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[ CAS No. 5458-48-0 ]

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Chemical Structure| 5458-48-0
Chemical Structure| 5458-48-0
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Product Details of [ 5458-48-0 ]

CAS No. :5458-48-0 MDL No. :MFCD00130008
Formula : C12H15NO2 Boiling Point : 326.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :205.25 g/mol Pubchem ID :-
Synonyms :

Safety of [ 5458-48-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5458-48-0 ]

  • Downstream synthetic route of [ 5458-48-0 ]

[ 5458-48-0 ] Synthesis Path-Downstream   1~17

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  • [ 827-52-1 ]
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  • [ 92959-64-3 ]
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  • [ 827-52-1 ]
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  • [ 7137-56-6 ]
YieldReaction ConditionsOperation in experiment
With nitric acid; In acetic acid; for 6h;Cooling with ice; To a solution of 36 mL fuming HNO3, 18 mL acetic acid which was stirred at -10 C, 10 mL of cyclohexylbenzene dissolved in 18 mL acetic acid was added dropwise. It is recommended that the dropwise procedure should cost at least 30 minutes. The resulted solution was stirred in an ice-salt bath for about 6 h. When the reaction was complete, crushed ice was added, then extracted with CH2Cl2 (3×80 mL), and the organic layer was washed successively with water (100 mL), 10% NaOH (50 mL), saturated NaCl aqueous solution, and dried over anhydrous Na2SO4. Compound 1 was used without further purification.
  • 4
  • [ 5458-48-0 ]
  • [ 6373-50-8 ]
YieldReaction ConditionsOperation in experiment
0.805 g With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; A solution of the nitration compound 1 and Pd-C (10percent) in ethanol (100 mL) was stirred under hydrogen overnight at room temperature and then filtered through Celite and concentrated in vacuo. The crude product was purified by flash chromatography (PE:EtOAc = 20:1) to afford 0.805 g (46percent) compd. 2 and 0.219 g (17percent) compd. 2? as oil.
  • 5
  • [ 5458-48-0 ]
  • [ 80998-21-6 ]
YieldReaction ConditionsOperation in experiment
17% With ammonium chloride; zinc In ethanol; water; N,N-dimethyl-formamide for 1.5h; Ambient temperature;
  • 6
  • [ 827-52-1 ]
  • [ 7697-37-2 ]
  • [ 5458-48-0 ]
  • 7
  • [ 827-52-1 ]
  • [ 7697-37-2 ]
  • [ 5458-48-0 ]
  • [ 92959-64-3 ]
  • 8
  • [ 827-52-1 ]
  • [ 7697-37-2 ]
  • [ 64-19-7 ]
  • [ 5458-48-0 ]
  • [ 7137-56-6 ]
  • 9
  • [ 827-52-1 ]
  • [ 7697-37-2 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • [ 5458-48-0 ]
  • [ 92959-64-3 ]
  • [ 7137-56-6 ]
  • 10
  • [ 100-25-4 ]
  • [ 53535-83-4 ]
  • [ 5458-48-0 ]
YieldReaction ConditionsOperation in experiment
30 % Spectr. With potassium phenolate In tetrahydrofuran at 20℃; for 0.5h;
  • 11
  • [ 5458-48-0 ]
  • [ 51410-58-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 17 percent / NH4Cl, Zn / dimethylformamide; ethanol; H2O / 1.5 h / Ambient temperature 2: diethyl ether / 0.5 h / -10 °C
  • 12
  • [ 5458-48-0 ]
  • [ 29030-57-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tin; hydrochloric acid 2: benzene
Multi-step reaction with 2 steps 1: Raney nickel / Hydrogenation 2: zinc
  • 13
  • [ 5458-48-0 ]
  • [ 25109-28-8 ]
  • 14
  • [ 5458-48-0 ]
  • [ 62115-76-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cl2, FeCl3 / 60 °C 2: Fe, aq. HCl / Heating
With Potassium borohydride; iron(III) chloride In methanol; ice-water; water; ethyl acetate 104 3-Chloro-4-cyclohexylaniline EXAMPLE 104 3-Chloro-4-cyclohexylaniline A mixture of 1.0 g (5 mmol) of 4-cyclohexyl-nitrobenzene and 0.1 g of iron(III) chloride was heated to 60°. After the cyclohexyl-nitrobenzene had melted chlorine gas was conducted through the well-stirred mixture for 15 minutes. Then, 20 ml of ice-water were added and the mixture was extracted with ether. The ether was distilled off and the residue was dissolved in 60 ml of methanol. Then, the solution was treated with 2.5 g (25 mmol) of copper(I) chloride and portionwise with 1.6 g (29 mmol) of potassium borohydride. After stirring for 30 minutes the mixture was poured into 0.5 l of water and extracted with ether. Drying over sodium sulfate, distillation of the ether and chromatography over silica gel with hexane/ethyl acetate 9:1 gave 0.68 g of oil. MS: m/e (% basic peak)=209 (M+, 75), 166 (100), 140 (78), 131 (62).
  • 15
  • [ 5458-48-0 ]
  • [ 28022-30-2 ]
YieldReaction ConditionsOperation in experiment
56% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Reflux;
With N-Bromosuccinimide In tetrachloromethane; ethyl acetate 268.1 Step 1 Step 1 1-(1-Bromocyclohexyl)-4-nitrobenzene 4-Cyclohexylnitrobenzene (22.6 g, 0.11 mol) and N-bromosuccinimide (21.6 g, 0.12 mol) were suspended in tetrachloromethane (200 mL) and a catalytic amount of dibenzoylperoxide was added. The reaction mixture was stirred at 80° C. for 4.5 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (400 mL) and washed with water (100 mL). The aqueous phase was extracted with ethyl acetate (200 mL) and the combined organic phases were washed with water (3*150 mL), dried over MgSO4 and concentrated in vacuo. The residue was crystallized from ethyl acetate and heptane to give 18.4 g of 1-(bromocyclohexyl)-4-nitrobenzene. 1H NMR (DMSO-d6): δ1.29-1.40 (1H,m), 1.60-1.71 (3H,d), 1.73-1.85 (2H,m), (2H,m), 2.55 (2H,m), 7.92 (2H,d), 8.34 (2H,d). M.p.: 83.5-85.5° C. MA: calc 50.72%; C, 4.97%; H, 4.93%. N; Found: 50.65%; C, 5.10%; H, 4.91%; N.
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 80℃; for 4.5h; 268.L.1 4-Cyclohexylnitrobenzene (22.6 g, 0.11 mol) and N-bromosuccinimide (21.6 g, 0.12 mol) were suspended in tetrachloromethane (200 mL) and a catalytic amount of dibenzoylperoxide was added. The reaction mixture was stirred at 80°C for 4.5 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate (400 mL) and washed with water (100 mL). The aqueous phase was extracted with ethyl acetate (200 mL) and the combined organic phases were washed with water (3 x 150 mL), dried over MgSO4 and concentratedin vacuo. The residue was crystallised from ethyl acetate and heptane to give 18.4 g of 1-(bromocyclohexyl)-4-nitrobenzene.1H NMR (DMSO-d6): δ 1.29-1.40 (1H,m), 1.60-1.71 (3H,d), 1.73-1.85 (2H,m), 2.06-2.18 (2H,m), 2.55 (2H,m), 7.92 (2H,d), 8.34 (2H,d). M.p.: 83.5-85.5°C. MA: calc50.72% C, 4.97% H, 4.93% N; Found50.65% C, 5.10% H, 4.91% N.
  • 16
  • [ 5458-48-0 ]
  • 1-nitro-4-(1-(2-nitro-1-phenylethyl)cyclohexyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / Reflux 2: methyl 4-formylbenzoate; 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / methanol / 0 °C
  • 17
  • [ 5458-48-0 ]
  • [ 4180-23-8 ]
  • (S)-4-cyclohexyl-N-(1-(4-methoxyphenyl)propyl)aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With aluminum(III) fluoride; nickel(II) tetrafluoroborate hexahydrate; trimethoxysilane; (3aS,3'aS,8aR,8'aR)-8,8a,8',8'a-tetrahydro-3aH,3'aH-2,2'-biindeno[1,2-d]oxazole; sodium iodide; zinc In toluene at 0℃; for 24h; Inert atmosphere; Glovebox; enantioselective reaction;
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