tert-Butoxycarbonyl)-5-methyl-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: 100.0%

5-methylindole-1-carboxylic acid tert-butyl ester (129822-49-7) → {1-[(tert-butoxy)carbonyl]-5-methyl-1H-indol-2-yl}boronic acid (475102-14-8)

Guidance literature:

5-methylindole-1-carboxylic acid tert-butyl ester; With Triisopropyl borate; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 3h;

In tetrahydrofuran; pH=6; aq. phosphate buffer;

DOI:10.1039/c1ob06411h

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → {1-[(tert-butoxy)carbonyl]-5-methyl-1H-indol-2-yl}boronic acid (475102-14-8)

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: 85 percent / 2N HCl / tetrahydrofuran

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

DOI:10.1021/jo026087j

Reference yield:

5-methyl-1H-indole (614-96-0) → {1-[(tert-butoxy)carbonyl]-5-methyl-1H-indol-2-yl}boronic acid (475102-14-8)

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: 85 percent / 2N HCl / tetrahydrofuran

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

DOI:10.1021/jo026087j

upstream raw materials:

5-methylindole-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

5-methyl-1H-indole

Downstream raw materials:

β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose-3-(2-cyanoethyl N,N-diisopropylphosphoramidite)

β-D-1-(3-methyl-pyrimido[4,5-d]pyrimido[1,6-a]indol-10-yl)-5-O-(4,4'-dimethoxytrityl)-2-deoxyribose

C₂₉H₃₀N₂O₄S

Refernces

• 1、 Vazquez, Enrique,Davies, Ian W.,Payack, Joseph F.. "A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols". . p. 7551 - 7552. Retrieved 2007/10/03.