3-Chloro-5-fluorophenylboronic acid

Base Information

• Chemical Name: 3-Chloro-5-fluorophenylboronic acid
• CAS No.: 328956-61-2
• Molecular Formula: C6H5BClFO2
• Molecular Weight: 174.367
• Hs Code.: 29163990
• European Community (EC) Number: 675-619-8
• DSSTox Substance ID: DTXSID00572313
• Wikidata: Q72451147
• Mol file: 328956-61-2.mol

Synonyms:3-chloro-5-fluorophenylboronic acid;328956-61-2;(3-chloro-5-fluorophenyl)boronic acid;3-Chloro-5-fluorobenzeneboronic acid;3-Chloro-5-fluorophenlyboronic acid;MFCD06801741;Boronic acid, (3-chloro-5-fluorophenyl)-;3-Chloro-5-fluorophenylboronicacid;(3-chloro-5-fluoro-phenyl)boronic acid;SCHEMBL5524;DTXSID00572313;XYQDHVBKUNNLGZ-UHFFFAOYSA-N;3-chloro-5-fluoro-benzeneboronic acid;AKOS004113767;AB30220;CS-W003356;GS-6553;SY014161;AM20050344;C2914;EN300-117486;3-chloro-5-fluorobenzeneboronic acid, AldrichCPR;A821503;J-512268;Z1201623919;3-Chloro-5-fluorobenzeneboronic Acid (contains varying amounts of Anhydride);3-chloro-5-fluorophenylboronic acid (contains varying amounts of anhydride)

Chemical Property of 3-Chloro-5-fluorophenylboronic acid

Chemical Property:

• Melting Point: >200 °C
• Boiling Point: 308.135 °C at 760 mmHg
• PKA: 6.52±0.10(Predicted)
• Flash Point: 140.156 °C
• PSA: 40.46000
• Density: 1.416 g/cm³
• LogP: 0.15890
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 174.0055154
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

3-Chloro-5-fluorophenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC(=C1)Cl)F)(O)O
• Uses: 3-Chloro-5-fluorobenzeneboronic acid is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. suzuki reaction

Technology Process of 3-Chloro-5-fluorophenylboronic acid

There total 3 articles about 3-Chloro-5-fluorophenylboronic 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: 55.7%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-3-chloro-5-fluorobenzene (33863-76-2) → 3-fluoro-5-chlorophenylboronic acid (328956-61-2)

Guidance literature:

1-bromo-3-chloro-5-fluorobenzene; With magnesium; In tetrahydrofuran; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -70 - 20 ℃; for 16h;

With hydrogenchloride; water; In tetrahydrofuran; for 1h;

Reference yield:

C12H17BClFO2 → 3-fluoro-5-chlorophenylboronic acid (328956-61-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2003.08.058

Reference yield:

1-bromo-3-chloro-5-fluorobenzene (33863-76-2) → 3-fluoro-5-chlorophenylboronic acid (328956-61-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

1.2: tetrahydrofuran / -78 - 20 °C

2.1: HCl / tetrahydrofuran

With hydrogenchloride; n-butyllithium; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2003.08.058

upstream raw materials:

1-bromo-3-chloro-5-fluorobenzene

Trimethyl borate

Downstream raw materials:

C₁₅H₁₁ClFN₃

C₂₀H₁₇ClFN₃OS

C₃₀H₁₈ClF₁₁O

Refernces

• 1、 Hasvold, Lisa A.,Wang, Weibo,Gwaltney II, Stephen L.,Rockway, Todd W.,Nelson, Lissa T. J.,Mantei, Robert A.,Fakhoury, Stephen A.,Sullivan, Gerard M.,Li, Qun,Lin, Nan-Horng,Wang, Le,Zhang, Haiying,Cohen, Jerome,Gu, Wen-Zhen,Marsh, Kennan,Bauch, Joy,Rosenberg, Saul,Sham, Hing L.. "Pyridone-containing farnesyltransferase inhibitors: Synthesis and biological evaluation". . p. 4001 - 4005. Retrieved 2007/10/03.