220957-39-1

Basic information

• Product Name: 5-Bromofuro[2,3-b]pyridine
• Synonyms: 5-Bromofuro[2,3-b]pyridine;5-broMofuro[2
• CAS NO: 220957-39-1
• Molecular Formula: C₇H₄BrNO
• Molecular Weight: 198
• Mol File: 220957-39-1.mol

Chemical Properties

• Boiling Point: 226℃
• Flash Point: 91℃
• Appearance: /
• Density: 1.710
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-Bromofuro[2,3-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromofuro[2,3-b]pyridine(220957-39-1)
• EPA Substance Registry System: 5-Bromofuro[2,3-b]pyridine(220957-39-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 220957-39-1(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
5-Bromofuro[2,3-b]pyridine is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of biologically active molecules with potential therapeutic applications.
Used in Organic Synthesis:
In the realm of organic synthesis, 5-Bromofuro[2,3-b]pyridine is employed as a versatile building block for the preparation of a wide range of organic compounds. Its ability to form carbon-carbon and carbon-heteroatom bonds makes it an essential component in the synthesis of complex organic molecules.
Used as a Reagent in Chemical Reactions:
5-Bromofuro[2,3-b]pyridine also serves as a reagent in various chemical reactions, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. Its presence facilitates the synthesis of new compounds with desired properties and functions.
Used in the Synthesis of Biologically Active Molecules:
Due to its structural features, 5-Bromofuro[2,3-b]pyridine is extensively used in the synthesis of biologically active molecules. These molecules have potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.
Used in the Development of Materials:
5-Bromofuro[2,3-b]pyridine contributes to the development of novel materials with specific properties, such as conductivity, magnetism, or optical activity. Its integration into material science allows for the creation of advanced materials with potential applications in various industries.

Synthetic route

5-bromo-3-((trimethylsilyl)ethynyl)pyridin-2-oI (942589-70-0) → 5-bromofuro<2,3-b>pyridine (220957-39-1)

Conditions	Yield
With copper(l) iodide; triethylamine In ethanol at 70℃; for 3h;	32%

5-bromo-3-ethynyl-2(1H)-pyridinone (942589-71-1) → 5-bromofuro<2,3-b>pyridine (220957-39-1)

Conditions	Yield
In dimethyl sulfoxide at 120℃; for 0.5h; Irradiation;

5-nitrofuro<2,3-b>pyridine (34668-29-6) → 5-bromofuro<2,3-b>pyridine (220957-39-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: Al(Hg), water / diethyl ether / 3 h / Ambient temperature 2: 1.) 47 percent aq. HBr, NaNO2, 2.) CuBr, 37 percent aq. HBr / 1.) 0 deg C, 15 min View Scheme

furo[2,3-b]pyridin-5-ylamine (34668-30-9) → 5-bromofuro<2,3-b>pyridine (220957-39-1)

Conditions	Yield
With hydrogen bromide; copper(I) bromide; sodium nitrite 1.) 0 deg C, 15 min; Yield given; Multistep reaction;

5-bromofuro<2,3-b>pyridine (220957-39-1) → C7H4FNO3S

Conditions	Yield
Stage #1: 5-bromofuro<2,3-b>pyridine With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); N-Methyldicyclohexylamine; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In isopropyl alcohol at 110℃; for 1h; Microwave irradiation; Stage #2: With N-fluorobis(benzenesulfon)imide In isopropyl alcohol at 20℃; for 3h;	42%

methyl 3-[[(4-methylcyclohexyl)carbonyl](1-methylethyl)amino]-5-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-thiophenecarboxylate (942589-73-3) + 5-bromofuro<2,3-b>pyridine (220957-39-1) → methyl 5-(4-furo[2,3-b]pyridin-5-ylphenyl)-3-[[(4-methylcyclohexyl)carbonyl](1-methylethyl)amino]-2-thiophenecarboxylate (942589-74-4)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; for 0.3h; Irradiation;

Upstream product

• 34668-30-9 furo[2,3-b]pyridin-5-ylamine 
• 13466-38-1 5-bromopyridin-2-ol 
• 381233-75-6 5-bromo-2-hydroxy-3-iodopyridine 
• 942589-70-0 5-bromo-3-((trimethylsilyl)ethynyl)pyridin-2-ol 
• 942589-71-1 5-bromo-3-ethynyl-2(1H)-pyridinone 
• 34668-29-6 5-nitrofuro<2,3-b>pyridine 

Downstream Products

• 942589-74-4 methyl 5-(4-furo[2,3-b]pyridin-5-ylphenyl)-3-[[(4-methylcyclohexyl)carbonyl](1-methylethyl)amino]-2-thiophenecarboxylate 

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