109531-96-6

Basic information

• Product Name: N-METHYLFUROHYDROXAMIC ACID
• Synonyms: N-(2-FUROYL)-N-METHYLHYDROXYLAMINE;N-METHYLFUROHYDROXAMIC ACID;N-MFHA;2-Furancarboxamide,N-hydroxy-N-methyl-(9CI);N-Methylfurohydroxamic Acid [Chelating Reagent for HPLC];N-(2-Furanylcarbonyl)-N-methylhydroxylamine;N-Hydroxy-N-methyl-2-furancarboxamide;N-(2-Furoyl)-N-methylhydroxylamine N-MFHA
• CAS NO: 109531-96-6
• Molecular Formula: C6H7NO3
• Molecular Weight: 141.12
• Product Categories: AMIDE;Analytical Chemistry;Bipyridyls, etc. (Chelating Reagents);Chelating Reagents;Hydroxylamines;Hydroxylamines (N-Substituted)
• Mol File: 109531-96-6.mol

Chemical Properties

• Melting Point: 101 °C
• Boiling Point: 245.7°C at 760 mmHg
• Flash Point: 102.4°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 0.0151mmHg at 25°C
• Refractive Index: 1.535
• Water Solubility: almost transparency in hot Water
• CAS DataBase Reference: N-METHYLFUROHYDROXAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYLFUROHYDROXAMIC ACID(109531-96-6)
• EPA Substance Registry System: N-METHYLFUROHYDROXAMIC ACID(109531-96-6)

Safety Data

• Hazardous Substances Data: 109531-96-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 3530, 1994 DOI: 10.1021/jo00092a007

InChI:InChI=1/C6H7NO3/c1-7(9)6(8)5-3-2-4-10-5/h2-4,9H,1H3

Upstream product

• 88-14-2 2-furanoic acid 
• 4229-44-1 N-methylhydroxyamine hydrochloride 
• 144223-33-6 2-furoyl-1H-1,2,3-benzotriazole 
• 527-69-5 2-furancarbonyl chloride 

Downstream Products

• 156026-20-9 N-isopropoxymethyl-N-benzyl-2-furancarboxamide 

Relevant articles and documents

Late-Stage Photoredox C-H Amidation of N-Unprotected Indole Derivatives: Access to N-(Indol-2-yl)amides

The late-stage functionalization of N-unprotected indoles can be useful for modifying low-molecular-weight drugs and bioactive peptides. Whereas indole carboxamides are valuable in pharmaceutical applications, the preparation N-(indol-2-yl)amides with similar structures continues to be challenging. Herein we report on visible-light-induced late-stage photoredox C-H amidation with N-unprotected indoles and tryptophan-containing peptides, leading to the formation of N-(indol-2-yl)amide derivatives. N-Unprotected indoles and aryloxyamides that contain an electron-withdrawing group could be coupled directly to eosin Y as the photocatalyst by irradiation with a green light-emitting diode at room temperature. Mechanistic studies and density functional theory calculations indicate that the transformation might proceed through the oxidative C-H functionalization of indole with a PS? to PS?- cycle. This protocol provides a new toolkit for the late-stage modification labeling and peptide-drug conjugation of N-unprotected indole derivatives.

Efficient Conversions of Carboxylic Acids into O-Alkyl, N-Alkyl and O,N-Dialkylhydroxamic Acids

Carboxylic acids were conveniently converted into unsubstituted, N-alkyl-, O-alkyl-, and O,N-dialkylhydroxamic acids via acylbenzotriazole intermediates. The ready availability of the reagents, mild conditions, and easy handling of the intermediates are advantageous.

A Facile Preparation of N-(Isopropoxyalkyl) Amides by Generation and Trapping of N-Acyliminium Ions from Ionization-Rearrangement Reactions of N-Triflyloxy Amides

A series of hydroxamic acids were converted to N-triflyloxy amides which were heated in 2-propanol to give N-(1-isopropoxyalkyl) amides in high yields.The method is simple, direct, and extremely tolerant of structural diversity both in the N-acyl group, a