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Product Details of [ 51605-97-1 ]

CAS No. :51605-97-1 MDL No. :MFCD00051585
Formula : C9H12BrN Boiling Point : -
Linear Structure Formula :- InChI Key :WEMDUNBELVTSRP-UHFFFAOYSA-N
M.W : 214.10 Pubchem ID :521337
Synonyms :

Safety of [ 51605-97-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51605-97-1 ]

* 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 [ 51605-97-1 ]
  • Downstream synthetic route of [ 51605-97-1 ]

[ 51605-97-1 ] Synthesis Path-Upstream   1~7

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  • [ 150560-58-0 ]
Reference: [1] Synthesis, 2003, # 13, p. 2047 - 2052
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  • [ 5433-01-2 ]
YieldReaction ConditionsOperation in experiment
77%
Stage #1: With sulfuric acid; sodium nitrite In ethanol; water at -5℃; Inert atmosphere
Stage #2: With copper In ethanol; water for 4 h; Reflux; Inert atmosphere
2-Bromo-4-isopropylaniline 12 (2.65 g, 12.4 mmol, 1.0 eq.) was added over 15 min. to a mixture of ethanol 96percent (23 mL) and conc. sulfuric acid (2.5 mL) at -5°C under vigorous stirring. Then, a solution of sodium nitrite (1.42 g, 20.7 mmol, 1.67 eq.) in water (3 mL) was added at -5°C over 1 h and the resulting mixture was stirred for 30 minutes, followed by addition of copper powder (12.0 g). The reaction mixture was refluxed for 4 h and filtered through glass frit. The filtrated was poured into cold water (60 mL) and the organic product was extracted with DCM (4 x 50 mL). The combined organic extracts were dried over potassium carbonate and concentrated. Fractional distillation (11 mmHg, 89-90°C) of the residue gave 13 as yellowish oil (1.91g, 77percent yield).
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 19, p. 3301 - 3308
[2] Journal of the Chemical Society, 1939, p. 1299,1301
[3] Journal of Organic Chemistry, 1939, vol. 4, p. 20,26
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 794 - 797
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  • [ 5433-01-2 ]
Reference: [1] Patent: US2007/135596, 2007, A1,
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  • [ 5651-47-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 794 - 797
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  • [ 34246-57-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 794 - 797
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  • [ 544-92-3 ]
  • [ 549488-76-8 ]
YieldReaction ConditionsOperation in experiment
88% at 195℃; for 4 h; Heat a mixture of copper (I) cyanide (2. 5g, 28.02 mmol), and [2-BROMO-4-] isopropyl-phenylamine [(5.] [0G,] 23.35 mmol) in [1-METHYL-2-PYRROLIDINONE] (20 ml) to 195 [°C] for four hours. Dilute the reaction mixture with 100 ml of ethyl acetate and the dark solution, wash twice with 28percent aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride (brine) and twice with water. Collect the organic layer, dry over sodium sulfate and remove the solvent under reduced pressure. Purify the via flash chromatography eluting with a step gradient starting with hexanes and going to 80percent hexanes with 20percent ethyl acetate to obtain 3. [31 G] (20.66 mmol, 88percent yield) of the title compound as an orange oil: Mass Spectrum (m/e): 161 (M+1).
Reference: [1] Patent: WO2004/14895, 2004, A1, . Location in patent: Page 65-66
[2] Patent: WO2004/14895, 2004, A1, . Location in patent: Page 62
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  • [ 875550-89-3 ]
Reference: [1] Patent: WO2007/81569, 2007, A2,
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