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13454

Sigma-Aldrich

N-Benzylhydroxylamine hydrochloride

puriss., ≥99.0% (AT)

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About This Item

Linear Formula:
C6H5CH2NHOH · HCl
CAS Number:
29601-98-7
Molecular Weight:
159.61
Beilstein/REAXYS Number:
507948
MDL number:
MFCD00043377
UNSPSC Code:
12352100
PubChem Substance ID:
57647092
NACRES:
NA.22

grade

puriss.

Quality Level

100

assay

≥99.0% (AT)

form

solid

mp

~105 °C
108-110 °C (lit.)

SMILES string

Cl.ONCc1ccccc1

InChI

1S/C7H9NO.ClH/c9-8-6-7-4-2-1-3-5-7;/h1-5,8-9H,6H2;1H

InChI key

YSNXOQGDHGUKCZ-UHFFFAOYSA-N

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Application

N-Benzylhydroxylamine hydrochloride was used in the synthesis of sugar derived nitrones. It was used as starting reagent in the synthesis of fluoro isoxazoline and isoxazolidine derivatives using flouro nitrone.

Biochem/physiol Actions

N-Benzylhydroxylamine is a potential pharmacological agent in the prevention and progression of acrolein-induced damage to the retinal pigment epithelium.

Other Notes

Formation of nitrones from carbonyl compounds and [2+3]-cycloaddition with olefins to isoxazolidines, which are versatile intermediates; Pd-catalyzed hydroxylamination of allylic esters.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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R Herrera et al.
The Journal of organic chemistry, 66(4), 1252-1263 (2001-04-21)
Captodative olefins 1-acetylvinyl carboxylates proved to be highly regioselective dipolarophiles in 1,3-dipolar cycloadditon to propionitrile oxide, arylphenylnitrile imines, diazoalkanes, and nitrones to yield the corresponding 5-substituted heterocycles. The addition of the latter was also stereoselective, being slightly susceptible to steric
B.J. Wakefield
Sci. Synth., 11, 229-229 (2002)
Ionic liquid mediated synthesis of some novel fluoro isoxazolidine and isoxazoline derivatives using N-benzyl fluoro nitrone via cycloaddition reaction and their antimicrobial activities.
Chakraborty B, et al.
Indian J. Chem. B, 52(10), 1342-1351 (2013)
T. Kawakami et al.
Bulletin of the Chemical Society of Japan, 73, 2423-2423 (2000)
J.E. Baldwin et al.
Tetrahedron, 42, 3097-3097 (1986)
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