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[ CAS No. 89282-70-2 ] {[proInfo.proName]}

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Chemical Structure| 89282-70-2
Chemical Structure| 89282-70-2
Structure of 89282-70-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 89282-70-2 ]

CAS No. :89282-70-2 MDL No. :MFCD01821229
Formula : C5H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :ZSTYQALWKOGXOV-UHFFFAOYSA-N
M.W : 103.16 Pubchem ID :11789141
Synonyms :

Safety of [ 89282-70-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H302+H312+H332-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 89282-70-2 ]

* 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.

  • Upstream synthesis route of [ 89282-70-2 ]
  • Downstream synthetic route of [ 89282-70-2 ]

[ 89282-70-2 ] Synthesis Path-Upstream   1~10

  • 1
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Reference: [1] Patent: WO2006/97808, 2006, A1, . Location in patent: Page/Page column 66-67
[2] Patent: US4864051, 1989, A,
[3] Patent: US2009/298811, 2009, A1, . Location in patent: Page/Page column 56
  • 2
  • [ 19752-21-7 ]
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YieldReaction ConditionsOperation in experiment
78% With hydrogenchloride; sodium hydroxide; hydrazine In <i>N</i>-methyl-acetamide; methanol; chloroform; water EXAMPLE 3
Synthesis of 2-methoxyisobutylamine
Potassium phthalimide(3.70 g, 0.02 mol) was added to a solution of 2-methoxyisobutylbromide(3.34 g, 0.02 mol) in 100 ml of dimethylformamide.
Stirring and reflux were continued for 4 hours, and the temperature dropped slowly to 25° C.
After the addition of 200 ml of chloroform, the mixture was poured into 500 ml of cold water.
The aqueous phase was separated and extracted with two 50 ml portions of chloroform.
The combined chloroform extractants were washed with 100 ml of 0.2N sodium hydroxide and 100 ml of water.
After drying the chloroform was removed.
The residue was added to hydrazine (2 g, 0.04 mol) in 100 ml of methanol and was heated under reflux for an hour.
The methanol was removed by concentration under reduced pressure.
Concentrated hydrochloric acid was added to the residual aqueous solution and the mixture was heated under reflux for an hour.
The solution was then concentrated under reduced pressure to remove most of the hydrochloric acid.
The moist residue was adjusted pH=14 using sodium hydroxide and was poured into separatory funnel containing saturated K2 CO3 solution.
The resulting solution was distilled at atmospheric pressure and the product collected at 125° C. (1.6 g, 78percent yield).
IR(neat/ν cm-1):3280, 3065, 2960, 2920, 1640, 1430, 1365, 1075.
Reference: [1] Patent: US5210270, 1993, A,
  • 3
  • [ 82473-56-1 ]
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Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 2657,2659
[2] Patent: US4988827, 1991, A,
  • 4
  • [ 151-56-4 ]
  • [ 2658-24-4 ]
  • [ 60-29-7 ]
  • [ 7637-07-2 ]
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Reference: [1] Patent: US4988827, 1991, A,
  • 5
  • [ 1646-84-0 ]
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Reference: [1] Zhurnal Obshchei Khimii, 1952, vol. 22, p. 2121,2124;engl.Ausg.S.2175,2178
  • 6
  • [ 17860-39-8 ]
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Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 2657,2659
  • 7
  • [ 1023304-50-8 ]
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Reference: [1] Patent: US2008/102028, 2008, A1, . Location in patent: Page/Page column 9; -11
  • 8
  • [ 136918-14-4 ]
  • [ 22665-67-4 ]
  • [ 89282-70-2 ]
YieldReaction ConditionsOperation in experiment
70 %Chromat. With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 3 h; Diisopropylazodicarboxylate (524.38 g, 2.48 mol) was added dropwise to a solution of phthalimide (364.77 g, 2.48 mol), triphenylphosphine (652.84 g, 2.48 mol), and MIBOL (220.07 g, 97.7percent (GC), 2.06 mol) in anhydrous tetrahydrofuran (10815 mL). A duplicate solution was prepared. The solutions were stirred for a minimum of 3 hours and the reaction was monitored by TLC analysis (2:3 ethyl acetate/hexanes, detection with 254 nm UV light and p-anisaldehyde spray). When the disappearance of MIBOL was confirmed, the solvent was removed by rotary evaporation under reduced pressure and the reaction mixtures were combined. The resulting orange oil was triturated with hexanes (4275 mL) until obtaining a semi-solid. The solvent was removed by rotary evaporation under reduced pressure and the crude solid was dried under high vacuum. The solid was suspended in methanol (7875 mL) and hydrazine monohydrate (413.26 g, 8.26 mol) was added. The solution was heated to reflux with mechanical stirring. An additional portion of methanol (2000 mL) was added after 25 minutes of reflux to increase the fluidity of the suspension. After 45 minutes of reflux, disappearance of the phthalimide intermediate was confirmed by TLC analysis (Rf 0.4, 2:3 ethyl acetate/hexanes, detection with 254 nm UV light and p-anisaldehyde spray). The solution was cooled to room temperature. A solution of concentrated hydrochloric acid (609 mL) and methanol (609 mL) was added, and the solution was heated at reflux for 9 hours with magnetic stirring. After cooling to room temperature, the solution was filtered on Celite.(R). and the residue rinsed portionwise with methanol (5960 mL). The filtrate was evaporated under reduced pressure and dried under high vacuum. The product, a yellow solid, was triturated five times with IN hydrochloric acid (3600 mL, 2925 mL and 3 times 2250 mL). The fractions were combined and concentrated to 4645 mL by rotary evaporation under reduced pressure. The resulting solution was split in two batches of equal volume. Each batch was extracted with ethyl acetate (twice 640 mL). The aqueous layers were combined and concentrated to 4500 mL by rotary evaporation under reduced pressure. The resulting solution was basified to a pH of 11 by carefully adding pellets of sodium hydroxide (1427 g) yielding a green olive, almost black, extremely viscous oily solution. It was filtered and the residue rinsed with diethyl ether (3370 mL). The solution was extracted continuously three times with diethyl ether. The organic layer (18050 mL) resulting from the liquid-liquid extraction was dried over anhydrous MgSO4. The solution was distilled at atmospheric pressure on a Vigreux column yielding MIBA as a colorless liquid (299.51 g, 70percent yield, 97.0percent (GC), b.p.: 120.0-120.5° C.). TLC Rf 0.5 (90:9.75:0.25 CH2Cl2/CH3OH/NH4OH, detection with ninhydrine spray); FTIR(neat): 3386, 3314, 2971, 2935, 2826, 1597, 1468, 1381, 1364, 1306, 1259, 1223, 1195, 1155, 1118, 1074, 1013, 894, 847, 716 cm-1; 1H-NMR (600 MHz, CDCl3): δ 1.13 (s, 6H, 2 CH3), 2.62 (s, 2H, CH2), 3.19 (s, 3H, OCH3), 4.76 (br s, 2H, NH2); 13C-NMR (151 MHz, CDCl3): δ 22.6 (2 CH3), 49.4 (OCH3), 50.6 (CH2), 75.0 (C).
Reference: [1] Patent: US2008/102028, 2008, A1, . Location in patent: Page/Page column 9; 10-11
  • 9
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Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 6, p. 2248 - 2251[2] Angew. Chem., 2016, vol. 128, # 6, p. 2288 - 2292,5
  • 10
  • [ 2658-24-4 ]
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Reference: [1] Chemische Berichte, 1964, vol. 97, p. 510 - 519
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