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673862

Sigma-Aldrich

2-Nitrophenylboronic acid

≥95%

Synonym(s):

o-Nitrobenzeneboronic acid

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About This Item

Linear Formula:
(O2N)C6H4(B(OH)2)
CAS Number:
5570-19-4
Molecular Weight:
166.93
MDL number:
MFCD00161358
UNSPSC Code:
12352103
PubChem Substance ID:
24885182
NACRES:
NA.22

Assay

≥95%

form

powder

mp

155-160 °C

SMILES string

OB(O)c1ccccc1[N+]([O-])=O

InChI

1S/C6H6BNO4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4,9-10H

InChI key

SFUIGUOONHIVLG-UHFFFAOYSA-N

Application

Boronic acid catalyst used for:
  • Mild and selective dipolar cycloadditions of unsaturated carboxylic acids with azides
  • Transposition of allylic alcohols and Meyer-Schuster rearrangements

Reactant involved in:
  • Suzuki-Miyaura cross-coupling reactions with aryl halides or nitroarenediazonium tetrafluoroborates
  • Copper-catalyzed halogenation
  • Oxidative arylation of aminopyrazolyl disulfides
Used in a preparation of unsymmetrical 2,2′-dinitrobiphenyls via Suzuki-Miyaura cross-coupling with nitrophenyl halides.

Other Notes

May contain varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - 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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

673862-VAR:
673862-BULK:
673862-5G:
673862-1G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM6300
MKCF5224
MKBT0423V
MKBP8593V
MKBM3975V

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Raquel Rodríguez González et al.
The Journal of organic chemistry, 70(23), 9591-9594 (2005-11-05)
[Reaction: see text]. Mechanistic investigations and protocols for the synthesis of 2-nitrobiphenyls and 2,2'-dinitrobiphenyls are disclosed. It is revealed that obstacles appear during the transmetalation step when the phenylboronic acid is substituted with a nitro group in the 2-position, whereas

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