8-Aminoquinoline
QUINOLIN-8-AMINE · 8-QUINOLINAMINE · Quinolin-8-ylaMine · nc066 · wr6920 · AS-232 · 8-Amino · AKOS 91147
식별자 및 물리적 특성
| CAS No. | 578-66-5 |
|---|---|
| 분자식 | C9H8N2 |
| 평균 분자량 | 144.17 g/mol |
| 단동위원소 질량 | 144.06874826 g/mol |
| SMILES | Nc1cccc2cccnc12 |
| InChIKey | WREVVZMUNPAPOV-UHFFFAOYSA-N |
| PubChem CID | 11359 |
| ChEMBL | CHEMBL99932 |
| EC No. | 209-427-9 |
| DTXSID | DTXSID4060369 |
화학 및 물리적 성질
| XLogP | 1.8 |
|---|---|
| 극성 표면적 | 38.9 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 136 |
| 증기압 | 0.00055 [mmHg] |
| Physical Description | Yellow solidified mass or fragments[Aldrich MSDS] |
| 녹는점 | 60-65 °C (lit.) |
| 끓는 점 | 174 °C/26 mmHg (lit.) |
| 밀도 | 1.1148 (estimate) |
| 굴절률 | 1.7080 (estimate) |
| 인화점 | 174°C/26mm |
| 저장 조건 | Keep in dark place,Inert atmosphere,Room temperature |
| pKa(산도 계수) | pK1: 3.99(+1) (20°C,μ=0.01) |
| 물리적 상태 | 결정성 분말 |
| 색상 | 녹색에서 베이지색 갈색 |
| 용해도 | 약간 용해됨 |
| BRN | 114474 |
| InChI | 1S/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2 |
| InChIKey | WREVVZMUNPAPOV-UHFFFAOYSA-N |
| SMILES | Nc1cccc2cccnc12 |
| NIST | 8-Quinolinamine(578-66-5) |
| EPA | 8-Quinolinamine (578-66-5) |
화학적 성질
green to beige-brown crystalline powder
안전 및 규제
| GHS 분류 | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (19.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H341 (11.5%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, 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 52 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.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. |
|---|---|
| 규제 정보 | Chemical: 8-Quinolinamine8-Aminoquinoline: Does not have an individual approval but may be used under an appropriate group standard |
| 유해성 요약 | A skin and strong eye irritant[Aldrich MSDS] See 5-Aminoquinoline. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2A (100%)STOT SE 3 (19.2%)Muta. 2 (11.5%) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | VA9627000 |
| 운송 번호(UN) | UN2811 |
| 독성 | mmo-sat 50 mg/plate MUREAV 39,285,77 |
| 관세 코드 | 29334990 |
| 위험 문구(R) | 68-36/37/38-20/21/22-36/38 |
| 위험 표시 | Xn,Xi |
용도
용도
8-Aminoquinoline is used as pesticide and pharmaceutical intermediate. It has been used in the preparation of base-stabilized terminal borylene complex of osmium. It is also used in the spectrophotometric determination of bivalent palladium.
일반 설명
8-Aminoquinoline fluoresce moderately to weakly in low dielectric media but not in strongly hydrogen-bonding or acidic aqueous media. The reaction of 8-aminoquinoline with chromium (III), manganese (II), iron (II) and (III), cobalt (II), nickel (II), copper (II), zinc (II), cadmium (II) and platinum (II) salts has been studied.
제조 및 합성 방법
제조 방법
Synthesis of 8-aminoquinoline: Under an ice bath, sulfuric acid (2.0 mL) was added onto quinoline (5 mmol, 1.0 equiv) then 65% nitric acid (3.0 equiv) were added dropwise and stirred for 4h at rt. The mixture was poured into the ice water and neutralized with NaOH; and then extracted with dichloromethane. After dried over Na2SO4 and evaporated in vacuo, used next step without purification.Mixture of nitroquinolines and 5% Pd/C was solved in ethanol and suspension was saturated with hydrogen gas under atmospheric pressure at 40°C until the starting material was consumed. 2 h later, the mixture was filtered and evaporated. The crude product was purified by silica gel column chromatography, eluting with EtOAc in hexanes to yield the desired 8-aminoquinoline is isolated as a brown solid in a yield of 32%.Obtained as a brown solid (231 mg, 32%); 1H NMR (500 MHz, CDCl3) δ 8.71 – 8.60 (m, 1H), 7.93 (d, J = 8.2 Hz, 1H), 7.29 – 7.16 (m, 2H), 7.02 (d, J = 8.1 Hz, 1H), 6.80 (d, J = 7.4 Hz, 1H), 4.89 (s, 2H).