3-BROMOQUINOLIN-8-AMINE

Base Information

• Chemical Name: 3-BROMOQUINOLIN-8-AMINE
• CAS No.: 139399-67-0
• Molecular Formula: C9H7BrN2
• Molecular Weight: 223.072
• Hs Code.: 2933499090
• Mol file: 139399-67-0.mol

Synonyms:3-Brom-[8]chinolylamin;3-bromo-8-aminoquinoline;3-bromo-quinolin-8-ylamine;8-amino-3-bromoquinoline;3-bromo-[8]quinolylamine;QC-3976;8-Quinolinamine,3-bromo;

Chemical Property of 3-BROMOQUINOLIN-8-AMINE

Chemical Property:

• PSA: 38.91000
• LogP: 3.16070

Purity/Quality:

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

3-Bromoquinolin-8-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Bromoquinolin-8-amine acts as a reagent for the synthesis and structure activity relationship of 3-(arylsulfonyl)-8-(piperidin-4-yl amino)quinoline derivatives as 5-HT6 receptor antagonists for the treatment of Alzheimer''s disease and Schizophrenia. Also acts as a reagent for the synthesis of certain 8-aminoquinolines and antimalarias.

Technology Process of 3-BROMOQUINOLIN-8-AMINE

There total 5 articles about 3-BROMOQUINOLIN-8-AMINE 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: 96.0%

8-nitro-3-bromoquinoline (5341-07-1) → 3-bromo-8-aminoquinoline (139399-67-0)

Guidance literature:

With iron(III) chloride; pyrographite; hydrazine hydrate; In methanol; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c6ob01325b

Reference yield:

8-nitroquinoline (607-35-2) → 3-bromo-8-aminoquinoline (139399-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NBS / acetic acid / 2 h

2: 92 percent / H₂ / 10percent Pd-C / methanol / 2280 Torr

With N-Bromosuccinimide; hydrogen; palladium on activated charcoal; In methanol; acetic acid;

DOI:10.1007/BF00823423

Reference yield:

3-bromoquinoline (5332-24-1) → 3-bromo-8-aminoquinoline (139399-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid monohydrate; fuming nitric acid

2: tin dichloride; alcoholic hydrochloric acid

With hydrogenchloride; sulfuric acid; nitric acid; tin(ll) chloride;

upstream raw materials:

8-nitro-3-bromoquinoline

hydrogenchloride

8-nitroquinoline

3-bromoquinoline

Downstream raw materials:

3-bromo-8-methoxyquinoline

3-bromo-8-fluoroquinolin-8-amine

3-iodo-8-quinolinol

Refernces

• 1、 Mehndiratta, Samir,Chen, Mei-Chuan,Chao, Yuh-Hsuan,Lee, Cheng-Hsin,Liou, Jing-Ping,Lai, Mei-Jung,Lee, Hsueh-Yun. "Effect of 3-subsitution of quinolinehydroxamic acids on selectivity of histone deacetylase isoforms". . p. 74 - 84. Retrieved 2020/11/10.
• 2、 Kuninobu, Yoichiro,Nishi, Mitsumi,Kanai, Motomu. "5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives". supporting information. p. 8092 - 8100. Retrieved 2016/09/09.