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1-Adamantanecarboxylic acid

CAS No.828-51-3
Chemical Name:1-Adamantanecarboxylic acid
CBNumber:CB3145173
Molecular Formula:C11H16O2
Formula Weight:180.24
MOL File:828-51-3.mol

1-Adamantanecarboxylic acid Property

Melting point 172-174 °C (lit.)
Boiling point 253.08°C (rough estimate)
Density 0.9976 (rough estimate)
refractive index 1.4910 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform, Methanol (Slightly)
form Crystalline Powder
pka 4.86±0.20(Predicted)
color White to off-white
Water Solubility Insoluble in water. Solubility in methanol gives very faint turbidity. Soluble in ethanol, chloroform, and dichloromethane.
BRN 1910637
InChI InChI=1S/C11H16O2/c12-10(13)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2,(H,12,13)
InChIKey JIMXXGFJRDUSRO-UHFFFAOYSA-N
SMILES C12(C(O)=O)CC3CC(CC(C3)C1)C2
CAS DataBase Reference 828-51-3(CAS DataBase Reference)
EWG's Food Scores 1
NIST Chemistry Reference Adamantane-1-carboxylic acid(828-51-3)
UNSPSC Code 12352100
NACRES NA.22

Safety

Hazard Codes :Xi
Risk Statements :36/37/38
Safety Statements :22-24/25-36-26
WGK Germany :3
RTECS :AU4452200
Hazard Note :Irritant
HS Code :29162000

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H335-H315-H319
Precautionary statements P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

1-Adamantanecarboxylic acid Price More Price(5)

Brand: Sigma-Aldrich(India)
Product number: 106399
Product name : 1-Adamantanecarboxylic acid
Purity: 99%
Packaging: 25G
Price: ₹3864.53
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 106399
Product name : 1-Adamantanecarboxylic acid
Purity: 99%
Packaging: 100G
Price: ₹11138.93
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: A0742
Product name : 1-Adamantanecarboxylic Acid
Purity: min. 98.0 %
Packaging: 25G
Price: ₹4800
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: A0742
Product name : 1-Adamantanecarboxylic Acid
Purity: min. 98.0 %
Packaging: 100G
Price: ₹10800
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: A0742
Product name : 1-Adamantanecarboxylic Acid
Purity: min. 98.0 %
Packaging: 500G
Price: ₹17000
Updated: 2022/05/26
Buy: Buy

1-Adamantanecarboxylic acid Chemical Properties,Usage,Production

Chemical Properties white to off-white crystalline powder
Uses 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.
Uses 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.
Uses Adamantoic Acid is an inhibitor of chorismate mutase activity and hydroxyphenylpyruvate synthase. It inhibits TTR conformational changes facilitating amyloid fibril formation.
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.]