N-Bromosuccinimide N-溴代丁二酰亚胺
CAS 128-08-5 MFCD00005510
化学结构图
SMILES: O=C1CCC(=O)N1Br
化学属性
| Mol. Formula | C4H4BrNO2 |
|---|---|
| Mol. Weight | 177.98 |
| Melting Point | 175-180°C |
| Density | 2.098 |
| TSCA | Yes |
| Stability | 对光敏感.热和湿度敏感 |
| Appearance | 白色或乳白色细粒结晶，182℃ 时分解。活性溴最小含量44.5%。 |
| Solubility | 溶于丙酮、乙酸乙酯、醋酸酐，难溶于水、苯、四氯化碳、氯仿等。 |
| Boiling Point | 221.4 °C at 760 mmHg |
别名和识别编码
| Chemical Name | N-Bromosuccinimide |
|---|---|
| CAS Number | 128-08-5 |
| Synonym | 1-Bromo-2,5-pyrrolidinedione {LY} 1-Bromo-2,5-pyrrolidinedione {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {} {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1-Bromo-2,5-pyrrolidinedione {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1-Br |
| PubChem Substance ID | 87563662 |
| EC Number | 204-877-2 |
| Beilstein Registry Number | 21(5)9,543 |
| MDL Number | MFCD00005510 |
| Merck Number | 1438 |
| Alfabeta Name | BROMODIHYDROPYRROLEDIONE H1125-----, |
| Reaxys-RN | 113916 |
| Chemical Name Translation | N-溴代丁二酰亚胺 |
| LabNetwork Molecule ID | LN00195931 |
| InChI | InChI=1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2 |
| Canonical SMILES | O=C1N(C(CC1)=O)Br |
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分类
- Active Esters/Additives, Bromination, C-X Bond Formation (Halogen), Chemical Biology, Chemical Synthesis, Essential Chemicals, Inorganic Salts, Solutions and Reagents, Peptide Chemistry, Peptide Coupling, Reagent Plus, Research Essentials, Synthetic Reagents
- {SNA} Active Esters/Additives, Bromination, C-X Bond Formation (Halogen), Chemical Biology, Chemical Synthesis, Peptide Chemistry, Peptide Coupling, Synthetic Reagents
- {SA} Active Esters/Additives, Bromination, C-X Bond Formation (Halogen), Chemical Biology, Chemical Synthesis,
产品应用
- 多功能溴化剂。用于色氨酸的氧化反应，但酪氨酸、组氨酸和甲硫氨酸残基被氧化的程度可能较低。也可用于核糖体巯基的改性。
- 通用溴化剂。在 AIBN 存在的条件下，可将硅基醚氧化为醛。
相关文献及参考
- In acetonitrile, NBS is a mild and regiospecific nuclear brominating agent for activated aromatics such as methoxybenzenes and naphthalenes: J. Org. Chem., 60, 5328 (1995). Deactivated aromatics, e.g. nitroarenes and benzotrifluorides, can be m-brominated under mild conditions in good yield with NBS in TFA, in the presence of H2SO4: Synlett, 1245 (1999).
- Both aliphatic and aromatic aldehydes are converted to acyl bromides under free-radical conditions: Tetrahedron Lett., 3809 (1979); Synlett, 347 (1990); Tetrahedron Lett., 31, 7237 (1990).
- Source of free-radical or positive bromine. For examples of radical benzylic bromination (Wohl-Ziegler), see: Org. Synth. Coll., 4, 921 (1963); 5, 145, 329, 825 (1973). The use of the ozone depleting solvent CCl4 has been avoided by the use of the ionic liquid 1-n-Butyl-3-methylimidazolium hexafluorophosphate, L19086: Synlett, 702 (2003). Cleavage of carbohydrate benzyl ethers: J. Org. Chem., 55, 378 (1990), and of benzyl esters: Synlett, 219 (1994), occur under mild conditions; the benzyl group is converted to benzaldehyde. For allylic bromination, see e.g.: Org. Synth. Coll., 4, 108 (1963);.9, 112, 191 (1998) review: Chem. Rev., 43, 271 (1948).
- In the presence of a phosphine or phosphite, converts alcohols to alkyl bromides with inversion: Tetrahedron Lett., 3937 (1973). For a review of this and related reactions, see: Org. React., 29, 1 (1983).
- Alberola, A. et al.: Anal. Quim., 74, 761 (1968); Kobayashi, T. et al.: J. Chem. Soc. Perk. Trans., 12, 1372 (2001); Paulini, K. et al.: CHem. Ber., 127, 685 (1994);
- Short: II/27C
- For a brief feature on uses in synthesis, see: Synlett, 498 (2006). See also 1,3-Dibromo-
- Merck: 14,1438 Beilstein:21(5)9,543
- In the presence of DBU in MeOH, amides rearrange to amines in good yields, providing a mild and efficient alternative to the classical Hofmann halogen/ caustic alkali conditions: J. Org. Chem., 62, 7495 (1997).
安全信息
GHS Symbol
- H290 May be corrosive to metals 可能腐蚀金属。
- H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
- H302 Harmful if swallowed 吞食有害
- P234 Keep only in original container. 只保留在原来的容器中。
- P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
- P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
- P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
- P301+P330+P331
- P301+P330+P331+P310
- P303+P361+P353+P310+P363
- P304+P340+P310
- P305+P351+P338
- P305+P351+P338+P310
- P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
- P390 Absorb spillage to prevent material damage. 吸收溢出物，防止重大损害。
- P405 Store locked up. 上锁保管。
- P406 Store in corrosive resistant/… container with a resistant inner liner. 存放在耐腐蚀/具有耐性的内衬容器。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
- S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
- S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护；
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
- R22 Harmful if swallowed 吞咽有害
- R34 Causes burns 会导致灼伤
- R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
其他信息
- 用途四:有机合成原料，用于调节低能溴化反应，也用于生产橡胶助剂和医药品。可合成溴乙腈医药。农药工业用于合成噻菌灵，还可用作水果保鲜剂以及防腐、防霉剂等。
- 储运特性:库房通风低温干燥; 与苯胺; 二烷基硫; 水合肼,过氧化物, 丙腈分开存放
- 可燃性危险特性:对人眼睛,皮肤和黏膜有刺激性; 热分解排出有毒氮氧化物和溴化物烟雾
- 上游原料:丁二酸 --> 丁二酰亚胺
- TCI Shanghai:N-溴代丁二酰亚胺 N-Bromosuccinimide,>;98.0%(T)(128-08-5)
- Acros Organics:n-溴琥珀酰亚胺 N-Bromosuccinimide, 99%(128-08-5)
- 急性毒性:腹腔-小鼠 LDL0: 256 毫
- {Chemicalb
- Hazard Note:Harmful
- N-溴代丁二酰亚胺价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 30028616 N-溴代丁二酰亚胺 100g 80.5元 2011/08/23 30028626 N-溴代丁二酰亚胺 100g 70元 2011/04/16 B0656 N-溴代丁二酰亚胺 N-Bromosuccinimide 100G 280元
- MOL 文件:128-08-5.mol
- 存储注意事项:湿度敏感;光敏感
- Sigma Aldrich:128-08-5(sigmaaldrich)
- 微有溴气味。能溶于丙酮，微溶于水、叔丁醇、四氯化碳、己烷和冰乙酸。活性溴的最小含量44.5%。
- 方法一:1.由丁二酰亚胺溴化而得。将丁二酰亚胺磨细投入反应锅，加入碎冰和氢氧化钠溶液，搅拌溶解。在剧烈搅拌和冷却的情况下
- 用途三:用作鉴别伯、仲、叔醇试剂
- 海关编码:29251995
- 爆炸物危险特性:与苯胺, 二烷基硫, 水合肼反应爆炸; 105℃加热24小时与丙腈反应爆炸
- 类别:有毒物质
- Alfa Aesar:N-
- 方法一:1.由丁二酰亚胺溴化而得。将丁二酰亚胺磨细投入反应锅，加入碎冰和氢氧化钠溶液，搅拌溶解。在剧烈搅拌和冷却的情况下，加入溴和四氯化碳的混合液，搅拌2分钟后迅速过滤。用
- 用途一:可合成溴乙腈药物，农药工业用于合成噻菌灵，可用作水果保鲜剂以及防腐、防霉剂等
- 用途五
- 用途二:用作鉴别伯、仲与叔醇的试剂及橡胶制品附加剂，也用于有机合成
- 下游产品:1,4-二(溴甲基)苯 --> 1H-吡唑-4-甲酸 --> 5-溴-4-氯-7H-吡咯并[2,3-d]嘧啶 --> 5-溴-4-氯-2-甲硫-7H-吡咯[2,3-D]嘧啶 --> 咪唑并[1,2-A!吡啶-2-羧酸 --> 5-溴-2-(哌啶-1-基)嘧啶 --> 3-[(1-吗啉基)甲基]苯甲酸甲酯 --> 4-溴巴豆酸乙酯 --> 5-溴-2-氯-4,6-二甲基尼古丁腈 --> 5-溴-4,6-二甲氧基嘧啶 --> 5-甲基-4-溴-1H-吡唑-3-羧酸 --> 2,5-二氯-3-噻吩甲酸 --> 3-溴-5-(三氟甲基)苯磺酰氯 --> 4-溴-2-甲氧基苯酚 --> 5-溴氧化吲哚 --> 2-羟基-5-溴吡啶 --> 3-硝基溴苄 --> 双(3-甲基-1-苯基-5-吡唑啉酮) --> 3-甲氧基-4-溴甲基苯甲酸甲酯 --> 2,6-二溴-3-氨基吡啶 --> 咪唑并[1,2-A]吡啶-2-羧酸乙酯 --> 2-氨基-5-溴吡嗪 --> 4-二甲基氨甲基-苯胺 --> 3-溴甲基苯甲酸 --> 2-溴甲基苯甲酸甲酯 --> 2-(溴甲基)吡啶氢溴酸盐 --> 5-溴-2-(吗啉-4-基)嘧啶 --> 溴乙腈 --> 4-甲基磺酰苄溴 --> 雷替曲塞
- 检测方法:T(Iodometry)
- 毒性分级:高毒
- 急性毒性:腹腔-小鼠 LDL0: 256 毫克/公斤
