1,3-Adamantanedicarboxylic acid Chemical Properties

Melting point:

276-278 °C (lit.)

Boiling point:

380.6±15.0 °C(Predicted)

Density 

1.461±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Sparingly), Methanol (Slightly, Heated)

form 

Solid

pka

4.24±0.40(Predicted)

color 

White to Off-White

CAS DataBase Reference

39269-10-8(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

RTECS 

YD1994000

HS Code 

29172090

MSDS

• Language:English Provider:SigmaAldrich

1,3-Adamantanedicarboxylic acid Usage And Synthesis

Uses

1,3-Adamantanedicarboxylic acid is a carboxylic acid derivative of adamantane. It is widely used in drug industry, polymer synthesis and fine chemicals as key intermediates. It is also used as antidepressants or antiparkinsonic drugs in clinical practice.

Preparation

1,3-Adamantanedicarboxylic acid was synthesized from 1-adamantane carboxylic acid by one-pot method. In this process, the ratio of mixed acid (nitric acid and sulfuric acid) have important effect on the yield, the role of sulfuric acid not only is solvent, but also can improve the oxidate ability of nitric acid.
Efficient Synthesis of 1,3-Adamantanedicarboxylic Acid and 1,3-Diaminoadamantane

Reaction: 1-Adamantane carboxylic acid (20 g), nitric acid (65 %, 20 mL) and sulfuric acid (98 %, 160 mL) were placed in a three-necked roundbottom flask fitted with an efficient magnetic stirrer and a thermometer. Cooled to 0 oC and held at 0 oC, anhydrous formic acid (80 %, 70 mL) was added dropwise in 5 h and reacted for 1 h. poured to crushed ice, filtered and then washed the precipitate several times with water to give a white solid. Then the white solid was dissolved in aqueous NaOH solution and the upper clear solution was separated and acidified by HCl to pH = 3. Filtered, washed with water, dried in vacuum, recrystallized from ethanol. White solid, yield 22.9 g (92 %). m.p.: 275- 276 oC
1H NMR (DMSO-d6, 400 MHz) δ: 1.616 (m, 2H), 1.691-1.727 (m, 4H), 1.759-1.791 (m, 4H), 1.850-1.882 (m, 2H), 2.059 (m, 1H), 12.062 (br, s, 2H, COOH); 13C NMR (100 MHz, DMSO-d6) δ 27.37 (C-5, C-7), 34.98 (C-6), 37.66 (C-4, C-8, C-9, C-10), 39.78 (C-2), 39.89 (C-2, C-3), 177.76 (COOH). IR (KBr, νmax, cm-1) : 2913, 2851, 2636, 1691, 1451, 1410, 1344, 1249, 1103, 1084, 952, 743, 670, 528; Anal. calcd for C12H16O4: C 64.29, H 7.14; found C 64.55, H 7.22.

Purification Methods

Dissolve the acid in aqueous NaOH, treat with charcoal, filter and acidify with dilute HCl. It crystallises from MeOH. [Stetter & Wulff Chem Ber 93 1366 1960, Beilstein 9 III 4066, 9 IV 2997.]

1,3-Adamantanedicarboxylic acid(39269-10-8)Related Product Information

• 1,3-Adamantanediol
• Adamantane
• Folic acid
• Altrenogest
• Amantadine
• OXALIC ACID
• Decane
• Ethyl 2-(Chlorosulfonyl)acetate
• Glycine
• Cyclohexanepropionic acid
• 1,3-adamantanedimethanol
• Azelaic acid
• Cyclooctanecarbaldehyde
• 2,2-Dimethylglutaric acid
• 1,3-Dimethyladamantane
• Dimethyl 1,3-adamantanedicarboxylate
• 1,3-Cyclohexanedicarboxylic acid
• CYCLOOCTANEMETHANOL