372147-50-7

Basic information

• Product Name: Imidazo[1,2-a]pyridine-5-carboxaldehyde (9CI)
• Synonyms: Imidazo[1,2-a]pyridine-5-carboxaldehyde (9CI);IMidazo[1,2-a]pyridine-5-carboxaldehyde;Imidazo[1,2-a]pyridine-5-carbaldehyde
• CAS NO: 372147-50-7
• Molecular Formula: C8H6N2O
• Molecular Weight: 146.14604
• Product Categories: AMINETERTIARY;ALDEHYDE
• Mol File: 372147-50-7.mol

Chemical Properties

• Melting Point: 123-126°C
• Appearance: /
• Density: 1.25 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.75±0.50(Predicted)
• CAS DataBase Reference: Imidazo[1,2-a]pyridine-5-carboxaldehyde (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Imidazo[1,2-a]pyridine-5-carboxaldehyde (9CI)(372147-50-7)
• EPA Substance Registry System: Imidazo[1,2-a]pyridine-5-carboxaldehyde (9CI)(372147-50-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 372147-50-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Imidazo[1,2-a]pyridine-5-carboxaldehyde (9CI) is used as a pharmaceutical candidate for its anti-cancer properties, targeting various types of cancer through its ability to modulate multiple signaling pathways involved in tumor growth and progression.
Used in Anti-inflammatory Applications:
Imidazo[1,2-a]pyridine-5-carboxaldehyde (9CI) is utilized as an anti-inflammatory agent, leveraging its capacity to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Neurodegenerative Disease Treatment:
Imidazo[1,2-a]pyridine-5-carboxaldehyde (9CI) is employed as a potential therapeutic agent for neurodegenerative diseases, due to its demonstrated neuroprotective effects and ability to target the underlying mechanisms of such conditions.
Used in Organic Synthesis:
As a building block in organic synthesis, Imidazo[1,2-a]pyridine-5-carboxaldehyde (9CI) is used for the preparation of other complex chemical compounds, contributing to the development of new pharmaceuticals and materials.

Upstream product

• 177485-39-1 ethyl (imidazo[1,2-a]pyridin-5-yl)carboxylate 
• 167884-17-5 5-hydroxymethylimidazo[1,2-a]pyridine 
• 69142-64-9 ethyl 6-aminopicolinate 

Downstream Products

• 429690-43-7 3-bromoimidazo[1,2-a]pyridine-5-carbaldehyde 
• 429690-44-8 3-nitroimidazo[1,2-a]pyridine-5-carbaldehyde 
• 372147-66-5 (Z)-ethyl α-[(triphenylphosphoranylidene)amino]-β-(imidazo[1,2-a]pyridin-5-yl)propenoate 

Relevant articles and documents

BENZISOXAZOLE COMPOUND

Disclosed is a compound represented by the general formula (I) or a salt thereof: wherein any one of R1, R2 and R3 represents a group represented by the formula: -(CH2)m-NR11R12 (wherein m is 1 or 2; and R11 and R12 independently represent a hydrogen atom or a C1-6 alkyl group or may, together with a nitrogen atom to which R11 and R12 are bound, form a 4- or 5-membered cyclic group); the remaining two or R1, R2 and R3 independently represent a group represented by the formula: -(O)n-R21 (wherein n is 0 or 1; and R21 represents a hydrogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, or the like); and R4 represents a C1-6 alkyl group which may have a substituent or the like.

Efficient synthesis of new polyfunctionalized thiadiazaacenaphthylenes from imidazo[1,2-a]pyridines

New heterocycles containing sulfur and nitrogen with an azaindolizine moiety were synthesized. The imidazo[1,2-a]pyridine-2,5-dicarboxylates (9a, b, 10a, b) and 5-formylimidazo[1,2-a]pyridine-2-carboxylates (17a, b) treated with ethyl thioglycolate and lithium hydroxide underwent ring closure yielding the multifunctional[2,3,3]cyclazines (13) and (18). Under similar conditions, the imidazo[1,2-a]pyridinecarbaldehydes (22a, b) and (29a, b) were converted into the linearly cyclized compounds thieno[3,2-b]imidazo[1,2-a]pyridines (23, 31) and a peri annulated product thiadiazaacenaphthylene (30).

Heterocyclization of functionalized vinylic derivatives of imidazo[1,2-α]pyridines

Heterocyclization of functionalized vinylic derivatives of imidazo[1,2-α]pyridines was explored experimentally and theoretically using semiempirical AM1 and ab initio methods. A range of functionalized vinylic derivatives (azido, amino, and carbodiimide groups) were prepared for conversion into pyrroloazaindoles 19-22, imidazo[1,x]-; (x=5, 6, 7, 8), [2,6]-, and [2,7]naphthyridines 28-30, 35-38 by thermal reaction. In the case of vinylic groups in the 5 position, peri annulation also was observed. The experimental and theoretical data are compared and discussed.