5,5-dimethyl-1-pyrroline N-oxide
DMPO · 2,2-DIMETHYL-3,4-DIHYDRO-2H-PYRROLE 1-OXIDE · 3,4-DIHYDRO-2,2-DIMETHYL-2H-PYRROLE 1-OXIDE · 5,5-dimethyl-1-pyrroline-1-oxide · Dimethyl N · spintrappingreagent · DMPO, hydrophilic spin trap · ,5-Dimethyl-1-pyrroline N-oxide
식별자 및 물리적 특성
| CAS No. | 3317-61-1 |
|---|---|
| 분자식 | C6H11NO |
| 평균 분자량 | 113.16 g/mol |
| 단동위원소 질량 | 113.08406397 g/mol |
| SMILES | CC1(C)CCC=[N+]1[O-] |
| InChIKey | VCUVETGKTILCLC-UHFFFAOYSA-N |
| PubChem CID | 1774 |
| ChEMBL | CHEMBL79824 |
| ChEBI | CHEBI:149489 |
| EC No. | 222-011-1 |
| DTXSID | DTXSID30186826 |
화학 및 물리적 성질
| XLogP | -0.3 |
|---|---|
| 극성 표면적 | 28.8 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 8 |
| 형식 전하 | 0 |
| 복잡도 | 126 |
| 물질 분류 | Other Uses -> Biochemical Research |
| Physical Description | White solidHighly hygroscopic[Merck Index] Light yellow, hygroscopic solidified mass or fragmentsmp = 25-29 deg C[Sigma-Aldrich MSDS] |
| 녹는점 | 25-29 °C (lit.) |
| 끓는 점 | 75 °C/0.4 mmHg (lit.) |
| 밀도 | 1.015 g/mL at 25 °C (lit.) |
| 굴절률 | n20/D 1.496(lit.) |
| 인화점 | 204 °F |
| 저장 조건 | -20°C |
| 용해도 | DMSO(최대 25mg/ml) 또는 에탄올(최대 25mg/ml)에 용해됩니다. |
| 물리적 상태 | 담황색 고체 또는 오일. |
| pKa(산도 계수) | 2.47±0.40(Predicted) |
| 색상 | 옅은 노랑 |
| Merck | 14,3393 |
| BRN | 107603 |
| 안정성 | 안정적이지만 빛에 민감하고 흡습성이 있으며 열에 민감합니다. 불활성 가스하에 어두운 곳에 보관하고 차갑게 보관하십시오. 강한 산화제, 습기와 호환되지 않습니다. |
| InChI | 1S/C6H11NO/c1-6(2)4-3-5-7(6)8/h5H,3-4H2,1-2H3 |
| InChIKey | VCUVETGKTILCLC-UHFFFAOYSA-N |
| SMILES | CC1(C)CCC=[N+]1[O-] |
화학적 성질
white to faintly yellow solid
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.Not ClassifiedAggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| 유해성 요약 | May cause irritation[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Not Classified |
| 수질 위해 등급(WGK) | 3 |
| 관세 코드 | 29339900 |
| 안전 문구(S) | 24/25 |
| 위험 등급 | IRRITANT |
| F 고인화성물질 | 8-10 |
| 저장 분류 | 10 - Combustible liquids |
용도
개요
Free radicals are highly reactive, short-lived species. Spin traps react with radicals, forming stable adducts that can be further studied. DMPO is a commonly-used spin trap that reacts with O-, N-, S-, and C-centered radicals. This allows their characterization when used in association with electron spin resonance and immuno-spin trapping. DMPO is water-soluble, rapidly penetrates lipid bilayers, has low toxicity, and can be used in vitro and in vivo.
용도
5,5-Dimethyl-1-pyrroline N-oxide is a reagent generally used either as a free-radical spin-trapping agent, or electrophilic component during the synthesis of pyrrolidine derivatives. It may also be considered as 1,3-dipole in cycloaddition processes.
제조 및 합성 방법
제조 방법
To a three-necked round bottom flask equipped with a condenser, addition funnel, thermometer, and mechanical stirrer and containing 300 ml. 95% ethanol precooled to 2°C is added, all at once, 14.5 g (0.1 mole) 4-methyl-4-nitropentanol, and 13.1 g (1.2 mole) zinc dust. With rapid agitation, the glacial acetic acid (24.0 g, 0.4 mole) is added dropwise over a 1-hr period while maintaining the reaction temperature below 15°C. The mixture is stirred vigorously for 2 hr and then stored in the refrigerator for 2 days, at approximately 1°C. Then the zinc acetate is filtered and rinsed with 100 ml of ethanol. The combined ethanol factions are rotoevapo-rated to give the crude nitrone. The crude nitrone is dissolved in a 200 ml portion of dichloromethane and the latter washed two times with saturated sodium bicarbonate solution. The organic layer is dried over sodium sulfate and the solvent rotoevaporated, to give 10.7 (94% yield) of the crude nitrone. The product was purified by double distillation (b.p. 53°C, 0.1 Torr), to give 6.8 g (60%) of the pure nitrone as a white hygroscopic solid. The H1 NMR (400 MH CDC13, Me4Si) is 6.80 (t, 2H, methylene bound to quaternary C, J = 7.2Hg), 1.43 (s, 6H, methyl), C13NMr (100 MH2, CDC13, Me4 Si) 5=132.4 (Vinyl), 73.5 (quaternary), 34.1 (Allyl), 25.3 (methylene bound to quaternary C), 24.4 (methyls).