1-(tert-butoxycarbonyl)-1H-indole-5-boronic acid

Base Information

• Chemical Name: 1-(tert-butoxycarbonyl)-1H-indole-5-boronic acid
• CAS No.: 317830-84-5
• Molecular Formula: C13H16 B N O4
• Molecular Weight: 261.085
• Hs Code.: 2933990090
• European Community (EC) Number: 888-323-0
• DSSTox Substance ID: DTXSID10593251
• Nikkaji Number: J2.986.010F
• Wikidata: Q82487693
• Mol file: 317830-84-5.mol

Synonyms:317830-84-5;1-(tert-butoxycarbonyl)-1H-indole-5-boronic acid;1-BOC-INDOLE-5-BORONIC ACID;1-(TERT-BUTOXYCARBONYL)-1H-INDOL-5-YLBORONIC ACID;(1-(tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid;[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-5-yl]boronic acid;{1-[(tert-butoxy)carbonyl]-1H-indol-5-yl}boronic acid;1-(TERT-BUTOXYCARBONYL)-1H-INDOL-5-YLBORONICACID;[1-(tert-Butoxycarbonyl)-1H-indol-5-yl]boronic acid;N-Boc-5-indoleboronic acid;n-boc-indole-5-boronic acid;1-(tert-butoxycarbonyl)-1H-indol-5-yl-5-boronic acid;SCHEMBL2081790;DTXSID10593251;LMSHKSBYXDUUBM-UHFFFAOYSA-N;1-Boc--1H-indole-5-boronic acid;MFCD06738850;1-(TERT-BUTOXYCARBONYL)-1H-INDOL-5-YLBORONIC ACID PINACOL ESTER;AKOS015969063;AB28033;BS-25251;DB-068526;CS-0175399;W13712;EN300-7375741;A875808;J-018538

Chemical Property of 1-(tert-butoxycarbonyl)-1H-indole-5-boronic acid

Chemical Property:

• Boiling Point: 443.5±55.0 °C(Predicted)
• PKA: 8.51±0.30(Predicted)
• PSA: 71.69000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 1.10430
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 261.1172382
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

97% ^*data from raw suppliers

1-Boc-indole-5-boronicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1-(tert-butoxycarbonyl)-1H-indole-5-boronic acid

There total 5 articles about 1-(tert-butoxycarbonyl)-1H-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: 54.0%

1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (777061-36-6) → (1-(tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid (317830-84-5)

Guidance literature:

With sodium periodate; ammonium acetate; water; In acetone; at 23 ℃; for 24h;

Reference yield: 54.0%

N-Boc-indole-5-boronic acid neopentylglycol ester (1167418-11-2) → (1-(tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid (317830-84-5)

Guidance literature:

With sodium periodate; ammonium acetate; water; In acetone; at 23 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ol901113t

Reference yield:

5-bromo-indole-1-carboxylic acid tert-butyl ester (182344-70-3) → (1-(tert-butoxycarbonyl)-1H-indol-5-yl)boronic acid (317830-84-5)

Guidance literature:

5-bromo-indole-1-carboxylic acid tert-butyl ester; With potassium hydride; In tetrahydrofuran; at 0 ℃; for 0.25h;

With tert.-butyl lithium; In tetrahydrofuran; pentane; for 0.183333h;

With Trimethyl borate; In tetrahydrofuran; pentane; at -78 - 20 ℃;

DOI:10.1021/jo0491612

upstream raw materials:

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

5-bromo-1H-indole

di-tert-butyl dicarbonate

N-Boc-indole-5-boronic acid neopentylglycol ester

Downstream raw materials:

Pd(C₅H₅N)(C₁₃H₈N₂SO₂C₆H₄NO₂)(C₆H₃C₂H₂NC(O)OC(CH₃)3)

tert‐butyl 5‐fluoroindole‐1‐carboxylate

1-(tert-butyloxycarbonyl)indole-5-carboxaldehyde