5,6-Difluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: 5,6-Difluoro-2-methyl-1,2,3,4-tetrahydroquinoline
• CAS No.: 80076-46-6
• Molecular Formula: C₁₀H₁₁F₂N
• Molecular Weight: 183.201
• DSSTox Substance ID: DTXSID70444659
• Nikkaji Number: J355.003F
• Mol file: 80076-46-6.mol

Synonyms:80076-46-6;5,6-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline;5,6-Difluoro-1,2,3,4-tetrahydro-2-methylquinoline;SCHEMBL9598979;DTXSID70444659;MFCD20681385;PB47941;AS-83319;CS-0369579;FT-0750590;E82730

Chemical Property of 5,6-Difluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Chemical Property:

• Boiling Point: 247.5±40.0oC (760 Torr)
• PKA: 4.40±0.40(Predicted)
• Flash Point: 103.5±27.3oC
• PSA: 12.03000
• Density: 1.139±0.06 g/cm3 (20oC 760 Torr)
• LogP: 2.84940
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 183.08595568
• Heavy Atom Count: 13
• Complexity: 186

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2=C(N1)C=CC(=C2F)F

Technology Process of 5,6-Difluoro-2-methyl-1,2,3,4-tetrahydroquinoline

There total 4 articles about 5,6-Difluoro-2-methyl-1,2,3,4-tetrahydroquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

8-bromo-5,6-difluoro-2-methylquinoline (131190-82-4) → (+/-)-5,6-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline (80076-46-6)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In acetic acid; at 50 ℃; under 760 - 3800 Torr;

DOI:10.1248/cpb.44.642

Reference yield:

3,4-difluoroaniline (3863-11-4) → (+/-)-5,6-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline (80076-46-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sulfuric acid / 0.5 h / 10 - 20 °C

2.1: acetic acid; bromine; sodium acetate / 60 - 80 °C

3.1: sodium 3-nitrobenzenesulfonate; ferrous(II) sulfate heptahydrate; boric acid; hydrogenchloride / water / 0.5 h / Reflux

3.2: 1 h / Reflux

4.1: palladium on activated carbon; acetic acid; sodium acetate / water / 50 °C

4.2: 6 h / 20 °C

With hydrogenchloride; ferrous(II) sulfate heptahydrate; sulfuric acid; palladium on activated carbon; bromine; sodium acetate; boric acid; acetic acid; sodium 3-nitrobenzenesulfonate; In water;

DOI:10.3390/molecules24081641

Reference yield:

3,4-difluoroacetanilide (458-11-7) → (+/-)-5,6-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline (80076-46-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid; bromine; sodium acetate / 60 - 80 °C

2.1: sodium 3-nitrobenzenesulfonate; ferrous(II) sulfate heptahydrate; boric acid; hydrogenchloride / water / 0.5 h / Reflux

2.2: 1 h / Reflux

3.1: palladium on activated carbon; acetic acid; sodium acetate / water / 50 °C

3.2: 6 h / 20 °C

With hydrogenchloride; ferrous(II) sulfate heptahydrate; palladium on activated carbon; bromine; sodium acetate; boric acid; acetic acid; sodium 3-nitrobenzenesulfonate; In water;

DOI:10.3390/molecules24081641

upstream raw materials:

8-bromo-5,6-difluoro-2-methylquinoline

3,4-difluoroaniline

3,4-difluoroacetanilide

N-(2-bromo-4,5-difluorophenyl)acetamide

Downstream raw materials:

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

Refernces

• 1、 Hashimoto, Koji,Okaichi, Yoshihiko,Nomi, Daisuke,Miyamoto, Hisashi,Bando, Masahiko,Kido, Masaru,Fujimura, Tsutomu,Furuta, Takuya,Minamikawa, Jun-Ichi. "A practical synthesis of (S)-(-)-nadifloxacin: Novel acid-catalyzed racemization of tetrahydroquinaldine derivative". . p. 642 - 645. Retrieved 2007/10/03.