1-Chloroadamantane

Base Information

• Chemical Name: 1-Chloroadamantane
• CAS No.: 935-56-8
• Molecular Formula: C10H15Cl
• Molecular Weight: 170.682
• Hs Code.: 2916.20
• European Community (EC) Number: 213-305-0
• NSC Number: 143629
• UNII: HOZ9S5Z71H
• DSSTox Substance ID: DTXSID1061318
• Nikkaji Number: J5.218C
• Wikidata: Q2806581
• Mol file: 935-56-8.mol

Synonyms:Adamantane,1-chloro- (6CI,7CI,8CI);1-Adamantyl chloride;3-Chloroadamantane;Adamantyl chloride;Tricyclo[3.3.1.13,7]decane,1-chloro-;

Chemical Property of 1-Chloroadamantane

Chemical Property:

• Appearance/Colour: white to light grey adhering crystalline solid
• Vapor Pressure: 0.088mmHg at 25°C
• Melting Point: 163-166 °C
• Refractive Index: 1.488 - 1.490
• Boiling Point: 232.8 °C at 760 mmHg
• Flash Point: 82.3 °C
• PSA: 0.00000
• Density: 1.12 g/cm³
• LogP: 3.19400
• Storage Temp.: 2-8°C
• Solubility.: DMSO, Methanol (Slightly)
• Water Solubility.: Poorly soluble in water. Soluble in hydrocarbons. But readily soluble in nonpolar organic solvents.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 170.0862282
• Heavy Atom Count: 11
• Complexity: 144

Purity/Quality:

99% ^*data from raw suppliers

1-Chloroadamantane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)(C3)Cl
• Uses: 1-Chloroadamantane, an adamantane derivative shown to exhibit virucidal activity against the Newcastle disease virus in chick embryo fibroblasts. (Adamantane EP Impurity A) 1-Chloroadamantane was employed as precursor for the synthesis of perfluoroadmantane derivatives via aerosol direct fluorination.

Technology Process of 1-Chloroadamantane

There total 145 articles about 1-Chloroadamantane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

diphenylmethanone O-(adamantane-1-carbonyl) oxime (107264-20-0) → benzophenone (119-61-9) + hexachloroethane (67-72-1) + 1-chloroadamantane (935-56-8) + benzophenone azine (983-79-9)

Guidance literature:

With tetrachloromethane; Yields of byproduct given; Ambient temperature; Irradiation;

DOI:10.1016/S0040-4039(00)82327-8

Reference yield: 77.2%

adamantane (281-23-2) → 1-Adamantyl bromide (768-90-1) + 2-Adamantanone (700-58-3) + 1-chloroadamantane (935-56-8) + 2-adamantyl bromide (7314-85-4) + 1-adamanthanol (768-95-6) + 1-adamantanol (700-57-2)

Guidance literature:

With Bromotrichloromethane; 3,3-dimethyldioxirane; In acetone; at 20 ℃; Product distribution; Mechanism;

DOI:10.1021/jo971226w

Reference yield: 58.0%

vinyl acetate (108-05-4,9003-20-7) → ethylidene diacetate (542-10-9) + 1-chloroadamantane (935-56-8) + 1-vinyladamantane (6600-42-6) + 1-acetyladamantane (1660-04-4)

Guidance literature:

With Wilkinson's catalyst; adamantane; In dichloromethane; at 170 ℃; for 8h;

DOI:10.1007/BF00959742

upstream raw materials:

1-adamanthanol

pyridine

adamantane

methanol

Downstream raw materials:

2-(1-adamantyl)-5-methylphenol

4-((3r,5r,7r)-adamantan-1-yl)-2-methylphenol

2-Methyl-6-(1-adamantyl)-phenol

N-(1-adamantyl)acetamide

Refernces

• 1、 Verstraelen,L. et al.. "". . p. 1285 - 1288. Retrieved 1976.
• 2、 Bleher, Katharina,Comba, Peter,Faltermeier, Dieter,Gupta, Ashutosh,Kerscher, Marion,Krieg, Saskia,Martin, Bodo,Velmurugan, Gunasekaran,Yang, Shuyi. "Non-Heme-Iron-Mediated Selective Halogenation of Unactivated Carbon?Hydrogen Bonds". supporting information. . Retrieved 2021/12/09.
• 3、 McMillan, Alastair J.,Sieńkowska, Martyna,Di Lorenzo, Piero,Gransbury, Gemma K.,Chilton, Nicholas F.,Salamone, Michela,Ruffoni, Alessandro,Bietti, Massimo,Leonori, Daniele. "Practical and Selective sp3 C?H Bond Chlorination via Aminium Radicals". supporting information. p. 7132 - 7139. Retrieved 2021/03/03.