3-Chlorophenylboronic acid

Bezeichnung:3-Chlorophenylboronic acid

CAS-Nr63503-60-6

Englisch Name:3-Chlorophenylboronic acid

CBNumberCB3486386

SummenformelC6H6BClO2

Molgewicht156.37

MOL-Datei63503-60-6.mol

3-Chlorophenylboronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	185-189 °C(lit.)
Siedepunkt	311.4±44.0 °C(Predicted)
Dichte	1.32±0.1 g/cm3(Predicted)
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	soluble in Methanol
Aggregatzustand	Crystalline Powder or Needles
pka	7.55±0.10(Predicted)
Farbe	White to light yellow-green
Wasserlöslichkeit	Slightly soluble in water. soluble in ether, tetrahydrofuran,, dimethyl sulfoxide, dimethyl formamide, methanol.
BRN	2936343
InChI	InChI=1S/C6H6BClO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H
InChIKey	SDEAGACSNFSZCU-UHFFFAOYSA-N
SMILES	B(C1=CC=CC(Cl)=C1)(O)O
CAS Datenbank	63503-60-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	20/21/22-36/37/38
S-Sätze:	36-37/39-26
WGK Germany	3
HazardClass	IRRITANT
HS Code	29163990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral

Gefahreninformationscode (GHS)

3-Chlorophenylboronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
white to light yellow-green crystalline powder
Verwenden
suzuki reaction
Verwenden
Reactant involved in:
- 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamides
- Suzuki-Miyaura reactions with dibromotrifluoromethylbenzene
- Cross-coupling reactions with diazoesters or potassium cyanate
- Synthesis of biarylketones and phthalides
- Synthesis of inhibitors including PDE4 inhibitors among others
Verwenden
3-Chlorophenylboronic acid 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.
Synthese
Using m-dichlorobenzene as the starting material, iodine particles and 1,2-dibromoethane as the initiator reacts with magnesium in an organic solvent to prepare 3-chlorophenyl magnesium chloride. Then, the trimethyl borate is reacted with an organic solvent to prepare 3-chlorophenyl borate dimethyl ester. Finally, the product 3-chlorophenylboronic acid is obtained through hydrolysis, extraction, and crystallization.
Solubility in organics
3-Chlorophenylboronic acid can be dissolved in organic solvents such as N, N-dimethylformamide, ethyl acetate, and dichloromethane. In addition, it also has specific solubility in low-polarity and non-polar organic solvents, but 3-chlorophenylboronic acid has poor solubility in water.
Einzelnachweise
[1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 590 - 603
[2] Organic Letters, 2005, vol. 7, # 21, p. 4757 - 4759
[3] Tetrahedron, 2007, vol. 63, # 35, p. 8529 - 8536

3-Chlorophenylboronic acid Upstream-Materialien And Downstream Produkte

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