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Chemical Structure| 130783-02-7 Chemical Structure| 130783-02-7

Structure of 130783-02-7

Chemical Structure| 130783-02-7

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Product Citations

Product Citations

Markwitz, Martyna ; Labrzycki, Klaudiusz ; Azcune, Laura ; Landa, Aitor ; Kucinski, Krzysztof ;

Abstract: A metal-free dehydrative thioetherification method has been reported, enabling the conversion of various alcs. and thiols into thioethers. By employing triflic acid as a catalyst or utilizing a recyclable NAFION superacid catalyst, these methods significantly improve the efficiency and practicality of sulfide preparation

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Product Details of [ 130783-02-7 ]

CAS No. :130783-02-7
Formula : C8H4F6S
M.W : 246.17
SMILES Code : SC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1
MDL No. :MFCD00042273
InChI Key :KCAQWPZIMLLEAF-UHFFFAOYSA-N
Pubchem ID :518690

Safety of [ 130783-02-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H311+H331-H315-H319
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405
Class:6.1
UN#:2810
Packing Group:

Application In Synthesis of [ 130783-02-7 ]

* 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 [ 130783-02-7 ]

[ 130783-02-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 130783-02-7 ]
  • [ 349-58-6 ]
  • 2
  • [ 10177-24-9 ]
  • [ 130783-02-7 ]
  • 2-(((3,5-bis(trifluoromethyl)phenyl)thio)methyl)-5-chloropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Preparation of 2-(((3,5-bis(trifluoromethyl)phenyl)thio)methyl)-5-chloropyridine (6A). Sodium hydroxide (2N, aqueous, 5.46 mL, 10.9 mmol) was added dropwise to a solution of 3,5-bis-trifluoromethyl benzenethiol (1.83 mL, 10.9 mmol) in MeOH (3 mL). This mixture was stirred for 5 minutes and then <strong>[10177-24-9]5-chloro-2-(chloromethyl)pyridine</strong> (1.77 g, 10.9 mmol) was added as a solution in MeOH (10 mL). This mixture was stirred 2 hours at r.t. and then it was concentrated to about half volume in vacuo. EtOAc and half saturated aqueous ammonium chloride were added, the layers were separated, and the aqueous layer was extracted with EtOAc (lx). The combined organic layers were dried over anhydrous MgSO/i, filtered, and concentrated in vacuo to give 2-(((3,5- bis(trifluoromethyl)phenyl)thio)methyl)-5-chloropyridine (6A) as a solid (4.1 g, 101% yield). MS m/z = 372 [M+H]+. NMR (400 MHz, CDC13) δ ppm 8.49 (d, J=2.35 Hz, 1 H) 7.75 (s, 2 H) 7.61 - 7.65 (m, 2 H) 7.32 (d, J=8.08 Hz, 1 H) 4.32 (s, 2 H).
4.1 g Sodium hydroxide (5.4 mL of 2 N solution, 10.8 mmol) was added dropwise to a solution of 3,5-bis-trifluoromethyl benzenethiol ( Sigma- Aldrich Chemical Company, Inc., St. Louis, MO, USA) (1.8 mL, 11 mmol) in MeOH (3 mL) at room temperature. This mixture was stirred for 5 minutes and then <strong>[10177-24-9]5-chloro-2-(chloromethyl)pyridine</strong> (Sigma-Aldrich Chemical Company, Inc., St. Louis, MO, USA) (1.8 g, 11 mmol) was added as a solution in MeOH (10 mL). This mixture was stirred for 2 hours at room temperature and then it was concentrated to about half volume in vacuo. EtOAc and half saturated aqueous ammonium chloride were added, the layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO/t, filtered, and concentrated in vacuo to give 2-(((3,5-bis(trifluoromethyl)phenyl)thio)methyl)-5- chloropyridine (8a) (4.1 g, 101% yield) as a solid. MS m/z = 372 [M+H]+. NMR (400 MHz, CDC13) δ ppm 8.49 (d, J = 2.35 Hz, 1H) 7.75 (s, 2H) 7.61 - 7.65 (m, 2H) 7.32 (d, J = 8.08 Hz, 1H) 4.32 (s, 2H).
With sodium hydroxide; In methanol; water; at 20℃; for 2h; Sodium hydroxide (2 N, aqueous, 5.4 mL, 10.8 mmol) was added dropwise to a solution of 3,5-bis-trifluoromethyl benzenethiol (Sigma-Aldrich Chemical Company, Inc., St. Louis, MO, USA) (1.8 mL, 10.9 mmol) in MeOH (3 mL). This mixture was stirred for 5 min and then <strong>[10177-24-9]5-chloro-2-(chloromethyl)pyridine</strong> (Sigma-Aldrich Chemical Company, Inc., St. Louis, MO, USA) (1.77 g, 10.9 mmol) was added as a solution in MeOH (10 mL). This mixture was stirred for 2 h at RT and then it was concentrated to about half volume in vacuo. EtOAc and half saturated aqueous ammonium chloride were added, the layers were separated, and the aqueous layer was extracted with EtOAc (1 x). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give 2-(((3,5-bis(trifluoromethyl)phenyl)thio)methyl)-5-chloropyridine (33a) as a solid (4.1 g, 101% yield). MS m/z = 372 [M+H]+. 1H NMR (400 MHz, CDCl3) ^ ^ppm 8.49 (d, J = 2.35 Hz, 1 H) 7.75 (s, 2 H) 7.61 - 7.65 (m, 2 H) 7.32 (d, J = 8.08 Hz, 1 H) 4.32 (s, 2 H).
 

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