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480134

Sigma-Aldrich

2-Naphthylboronic acid

≥95.0%

Synonym(s):

2-Naphthaleneboronic acid

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About This Item

Linear Formula:
C10H7B(OH)2
CAS Number:
32316-92-0
Molecular Weight:
171.99
Beilstein:
2936449
MDL number:
MFCD00236051
UNSPSC Code:
12352103
PubChem Substance ID:
24871549
NACRES:
NA.22

Assay

≥95.0%

mp

269-275 °C (lit.)

SMILES string

OB(O)c1ccc2ccccc2c1

InChI

1S/C10H9BO2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7,12-13H

InChI key

KPTRDYONBVUWPD-UHFFFAOYSA-N

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Application

Used in a study of an enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones leading to chiral, tertiary trifluoromethyl alcohols. Also employed in a study of a palladium-catalyzed addition of aryl boronic acids to nitriles providing aryl ketones and to aryloxy nitriles providing benzofurans.

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

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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Sébastien L X Martina et al.
Chemical communications (Cambridge, England), (39), 4093-4095 (2006-10-07)
The catalytic asymmetric 1,2-addition of a series of arylboronic acids to 2,2,2-trifluoroacetophenones is described with high isolated yields (up to 96%) and good enantioselectivities (up to 83% ee) using a rhodium(I)/phosphoramidite catalyst.
Jae-Ryung Cha et al.
Journal of fluorescence, 24(4), 1215-1224 (2014-05-27)
Blue light-emitting spiro[benzotetraphene-fluorene] (SBTF)-based host materials, 3-(1-naphthyl)-10-naphthylspiro[benzo[ij]tetraphene-7,9'-fluorene] (1), 3-(2-naphthyl)-10-naphthylspiro[benzo[ij]tetraphene-7,9'-fluorene] (2), and 3-[2-(6-phenyl)naphthyl]-10-naphthylspiro[benzo[ij]tetraphene-7,9'-fluorene] (3) were designed and prepared via multi-step Suzuki coupling reactions. Introducing various aromatic groups into SBTF core lead to a reduction in band gap and a determination of
Saikat Das et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 18(1), 79-86 (2016-10-28)
Nuclear magnetic resonance is applied to investigate the relative positions and interactions between cationic and non-ionic carbohydrate-based surfactants in mixed micelles with D
Baowei Zhao et al.
Organic letters, 8(26), 5987-5990 (2006-12-15)
[Structure: see text] A cationic palladium complex catalyzed addition of arylboronic acids to nitriles to yield aryl ketones with moderate to good yields was developed. A one-step synthesis of benzofurans from phenoxyacetonitriles under the catalysis of [(bpy)Pd+(micro-OH)]2(-OTf)2 or [(bpy)Pd2+(H2O)2](-OTf)2 was
Alessio Innocenti et al.
Bioorganic & medicinal chemistry letters, 19(10), 2642-2645 (2009-04-21)
Inhibition of the beta-carbonic anhydrases (CAs, EC 4.2.1.1) from the pathogenic fungi Cryptococcus neoformans (Can2) and Candida albicans (Nce103) with a series of aromatic, arylalkenyl- and arylalkylboronic acids was investigated. Aromatic, 4-phenylsubstituted- and 2-naphthylboronic acids were the best Can2 inhibitors
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