1,3-아다만탄디카르복실산
1,3-아다만탄디카르복실산 · ADAMANTANE-1,3-DICARBOXYLIC ACID · 1,3-DICARBOXYADAMANTANE · (1s,3s,5r,7r)-AdaMantane-1,3-dicarboxylic acid · AKOS BC-0656 · adamantane-1,3-dicarboxylate · 1,3-ADAMANTANEDICARBOXYLIC ACID · 1,3-Adamantanedicarboxylic Acid,97%
식별자 및 물리적 특성
| CAS No. | 39269-10-8 |
|---|---|
| 분자식 | C12H16O4 |
| 평균 분자량 | 224.25 g/mol |
| 단동위원소 질량 | 224.10485899 g/mol |
| SMILES | O=C(O)C12CC3CC(C1)CC(C(=O)O)(C3)C2 |
| InChIKey | PAVQGHWQOQZQEH-UHFFFAOYSA-N |
| PubChem CID | 64339 |
| EC No. | 254-395-1 |
| DTXSID | DTXSID40192519 |
| 현지명 | 1,3-아다만탄디카르복실산 |
화학 및 물리적 성질
| XLogP | 1.1 |
|---|---|
| 극성 표면적 | 74.6 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 16 |
| 형식 전하 | 0 |
| 복잡도 | 327 |
| 녹는점 | 276-278 °C (lit.) |
| 끓는 점 | 380.6±15.0 °C(Predicted) |
| 밀도 | 1.461±0.06 g/cm3(Predicted) |
| 저장 조건 | Sealed in dry,Room Temperature |
| 용해도 | DMSO(난용성), 메탄올(약간 용해됨,가열) |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | 4.24±0.40(Predicted) |
| 색상 | 흰색에서 황백색까지 |
| InChI | InChI=1S/C12H16O4/c13-9(14)11-2-7-1-8(4-11)5-12(3-7,6-11)10(15)16/h7-8H,1-6H2,(H,13,14)(H,15,16) |
| InChIKey | PAVQGHWQOQZQEH-UHFFFAOYSA-N |
| SMILES | C12(C(O)=O)CC3CC(CC(C(O)=O)(C3)C1)C2 |
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.WarningH315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (66.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (33.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 3 reports by companies.There are 2 notifications provided by 2 of 3 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (66.7%)Eye Irrit. 2A (66.7%)STOT SE 3 (33.3%) |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | YD1994000 |
| 관세 코드 | 29172090 |
| 위험 문구(R) | 36/37/38 |
| 안전 문구(S) | 26-36/37/39 |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
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.
제조 및 합성 방법
제조 방법
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-DiaminoadamantaneReaction: 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 oC1H 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.