621-07-8 Usage
Description
N,N-Dibenzylhydroxylamine is a white to slightly yellow crystalline compound that is known for its reactivity in chemical synthesis. It is characterized by its ability to undergo oxidation and participate in cycloaddition reactions with suitable dipolarophiles.
Uses
Used in Chemical Synthesis:
N,N-Dibenzylhydroxylamine is used as a reagent for the synthesis of N,N,O-trisubstituted hydroxylamines and arylamines. Its oxidation product, N-benzyl-α-phenylnitrone, is a key intermediate in the formation of these compounds, which are valuable in various chemical applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N,N-Dibenzylhydroxylamine is used as a building block for the development of new drugs. Its ability to form a variety of chemical structures makes it a versatile component in the synthesis of pharmaceutical compounds.
Used in Research and Development:
N,N-Dibenzylhydroxylamine is also utilized in research and development settings, where its unique chemical properties are explored for potential applications in creating new materials and compounds with specific properties and functions.
Preparation
A mixture of 14 gm (0.202 mole) of hydroxylamine hydrochloride and 50 gm (0.395 mole) of benzyl chloride in 200 ml of 70% ethanol is treated with 60 gm of crystalline sodium carbonate. The mixture is heated under a reflux condenser for 2 hr, cooled to room temperature, filtered, and the solids discarded. The filtrate is treated with sufficient ice water to cause precipitation of A^N-dibenzylhydroxylamine. The reaction mixture is then thoroughly cooled in a freezing mixture to permit complete precipitation of product to take place. The yield, upon filtration, is 26 gm (61.5%), m.p. 123°C. A similar preparation has recently been reported [13a].
Check Digit Verification of cas no
The CAS Registry Mumber 621-07-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 1 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 621-07:
(5*6)+(4*2)+(3*1)+(2*0)+(1*7)=48
48 % 10 = 8
So 621-07-8 is a valid CAS Registry Number.
InChI:InChI=1/C14H15NO/c16-15(11-13-7-3-1-4-8-13)12-14-9-5-2-6-10-14/h1-10,16H,11-12H2
621-07-8Relevant articles and documents
Late Stage Functionalization of Secondary Amines via a Cobalt-Catalyzed Electrophilic Amination of Organozinc Reagents
Gra?l, Simon,Chen, Yi-Hung,Hamze, Clémence,Tüllmann, Carl Phillip,Knochel, Paul
supporting information, p. 494 - 497 (2019/01/14)
A general preparation of polyfunctional hydroxylamine benzoates from the corresponding secondary amines is reported. This convenient synthesis allows the setup of a late-stage functionalization of various secondary amines, including pharmaceuticals and peptidic derivatives. Thus, a cross-coupling of hydroxylamine benzoates with various alkyl-, aryl-, and heteroaryl-zinc chlorides in the presence of 5 mol % CoCl2 (25 °C, 2 h) provides a range of polyfunctional tertiary amines. This method was used to prepare penfluridol and gepirone.
Copper-Catalyzed Ring Opening of Benzofurans and an Enantioselective Hydroamination Cascade
Xu-Xu, Qing-Feng,Liu, Qiang-Qiang,Zhang, Xiao,You, Shu-Li
supporting information, p. 15204 - 15208 (2018/10/24)
A copper(II) acetate/(R)-DTBM-SEGPHOS-catalyzed ring opening of benzofurans and enantioselective hydroamination cascade with dimethoxymethylsilane (DMMS) and hydroxylamine esters is described. Starting from readily available substituted benzofurans, a series of chiral N,N-dibenzylaminophenols, which are of high interest in pharmaceutical chemistry, were obtained with excellent enantioselectivities (up to 66 % yield, 94 % ee).
Selective Oxidation of Secondary Amines to N,N-Disubstituted Hydroxylamines by Choline Peroxydisulfate
Banan, Alireza,Valizadeh, Hassan,Heydari, Akbar,Moghimi, Abolghasem
, p. 2315 - 2319 (2017/10/06)
N,N-Disubstituted hydroxylamines were prepared directly from secondary amines by a reliable method using an oxidizing task-specific ionic liquid, choline peroxydisulfate. The operational simplicity, high selectivity, and green reaction conditions, make this method efficient and practical.