621-07-8

Basic information

• Product Name: N,N-Dibenzylhydroxylamine
• Synonyms: DIBENZYL HYDROXYLAMINE;TIMTEC-BB SBB000533;N,N-DIBENZYLHYDROXYAMINE;N,N-DIBENZYLHYDROXYLAMINE;DIBENZYLHYDROXYLAMINE ***REVERSE***;Dibenzylhydroxyamine;N,N-Dibenzylhydroxylamine,98%;N,N-Dibenzylhydroxyl
• CAS NO: 621-07-8
• Molecular Formula: C₁₄H₁₅NO
• Molecular Weight: 213.27
• EINECS: 210-667-1
• Product Categories: Hydroxylamines;Hydroxylamines (N-Substituted);Nitrogen Compounds;Organic Building Blocks
• Mol File: 621-07-8.mol
• Article Data: 30

Chemical Properties

• Melting Point: 125-128 °C(lit.)
• Boiling Point: 353.27°C (rough estimate)
• Flash Point: 200.4 °C
• Appearance: /
• Density: 1.0439 (rough estimate)
• Vapor Pressure: 1.92E-06mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 13.19±0.69(Predicted)
• Water Solubility: Insoluble in water
• BRN: 978234
• CAS DataBase Reference: N,N-Dibenzylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dibenzylhydroxylamine(621-07-8)
• EPA Substance Registry System: N,N-Dibenzylhydroxylamine(621-07-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 621-07-8(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly yellow adhering crystalline

Uses

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.

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].

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

Upstream product

• 60-29-7 diethyl ether 
• 52742-32-2 N,N-dibenzyl-O-benzoylhydroxylamine 
• 141-52-6 sodium ethanolate 
• 100-44-7 benzyl chloride 
• 622-30-0 N-benzyl hydroxylalmine 
• 932-90-1 Benzaldoxime 
• 28539-14-2 N,N-bis(benzotriazol-1-ylmethyl)hydroxylamine 
• 100-39-0 benzyl bromide 
• 103-49-1 dibenzylamine 
• 64-17-5 ethanol 
• 7647-01-0 hydrogenchloride 
• 932-90-1 syn-benzaldehyde oxime 
• 112408-47-6 N,N,O-tribenzylhydroxylamine 
• 55096-92-9 3-(dibenzylamino)propanenitrile 

Downstream Products

• 112408-47-6 N,N,O-tribenzylhydroxylamine 
• 100-52-7 benzaldehyde 
• 620-40-6 tribenzylamine 
• 622-30-0 N-benzyl hydroxylalmine 
• 100-46-9 benzylamine 
• 103-49-1 dibenzylamine 
• 52742-32-2 N,N-dibenzyl-O-benzoylhydroxylamine 
• 113659-09-9 N,N-dibenzyl-O-phenylcarbamoyl-hydroxylamine 
• 10479-25-1 N,N-dibenzylethanamine 
• 111-43-3 Dipropyl ether 
• 2315-68-6 propyl benzoate 
• 29334-77-8 O-acetyl-N,N-dibenzylhydroxylamine 
• 120-51-4 benzoic acid benzyl ester 
• 3287-99-8 benzylamine hydrochloride 

Relevant articles and documents

Late Stage Functionalization of Secondary Amines via a Cobalt-Catalyzed Electrophilic Amination of Organozinc Reagents

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

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).

Synthesis and characterization of N-methyl and N-benzyl cinnamohydroxamic acids

N-methyl and N-benzyl cinnamohydroxamic acid was prepared by coupling reaction between N-methyl hydroxylamine and N-benzyl hydroxylamine with cinnamoyl chloride. The compounds were structurally characterized with 1H NMR, IR and elemental analysis.