1,1,1-Triacetoxy-1,1-Dihydro-1,2-Benziodoxol-3(1H)-One 戴斯-马丁氧化剂
CAS 87413-09-0 MFCD00130127
化学结构图
SMILES: CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21
化学属性
| Mol. Formula | C13H13IO8 |
|---|---|
| Mol. Weight | 424.14 |
| Melting Point | 130-133°C |
| Density | 1.369 |
| Boiling Point | 40 °C at 760 mmHg |
| TSCA | No |
| Stability | 对光线敏感，对湿度敏感 |
| Flash Point | -11°C(lit.) |
| pH | :A |
别名和识别编码
| Chemical Name | 1,1,1-Triacetoxy-1,1-Dihydro-1,2-Benziodoxol-3(1H)-One |
|---|---|
| CAS Number | 87413-09-0 |
| Alfabeta Name | TRISACETYLOXYDIHYDROBENZIODOXOLONE H111111231(())-------,,,, |
| MDL Number | MFCD00130127 |
| Synonym | Dess-Martin periodinane {LY} Dess-Martin periodinane {} {LY} Dess-Martin periodinane {} {} {LY} Dess-Martin periodinane {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Dess-Martin periodinane {} {} {} {} {} {} {} {} |
| PubChem Substance ID | 87568496 |
| Merck Number | 2933 |
| Beilstein Registry Number | 4548207 |
| EC Number | 250-023-7 |
| Chemical Name Translation | 戴斯-马丁氧化剂 |
| Reaxys-RN | 4548207 |
| LabNetwork Molecule ID | LN00164239 |
| Canonical SMILES | CC(OI(OC(C)=O)(C(C=CC=C1)=C1C2=O)(O2)OC(C)=O)=O |
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分类
- {SNA} Chemical Synthesis, Hypervalent Iodine, Oxidizing Agents, Synthetic Reagents
产品应用
- 氧化剂，用于氧化羟基二氢卟啉（hydroxychlorins）生成二氢卟啉-α-二酮（chlorin-α-diones）和四酮。也用于把醇氧化成醛和酮。
相关文献及参考
- Hydroxamic acids are oxidized to acyl nitroso compounds which can undergo cycloaddition to dienes: Synth. Commun., 30, 47 (2000).
- For a detailed discussion of the scope an
- Merck: 14,2933
- Deprotection of thioacetals can be accomplished under extremely mild conditions: Org. L
- For use in the synthesis of imides, N-acyl vinylogous carbamates and ureas, and nitriles, by oxidation of amides and amines, see: Angew. Chem. Int. Ed., 44, 5992 (2005).
- One of the mildest reagents for the selective oxidation of primary and secondary alcohols to aldehydes and ketones. High yields can be obtained at ambient temperatures, under neutral conditions, in chloroform, dichloromethane or acetonitrile: J. Org. Chem., 48, 4155 (1983); J. Am. Chem. Soc., 113, 7277 (1991); (reviews): J. Prakt. Chem./ Chem. Ztg., 338, 588 (1996); Synlett, 278 (2000). Has been employed for the oxidation of a wide variety of sensitive substrates and is particularly valuable in multi-step syntheses of polyfunctional molecules with complex stereochemistry. For an example involving exclusive oxidation of one of four possible secondary OH groups in a synthesis of erythromycin B, see: J. Am. Chem. Soc., 119, 3193 (1997). Allylic and benzylic alcohols can be oxidized selectively in the presence of saturated alcohols, and give the carbonyl compounds cleanly without over-oxidation or cis-trans isomerization: Tetrahedron Lett., 29, 995 (1988); J. Org. Chem., 55, 1636 (1990).
- ɑ,ß-Unsaturated carboxylic acids undergo Hunsdiecker-type decaboxylative bromination with tetraethylammonium bromide in the presence of the reagent: Synlett, 2495 (2005).
- CAUTION! In the presence of moisture, may form iodoxybenzoic acid which has been reported to be explosive under excessive heating or impact: Chem. Eng. News, 68(29), 3 (1990).
- Has also been used for deoximation of ketoximes to ketones under mild conditions: Tetrahedron Lett., 39, 3209 (1998); Synthesis, 760 (1999).
安全信息
GHS Symbol
- P201 Obtain special instructions before use. 使用前获取专门指示。
- P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
- P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
- P220 Keep/Store away from clothing/…/combustible materials. 保持远离/贮存远离服装/....../可燃材料。
- P221 Take any precaution to avoid mixing with combustibles/… 采取一切防范措施，避免与可燃物混合/...
- P233 Keep container tightly closed. ?保持容器密闭。
- P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
- P241+P242+P243
- P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
- 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。
- P273 Avoid release to the environment. 避免释放到环境中。
- 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。
- P281 Use personal protective equipment as required. 使用所需的个人防护装备。
- P301+P312+P330
- P302+P352+P332+P313+P362+P364
- P304+P340
- P305+P351+P338
- P305+P351+P338+P337+P313
- P308+
- P308+P311
- P308+P313
- P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
- 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
- P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
- P403+P235
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
- H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
- H271 May cause fire or explosion; strong oxidizer 可能会引起火宅或爆炸；强氧化剂。
- H272 May intensify fire; oxidizer 可能加剧火势；氧化剂。
- H302 Harmful if swallowed 吞食有害
- H302+H312+H332
- H312 Harmful in contact with skin 皮肤接触有害
- H315 Causes skin irritation 会刺激皮肤
- H319 Causes serious eye irritation 严重刺激眼睛
- H331 Toxic if inhaled 吸入中毒
- H332 Harmful if inhaled 吸入有害
- H335 May cause respiratory irritation 可能导致呼吸道刺激
- H336 May cause drowsiness or dizziness 肯能导致嗜睡或头晕
- H351 Suspected of causing cancer 怀疑致癌
- S17 Keep away from combustible material 远离可燃物料；
- S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾；
- S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
- 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；
- S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
- S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
- S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
- 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
- R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
其他信息
- Alfa Aesar:戴斯-马丁试剂 Dess-Martin periodinane(87413-09-0)
- 存储注意事项:空气敏感;惰性气体保护;湿度敏感
- 戴斯-马丁氧化剂价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 D2045 戴斯-马丁氧化剂 Dess-Martin Periodinane 25G 7400元 2014/06/02 D2045 戴斯-马丁氧化剂 Dess-Martin Periodinane 1G 780元 2014/06/02 D2045 戴斯-马丁氧化剂 Dess-Martin Periodinane 5G 2100元
- MOL 文件:87413-09-0.mol
- 用途一:重要的氧化试剂
- Acros Organics:戴斯马丁氧化剂 Dess-Martin periodinane, 15 wt.% solution in dichloromethane(87413-09-0)
- TCI Shanghai:戴斯-马丁氧化剂 Dess-Martin Periodinane,>;95.0%(T)(87413-09-0)
- Sigma Aldrich:87413-09-0(sigmaaldrich)
- 有机高价碘化合物:近年来,有机高价碘化合物作为一种容易制备、性能温和、选择性高而且环境友好的有机合成新试剂被广泛地应用于现代有机合成化中。Dess-Martin高价碘化合物(DMP)是其中研究最多、应用最广的试剂之一。 戴斯-马丁氧化剂〔也称Dess-Martin高碘试剂〕是一种常用的、温和的、选择性好的氧化试剂。经常用于将伯醇氧化成醛、仲醇氧化成酮。其优点是反应条件温和、速度适中、用量少、后处理简单。其制备方法可以由价格便宜的邻碘苯甲酸用溴酸钾在适当浓度的硫酸溶液中氧化成环得到化合物，该化合物再经过醋酐的处理得Dess-Martin periodinane试剂。
- 下游产品:C-(3,4-二氢-2H-苯并[1,4]嗪-3-基)-甲胺
- 敏感性:Light Sensitive
- Hazard Note:Harmful/Light sensitive
- 上游原料:乙酸 --> 乙酐 --> 对甲苯磺酸 --> 溴酸钾 --> 2-碘苯甲酸 --> 2-碘酰基苯甲酸
- 用途二:氧化剂，用于氧化羟基二氢卟啉（hydroxychlorins）生成二氢卟啉-α-二酮（chlorin-α-diones）和四酮。也用于把醇氧化成醛和酮。
- MSDS 信息:(1,1,1-Triacetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one(87413-09-0).msds
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