1-bromopyrrolidine-2,5-dione

• ChemBase编号: 91856
• 分子式: C4H4BrNO2
• 平均质量: 177.98406
• 单一同位素质量: 176.94254037
• SMILES: N1(C(=O)CCC1=O)Br
• Canonical SMILES: BrN1C(=O)CCC1=O
• InChI: InChI=1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2
• InChIKey: PCLIMKBDDGJMGD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-bromopyrrolidine-2,5-dione
• IUPAC传统名: N-bromosuccinimide
• 别名: N-溴琥珀酰亚胺; N-溴丁二酰胺; 1-Bromopyrrolidine-2,5-dione; N-Bromosuccinimide; 1-Bromo-2,5-Pyrrolidinedione; Succinobromimide; NBS; 1-bromopyrrolidine-2,5-dione; Bromosuccinimide; NSC 16; Succinbromimide; N-Bromo succinimide; N-Bromosuccinimide; N-bromosuccinimide

登记号

• CAS号: 128-08-5
• EC号: 204-877-2
• MDL号: MFCD00005510
• Beilstein号: 113916
• 默克索引号: 141438
• PubChem SID: 24892048; 162078554; 24851059
• PubChem CID: 67184
• CHEBI ID: 53174
• Chemspider ID: 60528
• 维基百科标题: N-Bromosuccinimide

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.08120419
• LogD (pH = 7.4): -0.08120419
• Log P: -0.08120419
• 摩尔折射率: 30.2166 cm^3
• 极化性: 11.852916 Å^3
• 极化表面积: 37.38 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 1.47 g / 100 mL (25°C) in water; Insoluble (25°C) in CCl4
• 外观: White solid
• 熔点: 175 - 178°C; 175-180 °C (dec.); 175-180 °C (dec.)(lit.); 175-180°C; 175-180°C dec.; 180-183°C
• 沸点: 339 °C
• 密度: 2.098; 2.098 g/cm3 (solid); 2.098 g/ml

安全信息

• 保存条件: 2-8°C, Desiccate
• 保存注意事项: Corrosive/Harmful/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; Light Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); X
• 联合国危险货物编号: 1759; 3261; UN3261
• 德国WGK号: 3
• 联合国危险货物等级: 8
• 联合国危险货物包装类别(PG): 2; III
• 澳大利亚Hazchem: 2X
• 危险公开号: 22-34; R:34
• 安全公开号: 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• 欧盟危险货物分类: C10
• 欧盟危险识别号(EUHIN): 8B
• 美国ERG指导号: 154
• TSCA收录: 是
• GHS危险品标识: GHS05; GHS06; GHS07
• GHS警示词: Danger
• 主要危害: Irritant
• GHS危险声明: H301-H314-H318; H302-H314
• GHS警示性声明: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• 个人保护装置: 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
• RID/ADR: UN 3261 8/PG 2
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95.0% (RT); 95+%; 99%
• 级别: purum; ReagentPlus®
• Empirical Formula (Hill Notation): C4H4BrNO2

详细说明

MP Biomedicals - 02101152

Crystalline
Allylic bromination reagent. Cleaves peptide at Tryptophyl residues. Decarboxylates α-amino acids, peptides, and proteins in aqueous solutions.

Sigma Aldrich - B81255

Application
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。1,2
包装
1, 5 kg in poly bottle
100, 500 g in poly bottle
5 g in glass bottle
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 18350

Application
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。

Toronto Research Chemicals - B686995

N-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis.

参考文献

• Alberola, A. et al.: Anal. Quim., 74, 761 (1968)
• Kobayashi, T. et al.: J. Chem. Soc. Perk. Trans., 12, 1372 (1968)
• Paulini, K. et al.: CHem. Ber., 127, 685 (1968)
• 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).
• Alkenes undergo trans-addition reactions with NBS in combination with a nucleophile. For examples, see: Org. Synth. Coll., 6, 184, 560 (1988). With alcohols, bromohydrin ethers are formed. For use in the synthesis of cyclopropenone, see: Org. Synth. Coll., 6, 361 (1988):
  
• 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).
• Sulfides to sulfoxides: J. Org. Chem., 37, 3976 (1968). Oximes to nitrile oxides: J. Org. Chem., 37, 436 (1968). Secondary alcohol in the presence of primary: Tetrahedron Lett., 2745 (1979). (In DMSO): Alkynes to ɑ-diketones: Can. J. Chem., 49, 1099 (1979).
• (Free radical): Aldehydes to acyl bromides or amides: Tetrahedron Lett., 31, 7237 (1990). Benzyl silyl ethers to aldehydes: Synlett, 345 (1990). Aldehydes to esters: Synlett, 347 (1990).
• For a brief feature on uses in synthesis, see: Synlett, 498 (2006). See also 1,3-Dibromo-5,5-dimethylhydantoin, A15510.
• For free-radical ɑ-bromination of a Boc glycine ester, see: Org. Synth. Coll., 9, 526 (1998).
• 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).
• 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).
• Examples of the use of NBS as a mild, selective oxidizing agent:
• For use as a mild catalyst in acetalization reactions, see Triethyl orthoformate, A13587.