19158-51-1 Usage
Chemical Properties
White powder
Uses
Different sources of media describe the Uses of 19158-51-1 differently. You can refer to the following data:
1. p-Toluenesulfonyl cyanide can be used in:The preparation of polyfunctional nitriles.Free-radical cyanation of B-alkylcatecholboranes.The synthesis of 4-hyroxypyridines by hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers.
2. Tosyl cyanide is used in a free-radical cyanation of B-alkylcatecholboranes. Also used as a component in a hetero-Diels-Alder reaction with 1,3-bis-silyl enol ethers leading to 4-hyroxypyridines.
Synthesis Reference(s)
Tetrahedron Letters, 10, p. 3351, 1969 DOI: 10.1017/S0009838800024678
General Description
p-Toluenesulfonyl cyanide is an electron-deficient nitrile. It undergoes hetero-Diels-Alder reaction with silyl enol ether of cyclohexenone to yield hydrolytically sensitive [4+2] adduct. It also undergoes facile [2+3] cycloaddition reaction with azides to form 5-sulfonyl tetrazoles. p-Toluenesulfonyl cyanide also reacts with alcohols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield sulfinates.
Check Digit Verification of cas no
The CAS Registry Mumber 19158-51-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,1,5 and 8 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 19158-51:
(7*1)+(6*9)+(5*1)+(4*5)+(3*8)+(2*5)+(1*1)=121
121 % 10 = 1
So 19158-51-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H14N2/c1-11(2)9-5-3-8(7-10)4-6-9/h3-6H,7,10H2,1-2H3
19158-51-1Relevant articles and documents
Van Leusen et al.
, p. 440 (1968)
P-Anisaldehyde-Photosensitized Sulfonylcyanation of Chiral Cyclobutenes: Enantioselective Access to Cyclic and Acyclic Systems Bearing All-Carbon Quaternary Stereocenters
Pirenne, Vincent,Traboulsi, Iman,Rouvière, Lisa,Lusseau, Jonathan,Massip, Stéphane,Bassani, Dario M.,Robert, Frédéric,Landais, Yannick
supporting information, p. 575 - 579 (2020/01/09)
The photosensitized p-Anisaldehyde-mediated addition of sulfonylcyanides onto the I -system of cyclobutenes is shown to afford highly functionalized cyclobutanes in high yields and diastereocontrol. The homochiral cyclobutene precursors are accessible on multigram scale in two steps through an asymmetric [2 + 2] cycloaddition/vinyl thioether reduction sequence. The enantiopure cyclobutylnitriles can be elaborated further through SmI2-mediated ring opening or converted into new enantiopure cyclobutenes through base-mediated sulfone elimination.
Method for the preparation of citalopram
-
, (2008/06/13)
A method for the manufacture of citalopram characterized in (i) reaction of 1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-5-halophthalane with an activated magnesium to form the Grignard reagent [3-[1-(4-fluorophenyl)-1,3 dihydro-isobenzofuran-1-yl]propyl]dimethylamine 5-magnesium halide followed by (ii) reaction of [3-[1-(4-fluorophenyl)-1,3 dihydro-isobenzofuran-1-yl]propyl)dimethylamine 5-magnesium halide with a compound containing a —CN group bound to a leaving group to form citalopram.