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[ CAS No. 619-42-1 ] {[proInfo.proName]}

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Chemical Structure| 619-42-1
Chemical Structure| 619-42-1
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Product Details of [ 619-42-1 ]

CAS No. :619-42-1 MDL No. :MFCD00013531
Formula : C8H7BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :CZNGTXVOZOWWKM-UHFFFAOYSA-N
M.W :215.04 Pubchem ID :12081
Synonyms :

Calculated chemistry of [ 619-42-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.42
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 2.95
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 2.67
Log Po/w (SILICOS-IT) : 2.36
Consensus Log Po/w : 2.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.3
Solubility : 0.107 mg/ml ; 0.000497 mol/l
Class : Soluble
Log S (Ali) : -3.16
Solubility : 0.147 mg/ml ; 0.000684 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.33
Solubility : 0.0999 mg/ml ; 0.000465 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.22

Safety of [ 619-42-1 ]

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 [ 619-42-1 ]

* 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 [ 619-42-1 ]
  • Downstream synthetic route of [ 619-42-1 ]

[ 619-42-1 ] Synthesis Path-Upstream   1~37

  • 1
  • [ 619-42-1 ]
  • [ 51035-17-7 ]
Reference: [1] Patent: US2012/39804, 2012, A1,
[2] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 881 - 907
[3] European Journal of Medicinal Chemistry, 2018, vol. 148, p. 465 - 476
  • 2
  • [ 619-42-1 ]
  • [ 26000-33-9 ]
Reference: [1] Synlett, 2005, # 1, p. 127 - 133
  • 3
  • [ 619-42-1 ]
  • [ 29886-62-2 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2360 - 2364
  • 4
  • [ 67-56-1 ]
  • [ 57699-28-2 ]
  • [ 13195-79-4 ]
  • [ 619-42-1 ]
  • [ 99-73-0 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 5, p. 1490 - 1496
  • 5
  • [ 27329-70-0 ]
  • [ 619-42-1 ]
  • [ 53355-29-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 17, p. 4585 - 4600
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2159 - 2161
  • 6
  • [ 619-42-1 ]
  • [ 75-16-1 ]
  • [ 2077-19-2 ]
YieldReaction ConditionsOperation in experiment
90% at 0 - 20℃; for 5 h; To a solution of methyl 4-bromobenzoate (5 g, 23.25 mmol) in THF (50 mL) at 0°C was added methylmagnesium bromide (23.25 mL, 69.8 mmol) (3M in diethyl ether) dropwise. The resulted mixture was stirred at room temperature for 5 h. Aqueous citricacid (1 M) was added, and the mixture stirred for 1 h, then extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and purified by flash column chromatography (80 g silica gel, 20percent-50percent EtOAc/hexanes) to provide the product of Step 1 (4.5 g, 90percent yield) as a colorless oil. LC retention time: 2.63 mm.
79%
Stage #1: at -30 - 20℃; for 5 h;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether
Preparation 36 2-(4-Bromo-phenvl)-propan-2-ol; A solution of methyl p-bromobenzoate (3g, 13.2 mmol) in tetrahydrofuran (14 mL) cooled to-30°C was treated dropwise with methyl magnesium bromide (1 M in diethyl ether, 105.5 mmol, 105.5 mL). Upon completion of addition, the resulting suspension was allowed to warm to room temperature and was stirred for 5 hours. Saturated aqueous ammonium chloride (100 mL) was added slowly and the mixture was diluted with ethyl acetate (100 mL). The organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over magnesium sulfate, were filtered, and the solvent was removed in vacuo. Purification by silica gel chromatography (10: 1 hexanes-ethyl acetate) gave 2.2 g (79percent yield) of 2- (4-bromo-phenyl)-propan-2-ol. 13C NMR (100 MHz, CDCI3) d 148.4, 131. 4, 126.6, 120. 8, 72.5, 31.9 ; MS (AP/CI) 197.1, 199.1 (M+H) +
79% at -30 - 20℃; for 5 h; A solution of methyl p-bromobenzoate (3 g, 13.2 mmol) in tetrahydrofuran (14 mL) cooled to -30° C. was treated dropwise with methyl magnesium bromide (1 M in diethyl ether, 105.5 mmol, 105.5 mL). Upon completion of addition, the resulting suspension was allowed to warm to room temperature and was stirred for 5 h. Saturated aqueous ammonium chloride (100 mL) was added slowly and the mixture was diluted with ethyl acetate (100 mL). The organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate (3.x.50 mL). The combined organic layers were dried over magnesium sulfate, were filtered, and the solvent was removed in vacuo. Purification by silica gel chromatography (10:1 hexanes-ethyl acetate) gave 2.2 g (79percent yield) of 2-(4-bromo-phenyl)-propan-2-ol. 13C NMR (100 MHz, CDCl3) d 148.4, 131.4, 126.6, 120.8, 72.5, 31.9; MS (AP/CI) 197.1, 199.1 (M+H)+.
79%
Stage #1: at -30 - 20℃; for 5 h;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether
PREPARATION 51; EPO <DP n="83"/>2-(4-Bromophenyl)propan-2-olA solution of methyl p-bromobenzoate (3g, 13.2 mmol) in tetrahydrofuran (14 ml.) cooled to -3O0C was treated dropwise with methyl magnesium bromide (1 M in diethyl ether,105.5 mmol, 105.5 mL). Upon completion of addition, the resulting suspension was allowed to warm to rt and was stirred for 5 hours. Saturated aqueous ammonium chloride (100 mL) was added slowly and the mixture was diluted with EtOAc (100 mL). The organic and aqueous layers were separated and the aqueous layer was extracted with EtOAc (3 x 50 mL).The combined organic layers were dried over magnesium sulfate, were filtered, and the solvent was removed in vacuo. Purification by silica gel chromatography (10:1 hexanes - EtOAc) gave 2.2 g (79percent yield) of PP51. 13C NMR (100 MHz, CDCI3) d 148.4, 131.4, 126.6,120.8, 72.5, 31.9; MS (AP/CI) 197.1 , 199.1 (M+H)+.
79%
Stage #1: at -30 - 20℃; for 5 h;
Stage #2: With water; ammonium chloride In tetrahydrofuran; diethyl ether
A solution of methyl p-bromobenzoate (3g, 13.2 mmol) in tetrahydrofuran (14 mL) cooled to -300C was treated dropwise with methyl magnesium bromide (1 M in diethyl ether,105.5 mmol, 105.5 mL). Upon completion of addition, the resulting suspension was allowed to warm to room temperature and was stirred for 5 hours. Saturated aqueous ammonium chloride (100 mL) was added slowly and the mixture was diluted with ethyl acetate (100 mL).The organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over magnesium sulfate, were filtered, and the solvent was removed in vacuo. Purification by silica gel chromatography (10:1 hexanes - ethyl acetate) gave 2.2 g (79percent yield) of 2-(4-bromo-phenyl)- EPO <DP n="37"/>propan-2-ol. 13C NMR (100 MHz, CDCI3) 148.4, 131.4, 126.6, 120.8, 72.5, 31.9; MS (AP/CI) 197.1 , 199.1 (M+H)+.

Reference: [1] Patent: WO2015/27021, 2015, A1, . Location in patent: Page/Page column 67; 68; 81; 82
[2] Patent: WO2005/90300, 2005, A1, . Location in patent: Page/Page column 35
[3] Patent: US2006/25421, 2006, A1, . Location in patent: Page/Page column 14
[4] Patent: WO2006/48727, 2006, A1, . Location in patent: Page/Page column 81-82
[5] Patent: WO2006/106416, 2006, A1, . Location in patent: Page/Page column 34-35
[6] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 887 - 892
[7] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 7953 - 7967
  • 7
  • [ 619-42-1 ]
  • [ 865-48-5 ]
  • [ 59247-47-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 22, p. 4705 - 4713
  • 8
  • [ 619-42-1 ]
  • [ 16184-89-7 ]
Reference: [1] Tetrahedron, 2017, vol. 73, # 48, p. 6754 - 6762
  • 9
  • [ 619-42-1 ]
  • [ 213596-33-9 ]
  • [ 2675-79-8 ]
YieldReaction ConditionsOperation in experiment
95% With potassium phosphate In 1,4-dioxane at 110℃; for 18 h; A Schlenk tube was charged with aryl halide (0.67 mmol, 1.0 equiv), aryl boronate ester (0.81 mmol, 1.2 equiv), potassium phosphate or CsF (3.0 equiv), Pd catalyst (0.1 equiv), 2-(dicyclohexylphosphino)biphenyl (0.2 equiv) (co-ligand was used in the presence of Pd(OAc)2 as catalyst and CsF as base (see Table 8, entries 13-15); reaction was performed at rt) and a Teflon coated stirbar. The reaction mixture was evacuated three times for ten minutes under high vacuum and backfilled with N2. Dry dioxane was added via the T-neck and the reaction mixture was heated to 110 0C for 18 h. The reaction mixture was cooled to room <n="24"/>temperature and diluted with DCM (10 rnL). The solution was filtered and the filtrated washed with DCM (100 mL). The filtrate was concentrated and purified by silica gel chromatography.
Reference: [1] Patent: WO2009/137322, 2009, A2, . Location in patent: Page/Page column 21; 22; 29; 30; 31
  • 10
  • [ 619-42-1 ]
  • [ 96-34-4 ]
  • [ 52787-14-1 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 5, p. 1146 - 1153
  • 11
  • [ 619-42-1 ]
  • [ 99-90-1 ]
  • [ 7511-49-1 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 52, p. 9271 - 9274
  • 12
  • [ 619-42-1 ]
  • [ 10602-00-3 ]
Reference: [1] Macromolecules, 2005, vol. 38, # 17, p. 7205 - 7206
[2] Journal of Organic Chemistry, 1992, vol. 57, # 25, p. 6998 - 6999
[3] Synthesis, 1980, # 8, p. 627 - 630
[4] Macromolecules, 2010, vol. 43, # 14, p. 6014 - 6023
[5] Revue Roumaine de Chimie, 2010, vol. 55, # 11-12, p. 989 - 994
[6] Patent: US2013/65248, 2013, A1,
[7] Patent: WO2013/170030, 2013, A1,
[8] Patent: WO2014/82286, 2014, A1,
[9] Patent: US2015/51242, 2015, A1,
[10] Journal of Materials Chemistry B, 2015, vol. 3, # 3, p. 491 - 497
[11] Patent: US9290791, 2016, B2,
[12] Patent: CN107043352, 2017, A,
[13] Patent: CN107082762, 2017, A,
[14] Patent: CN107417618, 2017, A,
  • 13
  • [ 619-42-1 ]
  • [ 26114-12-5 ]
Reference: [1] Patent: EP2610243, 2013, A2,
  • 14
  • [ 619-42-1 ]
  • [ 10602-04-7 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15257 - 15264
  • 15
  • [ 619-42-1 ]
  • [ 5467-74-3 ]
  • [ 89901-03-1 ]
YieldReaction ConditionsOperation in experiment
13.7% With sodium carbonate In 1,4-dioxane; water for 5 h; Heating / reflux 2.52a.
methyl 4'-bromo-biphenyl-4-carboxylate
0.54 g (2.5 mmol) of methyl 4-bromo-benzoate is dissolved in 10 mL dioxane and 2.5 mL 2M-sodium carbonate solution. 0.6 g (3 mmol) of 4-bromophenyl-boric acid and 0.12 g (0.1 mmol) of tetrakis-(triphenylphosphine)-palladium are added successively and the reaction is refluxed for 5 hours.
The reaction mixture is combined with water and EtOAc, filtered and the phases are separated.
The aqueous phase is extracted with EtOAc and the combined organic phases are dried over MgSO4.
After elimination of the drying agent and solvent the residue is triturated with acetonitrile, suction filtered and dried in the air.
Yield: 100 mg (13.7percent of theory);
C14H11BrO2 (M=291.15);
calc.: molar peak (M+H)+: 291/293 fnd.: molar peak (M+H)+: 291/293;
Rf value: 0.68 (silica gel, petroleum ether/EtOAc 8:2).
Reference: [1] Patent: US2004/242572, 2004, A1, . Location in patent: Page/Page column 77
  • 16
  • [ 288-32-4 ]
  • [ 619-42-1 ]
  • [ 101184-08-1 ]
YieldReaction ConditionsOperation in experiment
78% With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 130℃; Inert atmosphere (1) Under N2 protection, 4-bromobenzoic acid methyl ester (4.3g, 20mmol), imidazole (2.04g, 30mmol), cesium carbonate (19.6,60mmol), and cuprous iodide (0.19g, 1mmol) were added to a three-necked flask with 100mL dry DMF. It was heated with stirring to 130°C. After monitoring reaction completion by TLC, 200mL of saturated saline solution was added and extracted with dichloromethane 200mL x 3. The organic phase was dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure and purified by column chromatography to give a white solid 3.15g, yield 78.00percent.
Reference: [1] Patent: CN105348327, 2016, A, . Location in patent: Paragraph 0055; 0057; 0058
[2] Chemical Communications, 2016, vol. 52, # 69, p. 10505 - 10508
  • 17
  • [ 619-42-1 ]
  • [ 1692-15-5 ]
  • [ 106047-17-0 ]
Reference: [1] Patent: US2008/275062, 2008, A1, . Location in patent: Page/Page column 11
  • 18
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  • [ 93830-58-1 ]
  • [ 106047-17-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 11, p. 4755 - 4763
  • 19
  • [ 1120-87-2 ]
  • [ 619-42-1 ]
  • [ 106047-17-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 3, p. 761 - 780
  • 20
  • [ 619-42-1 ]
  • [ 160598-47-0 ]
Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 15, p. 7436 - 7444
  • 21
  • [ 1040745-70-7 ]
  • [ 619-42-1 ]
  • [ 160598-47-0 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 6, p. 2195 - 2198
  • 22
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  • [ 160598-47-0 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 42, p. 13862 - 13865
  • 23
  • [ 137-43-9 ]
  • [ 619-42-1 ]
  • [ 160598-47-0 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 26, p. 8084 - 8087
  • 24
  • [ 619-42-1 ]
  • [ 6638-79-5 ]
  • [ 192436-83-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 20, p. 3337 - 3340
  • 25
  • [ 5419-55-6 ]
  • [ 619-42-1 ]
  • [ 99768-12-4 ]
YieldReaction ConditionsOperation in experiment
95.5% With n-butyllithium In tetrahydrofuran at -78℃; for 0.5 h; In 500mL three-necked flask,Methyl 4-bromobenzoate (20.2 g, 77.2 mmol) was dissolved in dry THF (200.0 mL)Triisopropyl borate (18.9 g, 100.3 mmol) was added,Cool to -78 ° C,N-Butyllithium (6.8 g, 96.5 mmol) was added dropwise,Maintain the reaction temperature 0.5h.The reaction is completed,Saturated aqueous ammonium chloride solution was quenched,1mol / L hydrochloric acid to adjust the pH to 1,Ethyl acetate (100.0 mL × 3), the organic phases were combined,Saturated brine (60 mL × 1), dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure, the residue was beaten with n-hexane,The filtrate was filtered to give 4-methoxycarbonyl phenylboronic acid 13.3g, a yield of 95.5percent.
Reference: [1] Patent: CN106565761, 2017, A, . Location in patent: Paragraph 0063; 0064
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  • [ 99768-12-4 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[2] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
  • 27
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  • [ 275386-60-2 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15257 - 15264
[2] Patent: EP2610243, 2013, A2,
  • 28
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  • [ 383127-22-8 ]
Reference: [1] Patent: EP3190113, 2017, A1,
[2] Patent: TWI558709, 2016, B,
  • 29
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  • [ 162046-66-4 ]
Reference: [1] Patent: US2018/141923, 2018, A1,
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  • [ 199678-06-3 ]
Reference: [1] Patent: WO2017/205538, 2017, A1,
  • 31
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  • [ 223127-49-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5812 - 5817
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  • [ 619-42-1 ]
  • [ 107317-58-8 ]
  • [ 957207-58-8 ]
Reference: [1] ACS Catalysis, 2018, vol. 8, # 4, p. 2839 - 2843
  • 33
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  • [ 76-05-1 ]
  • [ 107317-58-8 ]
  • [ 957207-58-8 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 1, p. 38 - 41
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  • [ 619-42-1 ]
  • [ 107317-58-8 ]
  • [ 957207-58-8 ]
Reference: [1] ACS Catalysis, 2018, vol. 8, # 4, p. 2839 - 2843
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  • [ 76-05-1 ]
  • [ 107317-58-8 ]
  • [ 957207-58-8 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 1, p. 38 - 41
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  • [ 165049-28-5 ]
Reference: [1] Organic Process Research and Development, 1999, vol. 3, # 3, p. 184 - 188
  • 37
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  • [ 1131622-50-8 ]
Reference: [1] Patent: WO2014/8197, 2014, A1,
[2] Patent: WO2015/95767, 2015, A1,
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