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HomeProduct name list1,3-Adamantanedicarboxylic acid

1,3-Adamantanedicarboxylic acid

Synonym(s):ADC

  • CAS NO.:39269-10-8
  • Empirical Formula: C12H16O4
  • Molecular Weight: 224.25
  • MDL number: MFCD00167790
  • EINECS: 254-395-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-04-27 16:27:43
1,3-Adamantanedicarboxylic acid Structural

What is 1,3-Adamantanedicarboxylic acid?

The Uses of 1,3-Adamantanedicarboxylic acid

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
Synthesis of 1,3-adamantane dicarboxylic 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.]

Properties of 1,3-Adamantanedicarboxylic acid

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 for 1,3-Adamantanedicarboxylic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for 1,3-Adamantanedicarboxylic acid

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