69975-67-3

Basic information

• Product Name: Indane-5-carbonitrile
• Synonyms: Indane-5-carbonitrile;1H-INDENE-5-CARBONITRILE, 2,3-DIHYDRO
• CAS NO: 69975-67-3
• Molecular Formula: C₁₀H₉N
• Molecular Weight: 143.18516
• Product Categories: Fused Ring Systems
• Mol File: 69975-67-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Indane-5-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: Indane-5-carbonitrile(69975-67-3)
• EPA Substance Registry System: Indane-5-carbonitrile(69975-67-3)

Safety Data

• Hazardous Substances Data: 69975-67-3(Hazardous Substances Data)

Upstream product

• 506-68-3 bromocyane 
• 496-11-7 INDANE 
• 24425-40-9 indan-5-amine 
• 28042-80-0 5-indancarboaldehyde azine 
• 30084-91-4 indan-5-carbaldehyde 
• 623-26-7 terephthalonitrile 
• 109-64-8 1,3-dibromo-propane 
• 330660-35-0 silver cyanide 

Relevant articles and documents

Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes

Aromatic nitriles are key structural units in organic chemistry and, therefore, highly attractive targets for C-H activation. Herein, the development of an arene-limited, nondirected C-H cyanation based on the use of two cooperatively acting commercially available ligands is reported. The reaction enables the cyanation of arenes by C-H activation in the absence of directing groups and is therefore complementary to established approaches.

Ligand-Promoted Non-Directed C?H Cyanation of Arenes

This article reports the first example of a 2-pyridone accelerated non-directed C?H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment (kH/kD=4.40) indicates that the C?H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method.

Reductive activation of arenes 22. Reactions of the terephthalonitrile radical anion and dianion with α,ω-dibromoalkanes. New evidence for the charge transfer complex as a key intermediate in the reactions of the dianion

The major products of reactions of the terephthalonitrile radical anion with α,ω-dibromoalkanes Br(CH2)nBr (n = 3-5) were 4-(ω-bromoalkyl)benzonitriles. Analogous reactions of the terephthalonitrile dianion mainly yielded α,ω-bis(4-cyanophenyl) alkanes. Both transformations are convenient one-step routes to otherwise not easily accessible compounds that are valuable as versatile building blocks. The results of alkylation allow one to suggest that reactions of the dianion with intermediate 4-(ω-bromoalkyl)benzonitriles proceed more rapidly than those with the starting α,ω-dibromoalkanes. This was confirmed by competitive reactions of the dianion with 4-(ω-bromoalkyl)benzonitriles and the corresponding alkyl bromides. To explain such a ratio of the reaction rates, a mechanism was proposed for the reaction of the dianion with 4-(ω-bromoalkyl)benzonitriles. According to this mechanism, a charge transfer complex is a key reaction intermediate.