2-Chlorophenylboronic acid

Base Information

• Chemical Name: 2-Chlorophenylboronic acid
• CAS No.: 3900-89-8
• Molecular Formula: C6H6BClO2
• Molecular Weight: 156.376
• Hs Code.: 29319090
• European Community (EC) Number: 670-392-1
• DSSTox Substance ID: DTXSID80370213
• Nikkaji Number: J1.483.164I
• Wikidata: Q72456611
• Mol file: 3900-89-8.mol

Synonyms:2-Chlorophenylboronic acid;3900-89-8;(2-chlorophenyl)boronic acid;2-chlorobenzeneboronic acid;o-chlorophenylboronic acid;2-chlorophenyl boronic acid;Boronic acid, (2-chlorophenyl)-;MFCD00674012;2-Chlorophenylboronicacid;2-Chlorophenylboronic aicd;o-chlorphenylboronic acid;o-chlorophenyl boronic acid;(2-chlorophenyl)boronicacid;2-chloro phenylboronic acid;2-chloro-phenylboronic acid;2-chlorophenyl-boronic acid;SCHEMBL4129;2-chlorobenzene boronic acid;2-chloro phenyl boronic acid;2-chloro-phenyl boronic acid;2-chloro-phenyl-boronic acid;2-chloro benzene boronic acid;2-chloro-benzene boronic acid;2-chloro-benzene-boronic acid;AKOS BRN-0009;(2-chlorophenyl) boronic acid;(2-chlorophenyl)-boronic acid;Benzeneboronic acid, o-chloro-;DTXSID80370213;RRCMGJCFMJBHQC-UHFFFAOYSA-N;BCP22739;CS-D1476;O-CHLORO-BENZENEBORONIC ACID;STK503705;AKOS000266633;AB06914;AC-5347;AS-2594;BCP9000256;OL10077;2-Chlorophenylboronic acid, >=95.0%;NCGC00249464-01;SY007772;A6555;AM20060349;C1705;FT-0601796;EN300-114510;Q-102201;Z381540900;(1-BENZYL-3-HYDROXY-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL)-ACETICACID

Chemical Property of 2-Chlorophenylboronic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00034mmHg at 25°C
• Melting Point: 92-102 °C(lit.)
• Refractive Index: 1.557
• Boiling Point: 306.3 °C at 760 mmHg
• PKA: 8.23±0.58(Predicted)
• Flash Point: 139 °C
• PSA: 40.46000
• Density: 1.32 g/cm³
• LogP: 0.01980
• Storage Temp.: 0-6°C
• Solubility.: Soluble in DMSO, 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

2-Chlorophenylboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1Cl)(O)O
• Uses: suzuki reaction 2-Chlorophenylboronic Acid used in the preparation of imidazo[1,2-a]pyridine amides which has tuberculostatic activity.

Technology Process of 2-Chlorophenylboronic acid

There total 10 articles about 2-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: 100.0%

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-chlorobenzene (870195-94-1) → 2-Chlorobenzeneboronic acid (3900-89-8)

Guidance literature:

2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-chlorobenzene; With potassium hydrogen difluoride; In methanol; at 20 ℃; for 0.25h;

With chloro-trimethyl-silane; water; In acetonitrile; for 1h;

DOI:10.1016/j.tetlet.2005.09.101

Reference yield: 98.0%

2-bromo-1-chlorobenzene (694-80-4) → 2-Chlorobenzeneboronic acid (3900-89-8)

Guidance literature:

With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexane; toluene; at -70 ℃; for 1.5h; Inert atmosphere;

Reference yield: 86.0%

borane-THF + 2-bromo-1-chlorobenzene (694-80-4) → 2-Chlorobenzeneboronic acid (3900-89-8)

Guidance literature:

With magnesium; In water;

upstream raw materials:

2-chlorophenylmagnesium bromide

triisobutyl borate

boric acid tributyl ester

2-bromo-1-chlorobenzene

Downstream raw materials:

tris(2-chloro phenyl)boroxine

1,1-dimethylethyl (2R,5R)-5-<<2'-chloro-5-<(diethoxyphopsphoryl)methyl>(1,1'-biphenyl)-3-yl>methyl>-2-(1,1-dimethylethyl)-3-methyl-4-oxoimidazolidine-1-carboxylate

1,1-dimethylethyl (2S,5S)-5-<<2'-chloro-5-<(diethoxyphopsphoryl)methyl>(1,1'-biphenyl)-3-yl>methyl>-2-(1,1-dimethylethyl)-3-methyl-4-oxoimidazolidine-1-carboxylate

(2R,5R)-5-[4-Acetoxy-2'-chloro-5-(diethoxy-phosphorylmethyl)-biphenyl-3-ylmethyl]-2-tert-butyl-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu. "Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids". . p. 164 - 171. Retrieved 2018/12/05.
• 2、 Zernickel, Anna,Du, Weiyuan,Ghorpade, Seema A.,Sawant, Dinesh N.,Makki, Arwa A.,Sekar, Nagaiyan,Eppinger, J?rg. "Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water". . p. 1842 - 1851. Retrieved 2018/02/23.