59236-37-2

Basic information

• Product Name: 2-Amino-4-chlorobenzaldehyde
• Synonyms: 2-Amino-4-chlorobenzaldehyde
• CAS NO: 59236-37-2
• Molecular Formula: C₇H₆ClNO
• Molecular Weight: 155.58
• Mol File: 59236-37-2.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 297.0±25.0 °C(Predicted)
• Appearance: /
• Density: 1.348±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -0.70±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-4-chlorobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-chlorobenzaldehyde(59236-37-2)
• EPA Substance Registry System: 2-Amino-4-chlorobenzaldehyde(59236-37-2)

Safety Data

• Hazardous Substances Data: 59236-37-2(Hazardous Substances Data)

Usage

Description

2-Amino-4-chlorobenzaldehyde is an organic compound characterized by its aldehyde and amino functional groups, along with a chlorine atom attached to the benzene ring. It is a versatile intermediate in the synthesis of various chemical and pharmaceutical products due to its unique structure and reactivity.

Uses

Used in Pharmaceutical Industry:
2-Amino-4-chlorobenzaldehyde is used as a reagent for the synthesis of pharmaceuticals, specifically for the production of robenidine analogues. These analogues exhibit significant activity against multidrug-resistant bacteria, such as MRSA (Methicillin-resistant Staphylococcus aureus) and VRE (Vancomycin-resistant enterococci). 2-Amino-4-chlorobenzaldehyde plays a crucial role in the development of new antibiotics to combat the growing threat of antibiotic resistance.

Upstream product

• 5551-11-1 4-Chloro-2-nitrobenzaldehyde 
• 32989-56-3 5-chloro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene 
• 89-59-8 4-chloro-2-nitrotoluene 
• 7439-89-6 iron 
• 37585-16-3 (2-amino-4-chlorophenyl)methanol 
• 89-77-0 2-Amino-4-chlorobenzoic acid 
• 214971-18-3 4-chloroanthranilic acid N-methoxy-N-methylamide 
• 84459-33-6 2-bromo-4-chlorobenzaldehyde 
• 22996-18-5 (4-chloro-2-nitrophenyl)methanol 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 171917-60-5 3-(Benzyloxy)-7-chloroquinoline-2-carboxylic acid 
• 171917-57-0 Methyl-3-(benzyloxy)-7-chloroquinoline-2-carboxylate 
• 530083-91-1 [(5-Chloro-2-formyl-phenylcarbamoyl)methyl] phosphonic Acid Diethyl Ester 
• 883149-58-4 7-chloro-3-(2,5-dimethoxyphenyl)-1H-quinolin-2-one 
• 355408-08-1 (7-chloro-2-oxo-6-sulphamoyl-1,2-dihydro-3-quinolyl)phosphonic acid 
• 355399-61-0 diethyl 7-chloro-2-oxo-6-phenyl-1,2-dihydroquinolin-3-ylphosphonate 
• 355399-80-3 [7-Chloro-6-(4-methylphenyl)-2-oxo-1,2-dihydro-3-quinolyl]-phosphonic acid diethyl ester 
• 355399-86-9 [7-Chloro-6-(4-fluorophenyl)-2-oxo-1,2-dihydro-3-quinolyl]-phosphonic acid diethyl ester 
• 355399-84-7 [7-Chloro-6-(4-cyanophenyl)-2-oxo-1,2-dihydro-3-quinolyl]-phosphonic acid diethyl ester 
• 355399-68-7 [7-Chloro-6-(4-nitrophenyl)-2-oxo-1,2-dihydro-3-quinolyl]-phosphonic acid diethyl ester 
• 355399-70-1 [7-Chloro-6-(3-nitrophenyl)-2-oxo-1,2-dihydro-3-quinolyl]-phosphonic acid diethyl ester 
• 355823-06-2 6-(Anilinosulphonyl)-7-chloro-2-oxo-1,2-dihydro-3-quinolylphosphonic Acid Diethyl Ester 

Relevant articles and documents

Cationic Iridium-Catalyzed Asymmetric Decarbonylative Aryl Addition of Aromatic Aldehydes to Bicyclic Alkenes

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Repurposing an Aldolase for the Chemoenzymatic Synthesis of Substituted Quinolines

Quinoline derivatives are important natural products and pharmaceuticals, but their synthesis can be challenging due to poor yields, harsh reaction conditions, and instability of starting materials. Here we report the chemoenzymatic synthesis of quinaldic acids under mild conditions using an aldolase, trans-o-hydroxybenzylidenepyruvate hydratase-aldolase (NahE, or HBPA). A series of 2-aminobenzaldehydes derived from reduction of the corresponding nitro analogue were reacted with pyruvate in the presence of NahE to give substituted quinolines in up to 93% isolated yield. This reaction differs from the aldol condensation catalyzed by NahE in vivo, instead resembling the heterocycle formation catalyzed by its homologue, dihydrodipicolinate synthase.