151446-29-6

Basic information

• Product Name: Benzaldehyde, 2-amino-5-chloro-3-methyl-
• Synonyms: Benzaldehyde, 2-amino-5-chloro-3-methyl-;2-Amino-5-chloro-3-methylbenzaldehyde
• CAS NO: 151446-29-6
• Molecular Formula: C₈H₈ClNO
• Molecular Weight: 169.61
• Mol File: 151446-29-6.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzaldehyde, 2-amino-5-chloro-3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 2-amino-5-chloro-3-methyl-(151446-29-6)
• EPA Substance Registry System: Benzaldehyde, 2-amino-5-chloro-3-methyl-(151446-29-6)

Safety Data

• Hazardous Substances Data: 151446-29-6(Hazardous Substances Data)

Usage

General Description

Benzaldehyde, 2-amino-5-chloro-3-methyl- is a chemical compound with the molecular formula C8H8ClNO. It is a derivative of benzaldehyde with a chlorine atom and an amino group attached to the aromatic ring. Benzaldehyde, 2-amino-5-chloro-3-methyl- is commonly used in organic synthesis and pharmaceutical research. It has potential applications in the development of pharmaceuticals and agrochemicals due to its structural properties and reactivity. Furthermore, benzaldehyde, 2-amino-5-chloro-3-methyl- is also used as a flavoring agent in the food industry due to its aromatic properties. Overall, this chemical compound has several potential uses and applications in various industries.

Upstream product

• 24596-18-7 4-chloro-2,6-dimethylaniline 
• 775331-65-2 (2-amino-5-chloro-3-methylphenyl)methanol 
• 20776-67-4 2-amino-5-chloro-3-methylbenzoic acid 

Downstream Products

• 1373758-65-6 3-bromo-N-(4-chloro-2-formyl-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1373758-69-0 3-bromo-N-(4-chloro-2-((dimethylamino)methyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1373758-70-3 3-bromo-N-(4-chloro-2-methyl-6-((methylamino)methyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide hydrochloride 
• 1373758-71-4 3-bromo-N-(4-chloro-2-((isopropylamino)methyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide hydrochloride 
• 1373758-72-5 N-(2-(((tert-butyl)amino)methyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide hydrochloride 
• 1373758-73-6 (Z)-3-bromo-N-(4-chloro-2-((hydroxyimino)methyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1373758-74-7 3-bromo-N-(4-chloro-2-((Z)-methoxyiminomethyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1373758-75-8 3-bromo-N-(4-chloro-2-methyl-6-(thiazolidin-2-yl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1373758-66-7 3-bromo-N-(4-chloro-2-methyl-6-((methylamino)methyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1373758-67-8 3-bromo-N-(4-chloro-2-((isopropylamino)methyl)-6-methylphenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1373758-68-9 N-(2-(((tert-butyl)amino)methyl)-4-chloro-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide 
• 1370337-78-2 C₁₇H₁₀BrCl₂N₅O 
• 1417565-54-8 C₁₈H₁₀Cl₂F₃N₅O 
• 1417565-57-1 C₁₉H₁₂Cl₂F₃N₅O₂ 

Relevant articles and documents

Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization

Asymmetric Prins cyclization of in situ generated quinone methides and o-aminobenzaldehyde has been developed with chiral phosphoric acid as an efficient catalyst. This unconventional method provides a facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives in excellent yield and with excellent diastereo- and enantioselectivities (up to 99% yield and 99% ee). Mechanistic studies suggested that the three adjacent tertiary stereocenters were constructed through the sequential formation of C-O, C-C, and C-N bonds.

Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes

A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.

Gold(I)-catalyzed unprecedented rearrangement reaction between 2-aminobenzaldehydes with propargyl amines: An expedient route to 3-aminoquinolines

Access to aminoquinolines: A gold(I)-catalyzed unprecedented rearrangement reaction between 2-aminobenzaldehydes with propargyl amine was studied. The study provided, for the first time, direct access to 3-aminoquinolines in one step starting from readily available starting materials (see scheme). Elegantly designed experiments were employed to unravel the mechanism of this unprecedented rearrangement, which are corroborated by DFT calculations.