23074-42-2

Usage

Uses

Used in Chemical Synthesis:
1-Adamantanecarbonitrile is used as a starting reagent for the synthesis of adamantyl-1,3,4-oxathiazol-2-one, a compound with potential applications in various fields.
Used in Coordination Chemistry:
1-Adamantanecarbonitrile is used as a ligand in coordination chemistry, reacting with W2(OCMe3)6 to yield W(CAd)(OCMe3)3 (Ad=1-adamantyl). This reaction demonstrates its ability to form stable complexes with metal centers, which can be useful in various applications, such as catalysis and materials science.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 5239, 1980 DOI: 10.1021/jo01314a003Synthesis, p. 1140, 1985 DOI: 10.1055/s-1985-31453

InChI:InChI=1/C11H15N/c12-7-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10H,1-6H2

Upstream product

• 768-90-1 1-Adamantyl bromide 
• 7677-24-9 trimethylsilyl cyanide 
• 935-56-8 1-chloroadamantane 
• 7314-85-4 2-adamantyl bromide 
• 281-23-2 adamantane 
• 768-95-6 1-adamanthanol 
• 143-33-9 sodium cyanide 
• 24225-08-9 methanesulfonyl cyanide 
• 91233-19-1 1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione 
• 5511-18-2 adamantane-1-carboxamide 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 70891-99-5 α-Azido-1-adamantylmethyl phenyl sulfone 
• 22110-53-8 1-adamantyl isocyanide 
• 85433-68-7 3-(1-Adamantyl)-3,5-dihydro-5,5-dimethyl-4H-1,2,3-triazol-4-on 

Downstream Products

• 67886-57-1 1-Amino-1-(1-adamantyl)-2-phenylsulfonylethen 
• 31919-47-8 1-benzoyladamantane 
• 173601-35-9 adamantane-1-carboximidamide 
• 17768-41-1 adamantylmethylamine 
• 55241-31-1 5-adamantan-1-yl-3-(3-nitro-phenyl)-[1,2,4]oxadiazole 
• 54608-95-6 5-adamantan-1-yl-3-(4-nitro-phenyl)-[1,2,4]oxadiazole 
• 281-23-2 adamantane 
• 3405-48-9 N-(1-adamantyl)formamide 
• 38256-01-8 di(1-adamantyl) ketone 
• 59223-70-0 3-hydroxy-1-adamantanecarbonitrile 
• 91120-86-4 3-fluoroadamantane-1-carbonitrile 
• 91120-88-6 3-Fluoro-4-oxa-tricyclo[4.3.1.1^3,8]undecane-1-carbonitrile 
• 712-74-3 1,2,4,5-benzenetetracarbonitrile radical anion 
• 828-51-3 1-Adamantanecarboxylic acid 

Relevant academic research and scientific papers

Reactions of 1,3-dehydroadamantane with inorganic oxygen-free acids

A convenient and efficient procedure has been developed for the synthesis of 1-azidoadamantane, 1-adamantyl isocyanate, and 1-adamantyl isothiocyanate by reaction of 1,3-dehydroadamantane with hydrazoic, isocyanic, and isothiocyanic acids, respectively, under mild conditions. The reaction of 1,3-dehydroadamantane with hydrogen cyanide under analogous conditions gives adamantane-1-carbonitrile in a poor yield which may be improved using hexane as solvent.

Lewis Acid-Catalyzed Preparation of Bridge-head Adamantanoid Nitriles from their Corresponding Halides and Trimethylsilyl Cyanide

Bridge-head adamantyl and diamantyl nitriles 2 have been prepared in good yields by refluxing the corresponding halides 1 with trimethylsilyl cyanide and tin(IV) chloride in dichloromethane.

Method for dehydrating primary amide into nitriles under catalysis of cobalt

The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.

Copper-Catalyzed Intermolecular Functionalization of Unactivated C(sp3)-H Bonds and Aliphatic Carboxylic Acids

Intermolecular functionalization of C(sp3)-H bonds and aliphatic carboxylic acids enables the efficient synthesis of high value-added organic compounds from readily available starting materials. Although methods involving hydrogen atom transfer have been developed for such functionalization, these methods either work for only activated C(sp3)-H bonds or bring in a narrow set of functional groups. Here we describe a Cu-catalyzed process for the diverse functionalization of both unactivated C(sp3)-H bonds and aliphatic carboxylic acids. The process is enabled by the trapping of alkyl radicals generated through hydrogen atom abstraction by arylsulfonyl-based SOMO-philes, which introduces a large array of C, N, S, Se, and halide-based functional groups. The chemoselectivity can be switched from C-H functionalization to decarboxylative functionalization by matching the bond dissociation energy of the hydrogen atom transfer reagent with that of the target C-H or O-H bond.

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.

Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).

Method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by Ru coordination compound

The invention discloses a method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by a Ru coordination compound. The method comprises: adding a Ru coordination compound, an alkali, a primary amine and an organic solvent into a reaction test tube according to a mol ratio of 1:100:(100-500):1000-3000, and carrying out a stirring reaction under the condition of 80 to120 DEG C; and when gas chromatography monitors that the raw materials completely disappear, stopping the reaction, collecting the reaction solution, centrifuging the reaction solution, taking the supernatant, extracting with dichloromethane, merging the organic phases, drying, filtering, evaporating the organic solvent under reduced pressure to obtain a filtrate, and carrying out column chromatography purification on the filtrate to obtain the target product nitrile. According to the invention, the catalyst is good in activity, single in catalytic system, good in product selectivity, simple in subsequent treatment and good in system universality after the reaction is finished, has a good catalytic effect on various aryl, alkyl and heteroaryl substituted primary amines, and also has a gooddehydrogenation performance on secondary amines.

Acceptorless dehydrogenation of amines to nitriles catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated bimetallic ruthenium (II) complex

We have developed a clean, atom-economical and environmentally friendly route for acceptorless dehydrogenation of amines to nitriles by combining a new dual N-heterocyclic carbene-nitrogen-phosphine ligand R(CNP)2 (R = o-xylyl) with a ruthenium precursor [RuCl2(η6-C6H6)]2. In this system, the electronic and steric factors of amines had a negligible influence on the reaction and a broad range of functional groups were well tolerated. All of the investigated amines could be converted to nitriles in good yield of up to 99% with excellent selectivity. The unprecedented catalytic performance of this system is attributed to the synergistic effect of two ruthenium centers chelated by R(CNP)2 and a plausible reaction mechanism is proposed according to the active species found via in situ NMR and HRMS.

Method for preparing nitrile

The invention provides a method for preparing nitrile. Aldoxime carboxylic ester is used as a reactant to prepare a nitrile compound. The aldoxime carboxylic ester can be completely converted into corresponding nitrile under common catalysis of ferric salt and phenol within a few minutes. The method for preparing the nitrile has the advantages of gentle reaction conditions, simple and easy-to-getused reagents, cheap and environment-friendly catalyst, wide substrate application range, simple operation, rapid reaction and the like.

OXIDATIVE CONVERSION OF ALIPHATIC ALDEHYDES TO NITRILES USING OXOAMMONIUM SALT

The present invention relates to an oxidative transformation method of aliphatic benzaldehydes to nitriles using NH_4OAc through oxoammonium salts. By using stoichiometric amounts of oxoammonium salts to establish optimal reaction conditions associated with the oxidative conversion of aliphatic benzaldehydes to nitriles, high yields of nitrile can be selectively obtained, and the oxoammonium salts used can be oxidized and reused in a simple method.COPYRIGHT KIPO 2020