4044-99-9

Basic information

• Product Name: 6-BROMO-2-METHYLIMIDAZO[1,2-A]PYRIDINE
• Synonyms: 6-BROMO-2-METHYLIMIDAZO[1,2-A]PYRIDINE;IMidazo[1,2-a]pyridine, 6-broMo-2-Methyl-
• CAS NO: 4044-99-9
• Molecular Formula: C₈H₇BrN₂
• Molecular Weight: 211.07
• Product Categories: Fused Ring Systems;Halides
• Mol File: 4044-99-9.mol

Chemical Properties

• Melting Point: 101.0-101.5 °C
• Appearance: /
• Density: 1.6 g/cm³
• Refractive Index: 1.663
• PKA: 5.47±0.10(Predicted)
• CAS DataBase Reference: 6-BROMO-2-METHYLIMIDAZO[1,2-A]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2-METHYLIMIDAZO[1,2-A]PYRIDINE(4044-99-9)
• EPA Substance Registry System: 6-BROMO-2-METHYLIMIDAZO[1,2-A]PYRIDINE(4044-99-9)

Safety Data

• Hazardous Substances Data: 4044-99-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
6-Bromo-2-methylimidazo[1,2-a]pyridine is used as a building block in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and properties allow for the development of new compounds with potential therapeutic and pesticidal effects.
Used in Research and Development:
6-Bromo-2-methylimidazo[1,2-a]pyridine serves as a valuable tool in research and development for studying the biological effects and mechanisms of action of similar compounds. Its mutagenic properties in certain studies also make it a potential carcinogen, providing insights into the development of safer and more effective drugs and agrochemicals.

InChI:InChI=1/C8H7BrN2/c1-6-4-11-5-7(9)2-3-8(11)10-6/h2-5H,1H3

Upstream product

• 1072-97-5 5-bromo-2-pyridylamine 
• 598-31-2 1-bromoacetone 
• 78-95-5 chloroacetone 

Downstream Products

• 1246184-50-8 6-bromo-3-iodo-2-methylimidazo[1,2-a]pyridine 
• 728864-58-2 6-bromo-2-methylimidazo [1,2-a]pyridine-3-carbaldehyde 

Relevant articles and documents

Identification of the Privileged Position in the Imidazo[1,2-a]pyridine Ring of Phosphonocarboxylates for Development of Rab Geranylgeranyl Transferase (RGGT) Inhibitors

Members of the Rab GTPase family are master regulators of vesicle trafficking. When disregulated, they are associated with a number of pathological states. The inhibition of RGGT, an enzyme responsible for post-translational geranylgeranylation of Rab GTPases represents one way to control the activity of these proteins. Because the number of molecules modulating RGGT is limited, we combined molecular modeling with biological assays to ascertain how modifications of phosphonocarboxylates, the first reported RGGT inhibitors, rationally improve understanding of their structure-activity relationship. We have identified the privileged position in the core scaffold of the imidazo[1,2-a]pyridine ring, which can be modified without compromising compounds' potency. Thus modified compounds are micromolar inhibitors of Rab11A prenylation, simultaneously being inactive against Rap1A/Rap1B modification, with the ability to inhibit proliferation of the HeLa cancer cell line. These findings were rationalized by molecular docking, which recognized interaction of phosphonic and carboxylic groups as decisive in phosphonocarboxylate localization in the RGGT binding site.

Rapid, metal-free and aqueous synthesis of imidazo[1,2-: A] pyridine under ambient conditions

A novel, rapid and efficient route to imidazo[1,2-a]pyridines under ambient, aqueous and metal-free conditions is reported. The NaOH-promoted cycloisomerisations of N-propargylpyridiniums give quantitative yield in a few minutes (10 g scale). A comparison of common green metrics to current routes showed clear improvements, with at least a one order of magnitude increase in space-time-yield.

TETRAHYDROIMIDAZOPYRIDINE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of substituted 5,6,7,8-tetrahydroimidazo[l,2-α]pyridine derivatives, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory di

FUSED IMIDAZOLE AND PYRAZOLE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of substituted benzimidazole, imidazo[1,2-a]pyridine and pyrazolo[1,5-a]pyridine derivatives, and analogues thereof, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

FUSED IMIDAZOLE AND PYRAZOLE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of substituted benzimidazole, imidazo[1,2-α]pyridine and pyrazolo[1,5- α]pyridine derivatives, and analogues thereof, being potent modulators of human TNFα activity, are accordingly of benefit in the treatment and/or prevention of various human a

IMIDAZOPYRIDINE DERIVATIVES AS MODULATORS OF TNF ACTIVITY

A series of imidazo[l,2-a]pyridine derivatives of formula (I), being potent modulators of human TNFa activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including autoimmune and inflammatory disorders; neurological and neurodegenerative disorders; pain and nociceptive disorders; cardiovascular disorders; metabolic disorders; ocular disorders; and oncological disorders.

HISTAMINE H3 INVERSE AGONISTS AND ANTAGONISTS AND METHODS OF USE THEREOF

Provided herein are fused imidazolyl compounds, methods of synthesis, and methods of use thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders and metabolic disorders. Compounds provided herein inhibit the activity of histamine H3 receptors and modulate the release of various neurotransmitters, such as histamine, acetylcholine, norepinephrine, and dopamine (e.g. at the synapse). Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.