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)

pka

4.86±0.20(Predicted)

form 

Crystalline Powder

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)

NIST Chemistry Reference

Adamantane-1-carboxylic acid(828-51-3)

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

1-Adamantanecarboxylic acid Chemical Properties,Usage,Production

Chemical Properties

white to off-white crystalline powder

Uses

Adamantoic Acid is an inhibitor of chorismate mutase activity and hydroxyphenylpyruvate synthase. It inhibits TTR conformational changes facilitating amyloid fibril formation.

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

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.]