397322-82-6

Usage

General Description

2-Amino-3-chlorobenzaldehyde is an organic compound with the chemical formula C7H6ClNO. It is a pale yellow to brownish solid with a strong, bitter almond odor. 2-Amino-3-chlorobenzaldehyde is mainly used as an intermediate in the production of various dyes, pharmaceuticals, and other organic compounds. It is also used in the synthesis of benzene derivatives and as a reagent in organic chemistry reactions. Additionally, 2-Amino-3-chlorobenzaldehyde has been studied for its potential antimicrobial and anticancer properties, though further research is needed to fully understand its biological activities. Due to its hazardous nature, proper handling and disposal procedures should be followed when working with this chemical.

InChI:InChI=1/C7H6ClNO/c8-6-3-1-2-5(4-10)7(6)9/h1-4H,9H2

Upstream product

• 53312-77-9 2-amino-3-chlorobenzonitrile 
• 22233-52-9 3-chloro-2-nitrobenzaldehyde 
• 61487-25-0 (2-amino-3-chlorophenyl)methanol 

Downstream Products

• 67092-20-0 2,8-dichloroquinazoline 
• 60610-15-3 8-Chlor-2-oxo-1,2-dihydrochinazolin 
• 915922-73-5 8-chloroquinoline-2-carboxylic acid 
• 1064578-06-8 8-chloro-2-(2-chlorophenyl)-quinolin-3-amine 

Relevant academic research and scientific papers

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.

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.

Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation

A small library of tunable chiral pyridine-aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio- and diastereoselectivity (up to 99% ee and >20:1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[b][1,4]diazepines.

Novel Mps1 kinase inhibitors: From purine to pyrrolopyrimidine and quinazoline leads

Mps1, also known as TTK, is a mitotic checkpoint protein kinase that has become a promising new target of cancer research. In an effort to improve the lead-likeness of our recent Mps1 purine lead compounds, a scaffold hopping exercise has been undertaken.

HETEROCYCLIC COMPOUNDS AND THEIR USE AS INHIBITORS OF PI3K ACTIVITY

Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorde

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.

α-amination of nitrogen heterocycles: Ring-fused aminals

Aromatic aminoaldehydes react with cyclic amines to produce ring-fused aminals under thermal conditions. This process is applied to two-step syntheses of the quinazolinone alkaloids deoxyvasicinone and rutaecarpine. Copyright