80076-46-6

Basic information

• Product Name: 5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline
• Synonyms: 5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline;($$+/-$$)-5,6-Difluoro-1,2,3,4-tetrahydroquinaldine;5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline(Nadifloxacin Intermediates)
• CAS NO: 80076-46-6
• Molecular Formula: C10H11F2N
• Molecular Weight: 183.19800
• Mol File: 80076-46-6.mol

Chemical Properties

• Boiling Point: 247.5±40.0℃ (760 Torr)
• Flash Point: 103.5±27.3℃
• Appearance: /
• Density: 1.139±0.06 g/cm3 (20 ºC 760 Torr)
• PKA: 4.40±0.40(Predicted)
• CAS DataBase Reference: 5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline(80076-46-6)
• EPA Substance Registry System: 5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline(80076-46-6)

Safety Data

• Hazardous Substances Data: 80076-46-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs. Its unique structure allows for specific interactions with biological targets, potentially leading to the creation of novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its incorporation can enhance the effectiveness of these products by improving their chemical stability and biological activity against target organisms.
Used in Drug Discovery:
5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline plays a significant role in drug discovery as a structural component of potential lead compounds. Its presence in molecular scaffolds can influence the pharmacokinetics and pharmacodynamics of drug candidates, facilitating the identification of new therapeutic agents.
Used in Material Science:
5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline is also used in the development of new materials and chemical processes within material science. Its unique structure and properties can contribute to the creation of advanced materials with specific characteristics, such as improved stability or reactivity.
Overall, 5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline is a versatile chemical entity with broad applications across various industries, particularly in the development of pharmaceuticals and agrochemicals, as well as in material science and chemical research.

InChI:InChI=1S/C10H11F2N/c1-6-2-3-7-9(13-6)5-4-8(11)10(7)12/h4-6,13H,2-3H2,1H3

Upstream product

• 3863-11-4 3,4-difluoroaniline 
• 458-11-7 3,4-difluoroacetanilide 
• 64695-81-4 N-(2-bromo-4,5-difluorophenyl)acetamide 
• 131190-82-4 8-bromo-5,6-difluoro-2-methylquinoline 

Downstream Products

• 154357-40-1 9,10-difluoro-2,3-dihydro-3S-methyl-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid 

Relevant articles and documents

Synthesis, antibacterial activities, mode of action and acute toxicity studies of new oxazolidinone-fluoroquinolone hybrids

To combat bacterial resistance, a series of new oxazolidinone-fluoroquinolone hybrids have been synthesized and characterized. All synthetic hybrids were preliminarily evaluated for their in vitro antibacterial activities against 6 standard strains and 3 clinical isolates. The majority of hybrids displayed excellent activities against Gram-positive bacteria, but limited activities against Gram-negative bacteria. Hybrids OBP-4 and OBP-5 were found to be the most promising compounds. Further, in vitro antibacterial activities, mode of action and acute toxicity in mice of hybrids OBP-4 and OBP-5 were investigated. Hybrids OBP-4 and OBP-5 exhibited potent activities against Gram-positive bacteria, including drug-resistant strains. Correspondingly, studies on the mode of action of hybrids OBP-4 and OBP-5 indicated a strong inhibitory activity on protein synthesis by binding the active site of 50S subunit, but a weak inhibitory action on DNA synthesis. In addition, LD50 values of hybrids OBP-4 and OBP-5 in the acute oral toxicity were larger than 2000 mg/kg, suggesting a good safety profile.

A practical synthesis of (S)-(-)-nadifloxacin: Novel acid-catalyzed racemization of tetrahydroquinaldine derivative

(S)-(-)-Nadifloxacin [(S)-(-)-9-fluro-6,7-dihydro-8-(4-hyroxy-1- piperidyl)-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid, (S)- (-)-OPC-7251], an antibacterial agent, was synthesized from (S)-(-)-5,6- difluoro-2-methyl-1,2,3,4-tetrahydroquinoline (DFTQ), which was prepared by the optical resolution of racemic DFTQ with 2,3-di-O-benzoyl-L-tartaric acid. Racemization of the undesired enantiomer [(R)-(+)-DFTQ] was studied in the presence of various acids and the best result was obtained in the case of methanesulfonic acid. The absolute configuraton of (-)-nadifloxacin was determined as S by X-ray crystallographic analysis.