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Chemical Structure| 20712-12-3
Chemical Structure| 20712-12-3
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Product Details of [ 20712-12-3 ]

CAS No. :20712-12-3 MDL No. :MFCD08234509
Formula : C7H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :GDCWZYRWKSOYGQ-UHFFFAOYSA-N
M.W : 202.05 Pubchem ID :11030874
Synonyms :

Calculated chemistry of [ 20712-12-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 44.67
TPSA : 46.25 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) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.39
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 1.63
Consensus Log Po/w : 1.56

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.35
Solubility : 0.91 mg/ml ; 0.0045 mol/l
Class : Soluble
Log S (Ali) : -1.96
Solubility : 2.19 mg/ml ; 0.0108 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.73
Solubility : 0.381 mg/ml ; 0.00188 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.12

Safety of [ 20712-12-3 ]

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

Application In Synthesis of [ 20712-12-3 ]

* 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 [ 20712-12-3 ]
  • Downstream synthetic route of [ 20712-12-3 ]

[ 20712-12-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 20712-12-3 ]
  • [ 29124-57-0 ]
YieldReaction ConditionsOperation in experiment
76% With manganese(IV) oxide In dichloromethane at 20℃; for 3 h; 1L round bottom flask was charged with 1B (9.7 g, 48.0 mmol), manganese dioxide (29 g, 336 mmol), dichloromethane(400 mL), stirred at room temperature for 3 h and the reaction was complete by TLC. Suction filtered, washed with dichloromethane, the combined filtrate, the solvent was evaporated under reduced pressure,1C was obtained as a beige solid (7.3 g, 76.0percent yield).
71% With manganese dioxide In acetone REFERENCE EXAMPLE 286
To acetone (300 ml) were added (2-amino-5-bromophenyl)methanol (23.32 g) and active manganese dioxide (58.5 g), and the mixture was stirred at room temperature for 17.5 hours and filtered.
The solvent was evaporated under reduced pressure to give 2-amino-5-bromobenzaldehyde (16.41 g, 71percent).
1 H NMR (200 MHz, CDCl3) δ 6.10-6.20 (2H, br), 6.57 (1H, d, J=8.8 Hz), 7.38 (1H, dd, J=8.8, 2.4 Hz), 7.59 (1H, d, J=2.4 Hz), 9.81 (1H, s).
8 g With manganese(IV) oxide In dichloromethane at 20℃; Step 2: Synthesis of 2-amino-5-bromobenzaldehyde A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and Mn02 (25.8 g, 296.6 mmol) in CH2C12 (400 mL) was stuffed at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the titlecompound as a light yellow solid (8 g, 8 1percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M + H].
8 g With manganese(IV) oxide In dichloromethane at 20℃; A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO2 (25.8 g, 296.6 mmol) in CH2Cl2 (400 mL) was stirred at RT overnight. LCMS showed the reaction was completed.
The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (8 g, 81percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M+H]+.
8 g With manganese(IV) oxide In dichloromethane at 20℃; A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO2 (25.8 g, 296.6 mmol) in CH2Cl2 (400 mL) was stirred at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (8 g, 81percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M+H]+.

Reference: [1] Organic Syntheses, 2013, vol. 90, p. 240 - 250
[2] ChemistryOpen, 2015, vol. 4, # 2, p. 107 - 110
[3] Patent: CN107304201, 2017, A, . Location in patent: Paragraph 0061; 0065
[4] Patent: US6166006, 2000, A,
[5] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1188 - 1196
[6] Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5530 - 5535
[7] Patent: WO2014/11900, 2014, A2, . Location in patent: Page/Page column 37; 38
[8] Patent: US2015/197519, 2015, A1, . Location in patent: Paragraph 0127; 0128
[9] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2191 - 2195
[10] Patent: US9695165, 2017, B2, . Location in patent: Page/Page column 38
[11] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
  • 2
  • [ 5794-88-7 ]
  • [ 20712-12-3 ]
YieldReaction ConditionsOperation in experiment
100% With borane-THF In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice 500mLAdd three bottles1A (10 g, 46.3 mmol), dissolved in anhydrous THF (100 mL),Nitrogen protection,Under ice-cooling, a borane tetrahydrofuran solution (1M) (231 mL, 231 mmol) was added dropwise. After the addition was completed, the mixture was warmed to room temperature, stirred overnight and quenched with water (150 mL) under ice-cooling. The resulting mixture was extracted with ethyl acetate, washed with water, Sodium hydride solution, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 1B (9.7 g, 100percent yield) as a white solid
96% With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5 h; General procedure: To a suspension of lithium aluminum hydride (20.4 mmol) in THF (10 mL) was added benzoic acid (8.5 mmol) dissolved in THF (24 mL) dropwise over 20 minutes at room temperature. The reaction continued to stir at room temperature for 3.5 h, and then was quenched at 0 °C with H2O (10 mL). The suspension was filtered through a Celite plug with EtOAc (100 mL), washed with brine (30 mL), dried with MgSO4 and concentrated in vacuo.
Reference: [1] ACS Catalysis, 2013, vol. 3, # 4, p. 622 - 624
[2] Chemical Communications, 2017, vol. 53, # 1, p. 216 - 219
[3] Organic Letters, 2017, vol. 19, # 12, p. 3219 - 3222
[4] Patent: CN107304201, 2017, A, . Location in patent: Paragraph 0061; 0064
[5] Tetrahedron Letters, 2017, vol. 58, # 40, p. 3795 - 3799
[6] Journal of Medicinal Chemistry, 2018,
[7] Journal of Medicinal Chemistry, 2010, vol. 53, # 17, p. 6506 - 6510
[8] Organic Letters, 2016, vol. 18, # 9, p. 2200 - 2203
[9] Synlett, 2011, # 6, p. 844 - 848
[10] Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4252 - 4255
[11] Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5530 - 5535
[12] Patent: WO2014/11900, 2014, A2, . Location in patent: Page/Page column 37
[13] Organic Syntheses, 2013, vol. 90, p. 240 - 250
[14] Tetrahedron, 2014, vol. 70, # 34, p. 5114 - 5121
[15] Tetrahedron, 2014, vol. 70, # 34, p. 5114 - 5121
[16] Synthesis (Germany), 2014, vol. 46, # 24, p. 3365 - 3373
[17] Patent: US2015/197519, 2015, A1, . Location in patent: Paragraph 0125; 0216
[18] Organic Letters, 2015, vol. 17, # 19, p. 4750 - 4753
[19] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2191 - 2195
[20] Patent: US9695165, 2017, B2, . Location in patent: Page/Page column 37; 38
[21] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
  • 3
  • [ 52727-57-8 ]
  • [ 20712-12-3 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2 h; Inert atmosphere
Stage #2: With water; sodium hydroxide In tetrahydrofuran
To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0° C. under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5-bromophenyl)methanol (1.0 g, 5.2 mmol, 59percent) as off-white solid.
59%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2 h; Inert atmosphere
Stage #2: With water; sodium hydroxide In tetrahydrofuran
To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0 0C under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5- bromophenyl)methanol (1.0 g, 5.2 mmol, 59 percent) as off-white solid.
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 7, p. 1171 - 1174
[2] Journal of Organic Chemistry, 2014, vol. 79, # 3, p. 1235 - 1246
[3] Patent: WO2007/115408, 2007, A1, . Location in patent: Page/Page column 136
[4] Organic Letters, 2016, vol. 18, # 21, p. 5572 - 5575
[5] Patent: US2011/112067, 2011, A1, . Location in patent: Page/Page column 33; 34
[6] Patent: WO2009/135651, 2009, A1, . Location in patent: Page/Page column 51
[7] Patent: WO2006/50940, 2006, A1, . Location in patent: Page/Page column 59-60
[8] Patent: WO2009/7749, 2009, A2, . Location in patent: Page/Page column 108
[9] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1188 - 1196
[10] Organic Letters, 2010, vol. 12, # 5, p. 1084 - 1087
[11] Patent: WO2006/50943, 2006, A1, . Location in patent: Page/Page column 45
[12] Patent: WO2011/19090, 2011, A1, . Location in patent: Page/Page column 47-48
[13] European Journal of Medicinal Chemistry, 2014, vol. 90, p. 788 - 796
  • 4
  • [ 5344-90-1 ]
  • [ 20712-12-3 ]
YieldReaction ConditionsOperation in experiment
72.5% With N-Bromosuccinimide In N,N-dimethyl-formamide for 2 h; Cooling with ice To the reaction flask was added anthranilic alcohol (5.00 g, 40.0 mmol, commercially available), DMF (25 ml) was stirred at ice bath was added portionwise NBS (7.23 g, 40.0 mmol), the ice bath for 2 hours the reaction stirring the reaction solution was directly poured into ice water, filtered, washed and dried to obtain a white solid 5.86 g, yield 72.5percent.
72.5% With N-Bromosuccinimide In N,N-dimethyl-formamide for 2 h; Cooling with ice Dissolve o-aminobenzyl alcohol (5.00 g, 40.0 mmol, commercially available) in 25 mL DMF.NBS (7.23 g, 40.0 mmol) was added in portions with ice-bath stirring.After 2 hours of ice bath reaction, the reaction solution was poured directly into ice water with stirring.filter,washing,dry,5.86 grams of white solidYield 72.5percent.
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 39, p. 6965 - 6968
[2] Patent: CN105732587, 2016, A, . Location in patent: Paragraph 0111; 0112; 0113
[3] Patent: CN104650038, 2018, B, . Location in patent: Paragraph 0123; 0124; 0125
  • 5
  • [ 13292-87-0 ]
  • [ 5794-88-7 ]
  • [ 20712-12-3 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide In tetrahydrofuran REFERENCE EXAMPLE 285
In THF (350 ml) was dissolved 5-bromoanthranilic acid (40.06 g), and the mixture was cooled to 0° C.
To the mixture was added dropwise a solution of 10.0M borane dimethylsulfide in THF (54.5 ml), and the mixture was stirred at room temperature for 4.5 hours.
The mixture was cooled to 0° C., and to the mixture was added dropwise 3N sodium hydroxide solution.
The mixture was stirred at room temperature overnight, and to the mixture was added granulated sodium hydroxide to adjust the mixture to pH 11.
The aqueous layer was saturated with potassium carbonate, and the THF layer was separated.
The aqueous layer was extracted with ether (100 ml*5).
The organic layers were combined and dried with magnesium sulfate.
The solvent was evaporated under reduced pressure to give (2-amino-5-bromophenyl)methanol (36.66 g, 100percent).
1 H NMR (200 MHz, CDCl3) δ 4.62 (2H, s), 7.20 (1H, s), 7.23-7.26 (1H, m).
Reference: [1] Patent: US6166006, 2000, A,
  • 6
  • [ 52727-57-8 ]
  • [ 5344-90-1 ]
  • [ 20712-12-3 ]
Reference: [1] Organic letters, 2001, vol. 3, # 26, p. 4217 - 4220
[2] Organic letters, 2001, vol. 3, # 26, p. 4217 - 4220
  • 7
  • [ 5344-90-1 ]
  • [ 20244-61-5 ]
  • [ 20712-12-3 ]
Reference: [1] Patent: US2002/151504, 2002, A1,
[2] Patent: US5843972, 1998, A,
  • 8
  • [ 20712-12-3 ]
  • [ 882672-05-1 ]
Reference: [1] Patent: WO2014/11900, 2014, A2,
[2] Patent: US2015/197519, 2015, A1,
[3] Patent: US9695165, 2017, B2,
[4] Patent: CN107304201, 2017, A,
  • 9
  • [ 20712-12-3 ]
  • [ 1538604-68-0 ]
Reference: [1] Patent: WO2014/11900, 2014, A2,
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