6,8-Dibromoimidazo[1,2-a]pyrazine

Base Information

• Chemical Name: 6,8-Dibromoimidazo[1,2-a]pyrazine
• CAS No.: 63744-22-9
• Molecular Formula: C6H3Br2N3
• Molecular Weight: 276.918
• Hs Code.: 2933990090
• European Community (EC) Number: 811-059-4
• ChEMBL ID: CHEMBL302560
• DSSTox Substance ID: DTXSID20567145
• Nikkaji Number: J848.048F
• Wikidata: Q72464455
• Mol file: 63744-22-9.mol

Synonyms:6,8-dibromoimidazo[1,2-a]pyrazine;63744-22-9;6,8-Dibromo-imidazo[1,2-a]pyrazine;MFCD08460056;6 pound not8-Dibromoimidazo[1 pound not2-a]pyrazine;IMIDAZO[1,2-A]PYRAZINE, 6,8-DIBROMO-;SCHEMBL103894;CHEMBL302560;DTXSID20567145;UQCZZGIPIMJBCL-UHFFFAOYSA-N;BCP13891;CS-M3157;6,8 dibromoimidazo[1,2-a]pyrazine;6.8-dibromoimidazo[1,2-a]pyrazine;6,8-dibromo imidazo[1,2-a]pyrazine;AKOS005256704;PB27935;PS-3924;6,8-dibromoimidazo[1,2-alpha]pyrazine;SY006840;AM20070424;D4967;EN300-101186;A834499;J-518178;Z808644654

Chemical Property of 6,8-Dibromoimidazo[1,2-a]pyrazine

Chemical Property:

• Melting Point: 165.0 to 169.0 °C
• Refractive Index: 1.802
• PKA: -0.36±0.30(Predicted)
• PSA: 30.19000
• Density: 2.36 g/cm³
• LogP: 2.25430
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 276.86732
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

98% ^*data from raw suppliers

6,8-Dibromoimidazo[1,2-a]pyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN2C=C(N=C(C2=N1)Br)Br
• Uses: 6,8-Dibromoimidazo[1,2-a]pyrazine is a imidazopyrazine derivative with uterine-relaxing, antibronchospastic, and cardiac-stimulating properties. 6,8-Dibromoimidazo[1,2-a]pyrazine also displays theophylline-like properties. It is an Intermediate in organic syntheses.

Technology Process of 6,8-Dibromoimidazo[1,2-a]pyrazine

There total 7 articles about 6,8-Dibromoimidazo[1,2-a]pyrazine 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: 100.0%

2-amino-3,5-dibromopyrazine (24241-18-7) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 6,8-dibromoimidazo[1,2-a]pyrazine (63744-22-9)

Guidance literature:

In tetrahydrofuran; water; at 20 ℃; for 19h; Reflux;

Reference yield: 99.0%

1-bromo-2,2-dimethoxyethane (7252-83-7) + 2-amino-3,5-dibromopyrazine (24241-18-7) → 6,8-dibromoimidazo[1,2-a]pyrazine (63744-22-9)

Guidance literature:

1-bromo-2,2-dimethoxyethane; 2-amino-3,5-dibromopyrazine; In water; at 20 ℃; for 2h; Reflux;

With sodium hydrogencarbonate; In water; for 0.25h;

Reference yield: 89.0%

2-chloroethanal (107-20-0) + 2-amino-3,5-dibromopyrazine (24241-18-7) → 6,8-dibromoimidazo[1,2-a]pyrazine (63744-22-9)

Guidance literature:

In water; isopropyl alcohol; Reflux;

DOI:10.1016/j.bmcl.2010.07.008

upstream raw materials:

2-chloroethanal

2-amino-3,5-dibromopyrazine

bromoacetaldehyde

1-bromo-2,2-dimethoxyethane

Downstream raw materials:

4-(6-bromo-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic acid ethyl ester

6-bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazine

N-cyclopropyl-4-{6-[5-(methylamino)-5-oxopent-1-yn-1-yl]-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl}benzamide

N-cyclopropyl-4-{6-[(E)-(1-methyl-5-oxopyrrolidin-2-ylidene)methyl]-8-[(2-methylpropyl)amino]imidazo[1,2-a]pyrazin-3-yl}benzamide

Refernces

• 1、 Huang, Boshi,Liang, Xin,Li, Cuicui,Chen, Wenmin,Liu, Tao,Li, Xiao,Sun, Yueyue,Fu, Lu,Liu, Huiqing,De Clercq, Erik,Pannecouque, Christophe,Zhan, Peng,Liu, Xinyong. "Fused heterocycles bearing bridgehead nitrogen as potent HIV-1 NNRTIs. Part 4: Design, synthesis and biological evaluation of novel imidazo[1,2-a]pyrazines". . p. 330 - 337. Retrieved 2015.
• 2、 Kumar, Gulshan,Goel, Richa,Paul, Kamaldeep,Luxami, Vijay. "Investigation of rotameric conformations of substituted imidazo-[1,2-a] pyrazine: Experimental and theoretical approaches". . p. 9707 - 9717. Retrieved 2018/03/23.