O-(2,4-dinitrophenyl)hydroxylamine
2,4-Dinitrophenylhydroxylamine · 2,4-DinitrophenoxyaMine · NSC 148499 · 2,4-NitrophenoxyaMine · 4-dinitrophenyl)hydroxylamine · 1-aMinooxy-2,4-dinitro-benzene · O-(2,4-dinitrophenyl)hydroxylamine · HydroxylaMine,O-(2,4-dinitrophenyl)-
식별자 및 물리적 특성
| CAS No. | 17508-17-7 |
|---|---|
| 분자식 | C6H5N3O5 |
| 평균 분자량 | 199.12 g/mol |
| 단동위원소 질량 | 199.02292026 g/mol |
| SMILES | NOc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] |
| InChIKey | YLACRFYIUQZNIV-UHFFFAOYSA-N |
| PubChem CID | 87140 |
| EC No. | 241-512-6 |
| DTXSID | DTXSID20169926 |
화학 및 물리적 성질
| XLogP | 0.7 |
|---|---|
| 극성 표면적 | 127 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 6 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 14 |
| 형식 전하 | 0 |
| 복잡도 | 235 |
| 녹는점 | 112.5°C |
| 끓는 점 | 336.62°C (rough estimate) |
| 밀도 | 1.6937 (rough estimate) |
| 굴절률 | 1.6910 (estimate) |
| 저장 조건 | 2-8°C(protect from light) |
| 용해도 | DMSO(적게), 메탄올(약간)에 용해됨 |
| 물리적 상태 | 고체 |
| pKa(산도 계수) | -1.07±0.70(Predicted) |
| 색상 | 노란색 |
| InChI | InChI=1S/C6H5N3O5/c7-14-6-2-1-4(8(10)11)3-5(6)9(12)13/h1-3H,7H2 |
| InChIKey | YLACRFYIUQZNIV-UHFFFAOYSA-N |
| SMILES | NOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O |
화학적 성질
Light yellow solid
안전 및 규제
| GHS 분류 | WarningH302 (95.6%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 45 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (95.6%) |
| TSCA 등재 상태 | No |
| 관세 코드 | 29221990 |
| 위험 문구(R) | 22-36/37/38 |
| 안전 문구(S) | 26 |
용도
용도
O-(2,4-Dinitrophenyl)hydroxylamine is a rapid active-site-directed inhibitor of D-amino acid oxidase; modification results in specific incorporation of an amine group into an accessible nucleophilic r esidue with concomitant release of 2,4-dinitrophenol.
제조 및 합성 방법
제조 방법
To a stirred solution of 13.3 gm (0.1 mole) of t-butyl JV-hydroxycar-bamate and 5.6 gm (0.1 mole) of potassium hydroxide in 200 ml of absolute ethanol is added 20.2 gm (0.1 mole) of 2,4-dinitrochlorobenzene. The resultant deep red solution is stirred at room temperature for 1 hr; then enough glacial acetic acid is added dropwise to produce a light yellow solution. The solution is poured into 1.5 liters of cold water. The yellow oil which separates is gradually converted to crystals. The solid -butyl JV-(2,4-dinitrophenoxy)carbamate is separated, dried, and recrystallized from an ethyl acetate-hexane mixture to afford 16.4 gm (53%), m.p. 74-75°C. To 15 ml of trifluoroacetic acid is added 4 gm (0.0133 mole) of the i-butyl J/V-(2,4-dinitrophenoxy)carbamate. After the evolution of carbon dioxide has subsided, the solution is poured into 100 ml of ice water. The resultant oily layer crystallizes on standing to afford 2.5 gm (95%), m.p. 112°C (from ethanol). Recently it was discovered that the alkylation of ethyl JV-hydroxy-carbamate under alkaline conditions, particularly in a DMF medium at 60°C in the presence of sodium bicarbonate, leads to the ultimate formation of O-alkylated hydroxylamines. On the other hand, at 80-85°C, the direct alkylation without the presence of a base ultimately leads to N-alkylhydrox-ylamines (see Table I) [59]. The reaction of ethylazidoformate with an alcohol, while perhaps hazardous, may have some merit (Eqs. 31-33). The overall yield, based on ethyl chloroformate, is said to be on the order of 60%.