1-iodopyrrolidine-2,5-dione

• ChemBase编号: 22338
• 分子式: C4H4INO2
• 平均质量: 224.98453
• 单一同位素质量: 224.92867637
• SMILES: C1CC(=O)N(C1=O)I
• Canonical SMILES: IN1C(=O)CCC1=O
• InChI: InChI=1S/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2
• InChIKey: LQZMLBORDGWNPD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-iodopyrrolidine-2,5-dione
• IUPAC传统名: N-iodosuccinimide; NIS
• 别名: N-碘化丁二酰胺; N-碘代琥珀酰亚胺; N-Iodosuccinimide; 1-Iodopyrrolidine-2,5-dione; 1-iodo-2,5-pyrrolidinedione; NIS; Succiniodimide; N-Iodosuccinimide; 1-Iodopyrrolidine-2,5-dione; 2,5-Dioxo-1-iodopyrrolidine

登记号

• CAS号: 516-12-1
• EC号: 208-221-6
• MDL号: MFCD00005512
• Beilstein号: 113917
• 默克索引号: 145045
• PubChem SID: 24853162; 160985645; 24881033
• PubChem CID: 120273

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): -0.093946725
• LogD (pH = 7.4): -0.093946725
• Log P: -0.093946725
• 摩尔折射率: 34.8222 cm^3
• 极化性: 14.219178 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

• 熔点: ~200 °C (dec.); 195°C(dec); 202(dec.)°C; 202-206 °C(lit.); ca 196°C dec.
• 密度: 2.245

安全信息

• 保存注意事项: Harmful/Irritant/Light Sensitive/Moisture Sensitive/Store under Argon/Keep Cold; IRRITANT, LIGHT SENSITIVE, MOISTURE SENSITIVE; Moisture & Light Sensitive
• RTECS编号: WN2817000
• 欧盟危险性物质标志: X; 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38; R:36/37/38
• 安全公开号: 26-36; 26-36/37; S:20-25-26-37/39
• TSCA收录: false; 否
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Warning
• GHS危险声明: H301-H315-H319-H335; H302-H315-H319-H335
• GHS警示性声明: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97.0% (RT); 95%; 97%
• 级别: purum
• Empirical Formula (Hill Notation): C4H4INO2

详细说明

MP Biomedicals - 05208506

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02155068

Crystalline

Sigma Aldrich - 220051

Application
从 1,6-二炔经过高效的两步工艺制备的高取代的碘苯。1与 TFA 一起使用，将硫苷化学选择性地水解为 1-羟基糖苷。2从烯烃和苯亚磺酸合成乙烯砜。3
包装
5, 25, 100 g in glass bottle

Sigma Aldrich - 58070

Other Notes
用于硫官能团的氧化滴定1；氧化剂2,3,4；碘化剂5

Toronto Research Chemicals - I719900

N-Iodosuccinimide is a iodo substituted succinimide that is used as an iodinating agent in chemical synthesis.

参考文献

• Castanet, A.-S. et al.: Tetrahed. Lett., 43, 5047 (2002)
• Source of positive iodine. Iodinates methoxy benzenes and naphthalenes in acetonitrile, e.g. anisole gives 95% yield of 4-iodoanisole: Tetrahedron Lett., 37, 4081 (1996).
• In combination with TFA and TFA anhydride, iodinates 2,4-diethoxypyrimidines or N-alkyluracils specifically to their 5-iodo-derivatives: Synth. Commun., 18, 855 (1988). With triflic acid, the "superelectrophile" iodine(I) triflate is formed. This species will iodinate even deactivated aromatics, e.g. nitrobenzene to the m-iodo derivative: J. Org. Chem., 58, 3194 (1993).
• Alone or with a catalytic amount of triflic acid, is a powerful coupling agent in oligosaccharide synthesis, particularly for thioglycosyl donors; see, e.g.: Tetrahedron Lett., 34, 8523 (1993). For reviews, see: Chem. Rev., 93, 1503 (1993); Contemp. Org. Synth., 3, 173 (1996).
• In the presence of triphenylphosphine or triphenyl phosphite, converts alcohols to iodides stereoselectively with inversion: Tetrahedron Lett., 3937 (1973). See also: Carbohydr. Res., 24, 45 (1972).
• In combination with the phase-transfer catalyst, Tetra-n-butylammonium iodide, A15484, oxidizes alcohols to carbonyl compounds in high yield under neutral conditions: Synthesis, 394 (1981). Glycols are cleaved to carbonyl compounds; the rate of reaction is increased by u.v. irradiation: J. Org. Chem., 46, 1927 (1981). Similarly, ɑ-hydroxyacids are oxidatively decarboxylated to ketones: J. Org. Chem., 47, 3006 (1982).
• Oxidative coupling of dianions of acyclic tertiary amides gives a stereoselective preparation of ?-lactams: J. Org. Chem., 57, 1864 (1992):
  
• Has been used in the construction of disulfide bridges in cystine peptides, from cysteine in a DMF-dichloromethane solvent: J. Org. Chem., 58, 3003 (1993).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 960 (2006).
• With K₂CO₃ in MeOH, aldehydes can be oxidized directly to methyl esters: J. Org. Chem., 54, 1213 (1989).