13454
N-Benzylhydroxylamine hydrochloride
puriss., ≥99.0% (AT)
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About This Item
Linear Formula:
C6H5CH2NHOH · HCl
CAS Number:
Molecular Weight:
159.61
Beilstein:
507948
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
grade
puriss.
Quality Level
Assay
≥99.0% (AT)
form
solid
mp
~105 °C
108-110 °C (lit.)
functional group
amine
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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B.J. Wakefield
Sci. Synth., 11, 229-229 (2002)
T. Kawakami et al.
Bulletin of the Chemical Society of Japan, 73, 2423-2423 (2000)
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
S. Murahashi et al.
Tetrahedron Letters, 29, 2973-2973 (1988)
Synthesis of trihydroxy quinolizidine alkaloids: 1, 3-addition reaction of allylmagnesium bromide to a sugar nitrone.
Dhavale DD, et al.
Tetrahedron, 60(13), 3009-3016 (2004)
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