1-Adamantanecarbonyl chloride

Base Information

• Chemical Name: 1-Adamantanecarbonyl chloride
• CAS No.: 2094-72-6
• Molecular Formula: C11H15ClO
• Molecular Weight: 198.692
• Hs Code.: 29162090
• European Community (EC) Number: 218-252-7
• NSC Number: 179368,249324
• DSSTox Substance ID: DTXSID20175108
• Nikkaji Number: J150.553J
• Wikidata: Q72436519
• Mol file: 2094-72-6.mol

Synonyms:1-adamantanecarbonyl chloride

Chemical Property of 1-Adamantanecarbonyl chloride

Chemical Property:

• Appearance/Colour: white to almost white crystalline solid
• Vapor Pressure: 0.00678mmHg at 25°C
• Melting Point: 49-51 °C(lit.)
• Refractive Index: 1.556
• Boiling Point: 270.6 °C at 760 mmHg
• Flash Point: 139 °C
• PSA: 17.07000
• Density: 1.239 g/cm³
• LogP: 2.96820
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: soluble in Toluene
• Water Solubility.: may decompose
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 198.0811428
• Heavy Atom Count: 13
• Complexity: 218

Purity/Quality:

98% purity ^*data from raw suppliers

1-Adamantanecarbonyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34-37
• Safety Statements: 26-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)(C3)C(=O)Cl
• Uses: 1-Adamantanecarbonyl chloride was used in the preparation of efficient amine-modified oligodeoxynucleotides for fabrication of DNA microarrays.

Technology Process of 1-Adamantanecarbonyl chloride

There total 5 articles about 1-Adamantanecarbonyl chloride 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: 100.0%

1-Adamantanecarboxylic acid (828-51-3) → 1-Adamantanecarbonyl chloride (2094-72-6)

Guidance literature:

With thionyl chloride; at 80 ℃; for 2h;

DOI:10.1021/acs.jmedchem.7b00908

Reference yield:

adamontoyltris(trimethylsilyl)germane (104164-53-6) → tris(trimethylsilyl)germyl chloride (104164-55-8) + {(CH3)3Si}2Ge{C(OSi(CH3)3)C10H15} + chloroform (67-66-3,8013-54-5) + 1-Adamantanecarbonyl chloride (2094-72-6)

Guidance literature:

In tetrachloromethane; byproducts: Me3SiCl, hexachloroethane; Irradiation (UV/VIS); NMR tubes contg. the acylgermane/CCl4 sealed under vac., irradiated (two 100W Hg lamps, λ>360 nm) for up to 3h, with cooling to -15°C), soln. remained colourless; not isolated, detected by NMR-spect.;

DOI:10.1016/0022-328X(86)84028-1

Reference yield:

1-Adamantyl bromide (768-90-1) → 1-Adamantanecarbonyl chloride (2094-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) magnesium, 1,2-dibromoethane / 1.) diethyl ether, 35 deg C

2: 90 percent / SOCl₂ / 1 h / Heating

With thionyl chloride; magnesium; ethylene dibromide;

DOI:10.1021/jo00142a023

upstream raw materials:

1-Adamantanecarboxylic acid

1-Adamantyl bromide

adamontoyltris(trimethylsilyl)germane

adamantane

Downstream raw materials:

1-(adamantan-1-yl)propan-1-one

eugenyl 1-adamantylmethanoate

2-[3-(5-Adamantan-2-yl-[1,3,4]oxadiazol-2-yl)-3,3-diphenyl-propyl]-2-aza-bicyclo[2.2.2]octane

ethyl 1-adamantanecarboxylate

Refernces

• 1、 Soselia, Marina,Geibel, Irina,Zurabishvili, Davit,Samsoniya, Shota. "The Synthesis of Adamantane Ring Containing Benzimidazole, Benzoxazole, and Imidazo[4,5-e]benzoxazole Derivatives from 3-Aminophenol". . p. 447 - 455. Retrieved 2018.
• 2、 Saeed, Aamer,Bolte, Michael,Erben, Mauricio F.,Pérez, Hiram. "Intermolecular interactions in crystalline 1-(adamantane-1-carbonyl)-3-substituted thioureas with Hirshfeld surface analysis". . p. 7551 - 7563. Retrieved 2015.
• 3、 Michels, Jasper J.,Huskens, Jurriaan.,Reinhoudt, David N.. "Noncovalent binding of sensitizers for lanthanide(III) luminescence in an EDTA-bis(β-cyclodextrin) ligand". . p. 2056 - 2064. Retrieved 2002.
• 4、 Zhao, Di,Chen, Yong,Liu, Yu. "Construction and DNA condensation of cyclodextrin-coated gold nanoparticles with anthryl grafts". . p. 1895 - 1903. Retrieved 2014.
• 5、 Zhang, Lei,He, Yilong,Zhang, Na,Liu, Daosheng,Han, Jiao,Gong, Weitao. "Construction of a novel INHIBIT logic gate through a fine-tuned assembly of anthryl fluorophores via selective anion recognition and host-guest interactions". . p. 805 - 809. Retrieved 2015.
• 6、 Zurabishvili, Davit S.,Bukia, Tinatin J.,Lomidze, Medea O.,Trapaidze, Marina V.,Elizbarashvili, Elizbar N.,Samsoniya, Shota A.,Doroshenko, Tamara V.,Kazmaier, Uli. "Preparation of 2-(1-adamantyl)-1H-benzimidazole and novel derivatives thereof". . p. 139 - 145. Retrieved 2015.
• 7、 Li, Rong,Pan, Chunyue,Xiong, Shaohui,Yu, Guipeng,Wang, Pingshan,Zou, Yingping,Zhang, Aiqing. "Highly disordered crystalline-phase transition of tetrakis(1- adamantanecarboxymethyl)methane". . p. 481 - 486. Retrieved 2012.
• 8、 Wang, Haoyu,Wang, Liang,Wang, Xiaoguang,Xu, Jiayun,Luo, Quan,Liu, Junqiu. "Self-assembled nanostructures from C60-containing supramolecular complex: Its stimuli-responsive reversible transition and biological antioxidative capacity". . p. 2632 - 2638. Retrieved 2011.
• 9、 Lee, Hyo-Jun,Huang, Xiao,Sakaki, Shigeyoshi,Maruoka, Keiji. "Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis". supporting information. p. 848 - 855. Retrieved 2021/02/09.
• 10、 Alsayed, Shahinda S. R.,Beh, Chau Chun,Bishai, William R.,Foster, Neil,Gunosewoyo, Hendra,Lun, Shichun,Luna, Giuseppe,Payne, Alan D.. "Design, synthesis, and biological evaluation of novel arylcarboxamide derivatives as anti-tubercular agents". . p. 7523 - 7540. Retrieved 2020/03/13.