N-Iodosuccinimide N-碘代丁二酰亚胺
CAS 516-12-1 MFCD00005512
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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
GHS Symbol
- 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;
- 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
- 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.....
- 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
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