6-Bromocinnolin-4-ol

Base Information

• Chemical Name: 6-Bromocinnolin-4-ol
• CAS No.: 876-88-0
• Molecular Formula: C8H5BrN2O
• Molecular Weight: 225.0421
• Hs Code.: 2933990090
• NSC Number: 114061
• UNII: 9VXF8HBE3X
• DSSTox Substance ID: DTXSID50236514
• Wikidata: Q83118485
• ChEMBL ID: CHEMBL1722545
• Mol file: 876-88-0.mol

Synonyms:6-Bromocinnolin-4-ol;876-88-0;552330-87-7;6-bromo-1H-cinnolin-4-one;6-Bromo-4-cinnolinol;4(1H)-Cinnolinone, 6-bromo-;NSC114061;9VXF8HBE3X;MLS002706546;NSC-114061;6-bromo-4(1H)-Cinnolinone;NSC 114061;UNII-9VXF8HBE3X;4-Cinnolinol, 6-bromo-;SCHEMBL796509;6-bromocinnolin-4 (1h)-one;6-bromanyl-1H-cinnolin-4-one;CHEMBL1722545;DTXSID50236514;VWMHMZLZLNLBPB-UHFFFAOYSA-N;6-bromo-1,4-dihydrocinnolin-4-one;MFCD09834642;MFCD16659039;AKOS016007238;AKOS016007903;CS-W023187;PB43041;AC-22861;AS-57379;SMR001573949;FT-0690108;FT-0712682;EN300-681456;F11858;A830544;A870247

Chemical Property of 6-Bromocinnolin-4-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 276-277 °C
• Boiling Point: 374.174°C at 760 mmHg
• PKA: 2.32±0.40(Predicted)
• Flash Point: 180.095°C
• PSA: 46.01000
• Density: 1.822g/cm³
• LogP: 2.09790
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 223.95853
• Heavy Atom Count: 12
• Complexity: 229

Purity/Quality:

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

6-Bromocinnolin-4-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C(=O)C=NN2

Technology Process of 6-Bromocinnolin-4-ol

There total 17 articles about 6-Bromocinnolin-4-ol 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: 88.0%

1-(2-amino-5-bromophenyl)ethanone (29124-56-9) → 6-bromocinnolin-4-ol (876-88-0)

Guidance literature:

1-(2-amino-5-bromophenyl)ethanone; With hydrogenchloride; In water; at 0 ℃; for 0.333333h;

With sodium nitrite; In water; at 0 ℃; Reflux;

Reference yield: 82.0%

1-(2-amino-5-bromophenyl)ethanone (29124-56-9) → 6-bromo-1H-cinnolin-4-one (876-88-0,552330-87-7)

Guidance literature:

1-(2-amino-5-bromophenyl)ethanone; With hydrogenchloride; In water; at 0 ℃; for 0.25h;

With sodium nitrite; at 0 ℃; Reflux;

DOI:10.1021/acs.jmedchem.5b00515

Reference yield: 70.0%

N-(2-acetyl-4-bromophenyl)acetamide (29124-64-9) → 6-bromo-1H-cinnolin-4-one (876-88-0,552330-87-7)

Guidance literature:

With hydrogenchloride; sodium nitrite; In tetrahydrofuran; water; at 0 ℃; for 22h; Reflux;

upstream raw materials:

6-bromo-4-oxo-1,4-dihydro-3-cinnolinecarboxylic acid

1-(2-amino-5-bromophenyl)ethanone

N-(2-acetyl-4-bromophenyl)acetamide

2-aminoacetophenone

Downstream raw materials:

2-(4-(6-bromo-3-nitrocinnolin-4-ylamino)phenyl)-2-methylpropanenitrile

2-(4-(3-amino-6-bromocinnolin-4-ylamino)phenyl)-2-methylpropanenitrile

2-(4-(8-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-1H-imidazo[4,5-c]cinnolin-1-yl)phenyl)-2-methylpropanenitrile

2-(4-(8-bromo-1H-imidazo[4,5-c]cinnolin-1-yl)phenyl)-2-methylpropanenitrile

Refernces

• 1、 -. "Cnoline compound PI3K kinase inhibitor as well as preparation method and application thereof in pharmacy". Paragraph 0082-0084. . Retrieved 2021/06/02.
• 2、 Yu, Tao,Li, Ning,Wu, Chengde,Guan, Amy,Li, Yi,Peng, Zhengang,He, Miao,Li, Jie,Gong, Zhen,Huang, Lei,Gao, Bo,Hao, Dongling,Sun, Jikui,Pan, Yan,Shen, Liang,Chan, Chichung,Lu, Xiulian,Yuan, Hongyu,Li, Yongguo,Li, Jian,Chen, Shuhui. "Discovery of Pyridopyrimidinones as Potent and Orally Active Dual Inhibitors of PI3K/mTOR". . p. 256 - 261. Retrieved 2018/03/21.