3-溴哒嗪
3-溴哒嗪 · 3-溴吡哒嗪 · 3-bromopyridazine · 3-bromo- (9CI) · Pyridazine, 3-broMo- · 3-Bromopyridazine ,97% · Pyridazine, 3-bromo- (9CI) · 3-broMopyridazine hydrobroMide
标识与物理属性
| CAS No. | 88491-61-6 |
|---|---|
| 分子式 | C4H3BrN2 |
| 平均分子量 | 158.98 g/mol |
| 单同位素质量 | 157.94796 g/mol |
| SMILES | Brc1cccnn1 |
| InChIKey | ILYSUJOMLYXAOC-UHFFFAOYSA-N |
| PubChem CID | 13126699 |
| EC No. | 811-583-3 |
| DTXSID | DTXSID10520082 |
| 中文名 | 3-溴哒嗪 |
化学与物理性质
| XLogP | 0.2 |
|---|---|
| 极性表面积 | 25.8 |
| 氢键供体 | 0 |
| 氢键受体 | 2 |
| 可旋转键 | 0 |
| 重原子 | 7 |
| 形式电荷 | 0 |
| 复杂度 | 57 |
| 熔点 | 73-74 °C |
| 沸点 | 270.0±13.0 °C(Predicted) |
| 密度 | 1.726±0.06 g/cm3(Predicted) |
| 储存条件 | Inert atmosphere,Store in freezer, under -20°C |
| 形态 | solid |
| pKa（酸度系数） | 0.99±0.10(Predicted) |
| 颜色 | Yellow to reddish brown |
| InChI | 1S/C4H3BrN2/c5-4-2-1-3-6-7-4/h1-3H |
| InChIKey | ILYSUJOMLYXAOC-UHFFFAOYSA-N |
| SMILES | BrC1=CC=CN=N1 |
| CAS 数据库 | 88491-61-6 |
安全与法规
| GHS 分类 | DangerH301+H311+H331 (16.7%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]H302 (83.3%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (33.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H319 (33.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332 (50%): Harmful if inhaled [Warning Acute toxicity, inhalation]H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 6 reports by companies from 4 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. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (83.3%)Skin Irrit. 2 (66.7%)Eye Dam. 1 (33.3%)Eye Irrit. 2A (33.3%)Acute Tox. 4 (50%)STOT SE 3 (66.7%) |
| 储存类别 | 11 - Combustible Solids |
| 海关编码 | 2933998090 |
| 危险类别 | Acute Tox. 4 Oral |
制备与合成方法
生产方法
3-溴哒嗪的合成：将溴氧化磷（158 g，552 mmol）置于机械搅拌下，加热至80℃直至完全熔融。随后，将3-羟基哒嗪（30.5 g，317 mmol）一次性加入熔融的溴氧化磷中，反应混合物颜色迅速由橙色变为黄色，最终形成黑色固体。将反应体系升温至120℃，维持此温度反应3小时。反应完成后，冷却反应混合物至室温，随后在冰水浴中进一步冷却。缓慢加入冰水（总量300 mL），注意控制加入速度以缓解放热现象（观察到白烟生成）。在搅拌过程中，部分固体未溶解，此时加入2M NaOH水溶液（180 mL），继续搅拌45分钟直至所有固体完全溶解。将得到的深红色/棕色溶液缓慢倒入预先冷却并含有2M NaOH水溶液（910 mL）的冰/水浴中，保持内部温度低于25℃。用2M NaOH水溶液（50 mL）调节溶液pH至约9.5。使用二氯甲烷（DCM，5×250 mL）对溶液进行萃取，合并黄色有机层，用无水硫酸钠（Na2SO4）干燥，过滤后真空浓缩，得到灰色/棕色固体粗产物。将粗产物吸附于二氧化硅（98 g）上，通过硅胶柱（200 g）用庚烷/乙酸乙酯（1:1）作为洗脱剂进行纯化。收集含目标产物的馏分，合并后真空浓缩，得到3-溴哒嗪（34.7 g，216 mmol，产率69%），为绿色/灰色固体。GCMS分析显示产物纯度>99%。参考文献：[1] Patent: WO2015/161928, 2015, A1. Location in patent: Page/Page column 68[2] Patent: WO2015/161924, 2015, A1. Location in patent: Page/Page column 19; 20