N-溴代丁二酰亚胺(NBS)

CAS: 128-08-5 货号: B105057 分子式: C4H4BrNO2 分子量: 177.98 Beilstein号: 113916 EC号: 204-877-2
有货
级别和纯度: AR ? 分析纯(AR)—— 符合严格含量限度的高纯度试剂,适用于实验室分析。当精度要求高、痕量杂质可能影响结果时使用。 ≥99%
别名
N-溴代琥珀酰亚胺,NBS | N-溴丁二酰胺
储存条件
2-8°C储存,避光,充氩
运输条件
低温运输
★
规格
库存
价格
数量
25g
B105057-25g
现货 Stock Image
¥39.90
100g
B105057-100g
现货 Stock Image
¥52.90
250g
B105057-250g
现货 Stock Image
¥72.90
500g
B105057-500g
现货 Stock Image
¥120.90
2.5kg
B105057-2.5kg
现货 Stock Image
¥449.90
5kg
B105057-5kg
现货 Stock Image
¥799.90
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为什么选择此级别

AR 级 提供 ≥99% 纯度,适用于对基线干扰要求严格的色谱和分析工作流程。

🌡

储存与运输

2-8°C储存,避光,充氩。低温运输 。请查阅批次 COA 获取详细规格。

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质量文档

SDS、COA、产品数据表及规格说明书均可下载。可通过批号查询获取批次 COA。

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文献证明

在色谱分析、有机合成和交叉偶联反应领域已被 212 篇同行评审文献引用。

概述

N-溴代琥珀酰亚胺(NBS)是一种有机化合物,常用作有机合成中的溴化剂。它是溴自由基的方便来源。它用于烯丙基和苄基位置的自由基溴化。此外,NBS 也被用作有机化学中亲电加成和亲电取代反应的试剂多功能溴化剂。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。 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%。


应用:
N-溴代丁二酰亚胺可用作试剂: 在沃尔-齐格勒反应中(通过自由基途径在烯丙基位置进行溴化)。以氢化安息香和 1,2-二醇为原料,以 CCl4 为溶剂合成联苯和脂肪族 1,2-二酮。
以吲哚-β-烯胺酯或 β-烯胺酮为原料,通过 Pictet-Spengler 环化反应制备三环氮杂并 [4,5-b]吲哚。
通过 2-硅烷基-1,3-二噻烷的氧化水解合成酰基硅烷。

Common brominating agent. Oxidizes silyl ethers to aldehydes in the presence of AIBN. Versatile brominating agent. For the oxidation of tryptophan though tyrosine, histidine and methionine residues may be oxidized to a lesser extent. Also used for the modification of ribosomal sulfhydryl groups.


Product Application:

N-Bromosuccinimide can be used as a reagent:
In the Wohl-Ziegler reaction (bromination at allylic positions via a radical pathway).
To synthesize benzils and aliphatic 1,2-diketones from hydrobenzoins and 1,2-diols in the presence of CCl4 as a solvent.
To prepare tricyclic azepino[4,5-b]indoles from indole-β-enaminoesters or β-enaminones via Pictet–Spengler cyclization.
To synthesize acylsilanes via oxidative hydrolysis of 2-silyl-1,3-dithianes.

规格

别名
N-溴代琥珀酰亚胺,NBS | N-溴丁二酰胺
英文别名
NSC 16 | SCHEMBL58 | Q286939 | Succinbromide | Succinibromimide | FT-0645778 | J-005565 | MFCD00005510 | N-bromosuccinimid | N-Bromosuccinimide (NBS) | CCRIS 2899 | N-brornosuccinimide | 2, 1-bromo- | BP-30011 | N-Bromopyrrolidine-2,5-dione | UNII-K8G1F2U
规格或纯度
AR, ≥99%
英文名称
N-Bromosuccinimide(NBS)
储存条件
2-8°C储存,避光,充氩
运输条件
低温运输
纯度
≥99%
名称和识别符
PubChem SID
EC号
204-877-2
分子类型
小分子
IUPAC Name
1-bromopyrrolidine-2,5-dione
INCHI
1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
InChi Key
PCLIMKBDDGJMGD-UHFFFAOYSA-N
Smiles
C1CC(=O)N(C1=O)Br
Isomeric SMILES
C1CC(=O)N(C1=O)Br
UN Number
Packing Group
III
分子量
177.98
Beilstein号
113916
Reaxy-Rn
113916
Reaxys-RN link address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=113916&ln=

技术文档

📋 安全数据表 (SDS)

全面的危险、操作、储存及法规合规文件。

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🔬 规格说明书

该级别的完整质量属性和验收标准。

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高级数据

系统学分类

分类树(Taxonomy Tree)

界(kingdom) 有机化合物
超类(Superclass) 有机杂环化合物
类(Class) 吡咯烷
亚类(Subclass) 吡咯烷酮
中间层级节点(Intermediate Tree Nodes) 暂无
直接上位类(Direct Parent) 吡咯烷-2-酮
其他上位类(Alternative Parents) 二羧酰亚胺  内酰胺类  氮杂环化合物  有机光子化合物  有机氮化合物  有机氧化物  碳氢化合物衍生物  羰基化合物  
分子骨架(Molecular Framework) 脂肪族杂单环化合物
取代基(Substituents) 2-吡咯烷酮 - 脂肪族杂单环化合物 - 氮杂环 - 羰基 - 羧酸衍生物 - 二羧酰亚胺 - 烃衍生物 - 肟 - 有机硝基化合物 - 有机氧化物 - 有机氧化合物 - 有机氮化合物 - 有机氧化合物 - 有机氮化合物
描述(Description) 该化合物属于吡咯烷-2-酮类有机化合物。这类化合物在吡咯烷环的2位带有C=O键。
外部描述符(External Descriptors) a bromide
三维结构
交互式化学结构模型





化学和物理性质
溶解性
Soluble in acetone, tetrahydrofuran, dimethyl formamide, dimethyl sulfoxide and acetonitrile. Slightly soluble in water and acetic acid. Insoluble in ether, hexane and carbon tetrachloride.
密度
2.098
敏感性
对光敏感.热和湿度敏感
沸点
339 °C
熔点
175-180°C
分子量
177.980 g/mol
XLogP3
-0.100
氢键供体数Hydrogen Bond Donor Count
0
氢键受体数Hydrogen Bond Acceptor Count
2
可旋转键计数Rotatable Bond Count
0
精确质量Exact Mass
176.943 Da
单同位素质量Monoisotopic Mass
176.943 Da
拓扑极表面积Topological Polar Surface Area
37.400 Ų
重原子数Heavy Atom Count
8
形式电荷Formal Charge
0
复杂度Complexity
129.000
同位素原子数Isotope Atom Count
0
定义的原子立体中心计数Defined Atom Stereocenter Count
0
未定义的原子立体中心计数Undefined Atom Stereocenter Count
0
定义的键立体中心计数Defined Bond Stereocenter Count
0
未定义的键立体中心计数Undefined Bond Stereocenter Count
0
所有立体化学键的总数The total count of all stereochemical bonds
0
共价键合单元计数Covalently-Bonded Unit Count
1
安全和危险性(GHS)
象形图
GHS03,   GHS05,   GHS07,   GHS08,   GHS09
信号词
危险
危险声明

H272: 可能加剧火灾; 氧化剂

H290: 可能腐蚀金属

H302: 吞食有害

H314: 造成严重的皮肤灼伤和眼睛损伤

H315: 引起皮肤刺激

H319: 引起严重眼睛刺激

H335: 可能引起呼吸道刺激

H400: 对水生生物有剧毒

预防措施声明

P210: 远离热源,热表面,火花,明火和其他点火源。 - 禁止抽烟。

P220: 远离衣物和其他可燃物。

P234: 仅保存在原始容器中

P260: 不要吸入灰尘/烟雾/气体/雾/蒸汽/喷雾。

P261: 避免吸入灰尘/烟雾/气体/雾/蒸汽/喷雾

P264: 处理后要彻底洗手。

P270: 使用本产品时,请勿进食、饮水或吸烟。

P271: 仅在室外或通风良好的地方使用。

P273: 避免释放到环境中。

P280: 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。

P321: 特殊处理(请参阅此标签上的...)。

P330: 漱口

P363: 再次使用之前,请清洗受污染的衣物。

P390: 吸收溢出物以防止材料损坏。

P391: 收集溢出物

P301+P330+P331: 如误吞咽:漱口。不要诱导呕吐。

P302+P352: 如皮肤沾染:用水充分清洗。

P304+P340: 如误吸入:将人转移到空气新鲜处,保持呼吸舒适体位。

P305+P351+P338: 如进入眼睛:用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出,取出隐形眼镜。继续冲洗。

P362+P364: 脱掉沾污的衣服,清洗后方可重新使用。

P370+P378: 火灾时:使用干砂、干粉或抗醇泡沫灭火。

P405: 密闭存放

P406: 存放在带有耐腐蚀内衬的耐腐蚀/ ...容器中。

P403+P233: 存放在通风良好的地方。保持容器密闭。

P501: 将内容物/容器处理到。。。

P264+P265: 处理后彻底洗手[和…]。不要触摸眼睛。

P301+P317: 如果被吞咽:请寻求医疗帮助。

P305+P354+P338: 如果进入眼睛:立即用水冲洗几分钟。取下隐形眼镜(如果有的话),并且操作简单。继续冲洗。

P337+P317: 如果眼睛刺激持续:寻求医疗帮助。

P332+P317: 如果出现皮肤刺激:请寻求医疗帮助。

P302+P361+P354: 如果接触皮肤:立即脱掉所有被污染的衣服。立即用水冲洗几分钟。

P316: 立即寻求紧急医疗救助。

P319: 如果你感到不适,请寻求医疗帮助。

WGK Germany
3
Class
8
Merck Index
1438
个人防护装备
Eyeshields,Faceshields,full-face particle respirator type N100 (US),Gloves,respirator cartridge type N100 (US),type P1 (EN143) respirator filter,type P3 (EN 143) respirator cartridges
质检证书(CoA,COO,BSE/TSE 和分析图谱)
C of A & Other Certificates(BSE/TSE, COO):
输入批号以搜索分析图谱:

通过匹配包装上的批号来查找并下载产品的 COA,每批产品都进行了严格的验证,您可放心使用!

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技术文档和文章
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Triphenylphosphine Dibromide (PPh₃Br₂) Is More Than Just a Brominating Reagent: Experimental Selection Logic from Alcohol-to-Alkyl Bromide Conversion to Carboxylic Acid Activation and One-Pot Esterification, Vinyl Bromide Formation, and Nitrile Constructi
三苯基膦参与的羧酸活化与酰胺键形成:活化路径、酸酐竞争与适用场景
Triphenylphosphine-Involved Carboxylic Acid Activation and Amide Bond Formation: Activation Pathways, Anhydride Competition, and Applicability Scenarios
N-Bromosuccinimide (NBS)
3-Chloroperoxybenzoic acid, m-CPBA
Dimethyl sulfoxide (DMSO)
氮杂三环烷烃的张力释放:三维氮杂桥环的桥位模块化官能团化与立体控制
Strain Release of Azatricycloalkanes: Modular Bridge-Position Functionalization and Stereochemical Control of Three-Dimensional Bridged Aza Scaffolds
三种四元环锍盐模块化构建九类螺[2.3]己烷骨架:合成方法与生物电子等排体评价
Modular Construction of Nine Classes of Spiro[2.3]hexane Scaffolds Using Three Four-Membered-Ring Sulfonium Salts: Synthetic Methodology and Bioisosteric Evaluation
如何绕开α-氟消除:α,α-二氟苄基阴离子的溴转移捕获与氧化偶联
How to Bypass α-Fluoride Elimination: Bromine-Transfer Capture and Oxidative Coupling of α,α-Difluorobenzylic Anions
含氟3,3-二取代氧杂环丁烷砌块的设计逻辑:结构构建及胺碱性、亲脂性与代谢稳定性调节
Design Logic of Fluorinated 3,3-Disubstituted Oxetane Building Blocks: Structural Construction and Modulation of Amine Basicity, Lipophilicity, and Metabolic Stability
1,8-萘啶型醛糖还原酶抑制剂:骨架构建、体外抑制活性与结构优化方向
1,8-Naphthyridine-Based Aldose Reductase Inhibitors: Scaffold Construction, In Vitro Inhibitory Activity, and Directions for Structural Optimization
LY3509754关键α-溴代酮的构建:β-氧代酯策略与酶促酯水解后的伴随脱羧
Construction of the Key α-Bromoketone Intermediate for LY3509754: A β-Keto Ester Strategy and Concomitant Decarboxylation Following Enzymatic Ester Hydrolysis
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引用文献
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105. Hong-Yun Zhu, Sheng-Gang Chen, Qilei Zhang, Dong-Qiang Lin, Shan-Jing Yao.  (2019)  Adsorption Characteristics of Human Immunoglobulin G on Five New Tetrapeptide Biomimetic Affinity Resins.  JOURNAL OF CHEMICAL AND ENGINEERING DATA,  [10.1021/acs.jced.8b01199]
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107. Qian Yang, Ling Li, Xue Lang Gao, Hong Yue Wu, Fang Hua Liu, Qiu Gen Zhang, Ai Mei Zhu, Chun Hui Zhao, Qing Lin Liu.  (2019)  Crown ether bridged anion exchange membranes with robust alkaline durability.  JOURNAL OF MEMBRANE SCIENCE,  [10.1016/j.memsci.2019.02.038]
108. Dong Pan, Pingping Liang, Xiangmin Zhong, Dong Wang, Hui Cao, Wenjun Wang, Wanli He, Zhou Yang, Xiaochen Dong.  (2019)  Self-Assembled Porphyrin-Based Nanoparticles with Enhanced Near-Infrared Absorbance for Fluorescence Imaging and Cancer Photodynamic Therapy.  ACS Applied Bio Materials,  [PMID:35021390] [10.1021/acsabm.8b00530]
109. Zhixiang Lu, Yanxiong Liu, Xiaolan Liu, Shuhan Lu, Yuan Li, Shaoxiong Yang, Yu Qin, Liyan Zheng, Hongbin Zhang.  (2019)  A hollow microshuttle-shaped capsule covalent organic framework for protein adsorption.  Journal of Materials Chemistry B,  7  (9): (1469-1474).  [PMID:32255018] [10.1039/C8TB02870B]
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116. Xinfeng Cheng, Xiuping Ju, Hongmei Du, Yan Zhang, Jinsheng Zhao, Yu Xie.  (2018)  Synthesis and characterization of novel donor–acceptor type electrochromic polymers containing diketopyrrolopyrrole as an acceptor and propylenedioxythiophene or indacenodithiophene as a donor.  RSC Advances,  8  (41): (23119-23129).  [PMID:35540135] [10.1039/C8RA03570A]
117. Tingting Zhu, Ji Xiong, Zhongbo Xue, Yu Su, Fengnan Sun, Ran Chai, Jialiang Xu, Yaqing Feng, Shuxian Meng.  (2018)  A novel amphiphilic fluorescent probe BODIPY–O-CMC–cRGD as a biomarker and nanoparticle vector.  RSC Advances,  8  (36): (20087-20094).  [PMID:35541689] [10.1039/C8RA02125B]
118. Zhixiang Lu, Yunming Liu, Shuhan Lu, Yuan Li, Xiaolan Liu, Yu Qin, Liyan Zheng.  (2018)  A highly selective TPE-based AIE fluorescent probe is developed for the detection of Ag+.  RSC Advances,  8  (35): (19701-19706).  [PMID:35541010] [10.1039/C8RA03591A]
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128. Zelin Chen, Bowen Li, Xin Xie, Fang Zeng, Shuizhu Wu.  (2017)  A sequential enzyme-activated and light-triggered pro-prodrug nanosystem for cancer detection and therapy.  Journal of Materials Chemistry B,  6  (17): (2547-2556).  [PMID:32254473] [10.1039/C7TB01989K]
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130. Tao Liu, James M. Angelo, Dong-Qiang Lin, Abraham M. Lenhoff, Shan-Jing Yao.  (2017)  Characterization of dextran-grafted hydrophobic charge-induction resins: Structural properties, protein adsorption and transport.  JOURNAL OF CHROMATOGRAPHY A,  [PMID:28855091] [10.1016/j.chroma.2017.07.090]
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135. Jinlei Wang, Ying Chen, Qi Wei, Shanzhong Yang, Huagao Fang, Haibing Wei, Yunsheng Ding.  (2017)  Adamantammonium as a novel functional group for anion exchange membranes with excellent comprehensive performances.  POLYMER,  [10.1016/j.polymer.2017.02.030]
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