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393606

Sigma-Aldrich

o-Tolylboronic acid

≥95.0%

Synonyma:

(2-Tolyl)boronic acid, 2-Methyl-1-phenylboronic acid, 2-Methylbenzeneboronic acid, 2-Methylphenylboronic acid, 2-Tolueneboronic acid, o-Boronotoluene, o-Methylphenylboronic acid, o-Tolueneboronic acid

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About This Item

Lineární vzorec:
CH3C6H4B(OH)2
Číslo CAS:
16419-60-6
Molekulová hmotnost:
135.96
MDL number:
MFCD00093526
UNSPSC Code:
12352103
PubChem Substance ID:
24864527
NACRES:
NA.22

assay

≥95.0%

form

solid

mp

162-164 °C (lit.)

SMILES string

Cc1ccccc1B(O)O

InChI

1S/C7H9BO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5,9-10H,1H3

InChI key

NSJVYHOPHZMZPN-UHFFFAOYSA-N

Application

Reagent used for
  • Palladium-catalyzed direct arylation of pyrazoles with phenylboronic acids
  • Pd-catalyzed arylation using Suzuki-Miyaura cross-coupling in water
  • Ruthenium catalyzed direct arylation reactions
  • Ligand-free copper-catalyzed coupling reactions
  • Copper-catalyzed cross-coupling reactions of diaryl diselenides
  • Phosphine-free Suzuki-Miyaura cross-coupling reactions
  • Rhodium-catalyzed asymmetric 1,4-addition reactions

Reagent used in Preparation of
  • Chiral monophosphorus ligands in asymmetric Suzuki-Miyaura coupling reaction
  • Palladium nanoparticles immobilized by click ionic copolymers as recyclable catalysts for Suzuki-Miyaura cross-coupling reaction in water
  • Human farnesyl pyrophosphate synthase inhibitors as antitumor agents for multiple myeloma cells

Other Notes

Contains varying amounts of anhydride

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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2-Chlorophenylboronic acid ≥95.0%

Sigma-Aldrich

445215

2-Chlorophenylboronic acid

2,4,6-Trimethylphenylboronic acid ≥95%

Sigma-Aldrich

542318

2,4,6-Trimethylphenylboronic acid

2-Bromotoluene 99%

Sigma-Aldrich

B82006

2-Bromotoluene

1,3-Diiodo-5,5-dimethylhydantoin ≥96%

Sigma-Aldrich

711624

1,3-Diiodo-5,5-dimethylhydantoin

Tetrahedron, 63, 6996-6996 (2007)
Yih-Shyan Lin et al.
Journal of medicinal chemistry, 55(7), 3201-3215 (2012-03-07)
Human farnesyl pyrophosphate synthase (hFPPS) controls intracellular levels of FPP and post-translational prenylation of small GTPase proteins, which are essential for cell signaling and cell proliferation. Clinical investigations provide evidence that N-BP inhibitors of hFPPS are disease modifying agents that
Xinwei Tian et al.
Journal of agricultural and food chemistry, 65(43), 9553-9558 (2017-10-11)
A novel near-infrared fluorescence off-on probe, (E)-3,3-dimethyl-1-propyl-2-(2-(6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)-2,3-dihydro-1H-xanthen-4-yl)vinyl)-3H-indolium (1), is developed and applied to benzoyl peroxide (BPO) detection in real samples and fluorescence imaging in living cells and zebrafish. When arylboronate as the recognition unit is connected to a stable hemicyanine
Wenjun Tang et al.
Organic letters, 14(9), 2258-2261 (2012-04-14)
A series of novel P-chiral monophosphorus ligands exhibit efficiency in asymmetric Suzuki-Miyaura coupling reactions, enabling the construction of an array of chiral biaryl products in high yields and excellent enantioselectivities (up to 96% ee) under mild conditions. The carbonyl-benzooxazolidinone moiety
Glycerol as a recyclable solvent for copper-catalyzed cross-coupling reactions of diaryl diselenides with aryl boronic acids
Ricordi, V. G.; et al.
Green Chemistry, 14, 1030-1034 (2012)
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