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Chemical Structure| 101184-85-4 Chemical Structure| 101184-85-4

Structure of 101184-85-4

Chemical Structure| 101184-85-4

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Product Details of [ 101184-85-4 ]

CAS No. :101184-85-4
Formula : C5H11NS
M.W : 117.21
SMILES Code : S1CCNCCC1
MDL No. :MFCD15209531

Safety of [ 101184-85-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H312-H332-H335-H314-H227
Precautionary Statements:P210-P260-P264-P270-P271-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378-P403+P233-P403+P235-P405-P501
Class:8
UN#:2735
Packing Group:

Application In Synthesis of [ 101184-85-4 ]

* 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 [ 101184-85-4 ]

[ 101184-85-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2896-98-2 ]
  • [ 101184-85-4 ]
YieldReaction ConditionsOperation in experiment
96% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 4h; To a solution of <strong>[2896-98-2]1,4-thiazepan-5-one</strong> (2.07 g, 15.7 mmol) in dry THF was added LiA1H4 (0.66 g, 17.3 mmol) at OD, then the mixture was stirred at rt for 4h. H20 (0.7 mL), 15% NaOH (0.7 mL) and H20 (2.1 mL) were added to the reaction in successively. The mixture was filtrated to give 1.77 g product in 96% yield.?H-NIVIR (400 IVIFIz, CDC13) : 3.07 (m, 2H), 2.98 (m, 2H), 2.75 (m, 4H), 1.93 (m, 2H).
75.7% With lithium aluminium tetrahydride; In tetrahydrofuran; at 60℃; for 2h; To a suspension of LiAlH4 (200 mg, 5.2 mmol) in THF (5 mL) was added compound 3 (370 mg, 2.8 mmol). The mixture was stirred at 60 C. for 2 hours. The reaction was quenched with H2O (0.2 mL), dried over Na2SO4, filtered, and the filtrates were concentrated to give desired compound 4 (250 mg, 75.7%) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) 6=3.08-3.02 (m, 1H), 2.99-2.92 (m, 1H), 2.89-2.82 (m, 1H), 2.81-2.66 (m, 5H), 2.00-1.85 (m, 2H)
(Ref: J. Org. Chem. 1960, 25, 1953-1956.) To a stirred solution of 1,4- thiazepan-5-one (9.16 g, 70 mmol) in THF (271 mL) at 0 0C is added dropwise over20 min LAH (IM in THF, 70 mL, 70 mol). The reaction mixture is stirred at 0 0C for 10 min and then warmed to RT, stirring is continued for 2 h. The reaction mixture is quenched with careful successive addition of H2O (2.5 mL), 5N aqeous NaOH (2.5 mL) and H2O (9 mL). A thick gel like precipitate formed. The reaction mixture is filtered through a small pad of Celite, and the filter cake is washed with ether (300 mL). The filtrate is concentrated to afford the title compound as an oil, which is used immediately in the next reaction. 1H NMR (400 MHz, DMSO) delta 2.89 (t, 2H), 2.84 (t, 2H), 2.69 (t, 2H), 2.59 (t,2H), 1.78 (m, 2H).
2.63 g (98%) With sodium hydroxide; LiAlH4; In tetrahydrofuran; water; To a solution of <strong>[2896-98-2]1,4-thiazepan-5-one</strong> (3.0 g) in distilled THF (90 mL) cooled to 0 C. is added dropwise a solution of LiAlH4 in THF (1M solution, 22.9 mL). The mixture is stirred at room temperature for 2 h. The reaction is quenched by successive addition of water (2 mL), 15% NaOH (2 mL) and water (2 mL). The reaction mixture is filtered to remove the aluminum salt that had precipitated. The filtrate was dried (Na2SO4), filtered, and concentrated to obtain 2.63 g (98%) of 1,4-thiazepane as a yellow residue. Physical characteristics are as follows: 1H NMR (300 MHz, CDCl3) delta3.07, 2.96, 2.75, 1.92.
With sodium hydroxide; In tetrahydrofuran; water; Step 2. Lithium aluminum hydride (5.5 mL of a 1M solution in THF) is added dropwise to a stirred solution of <strong>[2896-98-2]hexahydro-5-oxo-1,4-thiazepine</strong> (721.5 mg) in dry THF (21 mL) cooled to 0 C. The reaction mixture is stirred at 0 C. for 10 min, then at room temperature for 4 h. The reaction mixture is quenched by careful successive addition of water (0.2 mL), 5N aqueous NaOH (0.2 mL) and water (0.74 mL). The reaction mixture becomes very thick and gel-like. The reaction mixture is diluted with ether (50 mL) and filtered through a pad of celite. The filter cake is washed with ether (100 mL). The filtrate is concentrated to afford 616.6 mg of 1,4-hexahydrothiazepine which is used immediately in the next step.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 4.16667h; Step 2.. lithium aluminum hydride (5.5 ML of a 1M solution in THF) is added dropwise to a stirred solution of <strong>[2896-98-2]hexahydro-5-oxo-1,4-thiazepine</strong> (721.5 mg) in dry THF (21 ML) cooled to 0 C. The reaction mixture is stirred at 0 C. for 10 min, then at room temperature for 4 h.. The reaction mixture is quenched by careful successive addition of water (0.2 ML), 5 N aqueous NaOH (0.2 ML) and water (0.74 ML).. The reaction mixture becomes very thick and gel-like.. The reaction mixture is diluted with ether (50 ML) and filtered through a pad of celite.. The filter cake is washed with ether (100 ML).. The filtrate is concentrated to afford 616.6 mg of 1,4-hexahydrothiazepine which is used immediately in the next step.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 0.5h; To a mixture of lithium aluminum hydride (2.31 g) and tetrahydrofuran (100 mL) was added a solution of <strong>[2896-98-2]1,4-thiazepan-5-one</strong> (4.0 g) in'tetrahydrofuran (30 mL) with stirring under ice-cooling and the mixture was stirred at room temperature for 30 min. 2N Sodium hydroxide was added to the reaction mixture until aluminum hydroxide precipitated, and the solid was filtered off. The filtrate was concentrated until the liquid amount became half, and di-tert-butyl dicarbonate (7.32 g) was added dropwise with stirring under ice-cooling. The mixture was stirred at room temperature for 2 hrs., and the reaction mixture was concentrated, diluted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and tert-butyl 1,4-thiazepan-4-carboxylate was obtained as a colorless oil (6.00 g, yield 91%) from a fraction eluted with ethyl acetate-hexane (1:4,volume ratio). NMR(CDCl3) delta:1.46(9H, s), 1.92-2.10(2H, m), 2.60-2.76(4H, m), 3.50-3.68(4H, m).
With lithium aluminium tetrahydride; In tetrahydrofuran; at 60℃; for 2h; To a suspension of LiAlH4 (200 mg, 5.2 mmol) in THF (5 mL) was added compound 3 (370 mg, 2.8 mmol). The mixture was stirred at 60 C. for 2 hours. The reaction was quenched with H2O (0.2 mL), dried over Na2SO4, filtered, and the filtrates were concentrated to give desired compound 4 (250 mg, 75.7%) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) 6=3.08-3.02 (m, 1H), 2.99-2.92 (m, 1H), 2.89-2.82 (m, 1H), 2.81-2.66 (m, 5H), 2.00-1.85 (m, 2H)

  • 2
  • [ 1072-72-6 ]
  • [ 2896-98-2 ]
  • [ 101184-85-4 ]
YieldReaction ConditionsOperation in experiment
4.30 g (81%) With sodium carbonate; In hydrogenchloride; water; Preparation 34 1,4-Thiazepane To a stirred solution of tetrahydrothiopyran-4-one (4.74 g) in conc. HCl (20.7 mL) cooled to 0 C. is added portion-wise sodium azide (3.98 g, 61.2 mmol). After addition is complete, the reaction is stirred at room temperature for 4 h. Solid sodium carbonate is then added portion-wise until the solution was slightly alkaline (pH=9). Water is added during addition of sodium carbonate to dissolve the salt. The alkaline solution is diluted with CHCl3 (125 mL), and the phases are separated. The aqueous layer is extracted with CHCl3 (2*75 mL). The combined organic layers are dried (Na2SO4), filtered, and concentrated. The crude product is recrystallized from CH2Cl2/hexanes to afford 4.30 g (81%) of 1,4-thiazepan-5-one as a white solid. Physical characteristics are as follows: Mp 114-116 C.; 1H NMR (300 MHz, CDCl3) delta6.41, 3.66, 2.96, 2.76.
 

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