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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:
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

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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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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