Boronic acid, [4-(hexylthio)phenyl]-

Base Information

• Chemical Name: Boronic acid, [4-(hexylthio)phenyl]-
• CAS No.: 151588-39-5
• Molecular Formula: C12H19BO2S
• Molecular Weight: 238.159
• DSSTox Substance ID: DTXSID70479168
• Wikidata: Q82313107
• Mol file: 151588-39-5.mol

Synonyms:151588-39-5;(4-(Hexylthio)phenyl)boronic acid;[4-(hexylsulfanyl)phenyl]boronic acid;Boronic acid, [4-(hexylthio)phenyl]-;starbld0019265;SCHEMBL2490739;4-(hexylthio)phenylboronic acid;DTXSID70479168;AFWKCJULYLAZEN-UHFFFAOYSA-N

Chemical Property of Boronic acid, [4-(hexylthio)phenyl]-

Chemical Property:

• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 238.1198812
• Heavy Atom Count: 16
• Complexity: 170

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)SCCCCCC)(O)O

Technology Process of Boronic acid, [4-(hexylthio)phenyl]-

There total 5 articles about Boronic acid, [4-(hexylthio)phenyl]- 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: 39.0%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-4-(hexylsulfanyl)benzene (76542-21-7) → 4-(n-hexylsulfanyl)phenylboronic acid (151588-39-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; 1 h at -78°C, B compd. added -78°C to room temp. for 1 h, acid hydrolysis;

DOI:10.1039/b210493h

Reference yield:

1-bromo-hexane (111-25-1) → 4-(n-hexylsulfanyl)phenylboronic acid (151588-39-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / NaH / dimethylformamide / 70 °C

2.1: BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: tetrahydrofuran / 1 h / -78 - 20 °C

3.1: Acid hydrolysis

With n-butyllithium; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/b210493h

Reference yield:

para-bromobenzenethiol (106-53-6) → 4-(n-hexylsulfanyl)phenylboronic acid (151588-39-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / NaH / dimethylformamide / 70 °C

2.1: BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: tetrahydrofuran / 1 h / -78 - 20 °C

3.1: Acid hydrolysis

With n-butyllithium; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/b210493h

upstream raw materials:

1-bromo-hexane

para-bromobenzenethiol

1-bromo-4-(hexylsulfanyl)benzene

Trimethyl borate

Downstream raw materials:

C₁₄₀H₁₈₄O₄S₄

C₃₄H₄₈OS₂

C₃₈H₅₀OS₃

C₄₂H₅₂OS₄