7131-11-5

Basic information

• Product Name: 1-benzyl(adamantane)
• Synonyms: 1-benzyl(adamantane)
• CAS NO: 7131-11-5
• Molecular Weight: 226.362
• Mol File: 7131-11-5.mol

Chemical Properties

• CAS DataBase Reference: 1-benzyl(adamantane)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl(adamantane)(7131-11-5)
• EPA Substance Registry System: 1-benzyl(adamantane)(7131-11-5)

Safety Data

• Hazardous Substances Data: 7131-11-5(Hazardous Substances Data)

Upstream product

• 770-70-7 1-chloromethyladamantane 
• 71-43-2 benzene 
• 27011-47-8 homoadamantanyl chloride 
• 63534-35-0 3-azidohomoadamantane 
• 786-08-3 adamantan-1-yl(phenyl)methanol 
• 24569-89-9 1,3-dehydroadamantane 
• 108-88-3 toluene 
• 100-52-7 benzaldehyde 
• 768-90-1 1-Adamantyl bromide 
• 1589-82-8 phenylmagnesium bromide 
• 31919-47-8 1-benzoyladamantane 
• 23074-42-2 1-adamantanecarbonitrile 
• 770-71-8 1-adamantanemethanol 
• 14651-42-4 1-(bromomethyl)adamantane 

Downstream Products

• 7131-12-6 α-(1-adamantyl)-p-nitrotoluene 
• 7131-13-7 α-(1-adamantyl)-o-nitrotoluene 
• 56714-76-2 (4-Adamantan-1-ylmethyl-phenyl)-carbamic acid ethyl ester 
• 76271-59-5 α-1-Adamantyl-o-toluidin 
• 76271-60-8 N-Methyl-α-1-adamantyl-p-toluidin 
• 7131-15-9 1-<4-Brom-benzyl>-adamantan 
• 77817-09-5 1-adamantylcyclohexylmethane 

Relevant articles and documents

Exhaustive One-Step Bridgehead Methylation of Adamantane Derivatives with Tetramethylsilane

A methylation protocol of adamantane derivatives was investigated and optimized using AlCl3 and tetramethylsilane as the methylation agent. Substrates underwent exhaustive methylation of all available bridgehead positions with yields ranging from 62 to 86 %, and up to six methyl groups introduced in one step. Scaling-up of the reaction was demonstrated by performing the >40 gram-scale synthesis of 1,3,5,7-tetramethyladamantane with 62 % yield. For several substrates, rearrangements were observed, as well as cleavage of functional groups or Csp3?Csp2 bonds or even cyclohexyl-adamantyl bonds. Based on mechanistic studies, it is suggested that a reactive methylation complex is formed from tetramethylsilane and AlCl3. X-ray diffraction structures of hexamethylated bis-adamantyls reveal elongation or widening of sp3 carbon bonds between adamantyl moieties to 1.585(3) ? and 125.26(9)° due to repulsive H???H contacts.

Chemical Transformations of Tetracyclo[3.3.1.13,7.01,3]decane (1,3-Dehydroadamantane): IX. Noncatalytic Reactions with Alkylarenes

Abstract: The reaction of 1,3-dehydroadamantane with alkylbenzenes was studied for the first time. It involved the C–H bond of the alkyl substituent in the α-position with respect to the aromatic ring. The proposed radical mechanism of the reaction was co

Nickel-catalyzed cross-coupling of umpolung carbonyls and alkyl halides

An effective nickel-catalyzed cross-coupling of Umpolung carbonyls and alkyl halides was developed. Complementary to classical alkylation techniques, this reaction utilizes Umpolung carbonyls as the environmentally benign alkyl nucleophiles, providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Nickel-Catalyzed Cross-Coupling of Umpolung Carbonyls and Alkyl Halides

An effective nickel-catalyzed cross-coupling of Umpolung carbonyls and alkyl halides was developed. Complementary to classical alkylation techniques, this reaction utilizes Umpolung carbonyls as the environmentally benign alkyl nucleophiles, providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Silver-catalyzed benzylation and allylation reactions of tertiary and secondary alkyl halides with grignard reagents

Treatment of alkyl halides, including tertiary alkyl bromides, with benzylic or allylic Grignard reagent in the presence of a catalytic amount of silver nitrate in ether yielded the corresponding cross-coupling products in high yields. The coupling reactions of tertiary alkyl halides provide efficient access to quaternary carbon centers.

Formation of (1-adamantylcarbinyl)arenes from 3-azidohomoadamantane-aluminum chloride-aromatic substrates

Reaction of 3-azidohomoadamantane with aromatic substrates catalyzed by aluminum chloride at 80 °C gave the corresponding (1-adamantylcarbinyl)arene in >90% yield. The reaction proceeds exclusively with elimination of azide ion. Competitive reaction with toluene (T)-benzene (B) gave an average kT/kB of ～14/1. The results indicate that a straightforward primary cation is probably not the actual attacking electrophile. The possible intervention of a bridged ion is discussed.

Hypobetalipoproteinemic agents. II. Compounds related to 4-(1- adamantyloxy)aniline

While the previously used displacement reaction of sodium 1-adamantyl oxide on 4-fluoronitrobenzene was applicable to the preparation of 4-(1-adamantyloxy) aniline and several related compounds, certain derivatives were not easily accessible by this route

Polycyclophenylpyrrolidines, their compositions and use

Compounds of the formula STR1 where R4 X is a polycyclocoupled group and R1 and R2 are H or simple hydrocarbon and R3 has the same value and additionally simple acyl, can be made by a variety of syntheses. They have hypolipedemic and antiatherosclerotic properties, and are useful in that field.