Skip to Content
Merck
All Photos(1)

Documents

483532

Sigma-Aldrich

4-(Dimethylamino)phenylboronic acid

≥95.0%

Synonym(s):

4-(N,N-Dimethylamino)phenylboronic acid, 4-N,N-Dimethylaminobenzeneboronic acid, 4-N,N-Dimethylphenylboronic acid, 4-Dimethylaminobenzeneboronic acid, p-(Dimethylamino)-benzeneboronic acid, [4-(Dimethylamino)phenyl-1-yl]boronic acid, [4-(Dimethylamino)phenyl]boric acid

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
(CH3)2NC6H4B(OH)2
CAS Number:
28611-39-4
Molecular Weight:
165.00
MDL number:
MFCD01074642
UNSPSC Code:
12352103
PubChem Substance ID:
24871900

Assay

≥95.0%

mp

227 °C (lit.)

SMILES string

CN(C)c1ccc(cc1)B(O)O

InChI

1S/C8H12BNO2/c1-10(2)8-5-3-7(4-6-8)9(11)12/h3-6,11-12H,1-2H3

InChI key

RIIPFHVHLXPMHQ-UHFFFAOYSA-N

Application

Reagent used for
  • Suzuki-Miyaura cross-coupling reaction
  • Nickel (Ni)-catalyzed Suzuki-Miyaura cross-coupling
  • Rhodium (Rh)-catalyzed asymmetric addition reactions
  • Palladium (Pd)-catalyzed C-OH bond activation

Reagent used in Preparation of
  • Push-pull arylvinyldiazine chromophores
  • Helical ortho-phenylene oligomers with terminal push-pull substitution
  • Alginate-supported cation-Pd nanoparticle gels as catalysts for the Suzuki-Miyaura cross-coupling reaction
  • Organic dyes for dye-sensitized solar cells

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Mamoru Tobisu et al.
Journal of the American Chemical Society, 133(48), 19505-19511 (2011-10-26)
Two protocols for the nickel-catalyzed cross-coupling of aryl fluorides with aryl boronic esters have been developed. The first employs metal fluoride cocatalysts, such as ZrF(4) and TiF(4), which enable Suzuki-Miyaura reactions of aryl fluorides bearing electron-withdrawing (ketones, esters, and CF(3))
Dramatic Effect of the Gelling Cation on the Catalytic Performances of Alginate-Supported Palladium Nanoparticles for the Suzuki-Miyaura Reaction
Chtchigrovsky, M.; et al.
Chemistry of Materials, 24, 1505-1510 (2012)
Organic dyes incorporating the cyclopentadithiophene moiety for efficient dye-sensitized solar cells
Cheng, X.; et al.
Dyes and Pigments, 92, 1292-1299 (2012)
Rapid access to 4-substituted-pyrones and 2(5H)-furanones via a palladium-catalyzed C-OH bond activation
Hu, Y.; et al.
Tetrahedron, 67, 7258-7262 (2011)
Jian He et al.
Organic & biomolecular chemistry, 10(17), 3398-3405 (2012-03-17)
ortho-Phenylenes are an emerging class of helical oligomers and polymers. We have synthesized a series of push-pull-substituted o-phenylene oligomers (dimethylamino/nitro) up to the octamer. Conformational analysis of the hexamer using a combination of low-temperature NMR spectroscopy and ab initio predictions
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service