248835
4-甲苯磺酰氰
technical grade, 95%
别名:
Tosyl cyanide, 对甲苯磺酰氰
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线性分子式:
CH3C6H4SO2CN
化学文摘社编号:
分子量:
181.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
242-849-1
Beilstein/REAXYS Number:
2048159
MDL number:
Assay:
95%
Form:
solid
产品名称
4-甲苯磺酰氰, technical grade, 95%
InChI key
JONIMGVUGJVFQD-UHFFFAOYSA-N
InChI
1S/C8H7NO2S/c1-7-2-4-8(5-3-7)12(10,11)6-9/h2-5H,1H3
SMILES string
Cc1ccc(cc1)S(=O)(=O)C#N
grade
technical grade
assay
95%
form
solid
bp
105-106 °C/1 mmHg (lit.)
mp
47-50 °C (lit.)
functional group
sulfone
thiocyanate
storage temp.
2-8°C
Quality Level
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Application
p-甲苯磺酰氰可用于：
- 多官能腈的制备。
- B-烷基儿茶酚硼烷的自由基氰化。
- 通过与1,3-双硅烯醇醚进行杂原子Diels-Alder反应合成4-羟基吡啶。
General description
p-甲苯磺酰氰是一种缺电子腈。它与环已烯酮的硅烯醇醚进行杂原子Diels-Alder反应，生成水解敏感性 [4+2]加合物。它还可与叠氮化物进行温顺[2+3]环加成反应，生成5-磺酰基四唑。p-甲苯磺酰氰也可以在存在1,8-二氮杂双环[5.4.0]十一碳-7-烯 (DBU) 或1,4-二叠氮双环[2.2.2]辛烷 (DABCO) 的情况下与醇类反应生成亚磺酸盐。
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Eye Dam. 1 - Skin Corr. 1B
存储类别
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Preparation of polyfunctional nitriles by the cyanation of functionalized organozinc halides with p-toluenesulfonyl cyanide.
Klement I, et al.
Tetrahedron Letters, 34(29), 4623-4626 (1993)
Synthesis of 2-(Arylsulfonyl)-4-hydroxypyridines by Hetero-Diels-Alder Reaction of 1,3-Bis-Silyl Enol Ethers with Arylsulfonyl Cyanides
Thomas Emmrich, et al.
Synthesis, 2551-2555 (2006)
A click chemistry approach to tetrazoles by Huisgen 1,3-dipolar cycloaddition: synthesis of 5-acyltetrazoles from azides and acyl cyanides.
Zachary P Demko et al.
Angewandte Chemie (International ed. in English), 41(12), 2113-2116 (2002-06-17)
Cynthia K McClure et al.
The Journal of organic chemistry, 68(21), 8256-8257 (2003-10-11)
The hetero-Diels-Alder reaction of an electron-deficient nitrile, p-toluenesulfonyl cyanide, with the silyl enol ether of cyclohexenone produced a hydrolytically sensitive [4 + 2] adduct in good yield. Use of Mander's reagent, ethyl cyanoformate, with the same diene, produced an unstable
O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide.
Barton DHR, et al.
Tetrahedron, 47(44), 9167-9178 (1991)
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