(4'-Methoxy-[1,1'-biphenyl]-4-yl)boronic acid

Base Information

• Chemical Name: (4'-Methoxy-[1,1'-biphenyl]-4-yl)boronic acid
• CAS No.: 156642-03-4
• Molecular Formula: C13H13BO3
• Molecular Weight: 228.055
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID60400704
• Nikkaji Number: J2.494.767J
• Wikidata: Q72489352
• Mol file: 156642-03-4.mol

Synonyms:156642-03-4;(4'-Methoxy-[1,1'-biphenyl]-4-yl)boronic acid;[4-(4-methoxyphenyl)phenyl]boronic Acid;4'-METHOXYBIPHENYL-4-YLBORONIC ACID;4-(4-methoxyphenyl)phenylboronic acid;4'-METHOXY-4-BIPHENYLBORONIC ACID;4'-Methoxybiphenyl-4-boronic acid;4-Methoxybiphenyl-4-ylboronic acid;4-(4-Methoxyphenyl)phenylboronic acid;{4'-methoxy-[1,1'-biphenyl]-4-yl}boronic acid;4-(4-Methoxyphenyl)benzeneboronic acid;(4'-Methoxy-[1,1'-biphenyl]-4-yl)boronicacid;SCHEMBL257917;4/'-Methoxybiphenylboronic acid;DTXSID60400704;VIHQQLWZRRVBNE-UHFFFAOYSA-N;BORONIC ACID, B-(4'-METHOXY[1,1'-BIPHENYL]-4-YL)-;MFCD04039030;AKOS004116108;(4'-Methoxybiphenyl-4-yl)boronic acid;AB17286;AS-3122;CS-0174836;(4'-Methoxy[1,1'-biphenyl]-4-yl)boronic acid;(4\'-Methoxy-[1,1\'-biphenyl]-4-yl)boronic acid

Chemical Property of (4'-Methoxy-[1,1'-biphenyl]-4-yl)boronic acid

Chemical Property:

• Melting Point: 209-211°C
• Boiling Point: 418.616 °C at 760 mmHg
• PKA: 8.52±0.16(Predicted)
• Flash Point: 206.972 °C
• PSA: 49.69000
• Density: 1.205 g/cm³
• LogP: 1.04200
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 228.0957744
• Heavy Atom Count: 17
• Complexity: 219

Purity/Quality:

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

4''-Methoxybiphenyl-4-ylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C2=CC=C(C=C2)OC)(O)O
• Uses: 4''-Methoxybiphenyl-4-ylboronic Acid is a 4,4''-Disubstituted biphenyl boronic acid (BBA) and a push-pull fluorophore with turn-on fluorescence properties. Upon carbohydrate triol binding, BBA boronate esters can participate in photon-induced electron transfer, giving a twisted intramol. charge transfer (TICT) complex.

Technology Process of (4'-Methoxy-[1,1'-biphenyl]-4-yl)boronic acid

There total 1 articles about (4'-Methoxy-[1,1'-biphenyl]-4-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:

4-bromo-4'-hydroxybiphenyl (29558-77-8) → 4'-methoxy-biphenyl-4-boronic acid (156642-03-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / ethanol; H₂O / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / -78 - -65 °C

2.2: B(OCH₃)3 / tetrahydrofuran; hexane / -65 - 20 °C

2.3: aq. HCl / tetrahydrofuran; hexane / 20 °C

With sodium hydroxide; n-butyllithium; In tetrahydrofuran; ethanol; hexane; water;

DOI:10.1080/10587250008031039

Reference yield: 91.0%

C12H12O2 + 4'-methoxy-biphenyl-4-boronic acid (156642-03-4) → C25H22O2

Guidance literature:

With silver hexafluoroantimonate; tetrafluoroboric acid; [Pd((S,S)-chiraphos)(PhCN)2](SbF₆)2; In water; isopropyl alcohol; at 10 ℃; for 21h;

DOI:10.1055/s-2007-990964

Reference yield: 85.0%

3-Bromothianaphthene (7342-82-7) + palladium diacetate (3375-31-3) + 4'-methoxy-biphenyl-4-boronic acid (156642-03-4) → 3-(4'-Methoxy-biphenyl-4-yl)-benzo[b]thiophene (250279-13-1)

Guidance literature:

With potassium carbonate; In water; acetone;

upstream raw materials:

4-bromo-4'-hydroxybiphenyl

Downstream raw materials:

3-(4'-Methoxy-biphenyl-4-yl)-benzo[b]thiophene

1-benzyl-2-(4'-methoxy-biphenyl-4-yl)-1H-benzoimidazole

3-benzyl-2-(4'-methoxy-biphenyl-4-yl)-3H-imidazo[4,5-b]pyridine

2-benzyl-3-(4'-methoxy[1,1'-biphenyl]-4-yl)furo[2,3-b]pyridine

Refernces

• 1、 Zang, Zhi-Qian,Zhang, Dong,Wan, Xin-Hua,Zhou, Qi-Feng. "Synthesis and property of liquid crystalline 4-alkoxyl-4″-cyano-p-terphenyls". . p. 145 - 158. Retrieved 2007/10/03.