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Chemical Structure| 629-19-6 Chemical Structure| 629-19-6

Structure of Dipropyl disulfide
CAS No.: 629-19-6

Chemical Structure| 629-19-6

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Product Citations

Product Citations

Robert Kawȩcki ;

Abstract: N-Sulfenylimines (sulfenimines, thiooximes, N-alkylidenesulfenamides) were efficiently synthesized through the reaction of primary amines and disulfides with NBS or bromine. This reaction can be carried out in an open flask at room temperature without the need for any transition-metal-containing additives. The use of thiols instead of disulfides gave similar results. A wide range of amines were reacted with aryl and alkyldisulfides, resulting in the formation of sulfenimines in a yield of 44–99%.

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Product Details of [ 629-19-6 ]

CAS No. :629-19-6
Formula : C6H14S2
M.W : 150.31
SMILES Code : CCCSSCCC
MDL No. :MFCD00009378
InChI Key :ALVPFGSHPUPROW-UHFFFAOYSA-N
Pubchem ID :12377

Safety of [ 629-19-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H319-H335-H411-H372
Precautionary Statements:P233-P260-P261-P264-P271-P273-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P391-P403-P403+P233-P405-P501
Class:9
UN#:3334
Packing Group:

Application In Synthesis of [ 629-19-6 ]

* 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 [ 629-19-6 ]

[ 629-19-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 214045-86-0 ]
  • [ 629-19-6 ]
  • [ 630419-50-0 ]
YieldReaction ConditionsOperation in experiment
36% To a chilled(-78 C) solution of 1-chloro-6-fluoro isoquinoline (59mg, 0.32 mmol) in 2 mL of THF was added LDA solution in cyclohexane (1.5 Molar, 0.23 mL, 0.35 mmol). The orange solution was stirred for 2 hrs before it was treated with n-propyl disulfide (60ZL, neat material, excess). The reaction was allowed to warm to room temperature over 30 min. It was quenched with a solution of half saturatedNH4CI, the organic residues were extracted into ethyl acetate. LC-MS analysis indicated about50% conversion into the desired product along with mainly starting material. The desired product was purified by a short column (4 cm X 2 cm, silica gel type-H) eluted with 5% ether in hexanes, 29mg (36% yield) of the desired product was obtained. LC/MSRt-min(MH+) [method C] : 3.79(256).'H NMR (400 MHz, CHLOROFORM-D)8 ppm 0.96 (t, J=7. 34 Hz, 3 H) 1.52 (m, 2 H) 2.86 (m, 2 H) 7.45 (dd, J=9.29, 8.56 Hz,1 H) 8.34 (d,J=0. 73 Hz, 2 H) 8.37 (m,1 H).
The following procedure is equally applicable to other 5-alkylthio-6-alkoxy isoquinolines by changing the reagents shown here. To a solution of 1-chloro-6- fluoro isoquinoline (88mg, 0.48 mmol) in 2.0mL THF under nitrogen at-78 C was added LDA (1.5 Molar in cyclohexane, 0.42 mL, 0.63 mmol) forming a dark brownish solution. Neat n-propyl disulfide(85, uL, excess) was introduced after it was stirred at-78 C for 30 min. The reaction was allowed to warm to room temperature over a period of 30 min. It was quenched with a solution of half saturatedNH4Cl, the organic residues were extracted into ethyl acetate. The organic layers were combined and dried under vacuum to 50 microns (Hg). The crude product was taken into 2 mL of THF, cooledto-78 C, added with excess potassium ethoxide (60mg). The isoquinoline intermediate was finally purified by a silica gel column (type-H, Merck) eluted with ether-hexanes mixture, 32.2mg (24%) of the pure compound was obtained. LC-MS showed 1-chloro-5-propylthio-6-ethoxyl isoquinoline at rt-min(MH+) [method C]: 3.77 (282).'H NMR (400 MHz, CHLOROFORM-D)8 ppm 0.94 (t, J=7. 34 Hz, 3 H)1. 46 (m, 2 H) 1.55 (t, J=6. 97 Hz, 3 H) 2.83 (t, J=7. 21 Hz, 2 H) 4.32 (q,J=6. 85 Hz, 2 H) 7.36 (d,J=9. 29 Hz,1 H) 8.22 (d, J=6. 11 Hz, 1 H) 8.32 (d, J=9. 29 Hz,1 H) 8.35 (d, J=6. 11 Hz,1 H).
  • 2
  • [ 1005-38-5 ]
  • [ 629-19-6 ]
  • [ 1314704-84-1 ]
YieldReaction ConditionsOperation in experiment
81% With copper(l) chloride; isopentyl nitrite; In acetonitrile; at 20 - 60℃; for 2h;Inert atmosphere; General procedure: Compound 3a or 3b (5.85 mmol) was added into the dry acetonitrile (35 mL) containing appropriate dialkyl(aryl) disulfide (40.95 mmol) and CuCl (0.29 m mol). The mixture was purged thoroughly with N2 and stirred at room temperature for 30 min. Isoamyl nitrite (4.25 g, 36.3 mmol) was added to the solution immediately, the reaction was stirred for 30 min at room temperature, and then the mixture was heated at 60 °C. The reaction time was listed in Table 2. The disappearance of the starting material was monitored by TLC (EtOAc/P.E., 1:10, v/v). After removing CuCl, the solvent and other volatiles were removed under reduced pressure. The residue was purified by column chromatography (Et3N-neutralized silica gel, gradient elution separation with EtOAc/P.E., 1:40-1:20, v/v) to afford the product as colorless or yellow oil.
  • 4
  • [ 93107-30-3 ]
  • [ 629-19-6 ]
  • 1-cyclopropyl-6,7-difluoro-3-(propylthio)quinolin-4(1H)-one [ No CAS ]
 

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