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393606

Sigma-Aldrich

o-Tolylboronic acid

≥95.0%

Synonym(s):

(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

Linear Formula:
CH3C6H4B(OH)2
CAS Number:
16419-60-6
Molecular Weight:
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

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

11 - Combustible Solids

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
SHBK9074
SHBF2995V
SHBD2665V
07912PC
08308TC

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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
Tetrahedron, 63, 6996-6996 (2007)
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
(S)-Phenylalanine-derived chiral phosphorus-olefin ligands in rhodium-catalyzed asymmetric 1,4-addition reactions
Narui, R.; et al.
Tetrahedron Asymmetry, 23, 284-293 (2012)
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