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1-Adamantanecarboxylic acid

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1-Adamantanecarboxylic acid Basic information

Product Name:
1-Adamantanecarboxylic acid
Synonyms:
  • 1-Adamantanecarboxylic
  • Adamantane-1-carboxylic acid 99%
  • 1-ADMANTANE CARBOXYLIC ACID
  • 1-Adamantane-1-carboxylic acid
  • 1-Adamantanecarboxylic acid ,99%
  • 3-adamantanecarboxylicacid
  • adamantanecarboxylic acid
  • Adamantoic acid
CAS:
828-51-3
MF:
C11H16O2
MW:
180.24
EINECS:
212-584-6
Product Categories:
  • C11 to C12
  • Carbonyl Compounds
  • Organic acids
  • Adamantanes
  • Carboxylic Acids
Mol File:
828-51-3.mol
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1-Adamantanecarboxylic acid Chemical Properties

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)
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Safety Information

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

MSDS

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1-Adamantanecarboxylic acid Usage And Synthesis

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.]

1-Adamantanecarboxylic acid Preparation Products And Raw materials

Preparation Products

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