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[ CAS No. 38191-34-3 ]

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Chemical Structure| 38191-34-3
Chemical Structure| 38191-34-3
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Product Details of [ 38191-34-3 ]

CAS No. :38191-34-3 MDL No. :MFCD03095028
Formula : C6H6BrNO Boiling Point : 265°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :188.02 g/mol Pubchem ID :14320605
Synonyms :

Safety of [ 38191-34-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 38191-34-3 ]

  • Upstream synthesis route of [ 38191-34-3 ]
  • Downstream synthetic route of [ 38191-34-3 ]

[ 38191-34-3 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 55305-43-6 ]
  • [ 38191-34-3 ]
  • [ 52112-66-0 ]
YieldReaction ConditionsOperation in experiment
94% With lithium hexamethyldisilazane In tetrahydrofuran; hexane at 5 - 20℃; for 1 h; Green chemistry General procedure: To a solution of o-aminophenol (400 mg, 3.67 mmol) and NCTS (998 mg, 3.67 mmol) in THF (6 mL), 1 M LiHMDS in hexane (3.67 mL, 3.67 mmol) was added and stirred at 5 °C to r.t. for 1h. Then the reaction mixture was poured in ice water and stirred for 15 min. Then extracted with EtOAc, the organic layer was separated. The organic layer was washed with brine solution.Then organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtained pure 2-aminobenzaxozole in 90percent yield (471 mg).
Reference: [1] Synlett, 2015, vol. 26, # 7, p. 897 - 900
  • 2
  • [ 38191-34-3 ]
  • [ 52112-66-0 ]
Reference: [1] Patent: WO2014/151147, 2014, A1,
[2] Patent: US2014/357651, 2014, A1,
[3] Patent: US9174994, 2015, B2,
  • 3
  • [ 32315-10-9 ]
  • [ 38191-34-3 ]
  • [ 19932-85-5 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine In dichloromethane at 0 - 20℃; [0950] To a solution of XXXV-1 (3 g, 16 mmol) in dry DCM (50 mL) was added TEA (3.2 g, 32 mmol). The reaction mixture was cooled to 0°C, triphosgene (1.6 g, 5.3 mmol) was added slowly. The mixture was stuffed overnight at rt, then quenched with water, extracted with DCM (80 mLx3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (PE/EA=10/1) to afford XXXV-2b (2.7g, 79percent yield).
Reference: [1] Patent: WO2015/153683, 2015, A1, . Location in patent: Paragraph 0950
  • 4
  • [ 19213-72-0 ]
  • [ 38191-34-3 ]
  • [ 19932-85-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 103, p. 59594 - 59602
  • 5
  • [ 38191-34-3 ]
  • [ 78-39-7 ]
  • [ 151230-42-1 ]
YieldReaction ConditionsOperation in experiment
88.5% at 25℃; for 0.166667 h; 2-Amino-5-bromophenol (561 mg, 3.00 mmol)Was added to triethyl orthoacetate (656 μL, 3.6 mmol),1,3-Dibromo-5,5-dimethylhydantoin (17.2 mg, 6.00 × 10 -2 mmol) was added,And the mixture was stirred at room temperature for 10 minutes.And extracted with ethyl acetate (50 mL × 2).The organic layer was washed with saturated brine,After dehydration with anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure,The residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/4 (volume ratio)) as an elution solvent,Compound 16 was obtained in a yield of 560 mg (88.5percent).
65% for 0.5 h; Reflux To 2-amino-5- bromophenol ( l .OOg, 5.32 mmol) , acetic acid ((0.006 ml) and triethylorthoacetate ( 1.75 ml, 9.58 mmol) were added and refluxed for 3o min. The reaction mixture was quenched with water, extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate : petroleum ether to afford the title compound as a orange solid ((0.756 g, 65percent). -NMR (δ ppm, CDC13, 400 MHz): δ 7.64 (d, 7 = 1.7 Hz, 1 H), 7.51 (d, 7 = 8.4 Hz, 1 H), 7.43 (dd, 7 = 8.4, 1.7 Hz, 1 H), 2.67 (s, 3H).
65% for 0.5 h; Reflux Intermediate 126
6-bromo-2-methylbenzo[d]oxazole:
To 2-amino-5-bromophenol (1.00 g, 5.32 mmol), acetic acid ((0.006 ml) and triethylorthoacetate (1.75 ml, 9.58 mmol) were added and refluxed for 30 min.
The reaction mixture was quenched with water, extracted with ethyl acetate, dried over sodium sulphate and concentrated.
The crude product was column chromatographed with ethyl acetate:
petroleum ether to afford the title compound as a orange solid ((0.756 g, 65percent).
1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.64 (d, J=1.7 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.43 (dd, J=8.4, 1.7 Hz, 1H), 2.67 (s, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7241 - 7257
[2] Patent: JP2016/79108, 2016, A, . Location in patent: Paragraph 0063
[3] Patent: WO2012/151525, 2012, A1, . Location in patent: Page/Page column 128
[4] Patent: US2012/289496, 2012, A1, . Location in patent: Page/Page column 113
  • 6
  • [ 1445-45-0 ]
  • [ 38191-34-3 ]
  • [ 151230-42-1 ]
YieldReaction ConditionsOperation in experiment
85% for 0.5 h; Reflux To an AcOH (1.521 μl, 0.027 mmol) were added 2-amino-5-bromophenol 23 (500 mg, 2.66 mmol) and 1,1,1-trimethoxyethane (600 μl, 4.79 mmol), then the reaction mixture was refluxed for 30 minutes. To the reaction solution was added water, then the reaction solution was extracted with ethyl acetate. The extraction was washed with brine and dried over magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by column chromatography to give Compound 24 (481 mg, 85percent).Compound 24; 1H-NMR (CDCl3) δ: 2.63 (s, 3H), 7.42 (dd, J=8.62, 2.03 Hz, 1H), 7.51 (d, J=8.62 Hz, 1H), 7.64 (d, J=2.03 Hz, 1H).
Reference: [1] Patent: US2012/253040, 2012, A1, . Location in patent: Page/Page column 31
  • 7
  • [ 27684-84-0 ]
  • [ 38191-34-3 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With sodium hydroxide; sodium dithionite In water at 20℃; for 0.25 h;
3-Bromo-6-nitrophenol (0.292 gms, 1. 34 mmole) was stirred in an 0.5percent aqueous sodium hydroxide solution (30 mL). Sodium hydrosulphite (2.00 gms of 85percent, 9.76 mmole) was added to the reaction flask and this was stirred at room temperature for 15 minutes. The reaction flask was then acidified with diluted hydrochloric acid until a pH of 5 was obtained. The reaction was then extracted three times with 40 mL portions of diethyl ether, the combined organic layers dried over anhydrous sodium sulfate, and concentrated to provide crude 2-amino-5-bromophenol (0.533 gms, m. p. 99.5-100. 5 C), which was recrystallized from ethyl ether/hexanes to provide the pure product (0.151 gms, 0.80 mmole, 60percent yield; m. p. 125-127 C (decompose) (reported m. p. 149.5-150. 5 C (Boyland, E et al., 1954) ;'H NMR (CD3CN, 500 MHz) 8 7.08 (bs, 1H), 6.82 (d, 1H, J= 2 Hz), 6.78 (dd, 1H, J= 8,2 Hz), 6.56 (d, 1H, J= 8 Hz), 4.03 (bs, 2H); IR (KBr) 3496 (broad), 3377,3298, 1598,1502, 1431,1269, 1210,916, 877 cm'') 5apos
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 9, p. 2736 - 2742
[2] Chemistry - A European Journal, 2011, vol. 17, # 33, p. 9076 - 9082
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597
[4] MedChemComm, 2015, vol. 6, # 7, p. 1375 - 1380
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 16, p. 4960 - 4971
[6] Patent: WO2005/95347, 2005, A1, . Location in patent: Page/Page column 40
[7] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 108 - 119
[8] Journal of the Chemical Society, 1928, p. 2703
[9] Fortsch.Ch.Phys., 1924, vol. 18, p. Heft 2,S.30
[10] Patent: EP1956013, 2008, A1, . Location in patent: Page/Page column 37
[11] Patent: WO2010/51042, 2010, A1, . Location in patent: Page/Page column 134
[12] Patent: US2007/203143, 2007, A1, . Location in patent: Page/Page column 48
[13] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00502
[14] Patent: US2014/357651, 2014, A1, . Location in patent: Paragraph 0485
[15] Patent: US9174994, 2015, B2, . Location in patent: Page/Page column 116
  • 8
  • [ 16394-40-4 ]
  • [ 38191-34-3 ]
YieldReaction ConditionsOperation in experiment
89%
Stage #1: With hydrogenchloride; water In ethanol at 100℃; for 3 h;
Stage #2: With sodium carbonate In ethanol; water
INTERMEDIATE B3 2-Amino-5-bromophenol A suspension of iV-(4-bromo-2-hydroxyphenyl)acetamide (Intermediate B2; 1.35 g, 5.87 mmol) in EtOH (30 mL) and 3 M HCl (30 mL) was heated to 100 0C (reflux) for 3 h. To the mixture was then added 1 M Na2CO3 (45 mL) and the ethanol was removed under reduced pressure. The residue was extracted with DCM (3 x 250 mL), dried and concentrated. Yield 988 mg (89percent). Analytical HPLC: purity 100percent (System A); LRESIMS (ESI+) m/z = 188/190 (M+H)+.
Reference: [1] Patent: WO2009/150144, 2009, A1, . Location in patent: Page/Page column 138
  • 9
  • [ 95-55-6 ]
  • [ 38191-34-3 ]
Reference: [1] Polyhedron, 2013, vol. 52, p. 246 - 254
[2] Russian Journal of Applied Chemistry, 2009, vol. 82, # 9, p. 1570 - 1576
  • 10
  • [ 591-20-8 ]
  • [ 38191-34-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 16, p. 4960 - 4971
[2] Journal of Organic Chemistry, 1990, vol. 55, # 9, p. 2736 - 2742
[3] Chemistry - A European Journal, 2011, vol. 17, # 33, p. 9076 - 9082
[4] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 108 - 119
[5] Patent: WO2014/151147, 2014, A1,
[6] Patent: US2014/357651, 2014, A1,
[7] Patent: US9174994, 2015, B2,
  • 11
  • [ 5676-60-8 ]
  • [ 38191-34-3 ]
Reference: [1] Patent: WO2009/150144, 2009, A1,
  • 12
  • [ 5683-43-2 ]
  • [ 38191-34-3 ]
Reference: [1] Patent: WO2009/150144, 2009, A1,
  • 13
  • [ 19932-85-5 ]
  • [ 38191-34-3 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 321,326
  • 14
  • [ 441019-63-2 ]
  • [ 38191-34-3 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 980,984
  • 15
  • [ 106-40-1 ]
  • [ 38191-34-3 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 980,984
  • 16
  • [ 2101-88-4 ]
  • [ 38191-34-3 ]
Reference: [1] Journal of the Chemical Society, 1963, p. 5571 - 5572
  • 17
  • [ 7664-93-9 ]
  • [ 10468-46-9 ]
  • [ 615-57-6 ]
  • [ 38191-34-3 ]
  • [ 106-40-1 ]
  • [ 1215-42-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1921, vol. 424, p. 300[2] Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 303
  • 18
  • [ 38191-34-3 ]
  • [ 858855-11-5 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With boron trifluoride diethyl etherate In tetrahydrofuran at -40 - -30℃; for 0.166667 h; Inert atmosphere
Stage #2: With tert.-butylnitrite In tetrahydrofuran at -30 - 20℃; for 1.5 h; Inert atmosphere
Stage #3: With iodine; potassium iodide In acetonitrile at 20℃; for 4 h; Inert atmosphere
To a solution of 1 (2.50 g, 13.30 mmol) in dry THF (12 mL) at -30 to -40 °C in a dry ice- MeCN bath was added boron trifluoride diethyl etherate (BF3 Et20, 4.92 mL, 39.90 mmol) dropwise under N2. After the mixture was stirred at -30 °C for 10 min, lBuONO (2.39 mL, 19.94 mmol) was added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 1.5 h to give a suspension. Petroleum ether (50 mL) was added to give more precipitate. The supernatant was removed by decantation and the solid left was washed with petroleum ether to afford a white solid. This solid was dissolved in dry MeCN (20 mL) and cooled in an ice bath. KI (11.00 g, 66.26 mmol) and I2 (6.00 g, 23.64 mmol) were added. The reaction mixture was stirred at room temperature for 4 h before saturated Na2S203 solution (50 mL) was added to quench the reaction. The mixture was extracted with ethyl acetate three times. The combined organic extracts were washed with water followed by brine, dried over anhydrous Na2S04, and filtered through a pad of Celite. The solvent was removed and the resultant residue was purified by silica gel column chromatography using a mixture of ethyl acetate and petroleum ether (v/v 1 :9) as eluent to give 2 as a pale solid (2.83 g, 71percent); 1H NMR (CDC13) δ 7.50 (d, J= 8.5 Hz, 1H), 7.16 (d, J= 2.2 Hz, 1H), 6.84 (dd, J = 2.2, 8.5 Hz, 1H), 5.39 (s, 1H) ppm.
Reference: [1] Patent: WO2015/23355, 2015, A1, . Location in patent: Page/Page column 162
[2] Journal of the Chemical Society, 1934, p. 137
  • 19
  • [ 38191-34-3 ]
  • [ 79-04-9 ]
  • [ 321436-06-0 ]
YieldReaction ConditionsOperation in experiment
77% With sodium hydrogencarbonate In 2,8-dimethylnonan-5-one; water Part 2.
A solution of 2-amino-5-bromophenol (2.53 g, 18.2 mmol, 1.0 equiv) in 15 mL of isobutylmethyl ketone and 15 mL of water was cooled to 0° C., NaHCO3 (3.67 g, 2.4 equiv) and then chloroacetyl chloride (2.36 g, 1.67 mL, 1.15 equiv) were added.
The mixture was heated to reflux overnight, then cooled to room temperature.
The mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, and concentrated in vacuo.
Flash chromatography on silica gel gave 7-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one in 77percent yield. LRMS found for C9H10NO3 (M+H)+: 180.1.
55% With potassium carbonate In N,N-dimethyl-formamide at 20℃; Cooling with ice; Inert atmosphere Ice bath,The compound 5-bromo-2-aminophenol (3.0 g, 16 mmol)And potassium carbonate (5.53 g, 40 mmol) were dissolved in N, N-dimethylformamide (15 mL)Under nitrogen protection,Chloroacetyl chloride (2.16 g, 19.1 mmol) was added dropwise to the reaction system,Stir at room temperature.After completion of the reaction, the reaction solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried over anhydrous sodium sulfate, filtered and dried. The crude product was purified by column chromatography (petroleum ether / ethyl acetate: 1) 7-bromo-2H-benzo [b] [1,4] oxazin-3 (4H) -one(2.0 g) in 55percent yield.
52% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate In tetrahydrofuran at 0 - 60℃; for 14 h; Inert atmosphere To a mixture of 2-amino-5-bromophenol (26.59 mmol), Triethyl benzyl ammonium chloride (TEBA) (30 mmol) and NaHCO3 (120 mmol) in Tetrahydrofuran (THF) (30 mL) was added a solution of 2-chloroacetyl chloride (53.2 mmol) in THF (10 mL) at 0–5 °C. The reaction mixture was stirred for 2 h at room temperature and then heated to 60 °C for 12 h under inert atmosphere. After completion of reaction, the resulting mixture was concentrated under vacuum and then 50 mL of water was added. The precipitate was collected and washed with hexane to afford 7-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one as a yellow solid (52percent yield). ESI–MS (m/z): 229[M+H]+.
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 1, p. 222 - 236
[2] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597
[3] MedChemComm, 2015, vol. 6, # 7, p. 1375 - 1380
[4] ChemMedChem, 2015, vol. 10, # 11, p. 1821 - 1836
[5] Patent: US6534535, 2003, B1,
[6] Patent: CN106349241, 2017, A, . Location in patent: Paragraph 0515; 0516; 0517; 0518; 0519
[7] Medicinal Chemistry Research, 2016, vol. 25, # 9, p. 1781 - 1793
[8] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 16, p. 4700 - 4704
  • 20
  • [ 38191-34-3 ]
  • [ 106-93-4 ]
  • [ 105679-22-9 ]
Reference: [1] Patent: WO2016/49099, 2016, A1, . Location in patent: Page/Page column 94
  • 21
  • [ 38191-34-3 ]
  • [ 105679-22-9 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597
  • 22
  • [ 38191-34-3 ]
  • [ 149-73-5 ]
  • [ 375369-14-5 ]
YieldReaction ConditionsOperation in experiment
93% at 80℃; for 1 h; Inert atmosphere A mixture of 2-amino-5-bromophenol (1.0 g, 5.34 mmol), p-toluene sulphonic acid (100 mg, 0.581 mmol) and trimethoxymethane (6 mL) was stirred at 80 oC under N2 for 1 h, and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EA = 9:1) to afford 6-bromobenzo[d]oxazole (980 mg, 93percent) as a brown solid. LC-MS m/z: no mass. tR = 1.73 min.
Reference: [1] Patent: WO2017/176961, 2017, A1, . Location in patent: Paragraph 00510
  • 23
  • [ 38191-34-3 ]
  • [ 122-51-0 ]
  • [ 375369-14-5 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 81, p. 15059 - 15062
[2] Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11743 - 11750
  • 24
  • [ 38191-34-3 ]
  • [ 1361110-64-6 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 5, p. 592 - 597
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