76790-15-3

Basic information

• Product Name: N-hydroxy-N-methylnaphthalene-2-carboxamide
• Synonyms: 2-naphthalenecarboxamide, N-hydroxy-N-methyl-; N-Hydroxy-N-methyl-2-naphthamide
• CAS NO: 76790-15-3
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.2212
• Mol File: 76790-15-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 380.4°C at 760 mmHg
• Flash Point: 183.8°C
• Density: 1.258g/cm³
• Vapor Pressure: 1.83E-06mmHg at 25°C
• Refractive Index: 1.665
• CAS DataBase Reference: N-hydroxy-N-methylnaphthalene-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-N-methylnaphthalene-2-carboxamide(76790-15-3)
• EPA Substance Registry System: N-hydroxy-N-methylnaphthalene-2-carboxamide(76790-15-3)

Safety Data

• Hazardous Substances Data: 76790-15-3(Hazardous Substances Data)

Upstream product

• 4229-44-1 N-methylhydroxyamine hydrochloride 
• 2243-83-6 2-naphthaloyl chloride 

Downstream Products

• 93-09-4 naphthalene-2-carboxylate 

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.