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Chemical Structure| 23347-22-0 Chemical Structure| 23347-22-0

Structure of 23347-22-0

Chemical Structure| 23347-22-0

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Product Details of [ 23347-22-0 ]

CAS No. :23347-22-0
Formula : C4N4S
M.W : 136.13
SMILES Code : N#CC1=NSN=C1C#N
MDL No. :MFCD00965211

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Application In Synthesis of [ 23347-22-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 23347-22-0 ]

[ 23347-22-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1835-65-0 ]
  • [ 873-51-8 ]
  • [ 23347-22-0 ]
  • 5,6,7,8,10,11,12,13-octafluoro(1,2,5-thiadiazolo[3,4-b]dibenzo[g,l]subporphyrazinato)phenylboron(III) [ No CAS ]
  • (9,10,11,12-tetrafluoro-di(1,2,5-thiadiazolo)[3,4-b,g]benzo[l]subporphyrazinato)phenylboron(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
10%; 5% In chlorobenzene; for 2h;Reflux; 1,2,5-Thiadiazolo-3,4-dicarbonitrile (3) (330mg, 2.46 mmol) and <strong>[1835-65-0]tetrafluorophthalonitrile</strong> (4) (246mg, 1.23 mmol) were dissolved in 5 ml of freshly distilled chlorobenzene. Solutions was purged with argon and after addition of dichlorophenylboron (3) (2.25 ml of freshly prepared 2 M solution in chlorobenzene) the reaction mixture was refluxed for 2 h. After overnight staying at RT the mixture was poured into diethyl ether, the brown residue containing by-products was filtered and dark pink filtrate was evaporated. The light pink crystalline product contained the unreacted dinitriles which were removed by vacuum sublimation at 200 °C. The residue containing mixture of subporphyrazines was chromatographed on silica with CH2Cl2 as eluent. The low-symmetry porphyrazines [F8S1SubPABPh] and [F4S2SubPABPh] were eluted as the 2nd and 3rd fractions (Rf=0.83 and 0.52, respectively), while the 1st minor fraction contained perfluorosubphthalocyanine, [F12SubPcPh] (Rf=0.93). After additional purification by gel permeation chromatography (Bio-Beads S-X, CH2Cl2) [(F8SSubPA)BPh] (80 mg, 10 percent) and [(F4S2SubPA)BPh] (35 mg, 5 percent) were obtained as dark pink solids. [F8S1SubPABPh] (4): Mass-spectrum (LDI-TOF) m/z positive: 625.1 [M+H]+; negative: 582.5 (85 percent) [M-Ph+Cl]?, 624.6 (10 0percent) [M]?; 1H NMR (400.13 MHz, CDCl3) delta 6.82 (t, J=7.5Hz, 1H), 6.53 (t, J=7.5Hz, 2H), 5.40 (d, J=6.9Hz, 2H); 19F NMR (282.4 MHz, CDCl3) delta ?137.8 (m, 2F), ?138.1 (m, 2F), ?148.6 (m, 4F); 11B NMR (160.47 MHz, CDCl3) delta ?15.75; UV?vis (CH2Cl2) lambda/nm (logepsilon): 307 (4.59), 415 (3.51), 504 (4.24), 535 sh, 554 (4.49), 579 (4.65); Anal. calcd for C26H5BF8N8S (624.24): C, 50.03; H, 0.81; N, 17.95; S, 5.14; found: C, 50.25; H, 1.02; N, 17.64; S, 4.98. [F4S2SubPABPh] (5): Mass-spectrum (LDI-TOF) m/z positive: 559.9 [M]+; negative: 518.2 (70 percent) [M-Ph+Cl]?, 560.4 (100 percent) [M]?; 1H NMR (400.13 MHz, CDCl3) delta 6.83 (t, J=7.5Hz, 1H), 6.66 (t, J=7.5Hz, 2H), 5.40 (d, J=6.9Hz, 2H); 19F NMR (282. 4MHz, CDCl3) delta ?137.8 (d, 2F), ?148.5 (d, 2F); 11B NMR (160.47 MHz, CDCl3) delta ?15.46; UV?vis (CH2Cl2) lambda/nm (logepsilon): 304 (4.65), 407 (3.69), 502 (4.12), 526sh, 541 (4.44), 569 (4.52); Anal. calcd for C22H5BF4N10S2 (560.27): C, 47.16; H, 0.90; N, 25.00; S, 11.44percent; found: C, 47.35; H, 1.12; N, 24.76; S, 11.17percent.
 

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