828-51-3 Usage
Chemical Properties
white to off-white crystalline powder
Uses
Different sources of media describe the Uses of 828-51-3 differently. You can refer to the following data:
1. Adamantoic Acid is an inhibitor of chorismate mutase activity and hydroxyphenylpyruvate synthase. It inhibits TTR conformational changes facilitating amyloid fibril formation.
2. It can be used as a stabilizer in the synthesis of monodisperse, highly crystalline CoPt3 nanoparticles1 and porous platinum nanoparticles. It is a potent and reversible CerK inhibitor.
3. 1-Adamantanecarboxylic acid can be used as: A stabilizer in the synthesis of monodisperse, highly crystalline CoPt3?nanoparticles and porous platinum nanoparticles.An additive in polycondensation reactions to yield conjugated polymers as possible optoelectronic materials.An additive in the allylic substitution reaction, which is catalyzed by palladium in an aqueous medium.
Synthesis Reference(s)
Synthetic Communications, 18, p. 545, 1988 DOI: 10.1080/00397918808060749
Biochem/physiol Actions
1-Adamantanecarboxylic acid undergoes complexation reactions with cyclohexaamylose. It is an inhibitor of phenyl ester hydrolysis of cycloheptaamylose.
Purification Methods
Possible impurities are trimethylacetic acid and C9 and C13 acids. Dissolve 15g of the acid in CCl4 (300mL) and shake with 110mL of 15N aqueous NH3 whereby the ammonium salt separates and is collected. Acid impurities form soluble ammonium salts. The salt is washed with cold Me2CO (20mL) and suspended in H2O (250mL). This is treated with 12N HCl and extracted with CHCl3 (100mL). The dried (Na2SO4) extract was evaporated and the residue was recrystallised from a mixture of MeOH (30mL) and H2O (ca 10mL) to give the pure acid (10-11g). [Koch & Haaf Org Synth Coll Vol V 20 1973.] It was also recrystallised from absolute EtOH and dried under vacuum at 100o. Alternatively, the acid (5g) is refluxed for 2hours with 15mL of MeOH and 2mL of 98% H2SO4 (cool when mixing this solution). Pour into 10 volumes of H2O and extract with the minimum volume of CHCl3 to give clear separation of phases. The extract is washed with H2O, dried (CaCl2) and distilled. The methyl ester is collected at 77-79o/1mm, m 38-39o. The ester is hydrolysed with the calculated amount of N KOH and refluxed until clear. Acidification with HCl provides the pure acid with 90% recovery. The amide crystallises from cyclohexane, m 189o. [Stetter et al. Chem Ber 92 1629 1959.] [Beilstein 9 IV 253.]
Check Digit Verification of cas no
The CAS Registry Mumber 828-51-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 8 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 828-51:
(5*8)+(4*2)+(3*8)+(2*5)+(1*1)=83
83 % 10 = 3
So 828-51-3 is a valid CAS Registry Number.
InChI:InChI=1/C11H16O2/c12-10(13)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2,(H,12,13)/p-1
828-51-3Relevant articles and documents
Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate**
Pfennig, Victoria S.,Villella, Romina C.,Nikodemus, Julia,Bolm, Carsten
supporting information, (2022/01/22)
A one-pot, three-step protocol for the preparation of Grignard reagents from organobromides in a ball mill and their subsequent reactions with gaseous carbon dioxide (CO2) or sodium methyl carbonate providing aryl and alkyl carboxylic acids in up to 82 % yield is reported. Noteworthy are the short reaction times and the significantly reduced solvent amounts [2.0 equiv. for liquid assisted grinding (LAG) conditions]. Unexpectedly, aryl bromides with methoxy substituents lead to symmetric ketones as major products.
Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
supporting information, p. 6648 - 6653 (2021/09/08)
The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
Cleavage of Carboxylic Esters by Aluminum and Iodine
Sang, Dayong,Yue, Huaxin,Fu, Yang,Tian, Juan
, p. 4254 - 4261 (2021/03/09)
A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group. This method enables the selective cleavage of alkyl carboxylic esters in the presence of aryl esters.