221626-01-3

Basic information

• Product Name: 2-cyclohexyl-1-cyanobenzene
• Synonyms: 2-cyclohexyl-1-cyanobenzene
• CAS NO: 221626-01-3
• Molecular Weight: 185.269
• Mol File: 221626-01-3.mol

Chemical Properties

• CAS DataBase Reference: 2-cyclohexyl-1-cyanobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyclohexyl-1-cyanobenzene(221626-01-3)
• EPA Substance Registry System: 2-cyclohexyl-1-cyanobenzene(221626-01-3)

Safety Data

• Hazardous Substances Data: 221626-01-3(Hazardous Substances Data)

Upstream product

• 5400-91-9 2-cyclohexyl-aniline; hydrochloride 
• 108-85-0 1-bromocyclohexane 
• 100-47-0 benzonitrile 
• 873-32-5 2-Chlorobenzonitrile 
• 136-01-6 cyclohexanecarboxylic acid Na-salt 
• 85-01-8 phenanthrene 
• 91-15-6 phthalonitrile 
• 110-82-7 cyclohexane 
• 931-51-1 cyclohexylmagnesiumchloride 
• 2042-37-7 o-cyanobromobenzene 
• 931-50-0 cyclohexylmagnesium bromide 
• 59734-92-8 1-bromo-2-cyclohexylbenzene 
• 557-21-1 dicyanozinc 

Downstream Products

• 1276042-20-6 4-(p-tolyl)-4H-spiro[benzo[d][1,2]dioxine-1,1’-cyclohexan]-4-amine 
• 1537171-20-2 4-phenyl-4H-spiro[benzo[d][1,2]dioxine-1,1'-cyclohexane]-4-amine 
• 1537171-29-1 CCDC 891331 
• 1537171-27-9 4-(3-chlorophenyl)-4H-spiro[benzo[d][1,2]dioxine-1,1'-cyclohexan]-4-amine 
• 1537171-26-8 4-(4-chlorophenyl)-4H-spiro[benzo[d][1,2]dioxine-1,1'-cyclohexan]-4-amine 
• 1537171-25-7 4-(naphthalen-2-yl)-4H-spiro[benzo[d][1,2]dioxine-1,1'-cyclohexan]-4-amine 
• 1537171-23-5 C₂₅H₂₅NO₃ 
• 1537171-22-4 4-(2-methoxyphenyl)-4H-spiro[benzo[d][1,2]dioxine-1,1'-cyclohexane]-4-amine 
• 1537171-21-3 4-(4-methoxyphenyl)-4H-spiro[benzo[d][1,2]dioxine-1,1'-cyclohexan]-4-amine 
• 854181-78-5 (2-cyclohexylphenyl)methanamine 
• 97023-48-8 2-cyclohexylbenzoic acid 

Relevant articles and documents

Direct synthesis of 2- and 4-alkylbenzonitriles from alkylation of aromatic nitriles in the presence of pyridine transition metal complexes

Alkylation of aromatic nitriles in the presence of pyridine transition metal complexes yields 2- and 4-alkylbenzonitriles.

Direct arylation of strong aliphatic C–H bonds

Despite the widespread success of transition-metal-catalysed cross-coupling methodologies, considerable limitations still exist in reactions at sp3-hybridized carbon atoms, with most approaches relying on prefunctionalized alkylmetal or bromide coupling partners1,2. Although the use of native functional groups (for example, carboxylic acids, alkenes and alcohols) has improved the overall efficiency of such transformations by expanding the range of potential feedstocks3–5, the direct functionalization of carbon–hydrogen (C–H) bonds—the most abundant moiety in organic molecules—represents a more ideal approach to molecular construction. In recent years, an impressive range of reactions that form C(sp3)–heteroatom bonds from strong C–H bonds has been reported6,7. Additionally, valuable technologies have been developed for the formation of carbon–carbon bonds from the corresponding C(sp3)–H bonds via substrate-directed transition-metal C–H insertion8, undirected C–H insertion by captodative rhodium carbenoid complexes9, or hydrogen atom transfer from weak, hydridic C–H bonds by electrophilic open-shell species10–14. Despite these advances, a mild and general platform for the coupling of strong, neutral C(sp3)–H bonds with aryl electrophiles has not been realized. Here we describe a protocol for the direct C(sp3) arylation of a diverse set of aliphatic, C–H bond-containing organic frameworks through the combination of light-driven, polyoxometalate-facilitated hydrogen atom transfer and nickel catalysis. This dual-catalytic manifold enables the generation of carbon-centred radicals from strong, neutral C–H bonds, which thereafter act as nucleophiles in nickel-mediated cross-coupling with aryl bromides to afford C(sp3)–C(sp2) cross-coupled products. This technology enables unprecedented, single-step access to a broad array of complex, medicinally relevant molecules directly from natural products and chemical feedstocks through functionalization at sites that are unreactive under traditional methods.

Manganese-Catalyzed Cross-Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism

The substrate scope and the mechanism have been investigated for the MnCl2-catalyzed cross-coupling reaction between aryl halides and Grignard reagents. The transformation proceeds rapidly and in good yield when the aryl halide component is an aryl chloride containing a cyano or an ester group in the para position or a cyano group in the ortho position. A range of other substituents gave no conversion of the aryl halide or led to the formation of side products. A broader scope was observed for the Grignard reagents, where a variety of alkyl- and arylmagnesium chlorides participated in the coupling. Two radical-clock experiments were carried out, and in both cases an intermediate aryl radical was successfully trapped. The cross-coupling reaction is therefore believed to proceed by an SRN1 mechanism, with a triorganomanganate complex serving as the most likely nucleophile and single-electron donor. Other mechanistic scenarios were excluded based on the substrate scope of the aryl halide.

Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere via N-H imines as an intramolecular directing group

Copper-catalyzed benzylic C-H oxygenation under an oxygen atmosphere was developed starting from carbonitriles and Grignard reagents via N-H imine intermediates. The present process is characterized by the following two-step sequence in a one-pot manner: (1) addition of Grignard reagents to carbonitriles to form N-H imines and (2) benzylic C-H oxygenation (C=O bond formation) triggered by 1,5-hydrogen atom transfer with transient iminyl copper species.

Ruthenium-catalyzed para-selective oxidative cross-coupling of arenes and cycloalkanes

A novel, direct para-selective oxidative cross-coupling of benzene derivatives with cycloalkanes catalyzed by ruthenium was developed. A wide range of arenes bearing electron-withdrawing substituents was functionalized directly with simple cycloalkanes with high para-selectivity; arenes with electron-donating groups were mainly para-functionalized. Benzoic acid can be used directly.

Decarboxylative photosubstitution of dicyanobenzenes with aliphatic carboxylate ions

The photoreaction of dicyanobenzenes with aliphatic carboxylate ions afforded alkylcyanobenzenes and alkyldicyanobenzenes via decarboxylative substitution. The redox-photosensitized reaction system was effective in improving the product yield. The efficie

NEW COMPOUNDS I/418

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Manganese-catalyzed substitution of activated aryl halides (X = Cl, Br and F) and aryl ethers by organomagnesium reagents

In the presence of manganese chloride (10%), Grignard reagents readily react in THF with aryl bromides, chlorides and even fluorides, as well as aryl methyl ethers bearing in the ortho- or para-position an electron withdrawing activating group (CN, CH=NR, oxazoline). Aryl and N- or S- alkylmagnesium halides have been used successfully. The reaction is performed under mild conditions (0 °C to room temperature, 30 minutes to 24 hours) and leads to cross-coupling products in good yields.