70201-43-3

Basic information

• Product Name: 3-BROMO-4-FORMYLPYRIDINE
• Synonyms: 3-Bromoisonicotinaldehyde ,98%;3-Bromopyridine-4-carboxaldehyde ,98%;5-BroMopyridine-4-carboxaldehyde;CHEMBRDG-BB 4003258;3-BROMO-4-PYRIDINECARBOXALDEHYDE;3-BROMO-4-FORMYLPYRIDINE;3-BROMO-PYRIDINE-4-CARBALDEHYDE;3-BROMOPYRIDINE-4-CARBOXALDEHYDE
• CAS NO: 70201-43-3
• Molecular Formula: C₆H₄BrNO
• Molecular Weight: 186.01
• EINECS: -0
• Product Categories: C1 to C6;C5 to C6;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Organic Building Blocks;NULL;pharmacetical;Aldehydes;Pyridines;Pyridine;Building Blocks;Halogenated;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 70201-43-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 81-82 °C(lit.)
• Boiling Point: 246.2 °C at 760 mmHg
• Flash Point: 102.7 °C
• Appearance: /
• Density: 1.683 g/cm³
• Vapor Pressure: 0.0275mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• PKA: 0.90±0.18(Predicted)
• CAS DataBase Reference: 3-BROMO-4-FORMYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMO-4-FORMYLPYRIDINE(70201-43-3)
• EPA Substance Registry System: 3-BROMO-4-FORMYLPYRIDINE(70201-43-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/38-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 70201-43-3(Hazardous Substances Data)

Usage

Description

3-BROMO-4-FORMYLPYRIDINE, also known as 3-Bromo-4-pyridinecarboxaldehyde, is an organic compound with the molecular formula C6H4BrNO. It features a pyridine ring with a bromine atom at the 3-position and a formyl group (aldehyde) at the 4-position. 3-BROMO-4-FORMYLPYRIDINE is a versatile intermediate in organic synthesis and has potential applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
3-BROMO-4-FORMYLPYRIDINE is used as a reagent for the synthesis of 3,4,5-trisubstituted 4,5-dihydro-1,2,4-oxadiazoles agonists. These agonists interact with the G-protein-coupled bile acid receptor 1 (TGR5), which can induce insulin secretion. This interaction may be utilized as a potential treatment for diabetes mellitus, offering a novel approach to managing blood sugar levels in diabetic patients.

InChI:InChI=1/C6H4BrNO/c7-6-3-8-2-1-5(6)4-9/h1-4H

Upstream product

• 626-55-1 3-Bromopyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 872-85-5 pyridine-4-carbaldehyde 
• 865449-16-7 3-bromo-4-(dibromomethyl)pyridine 
• 3430-22-6 3-Bromo-4-methylpyridin 
• 108-18-9 diisopropylamine 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 107-31-3 Methyl formate 
• 2591-86-8 N-Formylpiperidine 
• 663170-90-9 3-bromo-4-(diethoxymethyl)pyridine 

Downstream Products

• 222167-48-8 3-(2-phenylethynyl)pyridine-4-carboxaldehyde 
• 263024-69-7 3-bromo-4-(cyclohex-2-enylmethanol)pyridine 
• 606123-02-8 2-[3,5-di-iso-propyl-6-(2,2,2-trifluoroethoxy)benzene]-4-formylpyridine 
• 650628-88-9 3-methylthioisonicotinaldehyde 
• 941608-71-5 C₁₂H₁₂BrNO₄ 
• 953805-52-2 C₁₂H₁₀BrNO₃ 
• 941608-87-3 C₂₀H₂₁F₂NO₂S 
• 870235-32-8 4-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid methyl ester 
• 871583-22-1 methyl 4-(methylthio)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate 

Relevant articles and documents

Pyridine analogues of spirocyclic σ1 receptor ligands

Spirocyclic benzopyrans 2 interact with high affinity and selectivity with σ1 receptors. Bioisosteric replacement of the benzene ring of the benzopyran substructure with the electron rich thiophene ring (3) led to increased σ1 affinity. Herein the synthesis and pharmacological evaluation of electron deficient pyridine bioisosteres 4 are reported. Homologation of the aldehyde 6 to afford the pyridylacetaldehyde derivative 8 was performed by a Wittig reaction. Bromine lithium exchange of the bromopyridine 8, addition to 1-benzylpiperidin-4-one and cyclization led to the spirocyclic pyrranopyridine 10. Hydrogenolytic removal of the N-benzyl moiety of 10 provided the secondary amine 11, which allowed the introduction of various N-substituents (12a-d). Cyclization of the hydroxy acetal 9 with HCl led to various modifications of the substituent in 3′-position. Generally the σ1 affinity of the pyridine derivatives is reduced compared with those of the benzene and thiophene derivatives 2 and 3. However, the relationships between the structure and the σ1 affinity follow the same rules as for the benzene and thiophene derivatives. The most promising σ1 ligand within this class of compounds is the pyranopyridine 15 with a double bond in the pyran ring revealing a Ki-value of 4.6 nM and a very high selectivity (>217-fold) over the σ2 subtype.

One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes

The transition metal-free coupling reactions of unactivated diazanaphthalenes were studied using only lithium tetramethylpiperidine (LiTMP) reagent. Symmetrical and nonsymmetrical bis-diazanaphthalenes were synthesized in moderate to high yield by homo- and cross-coupling of related monomers. In addition, the single-step synthesis of diquinoxalino [2,3-a: 2', 3'c] phenazine and 2,2': 3', 2″ - terquinoxaline using the appropriate equivalent amount of LiTMP was performed. The products were characterized by means of NMR spectroscopy and HRMS spectrometry.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof:wherein Y1 is of formula (?) or formula (y):Ring Y is a 5- to 6-membered heteroaryl ring; and V4, V5, Rx, x, y, and n are as defined herein. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.