6-Bromoimidazo[1,2-a]pyridine

Base Information

• Chemical Name: 6-Bromoimidazo[1,2-a]pyridine
• CAS No.: 6188-23-4
• Molecular Formula: C7H5BrN2
• Molecular Weight: 197.034
• Hs Code.: 2933990090
• European Community (EC) Number: 689-291-9
• DSSTox Substance ID: DTXSID80383767
• Nikkaji Number: J1.723.346G
• Wikidata: Q72457067
• Mol file: 6188-23-4.mol

Synonyms:6-Bromoimidazo[1,2-a]pyridine;6188-23-4;IMIDAZO[1,2-A]PYRIDINE, 6-BROMO-;MFCD06496200;6-Bromo-inidazo[1,2-a]-pyridine;Buttpark 154\50-43;6-Bromo-imidazo[1,2-a]pyridine;SCHEMBL408627;DTXSID80383767;FXPMFQUOGYGTAM-UHFFFAOYSA-N;6-bromoimidazo [1,2-a] pyridine;BBL101003;SC1092;STL554797;AKOS004910672;CS-W003293;PB20174;6-Bromoimidazo[1,2-a]pyridine, 97%;AC-25821;SY018826;AM20061376;FT-0650239;EN300-56468;A21572;7X-0903;CU-00000000274-1;J-518429;Z855892306

Chemical Property of 6-Bromoimidazo[1,2-a]pyridine

Chemical Property:

• Melting Point: 76-78 °C
• Refractive Index: 1.688
• Boiling Point: 165 °C(Press: 1.5 Torr)
• PKA: 5.10±0.50(Predicted)
• PSA: 17.30000
• Density: 1.69 g/cm³
• LogP: 2.09680
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: slightly soluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 195.96361
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

98%, ^*data from raw suppliers

6-Bromoimidazo[1,2-a]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=NC=CN2C=C1Br
• Uses: It is used in organic syntheses and as pharmaceutical intermediates. The best results were obtained with lactams that could be introduced on the 6-bromoimidazo[1,2-a]pyridine. 1,2-dihydro-5-imidazo [1,2-a]pyridin-6-yl-6-methyl-2-oxo-3-pyridinecarbonitrile hydrochloride monohydrate 6 was synthesized in 5 steps from 6-bromoimidazo[1,2-a] pyridine using [2- 14 C] cyanoacetamide as the source of the radiolabel.

Technology Process of 6-Bromoimidazo[1,2-a]pyridine

There total 7 articles about 6-Bromoimidazo[1,2-a]pyridine 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-chloroethanal (107-20-0) + 5-bromo-2-pyridylamine (1072-97-5) → 6-bromoimidazo[1,2-a]pyridine (6188-23-4)

Guidance literature:

2-chloroethanal; 5-bromo-2-pyridylamine; In ethanol; water; for 3h; Reflux;

With sodium hydrogencarbonate; In water;

Reference yield: 97.0%

5-bromo-2-pyridylamine (1072-97-5) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 6-bromoimidazo[1,2-a]pyridine (6188-23-4)

Guidance literature:

With hydrogen bromide; In ethanol; water; at 103 ℃;

DOI:10.1021/acs.jmedchem.5b01605

Reference yield: 87.2%

5-bromo-2-pyridylamine (1072-97-5) + bromoacetaldehyde diethyl acetal → 6-bromoimidazo[1,2-a]pyridine (6188-23-4)

Guidance literature:

With hydrogen bromide; In ethanol; water; at 100 ℃; for 8h;

upstream raw materials:

5-bromo-2-pyridylamine

Bromoacetaldehyde diethyl acetal

2-chloroethanal

chloroacetaldehyde dimethyl acetal

Downstream raw materials:

6-(4-(methylsulfanyl)phenyl)-imidazo[1,2-a]pyridine

3-bromo-6-bromo-imidazo[1,2-a]pyridine

6-bromoimidazo[1,2-a]pyridine-3-carbaldehyde

Refernces

• 1、 -. "INHIBITORS OF LIN28 AND METHODS OF USE THEREOF". Page/Page column 52; 69; 102-103. . Retrieved 2021/06/26.
• 2、 Zhang, Lingtian,Lakkaniga, Naga Rajiv,Bharate, Jaideep B.,Mcconnell, Nicholas,Wang, Xiuqi,Kharbanda, Anupreet,Leung, Yuet-Kin,Frett, Brendan,Shah, Neil P.,Li, Hong-yu. "Discovery of imidazo[1,2-a]pyridine-thiophene derivatives as FLT3 and FLT3 mutants inhibitors for acute myeloid leukemia through structure-based optimization of an NEK2 inhibitor". . . Retrieved 2021/09/04.