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Key Documents

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412260

Sigma-Aldrich

Benzhydroxamic acid

99%

Sinónimos:

N-Hydroxybenzamide

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About This Item

Fórmula lineal:
C6H5CONHOH
Número de CAS:
495-18-1
Peso molecular:
137.14
Beilstein/REAXYS Number:
1907585
EC Number:
207-797-6
MDL number:
MFCD00002109
UNSPSC Code:
12352100
PubChem Substance ID:
24865799
NACRES:
NA.22

assay

99%

mp

126-130 °C (lit.)

solubility

1 M NaOH: soluble 50 mg/mL, clear, colorless

functional group

amine
phenyl

storage temp.

2-8°C

SMILES string

ONC(=O)c1ccccc1

InChI

1S/C7H7NO2/c9-7(8-10)6-4-2-1-3-5-6/h1-5,10H,(H,8,9)

InChI key

VDEUYMSGMPQMIK-UHFFFAOYSA-N

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General description

Benzhydroxamic acid (BHA) reacts with BiPh3 or Bi(O(t)Bu)3 to afford novel mono- and di-anionic hydroxamato complexes, having anti-bacterial activity against Helicobacter pylori. Three-dimensional structure of recombinant horseradish peroxidase-BHA complex has been studied.

Application

Benzhydroxamic acid may be employed for the Pd-catalyzed synthesis of benzisoxazolones.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000401603
0000401603
0000329529
0000222471
0000210335

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N-Phenylhydroxylamine ≥95.0%

Sigma-Aldrich

671576

N-Phenylhydroxylamine

4-Hydroxybenzamide 98%

Sigma-Aldrich

270253

4-Hydroxybenzamide

Henrik R Hallingbäck et al.
Biochemistry, 45(9), 2940-2950 (2006-03-01)
The oxidation of melatonin by the mammalian myeloperoxidase (MPO) provides protection against the damaging effects of reactive oxygen species. Indole derivatives, such as melatonin and serotonin, are also substrates of the plant horseradish peroxidase (HRP), but this enzyme exhibits remarkable
Nicolas Guimond et al.
Journal of the American Chemical Society, 132(20), 6908-6909 (2010-05-04)
An external-oxidant-free process to access the isoquinolone motif via cross-coupling/cyclization of benzhydroxamic acid with alkynes is described. The reaction features a regioselective cleavage of a C-H bond on the benzhydroxamic acid coupling partner as well as a regioselective alkyne insertion.
Péter Buglyó et al.
Dalton transactions (Cambridge, England : 2003), (38)(38), 8063-8070 (2009-09-23)
Novel half-sandwich Ru(II)-benzohydroxamate complexes were synthesized. [Ru(eta(6)-p-cymene)(mu-bha)](2)Cl(2) (bhaH = benzohydroxamic acid) with (O,O) coordination of the ligand, was characterized by elemental analysis, spectroscopic ((1)H-NMR, IR) and ESI-MS methods. Replacement of the chloride of the precursor by CF(3)SO(3)(-) and reaction of
Xiong Ye et al.
Journal of the American Chemical Society, 128(5), 1444-1445 (2006-02-02)
Ultrafast kinetic measurements of NO rebinding to horseradish peroxidase (HRP) are reported for the first time. The geminate kinetics are found to be exponential for all HRP samples studied. The ferric forms of HRP have NO geminate recombination time constants
Amita Pathak et al.
Chemical communications (Cambridge, England), 50(96), 15232-15234 (2014-10-25)
Reaction of BiPh3 or Bi(O(t)Bu)3 with benzohydroxamic acid (H2-BHA) results in formation of novel mono- and di-anionic hydroxamato complexes; [Bi2(BHA)3]∞ 1, [Bi(H-BHA)3] 2, [Bi(BHA)(H-BHA)] 3, all of which display nM activity against Helicobacter pylori. Subsequent dissolution of [Bi2(BHA)3]∞ in DMSO/toluene
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