5854-52-4

Basic information

• Product Name: 1-CHLOROCARBONYLOXYADAMANTANE
• Synonyms: 1-CHLOROCARBONYLOXYADAMANTANE
• CAS NO: 5854-52-4
• Molecular Formula: C₁₁H₁₅ClO₂
• Molecular Weight: 214.6886
• Mol File: 5854-52-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 271°Cat760mmHg
• Flash Point: 119.4°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 0.00663mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: 1-CHLOROCARBONYLOXYADAMANTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLOROCARBONYLOXYADAMANTANE(5854-52-4)
• EPA Substance Registry System: 1-CHLOROCARBONYLOXYADAMANTANE(5854-52-4)

Safety Data

• Hazardous Substances Data: 5854-52-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 88, p. 1988, 1966 DOI: 10.1021/ja00961a024

Purification Methods

Crystallise it from pet ether (b 30-60o) at -20o. Also purify it as for 1-adamantyl fluoroformate below. Its IR has  max at 4.2, 5.6 and 8.4 (2380, 1786 and 1190 cm-1). [Haas et al. J Am Chem Soc 88 1988 1966, cf Moroder et al. Hoppe-Seyler’s Z Physiol Chem 357 1647 1976.]

InChI:InChI=1/C11H15ClO2/c12-10(13)14-11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 768-95-6 1-adamanthanol 
• 75-44-5 phosgene 

Downstream Products

• 935-56-8 1-chloroadamantane 
• 6221-74-5 1-methoxyadamantane 
• 6221-75-6 1-Adamantyl ethyl ether 
• 768-95-6 1-adamanthanol 
• 74975-65-8 1-adamantyl 2,2,2-trifluoroethyl ether 
• 37994-87-9 1-Adamantyl ethyl carbonate 
• 880-52-4 N-(1-adamantyl)acetamide 
• 85963-93-5 2,4,6-triphenyl-1--1,2,3,4-tetrahydro-1,2,4,5-tetrazine 
• 1439367-28-8 (2R,3S)-3-hydroxy-2-{[(tricyclo[3 .3.1.1 ^3’7]dec-1-yloxy)carbonyl]amino}butanoic acid 
• 123058-69-5 adamantan-1-yl benzylcarbamate 
• 1402165-55-2 adamantan-1-yl 3,4-dimethoxybenzylcarbamate 
• 1402165-56-3 adamantan-1-yl 4-chlorobenzylcarbamate 
• 1402165-25-6 adamantan-1-yl 1-(2,2-diphenylvinyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 4411-26-1 1-adamantylisothiocyanate 

Relevant articles and documents

Enantioselective Copper(I)/Chiral Phosphoric Acid Catalyzed Intramolecular Amination of Allylic and Benzylic C?H Bonds

Radical-involved enantioselective oxidative C?H bond functionalization by a hydrogen-atom transfer (HAT) process has emerged as a promising method for accessing functionally diverse enantioenriched products, while asymmetric C(sp3)?H bond amination remains a formidable challenge. To address this problem, described herein is a dual CuI/chiral phosphoric acid (CPA) catalytic system for radical-involved enantioselective intramolecular C(sp3)?H amination of not only allylic positions but also benzylic positions with broad substrate scope. The use of 4-methoxy-NHPI (NHPI=N-hydroxyphthalimide) as a stable and chemoselective HAT mediator precursor is crucial for the fulfillment of this transformation. Preliminary mechanistic studies indicate that a crucial allylic or benzylic radical intermediate resulting from a HAT process is involved.

DISUBSTITUTED BETA-LACTONES AS INHIBITORS OF N-ACYLETHANOLAMINE ACID AMIDASE (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.