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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

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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[1]
  • Nickel (Ni)-catalyzed Suzuki-Miyaura cross-coupling[2]
  • Rhodium (Rh)-catalyzed asymmetric addition reactions[3]
  • Palladium (Pd)-catalyzed C-OH bond activation[4]

Reagent used in Preparation of
  • Push-pull arylvinyldiazine chromophores[5]
  • Helical ortho-phenylene oligomers with terminal push-pull substitution[6]
  • Alginate-supported cation-Pd nanoparticle gels as catalysts for the Suzuki-Miyaura cross-coupling reaction[7]
  • Organic dyes for dye-sensitized solar cells[1]

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBG5202V
SHBD3613V
SHBD1723V
SHBB4007V
SHBB1453V

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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)
Feng Cai et al.
Journal of the American Chemical Society, 133(45), 18066-18069 (2011-10-07)
We demonstrate that allenes, chiral 1,2-dienes, appended with basic functionality can serve as ligands for transition metals. We describe an allene-containing bisphosphine that, when coordinated to Rh(I), promotes the asymmetric addition of arylboronic acids to α-keto esters with high enantioselectivity.
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