3-Chlorophenylboronic acid

Base Information

• Chemical Name: 3-Chlorophenylboronic acid
• CAS No.: 63503-60-6
• Molecular Formula: C6H6BClO2
• Molecular Weight: 156.376
• Hs Code.: 29163990
• European Community (EC) Number: 628-786-6
• DSSTox Substance ID: DTXSID40370214
• Nikkaji Number: J920.027D
• Wikidata: Q72456614
• ChEMBL ID: CHEMBL164616
• Mol file: 63503-60-6.mol

Synonyms:3-Chlorophenylboronic acid;63503-60-6;(3-chlorophenyl)boronic acid;3-chlorobenzeneboronic acid;3-chlorophenyl boronic acid;3-Chlorophenylboronicacid;m-chlorophenylboronic acid;MFCD00161354;3-chloro benzene boronic acid;Boronic acid, (3-chlorophenyl)-;3-chlorphenylboronic acid;3-chiorophenylboronic acid;m-chlorophenyl boronic acid;3-chloro phenylboronic acid;3-chloro-phenylboronic acid;3-chlorophenyl-boronic acid;5-chlorophenyl-boronic acid;3-chlorobenzene boronic acid;SCHEMBL11815;3-(chloro)phenylboronic acid;3-chloro phenyl boronic acid;3-chloro-phenyl boronic acid;3-chloro-phenyl-boronic acid;AKOS BRN-0010;(3-chlorophenyl) boronic acid;CHEMBL164616;(3-chloro-phenyl)-boronic acid;BDBM92718;B-(3-chlorophenyl)-boronic acid;DTXSID40370214;SDEAGACSNFSZCU-UHFFFAOYSA-N;2-Fluorenecarboxylic acid, 9-oxo-;BCP22738;(M-CHLOROPHENYL)BORONIC ACID;STK503700;AKOS000266634;AB04228;AC-5353;AS-2513;BCP9000257;CS-W002463;OL10078;SY005777;A8744;AM20060343;C1613;FT-0600032;EN300-53026;A1-03827;Q-102203;F9995-0212;Z381540932;3-chlorophenylboronic acid;3-CHLOROPHENYL BORONIC ACID

Chemical Property of 3-Chlorophenylboronic acid

Chemical Property:

• Appearance/Colour: white to light yellow-green crystalline powder
• Vapor Pressure: 0.000242mmHg at 25°C
• Melting Point: 185-189 °C(lit.)
• Refractive Index: 1.557
• Boiling Point: 311.4 °C at 760 mmHg
• PKA: 7.55±0.10(Predicted)
• Flash Point: 142.1 °C
• PSA: 40.46000
• Density: 1.32 g/cm³
• LogP: 0.01980
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Water Solubility.: Slightly soluble in water. soluble in ether, tetrahydrofuran,, dimethyl sulfoxide, dimethyl formamide, methanol.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 156.0149373
• Heavy Atom Count: 10
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

3-Chlorophenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)Cl)(O)O
• Uses: suzuki reaction It is employed as a reactant involved in 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamides, Suzuki-Miyaura reactions with dibromotrifluoromethylbenzene, cross-coupling reactions with diazoesters3 or potassium cyanate. It is involved in the synthesis of biarylketones and phthalides and synthesis of inhibitors including PDE4 inhibitors6 among others. Reactant involved in: 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamidesSuzuki-Miyaura reactions with dibromotrifluoromethylbenzeneCross-coupling reactions with diazoesters or potassium cyanateSynthesis of biarylketones and phthalidesSynthesis of inhibitors including PDE4 inhibitors among others

Technology Process of 3-Chlorophenylboronic acid

There total 11 articles about 3-Chlorophenylboronic 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: 97.0%

1-bromo-3-chlorobenzene (108-37-2) + Trimethyl borate (121-43-7,63156-11-6) → 3-chlorophenylboronic acid (63503-60-6)

Guidance literature:

1-bromo-3-chlorobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

Trimethyl borate; In tetrahydrofuran; hexane; at -30 ℃; Inert atmosphere; Flow reactor;

DOI:10.1021/acs.orglett.6b01681

Reference yield: 82.0%

borane (13283-31-3) + (3-chlorophenyl)magnesium bromide (36229-42-2) → 3-chlorophenylboronic acid (63503-60-6)

Guidance literature:

With water; In tetrahydrofuran; slow addn. of 10 mmol of the Grignard reagent to a stirred soln. of borane in THF (40 mmol); the mixt. was poured into ice-water and acidified with 10% HCl;; extn. into ether three-times; the combined extracts were dried over NaSO4; removal of solvent under reduced pressure; trituration with petroleum ether; recrystn. from H2O;;

DOI:10.1016/0022-328X(83)87176-9

Reference yield: 57.0%

C8H10BClO2 → 3-chlorophenylboronic acid (63503-60-6)

Guidance literature:

With sulfuric acid; In ethanol; toluene; at 0 - 40 ℃; Solvent; Reagent/catalyst;

upstream raw materials:

(3-chlorophenyl)magnesium bromide

3-iodochlorobenzene

1-bromo-3-chlorobenzene

borane

Downstream raw materials:

1-bromo-3-chlorobenzene

3-iodochlorobenzene

tert-butyl-2-({4-[((2-methoxyethyl){2-[3-chlorophenyl]pyrimidin-4-yl}amino)methyl]phenyl}-thio)-2-methylpropanoate

(E)-3-(2-methylphenyl)acrylic acid

Refernces

• 1、 -. "Preparation method of monohalogenated phenylboronic acid". Paragraph 0047-0053. . Retrieved 2020/09/20.
• 2、 Obermoser, Victoria,Mauersberger, Robert,Schuster, Daniela,Czifersky, Monika,Lipova, Marina,Siegl, Monika,Kintscher, Ulrich,Gust, Ronald. "Importance of 5/6-aryl substitution on the pharmacological profile of 4?-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1?-biphenyl]-2-carboxylic acid derived PPARγ agonists". supporting information. p. 590 - 603. Retrieved 2016/12/09.