1-Adamantaneacetic acid Chemical Properties

Melting point:

134-137 °C (lit.)

Boiling point:

270.73°C (rough estimate)

Density 

1.0086 (rough estimate)

refractive index 

1.4949 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Solubility in Methanol - almost transparency

form 

Crystalline Powder or Crystals

pka

5.00±0.10(Predicted)

color 

White to off-white

BRN 

641412

InChI

InChI=1S/C12H18O2/c13-11(14)7-12-4-8-1-9(5-12)3-10(2-8)6-12/h8-10H,1-7H2,(H,13,14)

InChIKey

AOTQGWFNFTVXNQ-UHFFFAOYSA-N

SMILES

C12(CC(O)=O)CC3CC(CC(C3)C1)C2

CAS DataBase Reference

4942-47-6(CAS DataBase Reference)

NIST Chemistry Reference

1-Adamantaneacetic acid(4942-47-6)

Safety Information

Hazard Codes 

Xi,Xn,F

Risk Statements 

36/37/38-15-10

Safety Statements 

22-24/25-43-7/8

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29162090

MSDS

• Language:English Provider:1-Adamantaneacetic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Adamantaneacetic acid Usage And Synthesis

Chemical Properties

white to off-white crystalline powder or crystals

Uses

1-Adamantaneacetic acid was used as an acylating agent in determining pharmacological characteristics of ten new analogues of bradykinin (Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg) that were modified in the N-terminal part of the molecule.

Biochem/physiol Actions

1-Adamantaneacetic acid is an inhibitor of chorismate mutase-prephenate dehydrogenase (EC 1.3.1.12) from Escherichia coli K12 (strain JP 232).

Synthesis

General procedure for synthesizing 1-adamantylacetic acid from methyl 2-(adamantan-1-yl)acetate and sodium bicarbonate: referring to the preparation of 2-adamantylacetic acid in Example 10, 2.53 g of sodium hydroxide was dissolved in 433 mL of methanol, and 1,125 mL of methanol solution containing 150 g (0.72 mol) of methyl 2-adamantylacetic acid was added, and the reaction was stirred at room temperature for 6 hours at room temperature with stirring. Upon completion of the reaction, the reaction mixture was concentrated under vacuum. To the concentrated residue was added aqueous sodium bicarbonate solution and the mixture was washed with ether. Subsequently, the aqueous layer was adjusted to pH 1 with 12N hydrochloric acid and extracted with ethyl acetate. The combined extracts were dried with anhydrous sodium sulfate. After filtration to remove the desiccant, the filtrate was concentrated in vacuum to give the target product 1-adamantaneacetic acid. Yield: 129.39 g, 93% yield.

Purification Methods

Dissolve the acid in hot NaOH, treat with charcoal, filter and acidify. Collect the solid, wash it with H2O, dry and recrystallise it from MeOH. [Stetter et al. Chem Ber 92 1629 1959.] The acid chloride [2094-72-6] has M 168.7, m 51-54o, and b 135-136o/1mm. LACHRYMATORY.

References

[1] Patent: US5658923, 1997, A

1-Adamantaneacetic acid(4942-47-6)Related Product Information

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