Home Cart 0 Sign in  

[ CAS No. 59278-65-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 59278-65-8
Chemical Structure| 59278-65-8
Structure of 59278-65-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 59278-65-8 ]

Related Doc. of [ 59278-65-8 ]

Alternatived Products of [ 59278-65-8 ]

Product Details of [ 59278-65-8 ]

CAS No. :59278-65-8 MDL No. :MFCD08458822
Formula : C7H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :ZZVUOSVSPAPBEJ-UHFFFAOYSA-N
M.W : 200.03 Pubchem ID :17914598
Synonyms :

Calculated chemistry of [ 59278-65-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.93
TPSA : 43.09 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) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 1.85
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 1.94
Consensus Log Po/w : 1.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.177 mg/ml ; 0.000887 mol/l
Class : Soluble
Log S (Ali) : -3.08
Solubility : 0.166 mg/ml ; 0.000829 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.84
Solubility : 0.286 mg/ml ; 0.00143 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.15

Safety of [ 59278-65-8 ]

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 [ 59278-65-8 ]

* 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 [ 59278-65-8 ]
  • Downstream synthetic route of [ 59278-65-8 ]

[ 59278-65-8 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 5551-12-2 ]
  • [ 59278-65-8 ]
YieldReaction ConditionsOperation in experiment
65% With vasicine In ethylene glycol at 80℃; for 48 h; General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80°C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.
64% With iron; acetic acid In ethanol at 0℃; for 0.666667 h; Inert atmosphere To a solution of 4-bromo-2-nitrobenzaldehyde (10 g, 43.47 mmol) in EtOH (50 mL) andacetic acid (50 mL) was added Fe powder (7.28 g, 130.42 mmol). The mixture was stirred at0 °C for 40 mm under a nitrogen atmosphere. Insoluble solid was filtered off and the filtratewas adjusted to pH= 8 by progressively adding solid NaI-1C03. The resulting solution wasextracted with EtOAc (300 mL x 2), washed with saturated NaHCO3 (100 mL) and brine(100 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The cruderesidue was purified by silica gel chromatography (petroleum ether EtOAc = 10: 1) to givethe title compound (6 g, 64 percent) as a yellow solid. ‘1-1 NMR (400 Mhz, DMSO-d6) 6 9.79 (s, IH), 7.48 (d,J= 8.4 Hz, IH), 7.27 (s, 2H), 6.99 (s, 1H), 6.78 (d,J 8.0 Hz, IH).
38% With iron; acetic acid In ethanol at 20℃; for 1.5 h; Step 3. 2-Amino-4-bromobenzaldehyde To a 0.2M solution of 4-bromo-2-nitrobenzaldehyde in acetic acid and ethanol (v/v 1:1) solvent system was added iron powder. The reaction mixture was stirred at ambient temperature under <n="335"/>PP028218.0002Argon for 1.5 h and LCMS showed the reaction was complete. Insoluble solid was filtered off and the filtrate was concentrated in vacuum. Residue was diluted with ethyl acetate and was washed with saturated sodium bicarbonate, brine, dried over sodium sulfate and concentrated. Crude product was purified by Biotage using 15percent ethyl acetate in hexane to give desired product in 38percent yield. ES/MS m/z 200/202 (MH+).
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 45, p. 5003 - 5008
[2] Patent: WO2016/86200, 2016, A1, . Location in patent: Page/Page column 219
[3] Patent: WO2007/117607, 2007, A2, . Location in patent: Page/Page column 333-334
[4] Chemische Berichte, 1909, vol. 42, p. 3697
[5] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2462 - 2467
[6] Synthesis, 2010, # 10, p. 1678 - 1686
[7] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6829 - 6833
[8] Patent: WO2016/30443, 2016, A1, . Location in patent: Page/Page column 99-100
  • 2
  • [ 5551-12-2 ]
  • [ 59278-65-8 ]
Reference: [1] Patent: US6599917, 2003, B1,
  • 3
  • [ 60956-26-5 ]
  • [ 59278-65-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2462 - 2467
  • 4
  • [ 99474-21-2 ]
  • [ 59278-65-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2462 - 2467
  • 5
  • [ 99277-71-1 ]
  • [ 59278-65-8 ]
Reference: [1] Patent: WO2007/117607, 2007, A2,
  • 6
  • [ 22996-19-6 ]
  • [ 59278-65-8 ]
Reference: [1] Patent: WO2007/117607, 2007, A2,
  • 7
  • [ 5551-12-2 ]
  • [ 59278-65-8 ]
Reference: [1] Chemische Berichte, 1909, vol. 42, p. 3697
  • 8
  • [ 59278-65-8 ]
  • [ 953039-66-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6829 - 6833
[2] Patent: WO2017/32840, 2017, A1,
[3] Patent: WO2007/117607, 2007, A2,
  • 9
  • [ 59278-65-8 ]
  • [ 98-86-2 ]
  • [ 1203578-65-7 ]
Reference: [1] Synthesis, 2010, # 10, p. 1678 - 1686
  • 10
  • [ 59278-65-8 ]
  • [ 1266322-58-0 ]
Reference: [1] Patent: WO2013/177253, 2013, A2,
[2] Patent: WO2014/8223, 2014, A2,
[3] Patent: WO2014/108858, 2014, A1,
[4] Patent: WO2013/28447, 2013, A1,
[5] Patent: WO2013/52716, 2013, A1,
  • 11
  • [ 2032-34-0 ]
  • [ 59278-65-8 ]
  • [ 1375108-40-9 ]
YieldReaction ConditionsOperation in experiment
75% With p-toluenesulfonic acid monohydrate In toluene for 3 h; Reflux A mixture of 3,3-diethoxypropanenitrile (1.80 mL, 12.00 mmol), 2-amino-4- bromobenzaldehyde (2 g, 10.00 mmol) and p-toluenesulfonic acid monohydrate (0.380 g, 2.000 mmol) in toluene (30 mL) was heated under reflux using Dean-Stark apparatus for 3 h. The reaction was cooled, evaporated under reduced pressure, and the residue was dissolved in a small amount of DMF, diluted with chloroform, and washed with aq. sodium bicarbonate solution. The aqueous layer was extracted with chloroform, and the combined extracts were washed with brine, dried (Na2S04), and concentrated in vacuo. Purification by flash chromatography (0-3percent methanol in dichloromethane) followed by trituration in diethyl ether provided the title compound (1.75 g, 75percent). 1H NMR (400 MHz, DMSO-de) δ ppm 7.95 (dd, J=8.72, 1.89 Hz, 1 H) 8.08 (d, J=8.84 Hz, 1 H) 8.38 (d, J=2.02 Hz, 1 H) 9.13 (d, J=1.52 Hz, 1 H) 9.21 (d, 1 H).
75% With toluene-4-sulfonic acid In toluene for 3 h; Dean-Stark; Reflux A mixture of 3,3-diethoxypropanenitrile (1.80 mL, 12.00 mmol), 2-amino-4-bromobenzaldehyde (2g, 10.00 mmol) and p-toluenesulfonic acid monohydrate (0.380 g, 2.000 mmol) in toluene (30 mL) was heated under reflux using Dean-Stark apparatusfor 3 h. The reaction was cooled, evaporated under reduced pressure, and the residue was dissolved in a small amount of N,N-dimethylformamide, diluted with chloroform, and washed with aq sodium bicarbonate solution. The aqueous layer was extracted with chloroform, and the combined extracts were washed with brine, dried (Na2504), and concentrated in vacuo. Purification of the residue by flash chromatography (0-3percentmethanol in dichloromethane) followed by trituration in diethyl ether provided the titlecompound (1.75 g, 75percent). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.95 (dd, J=8.72, 1.89Hz, 1H) 8.08 (d, J=8.84 Hz, 1H) 8.38 (d, J=2.02 Hz, 1H) 9.13 (d, J=1.52 Hz, 1H) 9.21(d, 1H).
75% With toluene-4-sulfonic acid In toluene for 3 h; Reflux a) 7-bromoquinoline-3 -carbonitrileA mixture of 3,3-diethoxypropanenitrile (1.801 mL, 12.00 mmol),2-amino-4-bromobenzaldehyde (2 g, 10.00 mmol) and p-toluenesulfonic acid monohydrate (0.380 g, 2.000 mmol) in toluene (30 mL) was heated under reflux using Dean-Starkapparatus for 3 h. The reaction was cooled, evaporated under reduced pressure, and the residue was dissolved in a small amount of DMF, diluted with chloroform, and washed with aq. NaHCO3 solution. The aqueous layer was extracted with chloroform, and the combined extracts were washed with brine, dried (Na2504), and concentrated in vacuo. Purification by flash chromatography (0-3percent methanol in dichloromethane) followed by trituration in diethylether provided the title compound (1.75 g, 75percent). ‘H NMR (400 MHz, DMSO-d6) ö ppm7.95 (dd, J8.72, 1.89 Hz, 1 H) 8.08 (d, J8.84 Hz, 1 H) 8.38 (d, J2.02 Hz, 1 H) 9.13 (d, J1.52 Hz, 1 H) 9.21 (d, 1 H).
75% With toluene-4-sulfonic acid In toluene for 3 h; Reflux; Dean-Stark A mixture of 3,3-diethoxypropanenitrile (1.80 mL, 12.00 mmol), 2-amino-4- bromobenzaldehyde (2 g, 10.00 mmol) and p-toluenesulfonic acid monohydrate (0.380 g, 2.000 mmol) in toluene (30 mL) was heated under reflux using Dean-Stark apparatus for 3 h. The reaction was cooled, evaporated under reduced pressure, and the residue was dissolved in a small amount of DMF, diluted with chloroform, and washed with aq. sodium bicarbonate solution. The aqueous layer was extracted with chloroform, and the combined extracts were washed with brine, dried (Na2S04), and concentrated in vacuo. Purification by flash chromatography (0-3percent methanol in dichloromethane) followed by trituration in diethyl ether provided the title compound (1.75 g, 75percent). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.95 (dd, J=8.72, 1.89 Hz, 1 H) 8.08 (d, J=8.84 Hz, 1 H) 8.38 (d, J=2.02 Hz, 1 H) 9.13 (d, J=1.52 Hz, 1 H) 9.21 (d, 1 H)

Reference: [1] Patent: WO2013/28447, 2013, A1, . Location in patent: Page/Page column 119-120
[2] Patent: WO2013/52716, 2013, A1, . Location in patent: Page/Page column 50; 65
[3] Patent: WO2013/177253, 2013, A2, . Location in patent: Page/Page column 61
[4] Patent: WO2014/8223, 2014, A2, . Location in patent: Page/Page column 73
  • 12
  • [ 59278-65-8 ]
  • [ 621-62-5 ]
  • [ 1246549-62-1 ]
YieldReaction ConditionsOperation in experiment
54% With toluene-4-sulfonic acid In toluene at 110℃; for 3 h; Dean-Stark A mixture of 2-chloro-1 , 1-diethoxyethane (4.50 ml_, 30.0 mmol), 2-amino-4- bromobenzaldehyde (3.00 g, 15.0 mmol), and p-toluenesulfonic acid monohydrate (0.285 g, 1.500 mmol) in toluene (50 ml_) was heated at 110 °C for 3 hours using a Dean/Stark trap. The solvent was then evaporated and the residue partitioned between ethyl acetate and saturated aq NaHC03. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were evaporated onto silica gel and purified by flash chromatography (20-50percent dichloromethane/hexanes) to give the title product (1.97 g, 8.12 mmol, 54percent yield) as a yellow solid. MS (ES+) m/e 241.8/243.8 Br pattern [M+H]+; H NMR (400 MHz, DMSO-d6) δ ppm 7.85 (dd, J=8.84, 2.02 Hz, 1 H) 7.98 (d, J=8.59 Hz, 1 H) 8.29 (d, J=1.77 Hz, 1 H) 8.65 (d, J=2.02 Hz, 1 H) 8.94 (d, J=2.53 Hz, 1 H).
Reference: [1] Patent: WO2014/108858, 2014, A1, . Location in patent: Page/Page column 37, 38
  • 13
  • [ 59278-65-8 ]
  • [ 123-38-6 ]
  • [ 1375108-41-0 ]
YieldReaction ConditionsOperation in experiment
72% With potassium hydroxide In ethanol for 3 h; Inert atmosphere; Reflux A solution of KOH (5.61 g, 100 mmol) dissolved in ethanol (50 mL) was added drop wise to a mixture of 2-amino-4-bromobenzaldehyde (60.6 g, 303 mmol) and propionaldehyde (17.6 g, 303 mmol) in absolute ethanol (200 mL) under nitrogen. The mixture was heated to reflux, and then maintained at reflux for 3 h. After cooling to room temperature, the reaction mixture was concentrated to remove the ethanol, then water was added and the mixture was extracted with methylene chloride (3 x 100 mL). The combined organic layers were washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was triturated from diethyl ether to provide the title product (48.6 g, 219 mmol, 72percent yield) as a light brown solid. MS(ES) m/e 221.9, 223.9 [M+H]+ (bromine pattern).
2.5 g With potassium hydroxide In ethanol; water at 95℃; To a solution of 4-bromo-2-nitrobenzaldehyde (5 g, 21.7 mmol) in ethanol (50 mL), iron powder (4.85 g, 86.9 mmol ) was added followed by HCl aqueous solution (0.1 N, 15 mL) . The resulting reaction mixture was vigorously stirred at 95 °C for 2 h. The reaction progression was followed by TLC. When the reduction was completed, propionaldehyde (1 .5 mL, 21.7 mmol) and KOH (1.46 g, 26.0 mmol, in two portions) were added at rt. The reaction mixture was stirred at 95 °C overnight. It was cooled to rt, diluted with DCM (30 mL) and filtered through celite. The filtrate was washed with water (50 mL) and the aqueous layer was extracted with DCM (2 x 100 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The resulting crude product was purified by flash chromatography, affording the title compound. Yield: 52percent (2.5 g, Pale yellow solid). 1 H NMR (400 MHz, DMSO-d6): δ 8.81 (s, 1H), 8.18-8.17 (m, 2H), 7.89 (d, J = 8.7 Hz, 1H), 7.72 (dd, J = 1.9, 8.7 Hz, 1H), 2.50 (s, 3H). LCMS: (Method D) 223.9 (M+H), Rt. 2.48 min, 99.58percent (Max).
Reference: [1] Patent: WO2014/108858, 2014, A1, . Location in patent: Page/Page column 36
[2] Patent: WO2016/30443, 2016, A1, . Location in patent: Page/Page column 99-100
  • 14
  • [ 4696-26-8 ]
  • [ 59278-65-8 ]
  • [ 1375108-41-0 ]
YieldReaction ConditionsOperation in experiment
57% With toluene-4-sulfonic acid In toluene for 18 h; Reflux; Inert atmosphere To a solution of 2-amino-4-bromobenzaldehyde (6 g, 28.2 mmol) in toluene (50 mE) was added (E)- 1 -ethoxyprop- 1 -ene (6.07g, 70.49mmol) and 4-methylbenzcnesulfonic acid (0.49 g, 2.82 mmol). The mixture was heated to reflux for 18 h under a nitrogen atmosphere. Aftercooling the reaction to room temperature, the mixture was concentrated in vacuo. The crude residue was purified by silica gel chromatography (petroleum ether EtOAc = 5 : 1) to give the title compound (4 g, 57 percent) as a yellow solid. ‘H NMR (400 MHz, DMSO-d6) 6 8.80 (s, IH), 8.19-8.17 (m, 2H), 7.88 (d,J= 8.8 Hz, 1H). 7,73 -7.70 (m, 11-1), 2.47 (s, 3H).
Reference: [1] Patent: WO2016/86200, 2016, A1, . Location in patent: Page/Page column 219
  • 15
  • [ 928-55-2 ]
  • [ 59278-65-8 ]
  • [ 1375108-41-0 ]
YieldReaction ConditionsOperation in experiment
25% With p-toluenesulfonic acid monohydrate; sodium sulfate In chloroformReflux A I L round bottom flask fitted with a stirbar, a Dean-Stark trap for solvents heavier than water, and a condenser was charged with 2-amino-4-bromobenzaldehyde (20 g, 100 mmol), sodium sulfate (71.0 g, 500 mmol), and /?-toluenesulfonic acid monohydrate (4.75 g, 25.00 mmol). The solids were taken up in anhydrous chloroform (498 mL) and the suspension treated with 1-ethoxyprop-l-ene (14.39 mL, 130 mmol). The mixture was then heated to reflux with stirring overnight. The reaction mixture was cooled to room temperature and transferred to a 2L separatory funnel. The solution was extracted twice with 200 mL saturated aq sodium bicarbonate and once with 200 mL water. The organic layer was isolated and the aqueous layers were combined and re-extracted twice with an additional 100 mL dichloromethane. The organics were then pooled, dried over sodium sulfate, filtered, and concentrated to a residue. The residue was purified by flash chromatography (0.2-1.9percent methanol: dichloromethane). Fractions containing the desired material were pooled and concentrated to afford the title compound as a bright orange solid (5.603 g, 25.2 mmol, 25percent yield). MS(ES)+ m/e 221.8 [M+H]+.
Reference: [1] Patent: WO2013/28447, 2013, A1, . Location in patent: Page/Page column 62
[2] Patent: WO2013/52716, 2013, A1, . Location in patent: Page/Page column 47
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 59278-65-8 ]

Aryls

Chemical Structure| 145123-24-6

[ 145123-24-6 ]

2-Amino-3-bromobenzaldehyde

Similarity: 0.94

Chemical Structure| 29124-57-0

[ 29124-57-0 ]

2-Amino-5-bromobenzaldehyde

Similarity: 0.88

Chemical Structure| 135484-74-1

[ 135484-74-1 ]

2-Amino-6-bromobenzaldehyde

Similarity: 0.84

Chemical Structure| 55830-09-6

[ 55830-09-6 ]

1-(2-Amino-6-bromophenyl)ethanone

Similarity: 0.83

Chemical Structure| 437998-34-0

[ 437998-34-0 ]

2-Amino-3-bromobenzamide

Similarity: 0.82

Bromides

Chemical Structure| 145123-24-6

[ 145123-24-6 ]

2-Amino-3-bromobenzaldehyde

Similarity: 0.94

Chemical Structure| 29124-57-0

[ 29124-57-0 ]

2-Amino-5-bromobenzaldehyde

Similarity: 0.88

Chemical Structure| 135484-74-1

[ 135484-74-1 ]

2-Amino-6-bromobenzaldehyde

Similarity: 0.84

Chemical Structure| 55830-09-6

[ 55830-09-6 ]

1-(2-Amino-6-bromophenyl)ethanone

Similarity: 0.83

Chemical Structure| 437998-34-0

[ 437998-34-0 ]

2-Amino-3-bromobenzamide

Similarity: 0.82

Aldehydes

Chemical Structure| 145123-24-6

[ 145123-24-6 ]

2-Amino-3-bromobenzaldehyde

Similarity: 0.94

Chemical Structure| 29124-57-0

[ 29124-57-0 ]

2-Amino-5-bromobenzaldehyde

Similarity: 0.88

Chemical Structure| 135484-74-1

[ 135484-74-1 ]

2-Amino-6-bromobenzaldehyde

Similarity: 0.84

Chemical Structure| 50910-55-9

[ 50910-55-9 ]

2-Amino-3,5-dibromobenzaldehyde

Similarity: 0.80

Chemical Structure| 5551-12-2

[ 5551-12-2 ]

4-Bromo-2-nitrobenzaldehyde

Similarity: 0.79

Amines

Chemical Structure| 145123-24-6

[ 145123-24-6 ]

2-Amino-3-bromobenzaldehyde

Similarity: 0.94

Chemical Structure| 29124-57-0

[ 29124-57-0 ]

2-Amino-5-bromobenzaldehyde

Similarity: 0.88

Chemical Structure| 135484-74-1

[ 135484-74-1 ]

2-Amino-6-bromobenzaldehyde

Similarity: 0.84

Chemical Structure| 55830-09-6

[ 55830-09-6 ]

1-(2-Amino-6-bromophenyl)ethanone

Similarity: 0.83

Chemical Structure| 437998-34-0

[ 437998-34-0 ]

2-Amino-3-bromobenzamide

Similarity: 0.82