4-Bromo-6,7-dimethoxycinnoline

Base Information

• Chemical Name: 4-Bromo-6,7-dimethoxycinnoline
• CAS No.: 879014-17-2
• Molecular Formula: C10H9BrN2O2
• Molecular Weight: 269.098
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70696919
• Wikidata: Q82626686
• Mol file: 879014-17-2.mol

Synonyms:4-BROMO-6,7-DIMETHOXYCINNOLINE;879014-17-2;Cinnoline, 4-bromo-6,7-dimethoxy-;SCHEMBL2209746;DTXSID70696919;4-Bromo-6,7-dimethoxycinnoline?;IZEOAYBTVXVTBB-UHFFFAOYSA-N

Chemical Property of 4-Bromo-6,7-dimethoxycinnoline

Chemical Property:

• Boiling Point: 382.3±52.0 °C(Predicted)
• PKA: 0.41±0.10(Predicted)
• PSA: 44.24000
• Density: 1.544±0.06 g/cm3(Predicted)
• LogP: 2.40950
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 267.98474
• Heavy Atom Count: 15
• Complexity: 218

Purity/Quality:

98%min ^*data from raw suppliers

4-Bromo-6,7-dimethoxycinnoline 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=CN=N2)Br)OC

Technology Process of 4-Bromo-6,7-dimethoxycinnoline

There total 2 articles about 4-Bromo-6,7-dimethoxycinnoline 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: 77.0%

6,7-dimethoxycinnolin-4-ol (99072-22-7) → 4-bromo-6,7-dimethoxy cinnoline (879014-17-2)

Guidance literature:

With phosphorus(V) oxybromide; In acetonitrile; at 70 ℃;

DOI:10.1016/j.bmcl.2012.01.086

Reference yield:

2-amino-4,5-dimethoxyacetophenone (4101-30-8) → 4-bromo-6,7-dimethoxy cinnoline (879014-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; sodium nitrite / water / 75 °C

2: phosphorus(V) oxybromide / acetonitrile / 70 °C

With hydrogenchloride; sodium nitrite; phosphorus(V) oxybromide; In water; acetonitrile;

DOI:10.1016/j.bmcl.2012.01.086

Reference yield: 95.6%

6-bromo-1H-indazole (79762-54-2) + 4-bromo-6,7-dimethoxy cinnoline (879014-17-2) → 4-(6-bromo-1H-indazol-1-yl)-6,7-dimethoxycinnoline

Guidance literature:

With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine; In toluene; at 115 ℃; for 24h;

upstream raw materials:

6,7-dimethoxycinnolin-4-ol

2-amino-4,5-dimethoxyacetophenone

Downstream raw materials:

4-(6,7-dimethoxycinnolin-4-yl)benzaldehyde

Refernces

• 1、 Yao, Xingjun,Yang, Hongfa,Wan, Yanhui,Bie, Li,Liu, Xinrui,Liu, Zhonghui. "Synthesis and evaluation of vascular endothelial growth factor receptor-2 inhibitory activity of 6,7-dimethoxycinnoline derivatives". . p. 984 - 988. Retrieved 2013/12/04.
• 2、 Hu, Essa,Ma, Ji,Biorn, Christopher,Lester-Zeiner, Dianna,Cho, Robert,Rumfelt, Shannon,Kunz, Roxanne K.,Nixey, Thomas,Michelsen, Klaus,Miller, Silke,Shi, Jianxia,Wong, Jamie,Hill Della Puppa, Geraldine,Able, Jessica,Talreja, Santosh,Hwang, Dah-Ren,Hitchcock, Stephen A.,Porter, Amy,Immke, David,Allen, Jennifer R.,Treanor, James,Chen, Hang. "Rapid identification of a novel small molecule phosphodiesterase 10A (PDE10A) tracer". experimental part. p. 4776 - 4787. Retrieved 2012/07/28.