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Sigma-Aldrich

4-Chlorophenylboronic acid pinacol ester

97%

Synonym(s):

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)chlorobenzene

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About This Item

Empirical Formula (Hill Notation):
C12H16BClO2
CAS Number:
195062-61-4
Molecular Weight:
238.52
MDL number:
MFCD05663875
UNSPSC Code:
12352103
PubChem Substance ID:
24882508
NACRES:
NA.22

assay

97%

form

solid

mp

50-55 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)OB(OC1(C)C)c2ccc(Cl)cc2

InChI

1S/C12H16BClO2/c1-11(2)12(3,4)16-13(15-11)9-5-7-10(14)8-6-9/h5-8H,1-4H3

InChI key

NYARTXMDWRAVIX-UHFFFAOYSA-N

Application

4-Chlorophenylboronic acid pinacol ester can be used as a reagent in Suzuki-Miyaura cross-coupling reaction to form C-C bonds by reacting with different aryl halides over palladium catalysts.
It can also be used as a reactant:
  • To prepare 2-(4-chlorophenyl)-4H-chromen-4-one by treating with 4-chromanone via one-pot palladium-catalyzed dehydrogenation and oxidative boron-Heck coupling reaction.
  • In the ligand-enabled C-H bond activation reaction in the presence of a palladium catalyst.
  • To synthesize biaryl amides via Cu-catalyzed C-H bond coupling of aryl arylamides.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H413

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A versatile approach to flavones via a one-pot Pd (II)-catalyzed dehydrogenation/oxidative boron-Heck coupling sequence of chromanones
Lee J, et al.
Organic & Biomolecular Chemistry, 14(2), 777-784 (2016)
Ligand-enabled cross-coupling of C (sp 3)-H bonds with arylboron reagents via Pd (II)/Pd (0) catalysis
Chan KSL, et al.
Nature Chemistry, 6(2), 146-146 (2014)
Cu (OAc) 2-catalyzed coupling of aromatic C-H bonds with arylboron reagents
Shang M, et al.
Organic Letters, 16(21), 5666-5669 (2014)
Enhanced heterogeneously catalyzed Suzuki-Miyaura reaction over SiliaCat Pd (0)
Pandarus V, et al.
Tetrahedron Letters, 54(35), 4712-4716 (2013)

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