1-(Phenylsulfonyl)-3-indoleboronic acid

Base Information

• Chemical Name: 1-(Phenylsulfonyl)-3-indoleboronic acid
• CAS No.: 129271-98-3
• Molecular Formula: C14H12BNO4S
• Molecular Weight: 301.131
• Hs Code.: 2933990090
• European Community (EC) Number: 696-122-2
• DSSTox Substance ID: DTXSID70379896
• Nikkaji Number: J1.926.753I
• Wikidata: Q82169918
• Mol file: 129271-98-3.mol

Synonyms:129271-98-3;1-(Phenylsulfonyl)-3-indoleboronic acid;1-(phenylsulfonyl)-1H-indol-3-ylboronic acid;(1-(Phenylsulfonyl)-1H-indol-3-yl)boronic acid;[1-(benzenesulfonyl)indol-3-yl]boronic Acid;1-(Phenylsulfonyl)-3-indolylboronic acid;1-(Phenylsulphonyl)-1H-indole-3-boronic acid;MFCD02681892;1-(PHENYLSULFONYL)-1H-INDOLE-3-BORONIC ACID;1-(Phenylsulfonyl)-1H-lndole-3-boronic acid;[1-(benzenesulfonyl)-1H-indol-3-yl]boronic acid;Boronic acid,b-[1-(phenylsulfonyl)-1H-indol-3-yl]-;Boronic acid, B-[1-(phenylsulfonyl)-1H-indol-3-yl]-;SCHEMBL819444;Boronic acid, [1-(phenylsulfonyl)-1H-indol-3-yl]-;DTXSID70379896;YKTZLHLBQGCFQX-UHFFFAOYSA-N;N-phenylsulfonylindole-3-boronic acid;AKOS004116601;AB12152;PS-9485;3-Borono-1-(phenylsulfonyl)-1H-indole;SY232262;[1-(phenylsulfonyl)indol-3-yl]boronic acid;[1-(benzenesulfonyl)-3-indolyl]boronic acid;AM20020374;CS-0131349;FT-0605854;1-benzenesulfonyl-1H-indol-3-yl-boronic acid;1-(Phenylsulfonyl)-1H-indole-3-ylboronic acid;(1-(Phenylsulfonyl)-1H-indol-3-yl)boronicacid;1-(Phenylsulfonyl)-3-indolylboronic acid, 97%;A805919;J-503592

Chemical Property of 1-(Phenylsulfonyl)-3-indoleboronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 144 °C
• Refractive Index: 1.633
• Boiling Point: 581.384 °C at 760 mmHg
• PKA: 7.98±0.30(Predicted)
• Flash Point: 305.41 °C
• PSA: 87.91000
• Density: 1.35 g/cm³
• LogP: 1.63890
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 301.0580092
• Heavy Atom Count: 21
• Complexity: 458

Purity/Quality:

97% ^*data from raw suppliers

1-(Phenylsulfonyl)-3-indolylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CN(C2=CC=CC=C12)S(=O)(=O)C3=CC=CC=C3)(O)O
• Uses: 1-(Phenylsulfonyl)-3-indolylboronic acid can be used for chemoselective cross-coupling to form carbon-carbon bonds.

Technology Process of 1-(Phenylsulfonyl)-3-indoleboronic acid

There total 7 articles about 1-(Phenylsulfonyl)-3-indoleboronic 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: 85.0%

3-bromo-1-phenylsulfonyl indole (99655-68-2) → 1-(phenylsulfonyl)-1H-indol-3-ylboronic acid (129271-98-3)

Guidance literature:

3-bromo-1-phenylsulfonyl indole; With Triisopropyl borate; tert.-butyl lithium; In tetrahydrofuran;

Further stages.; Acid hydrolysis;

DOI:10.1021/jm070040e

Reference yield:

indole (120-72-9) → 1-(phenylsulfonyl)-1H-indol-3-ylboronic acid (129271-98-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / NaOH; (n-Bu)4NHSO₄ / CH₂Cl₂

2.1: 95 percent / Br₂ / CCl₄

3.1: t-BuLi; B(O-i-Pr)3 / tetrahydrofuran

3.2: 85 percent / Acid hydrolysis

With sodium hydroxide; Triisopropyl borate; bromine; tert.-butyl lithium; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; tetrachloromethane; dichloromethane;

DOI:10.1021/jm070040e

Reference yield:

1-benzenesulfonylindole (40899-71-6) → 1-(phenylsulfonyl)-1H-indol-3-ylboronic acid (129271-98-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / Br₂ / CCl₄

2.1: t-BuLi; B(O-i-Pr)3 / tetrahydrofuran

2.2: 85 percent / Acid hydrolysis

With Triisopropyl borate; bromine; tert.-butyl lithium; In tetrahydrofuran; tetrachloromethane;

DOI:10.1021/jm070040e

upstream raw materials:

3-bromo-1-phenylsulfonyl indole

indole

1-benzenesulfonylindole

benzenesulfonyl chloride

Downstream raw materials:

N-(3,4-Dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]-2-[1-(phenylsulfonyl)-1H-indol-3-yl]benzenesulfonamide

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

1-Benzenesulfonyl-3-pyridin-3-yl-1H-indole