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D35457

Sigma-Aldrich

N,N-Dibenzylhydroxylamine

98%

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About This Item

Linear Formula:
(C6H5CH2)2NOH
CAS Number:
621-07-8
Molecular Weight:
213.28
EC Number:
210-667-1
MDL number:
MFCD00004772
UNSPSC Code:
12352100
PubChem Substance ID:
24893768
NACRES:
NA.22

Assay

98%

form

crystals

mp

125-128 °C (lit.)

SMILES string

ON(Cc1ccccc1)Cc2ccccc2

InChI

1S/C14H15NO/c16-15(11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10,16H,11-12H2

InChI key

GXELTROTKVKZBQ-UHFFFAOYSA-N

Application

N,N-Dibenzylhydroxylamine, upon oxidation, yields N-benzyl-α-phenylnitrone, which can undergo cycloaddition reaction with suitable dipolarophiles. It can be used to synthesize N,N,O-trisubstituted hydroxylamines and arylamines.

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 1

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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Synthesis of N,N,O-Trisubstituted Hydroxylamines by Stepwise Reduction and Substitution of O-Acyl N, N-Disubstituted Hydroxylamines.
Dhanju S and Crich D
Organic Letters, 18(8), 1820-1823 (2016)
Chemoselective Ligation of Peptide Phenyl Esters with N?Terminal Cysteines.
Fang GM, et al.
Chembiochem, 11(8), 1061-1065 (2010)
Recent developments in nitrone chemistry: some novel transformations.
Yang J
Synlett, 23(16), 2293-2297 (2012)
Synthesis of Arylamines via Aminium Radicals.
Svejstrup TD, et al.
Angewandte Chemie (International Edition in English), 56(47), 14948-14952 (2017)
Mechanistic studies lead to dramatically improved reaction conditions for the Cu-catalyzed asymmetric hydroamination of olefins.
Bandar JS, et al.
Journal of the American Chemical Society, 137(46), 14812-14818 (2015)

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