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Chemical Structure| 1139-52-2
Chemical Structure| 1139-52-2
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Product Details of [ 1139-52-2 ]

CAS No. :1139-52-2 MDL No. :MFCD00051598
Formula : C14H21BrO Boiling Point : -
Linear Structure Formula :- InChI Key :SSQQUEKFNSJLKX-UHFFFAOYSA-N
M.W : 285.22 Pubchem ID :70829
Synonyms :

Safety of [ 1139-52-2 ]

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

Application In Synthesis of [ 1139-52-2 ]

* 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 [ 1139-52-2 ]
  • Downstream synthetic route of [ 1139-52-2 ]

[ 1139-52-2 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 128-39-2 ]
  • [ 1139-52-2 ]
Reference: [1] Synthetic Communications, 2010, vol. 40, # 21, p. 3226 - 3232
[2] Organic Letters, 2008, vol. 10, # 23, p. 5429 - 5432
[3] Journal of the American Chemical Society, 2010, vol. 132, # 2, p. 863 - 872
[4] RSC Advances, 2018, vol. 8, # 32, p. 17806 - 17812
[5] Journal of Organic Chemistry, 1957, vol. 22, p. 1333
[6] Chemische Berichte, 1958, vol. 91, p. 2670,2679
[7] Tetrahedron Asymmetry, 2000, vol. 11, # 17, p. 3591 - 3607
[8] Tetrahedron Letters, 2006, vol. 47, # 4, p. 569 - 571
  • 2
  • [ 106-41-2 ]
  • [ 1139-52-2 ]
  • [ 10323-39-4 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 3179,3181
[2] Patent: US2459597, 1945, ,
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 3179,3181
[4] Patent: US2459597, 1945, ,
  • 3
  • [ 1144-36-1 ]
  • [ 719-22-2 ]
  • [ 1139-52-2 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 6, p. 2006 - 2012
[2] Journal of Organic Chemistry, 1996, vol. 61, # 6, p. 2006 - 2012
  • 4
  • [ 128-39-2 ]
  • [ 719-22-2 ]
  • [ 2455-14-3 ]
  • [ 1139-52-2 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 3, p. 858 - 867
  • 5
  • [ 106-41-2 ]
  • [ 507-20-0 ]
  • [ 1139-52-2 ]
Reference: [1] Journal of Chemical Research - Part S, 2000, # 12, p. 582 - 583
[2] Journal of Fluorine Chemistry, 2000, vol. 101, # 1, p. 81 - 83
  • 6
  • [ 67-56-1 ]
  • [ 128-39-2 ]
  • [ 719-22-2 ]
  • [ 1139-52-2 ]
  • [ 489-01-0 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 7156 - 7161
  • 7
  • [ 950-57-2 ]
  • [ 2966-50-9 ]
  • [ 2444-28-2 ]
  • [ 1139-52-2 ]
  • [ 7330-85-0 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 7156 - 7161
  • 8
  • [ 67-56-1 ]
  • [ 950-57-2 ]
  • [ 2444-28-2 ]
  • [ 719-22-2 ]
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  • [ 489-01-0 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 7156 - 7161
  • 9
  • [ 75-85-4 ]
  • [ 950-57-2 ]
  • [ 719-22-2 ]
  • [ 1139-52-2 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 7156 - 7161
  • 10
  • [ 64-17-5 ]
  • [ 950-57-2 ]
  • [ 2444-28-2 ]
  • [ 719-22-2 ]
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  • [ 5442-35-3 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 7156 - 7161
  • 11
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  • [ 67-63-0 ]
  • [ 2444-28-2 ]
  • [ 719-22-2 ]
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  • [ 22944-14-5 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 7156 - 7161
  • 12
  • [ 950-57-2 ]
  • [ 75-65-0 ]
  • [ 719-22-2 ]
  • [ 1139-52-2 ]
  • [ 7330-85-0 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 7156 - 7161
  • 13
  • [ 1144-36-1 ]
  • [ 719-22-2 ]
  • [ 2455-14-3 ]
  • [ 1139-52-2 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 6, p. 2006 - 2012
  • 14
  • [ 75697-72-2 ]
  • [ 719-22-2 ]
  • [ 1139-52-2 ]
  • [ 14035-34-8 ]
  • [ 6839-19-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 303 - 306
  • 15
  • [ 950-57-2 ]
  • [ 128-39-2 ]
  • [ 719-22-2 ]
  • [ 2455-14-3 ]
  • [ 40084-31-9 ]
  • [ 1139-52-2 ]
  • [ 489-01-0 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 6, p. 2006 - 2012
  • 16
  • [ 20017-35-0 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1595 - 1598
  • 17
  • [ 75697-72-2 ]
  • [ 17540-78-2 ]
  • [ 1139-52-2 ]
  • [ 489-01-0 ]
  • [ 14035-34-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1595 - 1598
  • 18
  • [ 75697-72-2 ]
  • [ 108-95-2 ]
  • [ 719-22-2 ]
  • [ 1139-52-2 ]
  • [ 14035-34-8 ]
  • [ 6839-19-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 303 - 306
  • 19
  • [ 1988-75-6 ]
  • [ 732-26-3 ]
  • [ 1139-52-2 ]
  • [ 20834-61-1 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1989, vol. 38, # 1.2, p. 124 - 126[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, vol. 38, # 1, p. 137 - 140
  • 20
  • [ 67-56-1 ]
  • [ 75697-72-2 ]
  • [ 719-22-2 ]
  • [ 17540-78-2 ]
  • [ 1139-52-2 ]
  • [ 489-01-0 ]
  • [ 14035-34-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1595 - 1598
  • 21
  • [ 1139-52-2 ]
  • [ 77-78-1 ]
  • [ 1516-96-7 ]
YieldReaction ConditionsOperation in experiment
95.2% With potassium carbonate In acetone at 22℃; for 13 h; Heating / reflux Reference Example 6
4-bromo-2,6-di-tert-butylanisole
Under an argon atmosphere, to a solution of 4-bromo-2,6-di-tert-butylphenol (50 g, 0.175 MoL) and potassium carbonate (96.7 g, 4.0 equivalents) in acetone (750 ML) was added dimethyl sulfate (38.6 g, 1.75 equivalents) at 22°C, and the mixture was stirred under reflux for 13 hrs..
Insoluble materials were filtered off and the solvent was evaporated under reduced pressure..
ethyl acetate (150 ML) and water (100 ML) were added, the mixture was partitioned, and the organic layer was washed successively with water (100 ML), 5percent aqueous NaHCO3 solution (100 ML) and 5percent aqueous NaCl solution (100 ML)..
The organic layer was dried over anhydrous magnesium sulfate, filtered by gravity, and the filtrate was concentrated under reduced pressure to give the title compound (56.1 g, brown oil)..
yield 95.2percent1H-NMR (300MHz, CDCl3, TMS) δ: 1.41 (s, 18H), 3.68 (s, 3H), 7.33 (s, 2H).
95.2% With potassium carbonate In acetone at 22℃; for 13 h; Heating / reflux Reference Example 2
4-Bromo-2,6-di-tert-butylanisole
Under argon atmosphere, to a solution of 4-bromo-2,6-di-tert-butylphenol (50 g, 0.175 mol) and potassium carbonate (96.7 g, 4.0 equivalents) in acetone (750 mL) was added dimethyl sulfate (38.6 g, 1.75 equivalents) at 22°C.
The mixture was stirred under reflux for 13 hours.
Insoluble substances were filtered off and the solvent was distilled off under reduced pressure.
By adding ethyl acetate (150 mL) and water (100 mL) to the residue, the reaction mixture was allowed to separate into layers.
An organic layer was washed successively with water (100 mL), a 5percent NaHCO3 aqueous solution (100 mL) and a 5percent NaCl aqueous solution (100 mL), dried over anhydrous magnesium sulfate and then naturally filtered.
The filtrate was concentrated under reduced pressure to obtain the title compound (56.1 g, brown oil).
Yield 95.2percent.
1H-NMR (300 MHz, CDCl3, TMS) δ: 1.41 (s, 18H), 3.68 (s, 3H), 7.33 (s, 2H).
Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 51, p. 16486 - 16487
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 33, p. 9738 - 9742[3] Angew. Chem., 2016, vol. 128, # 33, p. 9890 - 9894,5
[4] Patent: EP1452537, 2004, A1, . Location in patent: Page 27
[5] Patent: EP1568701, 2005, A1, . Location in patent: Page/Page column 13
[6] Synthesis, 2010, # 13, p. 2124 - 2128
  • 22
  • [ 1139-52-2 ]
  • [ 74-88-4 ]
  • [ 1516-96-7 ]
Reference: [1] Organic Letters, 2008, vol. 10, # 23, p. 5429 - 5432
[2] Chemistry - A European Journal, 2014, vol. 20, # 14, p. 4098 - 4104
[3] Chemistry - A European Journal, 2018, vol. 24, # 18, p. 4528 - 4531
[4] Journal of Organic Chemistry, 2008, vol. 73, # 3, p. 1143 - 1146
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1539 - 1543[6] Angew. Chem., 2017, vol. 129, # 6, p. 1561 - 1565,5
[7] Canadian Journal of Chemistry, 1966, vol. 44, p. 2855 - 2866
[8] Patent: US2011/166372, 2011, A1, . Location in patent: Page/Page column 24
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