N-Iodosuccinimide N-碘代丁二酰亚胺

CAS 516-12-1 MFCD00005512

化学结构图

516-12-1
SMILES: O=C1CCC(=O)N1I

化学属性

Mol. FormulaC4H4INO2
Mol. Weight224.98
Melting Point200-201°C
Density2.31
TSCANo
Solubility分解
Stability对光敏感
Appearance 白色针状结晶。熔点200-201℃,溶于丙酮、甲醇,略溶于二氧六环,几乎不溶于四氯化碳、乙醚。遇水分解。
Boiling Point249.6±23.0°C at 760 mmHg
Flash Point104.8±22.6°C

别名和识别编码

Chemical NameN-Iodosuccinimide
CAS Number516-12-1
Alfabeta NameIODOSUCCINIMIDE N-
MDL NumberMFCD00005512
Synonym N-Iodosuccinimide {LY} N-Iodosuccinimide {} {LY} N-Iodosuccinimide {} {} {LY} N-Iodosuccinimide {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} N-Iodosuccinimide {} {} {} {}
EC Number208-221-6
Beilstein Registry Number113917
PubChem Substance ID87571478
Merck Number5045
Chemical Name TranslationN-碘代丁二酰亚胺
Reaxys-RN113917
Wiswesser Line NotationT5VNVTJ BI
LabNetwork Molecule IDLN00117310
InChIInChI=1S/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2
Canonical SMILESO=C(CC1)N(I)C1=O
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分类

  • Heterocycles
  • {uni_hamburg} no charge; nitrogen heterocycle; alicycle; 5ring; amide; lactame; 1fragment
  • Miscellaneous Reagents
  • {SNA} C-X Bond Formation (Halogen), Chemical Synthesis, Iodination, Synthetic Reagents

产品应用

  • 用于有机合成,硫的氧化滴定试剂, 用作温和的碘化剂、硫苷催化剂等。

相关文献及参考

  • Oxidative coupling of dianions of acyclic tertiary amides gives a stereoselective preparation of ß-lactams: J. Org. Chem., 57, 1864 (1992):
  • 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).
  • Source of positiv
  • With K2CO3 in MeOH, aldehydes can be oxidized directly to methyl esters: J. Org. Chem., 54, 1213 (1989).
  • In combination
  • 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).
  • Castanet, A.-S. et al.: Tetrahed. Lett., 43, 5047 (2002);
  • 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 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).
  • Short: EINECS
  • Short: III/5a
  • 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).
  • For a brief feature on uses of the reagent in synthesis, see: Synlett, 960 (2006).

安全信息

Warnings IRRITANT, LIGHT SENSITIVE, MOISTURE SENSITIVE
Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • 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 Wear suitable protective clothing 穿戴适当的防护服;
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • 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+P312+P330
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P332+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
RTECSWN2817000
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Storage condition 2-8°C, protect from light {LY} 2-8°C, protect from light <0°C <;0 Moisture & Light Sensitive {} {LY} 2-8°C, protect from light {} {} {LY} 2-8°C, protect from light {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from li
Hazard Codes Xn Xn,Xi
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 180 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems
   Laboratory, NIOSH Exchange Chemicals.  (Aberdeen Proving Ground, MD 21010)
   Volume(issue)/page/year: NX#02815

其他信息

  • 用途一:主要作为生物制药中的医药中间体
  • 上游原料:1,4-二氧六环 --> 丁二酰亚胺 --> 二亚胺
  • Alfa Aesar:N-碘化丁二酰胺,97+% N-Iodosuccinimide, 97%(516-12-1)
  • MOL 文件:516-12-1.mol
  • 用途二:在有机合成中用于酮类、醛类的碘化。
  • Acros Organics:N-碘代琥珀酰亚胺 N-Iodosuccinimide, 98%(516-12-1)
  • 水中分解,溶于丙酮、甲醇,中度溶于二氧六环,微溶于二氯甲烷和醚,实际上不溶于四氯化碳。
  • 图谱信息:N-碘代丁二酰亚胺(516-12-1)核磁图( 13 CNMR) N-碘代丁二酰亚胺(516-12-1)红外图谱(IR2) N-碘代丁二酰亚胺(516-12-1)红外图谱(IR1) N-碘代丁二酰亚胺(516-12-1)核磁图( 1 HNMR)
  • 检测方法:T,NMR
  • 敏感性:Moisture Sensitive
  • F:8-9
  • Hazard Note:Harmful/Keep Cold/Moisture Sensitive
  • 下游产品:4,5-二甲氧基-3-碘苯甲醛 --> 2,4-二甲氧基-5-碘嘧啶 --> 2-氯-4-硝基苯-alpha-L-岩藻糖苷
  • TCI Shanghai:N-碘代琥珀酰亚胺 N-Iodosuccinimide,>;98.0%(T)(516-12-1)
  • 存储注意事项:氮气保护
  • 方法一:在避光条件下,使丁二酰亚胺与氧化银反应,制取N-丁二亚胺银。将其和碘在干燥的二氧六环中反应,生成N-碘琥珀酰亚胺。
  • 海关编码:29251995
  • 用途三:用于有机合成,硫的氧化滴定试剂, 用作温和的碘化剂、硫苷催化剂等。
  • N-碘代丁二酰亚胺价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 I0074 N-碘琥珀酰亚胺 N-Iodosuccinimide 100G 3150元 2014/06/02 I0074 N-碘琥珀酰亚胺 N-Iodosuccinimide 25G 1020元 2014/06/02 I0074 N-碘琥珀酰亚胺 N-Iodosuccinimide 5G 325元
  • Sigma Aldrich:516-12-1(sigmaaldrich)
  • MSDS 信息:1-Iodo-2,5-pyrrolidinedione(516-12-1).msds

系列性分类