14475-42-4

Basic information

• Product Name: N-(1-Butylpentylidene)hydroxylamine
• Synonyms: 5-Nonanone oxime;Dibutyl ketoneoxime;N-(1-Butylpentylidene)hydroxylamine
• CAS NO: 14475-42-4
• Molecular Formula: C₉H₁₉NO
• Molecular Weight: 157.2533
• Mol File: 14475-42-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 246.5°Cat760mmHg
• Flash Point: 139.2°C
• Appearance: /
• Density: 0.88g/cm³
• Vapor Pressure: 0.00877mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: N-(1-Butylpentylidene)hydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-Butylpentylidene)hydroxylamine(14475-42-4)
• EPA Substance Registry System: N-(1-Butylpentylidene)hydroxylamine(14475-42-4)

Safety Data

• Hazardous Substances Data: 14475-42-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H19NO/c1-3-5-7-9(10-11)8-6-4-2/h11H,3-8H2,1-2H3

Upstream product

• 502-56-7 nonanone-5 
• 821-74-9 4,5-nonadiene 
• 638-29-9 n-valeryl chloride 

Downstream Products

• 2763-67-9 di-n-butylformamide 
• 502-56-7 nonanone-5 
• 71350-26-0 di-n-butyl ketone oxime O-allyl ether 

Relevant articles and documents

Copper-Catalyzed Aza-Sonogashira Cross-Coupling To Form Ynimines: Development and Application to the Synthesis of Heterocycles

Nitrogen-substituted alkynes, such as ynamines and ynamides, are versatile synthetic building blocks. Ynimines bearing additional nucleophilic and electrophilic centers relative to ynamines and ynamides are expected to have high synthetic potential. However, their chemical reactivity remains unexplored owing mainly to the lack of synthetic accessibility. We report herein a versatile copper-catalyzed synthesis of ynimines from readily available O-acetyl ketoximes and terminal alkynes. A wide range of O-acetyl ketoximes derived from diaryl ketones, aryl alkyl ketones and dialkyl ketones underwent cross-coupling with a diverse set of terminal alkynes to afford the ynimines in good to excellent yields. An unprecedented [5+1] heteroannulation reaction exploiting the reactivity of the ynimine generated in situ was subsequently developed for the synthesis of medicinally important heterocycles, including isoquinolines, azaindoles, azabenzofurans, azabenzothiophenes and carbolines.

Iminyl Radical-Triggered Intermolecular Distal C(sp3)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade

An efficient iron-catalyzed intermolecular remote C(sp3)-H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls.

ENAMIDE PROCESS

A convenient method for converting oximes into enamides is disclosed. The process produces enamides without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines.