711-01-3

Basic information

• Product Name: ADAMANTANE-1-CARBOXYLIC ACID METHYL ESTER
• Synonyms: Adamantan-1-carboxylic acid, methyl ester;RARECHEM AQ TC 1002;LABOTEST-BB LT00007834;METHYL 1-ADAMANTANECARBOXYLATE;1-ADAMANTANECARBOXYLIC ACID METHYL ESTER;ADAMANTANE-1-CARBOXYLIC ACID METHYL ESTER;AKOS BC-0473;1-(Methoxycarbonyl)adamantane
• CAS NO: 711-01-3
• Molecular Formula: C₁₂H₁₈O₂
• Molecular Weight: 194.27
• EINECS: 1592732-453-0
• Product Categories: Adamantane derivatives;Aliphatics
• Mol File: 711-01-3.mol

Chemical Properties

• Melting Point: 35.0 to 39.0 °C
• Boiling Point: 79°C/1mmHg(lit.)
• Flash Point: 98.9 °C
• Appearance: Off-white solid
• Density: 1.13g/cm³
• Vapor Pressure: 0.0277mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: 0-10°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: ADAMANTANE-1-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: ADAMANTANE-1-CARBOXYLIC ACID METHYL ESTER(711-01-3)
• EPA Substance Registry System: ADAMANTANE-1-CARBOXYLIC ACID METHYL ESTER(711-01-3)

Safety Data

• Hazardous Substances Data: 711-01-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

A derivative of 1-Adamantanecarboxylic Acid

InChI:InChI=1/C12H18O2/c1-14-11(13)12-5-8-2-9(6-12)4-10(3-8)7-12/h8-10H,2-7H2,1H3

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 82094-57-3 1-(Prop-2-ene-1-sulfonyl)-adamantane 
• 828-51-3 1-Adamantanecarboxylic acid 
• 42711-75-1 3-hydroxyadamantane-1-carboxylic acid 
• 917-64-6 methyl magnesium iodide 
• 2094-72-6 1-Adamantanecarbonyl chloride 

Downstream Products

• 3732-31-8 1,1'-Biadamantane 
• 38256-01-8 di(1-adamantyl) ketone 
• 78743-65-4 2-<<(1-adamantyl)carbonyl>amino>ethanol 
• 80055-51-2 anti-periplanar o-tolyl-1,1'-diadamantylcarbinol 
• 214557-81-0 methyl 3,5-difluoroadamantane-1-carboxylate 
• 214557-84-3 methyl 3,5,7-trifluoroadamantane-1-carboxylate 
• 1214748-00-1 C₂₀H₂₄O₄ 
• 1214747-99-5 C₁₉H₂₃NO₃ 
• 17846-15-0 adamantane-1-carbohydrazide 
• 16269-16-2 3-(1-adamantyl)propanoic acid 
• 31685-38-8 3-(adamantan-1-yl)propan-1-ol 
• 1305348-89-3 methyl 4-[(1E)-4-(adamant-1-yl)but-1-en-1-yl]benzoate 
• 1305348-90-6 4-[(1E)-4-(adamant-1-yl)but-1-en-1-yl]benzoic acid 
• 1305348-91-7 4-[4-(adamant-1-yI)butyl]benzoic acid 

Relevant articles and documents

ADAMANTANYL-SUBSTITUTED BENZAMIDE COMPOUNDS AND THEIR USE AS P2X7 RECEPTOR ANTAGONISTS

The present invention relates to adamantanyl-substituted benzamide compounds and their use as antagonists of the P2X7 purinoreceptor. The invention further relates to methods for the treatment of disease and conditions associated with the P2X7 purinoreceptor.

Radical cyanocarbonylation using alkyl allyl sulfone precursors

Acyl cyanides have been prepared by the three-component coupling reactions comprised of alkyl allyl sulfones, carbon monoxide, and p-tolylsulfonyl cyanide under tin-free radical reaction conditions. Georg Thieme Verlag Stuttgart.

Dual Reaction Channels for Solvolyses of Acyl Chlorides in Alcohol-Water Mixtures

Rate constants are reported for solvolyses at 0 deg C of trimethylacetyl chloride (3) in 90-30percent v/v acetonitrile-, acetone-, ethanol- and methanol-water mixtures, of adamantane-1-carbonyl chloride (4) in 90-60percent acetone-, ethanol- and methanol-water mixtures, and of cyclopropanecarbonyl chloride (5) in 90-40percent acetone-water.Quantitative product data (acid and ester) are also reported for solvolyses of trimethylacetyl chloride in 98-20percent ethanol- and methanol-water mixtures.Product selectivities (S) show maxima in 90-95percent alcohol-water mixtures, similar to those, reported previously for solvolyses of p-chlorobenzoyl chloride (1a), benzoyl chloride (1b), 2,4,6-trimethylbenzenesulfonyl chloride (2a) and 4-methoxy-2,6-dimethylbenzenesulfonyl chloride (2b).Using rate-rate profiles, logarithms of rate constants are dissected into the competing reaction channels.Given the sharp maxima in S that occur at different alcohol compositions for different substrates, and the link to 'breaks' in rate-rate profiles, the results are consistent with competing mechanisms having different rate-limiting steps.The competing mechanisms involve two broad reaction channels: (1) nucleophilic attack by one molecule of solvent assisted by a second molecule of solvent acting as a general base catalyst-consequently, in aqueous alcohol there are four mechanistic combinations operating simultaneously within this one reaction channel; (2) nucleophilic attack by solvent occurs via a carbocationic reaction within the SN2-SN1 mechanistic spectrum, involving for example, a solvent-separated ion pair intermediate (SN1) or a concerted nucleophilic attack (SN2).

Synthesis of 1-adamantyl and 1-adamantylmethyl alkyl ketones

The reaction of 1-adamantanecarboxylic and 1-adamantylacetic acids with Grignard reagents in the presence of cuprous chloride or iodide gave the corresponding ketones.