Tosylmethyl Isocyanide 对甲基苯磺酰甲基异腈
CAS 36635-61-7 MFCD00000005
化学结构图
SMILES: [C-]#[N+]CS(=O)(=O)c1ccc(C)cc1
化学属性
| Mol. Formula | C9H9NO2S |
|---|---|
| Mol. Weight | 195.24 |
| Density | 1.422 |
| Melting Point | 109-113°C |
| TSCA | No |
| Stability | 对湿度敏感 |
| Solubility | insoluble |
| Boiling Point | 400.9°C at 760 mmHg |
| pH | :A |
别名和识别编码
| Chemical Name | Tosylmethyl Isocyanide |
|---|---|
| MDL Number | MFCD00000005 |
| CAS Number | 36635-61-7 |
| EC Number | 253-140-1 |
| Beilstein Registry Number | 3592382 |
| Reaxys-RN | 2331606 |
| PubChem Substance ID | 87576847 |
| Merck Number | 9556 |
| Synonym | 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {} {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {} {} {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {} {} {} {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {} {} {} {} {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {} {} {} {} {} {} {} {} {LY} 1-[(Isocyanomethyl)sulfonyl]-4-methylbenzene {} {} {} {} {} {} {} {} {} |
| Alfabeta Name | TOSYLMETHYLISOCYANIDE |
| Chemical Name Translation | 对甲基苯磺酰甲基异腈 |
| LabNetwork Molecule ID | LN00173745 |
| Canonical SMILES | CC1=CC=C(S(=O)(C[N+]#[C-])=O)C=C1 |
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分类
- Pharmaceuticals
- Sulfur & Selenium Compounds
- Aromatics
- Intermediates & Fine Chemicals
- {SNA} Building Blocks, Chemical Synthesis, Isocyanides, Nitrogen Compounds, Organic Building Blocks
产品应用
- Tosylmethyl Isocyanide is used as a synthetic reagent in the preparation of variety or biologically active heterocycles such as pyrroles and imidazoles. Tosylmethyl Isocyanide is reported to inhibit [
相关文献及参考
- In the presence of base (e.g. KO-t-Bu) in an aprotic solvent, e.g. DME, ketones are cyanated to give the homologous nitriles; see, e.g.: Org. Synth. Coll., 6, 41 (1988). Hindered ketones can be cyanated in DMSO: J.
- For a brief feature on uses of the reagent in synthesis, see: Synlett, 363 (2005).
- M
- Successive alkylation with different alkyl groups, followed by acid hydrolysis, leads to unsymmetrical ketones: Tetrahedron Lett., 4229 (1977). Similarly, dialkylation with ɑω-dihalides gives cyclobutanones: Synthesis, 325 (1980), or larger-ring ketones: Tetrahedron Lett., 22, 4193 (1981). Reaction of monoalkylated TosMIC with ɑω-dihalides is a useful route to 1,5- or 1,6-diketones: Rec. Trav. Chim., 104, 50 (1985):
- Shima, S. et al.: FEBS Lett., 585, 353 (2011); Yamada, N. et al.: Biosci. Biotechnol. Biochem., 56, 1943 (1992);
- Imidazoles by reaction with imidoyl chlorides: Tetrahedron Lett., 2373 (1972). Thiazoles by reaction with CS2 under phase-transfer conditions: Synthesis, 501 (1977). 1,2,4-Triazoles by reaction with diazonium salts, and pyrroles by reaction with Michael acceptors: Tetrahedron Lett., 5337 (1972). Pyrroles are also formed by reaction with aldehydes followed by either ethyl cyanoacetate to give 3-cyanopyrroles: J. Org. Chem., 57, 2245 (1992), or nitromethane to give 3-nitropyrroles: Tetrahedron, 47, 4639 (1991); Synthesis, 871 (1996). The same products are also obtained by reaction of TosMIC with nitroalkenes, from Henry reaction of the aldehydes with nitromethane:
- In contrast, aldehydes with K2CO3 in refluxing methanol lead to high yields of 5-substituted oxazoles: Tetrahedron Lett., 2369 (1972); with acid chlorides, the corresponding 4-tosyl oxazoles are obtained. For asymmetric induction in the oxazole synthesis by use of π-arylaldehyde-chromium tricarbonyl complexes, see: Tetrahedron: Asymmetry, 3, 287 (1992).
- Other applications in heterocyclic synthesis include the synthesis of:
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；
- S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后，立即用大量…（由生产厂家指定）冲洗；
- 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；
- S38 In case of insufficient ventilation wear suitable respiratory equipment 通风不良时，佩带适当的呼吸器；
- 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）；
- R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入，皮肤接触及吞食都有毒
- 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。
- P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
- 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+P310
- P301+P310+P330
- P302+P350
- P302+P352+P312+P361+P364
- P304+P340+P311
- P305+P351+P338
- P305+P351+P338+P337+P313
- P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
- P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适，呼叫解毒中心或医生/医师。
- P332+P313
- P337+P313
- P403+P233
- P405 Store locked up. 上锁保管。
- P501 Dispose of contents/container to..… 处理内容物/容器.....
- H301+H311+H331
- H331 Toxic if inhaled 吸入中毒
- H311 Toxic in contact with skin 皮肤接触中毒
- H301 Toxic if swallowed 吞食有毒
其他信息
- F:21
- 对甲基苯磺酰甲基异腈价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 T1046 对甲苯磺酰异氰酸酯 p-Toluenesulfonylmethyl Isocyanide 25G 952元 2014/06/02 T1046 对甲苯磺酰异氰酸酯 p-Toluenesulfonylmethyl Isocyanide 5G 308元 2010/06/21 182451000 对甲基苯磺酰甲基异腈 Tosylmethyl isocyanide 98% 100 GR 4539元
- Acros Organics:对甲苯磺酰异氰酸酯 Tosylmethyl isocyanide, 98%(36635-61-7)
- Alfa Aesar:对甲苯磺酰甲基异腈,97+% p-Toluenesulfonylmethyl isocyanide, 97+%(36635-61-7)
- MOL 文件:36635-61-7.mol
- Hazard Note:Irritant
- 海关编码:29299000
- Sigma Aldrich:36635-61-7(sigmaaldrich)
- 对甲基苯磺酰甲基异腈价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 T1046 对甲苯磺酰异氰酸酯 p-Toluenesulfonylmethyl Isocyanide 25G 1530元 2011/04/16 T1046 对甲苯磺酰异氰酸酯 p-Toluenesulfonylmethyl Isocyanide 5G 420元 2010/06/21 182451000 对甲基苯磺酰甲基异腈 Tosylmethyl isocyanide 98% 100 GR 4539元
- MSDS 信息:(p-Tolylsulfonyl)methyl isocyanide(36635-61-7).msds
- TCI Shanghai:对甲苯磺酰异氰酸酯 p-Toluenesulfonylmethyl Isocyanide,>;98.0%(LC)(N)(36635-61-7)
- 下游产品:3,4-二羟基苯基丙酸
- 敏感性:Moisture Sensitive
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