14631-43-7

Basic information

• Product Name: 2-Cyanotetrahydrofuran
• Synonyms: 2-Cyanotetrahydrofuran;tetrahydro-2-Furancarbonitrile
• CAS NO: 14631-43-7
• Molecular Formula: C₅H₇NO
• Molecular Weight: 97
• Mol File: 14631-43-7.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 2-Cyanotetrahydrofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyanotetrahydrofuran(14631-43-7)
• EPA Substance Registry System: 2-Cyanotetrahydrofuran(14631-43-7)

Safety Data

• Hazardous Substances Data: 14631-43-7(Hazardous Substances Data)

Usage

General Description

2-Cyanotetrahydrofuran, also known as CTHF, is a chemical compound with the formula C5H7NO. It is a colorless liquid with a faint odor, and it is soluble in water and alcohols. CTHF is used as a solvent and reagent in pharmaceutical and chemical industries for the synthesis of various compounds. It has also been studied for potential applications in biofuels and as a precursor to agricultural chemicals. Additionally, CTHF has been reported to have some potential health hazards, and caution should be exercised when handling and using this chemical.

Upstream product

• 23247-31-6 (E)-tetrahydrofuran-2-carbaldehyde oxime 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 91470-28-9 tetrahydrofuran-2-carboxamide 
• 13369-70-5 2-chlorotetrahydrofuran 
• 7677-24-9 trimethylsilyl cyanide 
• 13436-45-8 2-methoxytetrahydrofuran 
• 1608-67-9 2-acetoxytetrahydrofuran 
• 924899-41-2 1,1,1,3,3,3-hexafluoroisopropoxytetrahydrofuran 
• 109-99-9 tetrahydrofuran 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 38694-47-2 4-bromobutyraldehyde 
• 631-57-2 Acetyl cyanide 

Downstream Products

• 109-99-9 tetrahydrofuran 
• 1191-99-7 2,3-dihydro-2H-furan 
• 214262-61-0 cyanomethylene cyclopropane 
• 5648-87-3 2-cyclopropyl-2-hydroxyacetonitrile 
• 74-90-8 hydrogen cyanide 
• 1431558-32-5 C₁₇H₁₇N₃OS 

Relevant articles and documents

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

Decarboxylative alkynylation and cyanation of carboxylic acids using photoredox catalysis and hypervalent iodine reagents

Alkynes and nitriles are important functional groups that serve as versatile building blocks in organic synthesis and find applications in material and medicinal sciences. A convenient and straightforward access to both classes of compounds under mild conditions is, therefore, highly desirable. Herein, we disclose the decarb-oxylative alkynylation and cyanation of broadly available carboxylic acids using photoredox catalysis and hyper-valent iodine reagents. Choices of both catalysts and reagents were crucial. Computational and experimental studies revealed two different possible mechanisms that are dictated by the oxidation potential of the reagents: radical for alkynylation, ionic for cyanation.

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation

The one-step conversion of aliphatic carboxylic acids to the corresponding nitriles has been accomplished via the merger of visible light mediated photoredox and cyanobenziodoxolones (CBX) reagents. The reaction proceeded in high yields with natural and non-natural α-amino and α-oxy acids, affording a broad scope of nitriles with excellent tolerance of the substituents in the α position. The direct cyanation of dipeptides and drug precursors was also achieved. The mechanism of the decarboxylative cyanation was investigated both computationally and experimentally and compared with the previously developed alkynylation reaction. Alkynylation was found to favor direct radical addition, whereas further oxidation by CBX to a carbocation and cyanide addition appeared more favorable for cyanation. A concerted mechanism is proposed for the reaction of radicals with EBX reagents, in contrast to the usually assumed addition elimination process.