16269-13-9

Usage

Uses

1-Adamantaneacetonitrile is used as pharmaceutical intermediate.

InChI:InChI=1/C12H17N/c13-2-1-12-6-9-3-10(7-12)5-11(4-9)8-12/h9-11H,1,3-8H2

Upstream product

• 19026-73-4 2-(1-adamantyl)acetamide 
• 19835-38-2 1-adamantylacetyl chloride 
• 40430-66-8 1-ethynyladamantane 
• 2094-74-8 1-Adamantanecarbaldehyde 
• 52086-94-9 1-(2-Methoxy-vinyl)-adamantan 
• 18220-83-2 adamantan-1-ylacetaldehyde 
• 24569-89-9 1,3-dehydroadamantane 
• 75-05-8 acetonitrile 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 795-63-1 1-<(p-tolylsulfonyl)methoxy>adamantane 
• 151-50-8 potassium cyanide 

Downstream Products

• 698993-88-3 C₃₁H₃₂N₂ 
• 1425934-28-6 C₃₁H₃₂N₂*ClHO₄ 
• 40283-73-6 Thiosulfuric acid S-[N-(2-adamantan-1-yl-ethyl)-carbamimidoylmethyl] ester 
• 19026-73-4 2-(1-adamantyl)acetamide 
• 770-69-4 1-ethyladamantane 
• 768-91-2 1-methyl-adamantane 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 26482-53-1 2-(1-adamantyl)ethanamine 

Relevant academic research and scientific papers

Adamantylation of carbonitriles with 1,3-dehydroadamantane and its homologs

1,3-Dehydroadamantane and its methyl-substituted homologs react with carbonitriles at the α-carbon atom of the latter to give the corresponding α-adamantyl carbonitriles. This reaction provide a convenient one-step procedure for selective synthesis of branched nitriles which are difficult to obtain by traditional procedures.

One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions

A one-pot protocol to obtain C1-homologated aliphatic nitriles was achieved by treating aromatic and aliphatic aldehydes with the (methoxymethyl)triphenylphosphonium ylide followed by hydrolysis of the resulting methyl vinyl ethers with pTsOH (Ts = para-toluenesulfonyl) and treatment with molecular iodine and aqueous ammonia under metal cyanide free conditions. Neopentyl-type nitriles, which could not be obtained by conventional methods that involved conversion of the neopentyl alcohol into a tosylate and treatment with metal cyanide, were successfully obtained by using the present method.

Conversion of 3,3,3-Trisubstituted Prop-1-ynes with tert-Butylhydrazine into 3,3,3-Trisubstituted Propionitriles Catalyzed by TpRh(C2H4)2/P(2-furyl)3

The combination of TpRh(C2H4)2 (Tp = tris(pyrazol-1-yl)borate) and P(2-furyl)3 catalyzes the reaction of tertiary alkyl-substituted alkynes with tert-butylhydrazine, leading to the formation of 3,3,3-trisubstituted propionitrile derivatives. This reaction system is applicable to 1,1-disubstituted propargyl alcohols and amines to afford the corresponding β-cyanohydrins and β-amino nitriles, respectively. The catalytic cycle involves the formation of a vinylidenerhodium complex as a key intermediate.

A facile and efficient one-pot synthesis of nitriles from carboxylic acids

Direct transformation of aliphatic carboxylic acids to the corresponding nitriles can be easily performed with acetonitrile in the presence of sulfuric acid. Georg Thieme Verlag Stuttgart.