[ CAS No. 123858-51-5 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 123858-51-5
Chemical Structure| 123858-51-5
Structure of 123858-51-5

Quality Control of [ 123858-51-5 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 123858-51-5 ]

SDS

Product Details of [ 123858-51-5 ]

CAS No. :123858-51-5MDL No. :MFCD16659002
Formula :C8H8BrNOBoiling Point :-
Linear Structure Formula :-InChI Key :-
M.W :214.06Pubchem ID :14503614
Synonyms :

Computed Properties of [ 123858-51-5 ]

TPSA : 43.1 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.13 Rotatable Bond Count : 1

Safety of [ 123858-51-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 123858-51-5 ]

  • Upstream synthesis route of [ 123858-51-5 ]
  • Downstream synthetic route of [ 123858-51-5 ]

[ 123858-51-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 591-19-5 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
25% With hydrogenchloride; boron trichloride In toluene; acetonitrile Step A
Preparation of 1-(2-amino-4-bromophenyl)ethanone (162a)
Under an argon atmosphere a solution of 3-bromoaniline (31.3 g, 181.8 mmol) and acetonitrile (75 g, 1.818 mol) in anhydrous toluene (120 ml) was added dropwise to boron trichloride (23.4 g, 200 mmol) in (200 ml) hexanes under cooling in an ice bath and stirring over 2.5 hours.
After the addition was completed, aluminum chloride (26.6 g, 200 mmol) was added portion wise over 30 minutes.
The mixture was allowed to warm to ambient temperature and then heated at reflux for 16 hours with stirring.
A 3N HCl solution (100 ml) was added dropwise to the reaction mixture under stirring at 10° C.
After the addition was complete, the mixture was heated at reflux for 3.5 hours.
The reaction mixture was then cooled to room temperature, and the layers separated.
The aqueous layer was extracted with chloroform (3*250 ml).
Organic layers were combined, dried over magnesium sulfate, filtered, and the filtrate concentrated to give the title compound 162a (9.58 g, 25percent).
1H NMR (CDCl3, 300 MHz): δ 7.54 (d, 1H, J=8.8 Hz), 6.83 (d, 1H, J=1.9 Hz), 6.75 (dd, 1H, J=8.4, 1.8 Hz), 2.54 (s, 3H) ppm.
25% With hydrogenchloride; boron trichloride In toluene; acetonitrile Step A
Preparation of 1-(2-amino-4-bromophenyl)ethanone (162a)
Under an argon atmosphere a solution of 3-bromoaniline (31.3 g, 181.8 mmol) and acetonitrile (75 g, 1.818 mol) in anhydrous toluene (120 ml) was added dropwise to boron trichloride (23.4 g, 200 mmol) in (200 ml) hexanes under cooling in an ice bath and stirring over 2.5 hours.
After the addition was completed, aluminum chloride (26.6 g, 200 mmol) was added portion wise over 30 minutes.
The mixture was allowed to warm to ambient temperature and then heated at reflux for 16 hours with stirring.
A 3N HCl solution (100 ml) was added dropwise to the reaction mixture under stirring at 10° C.
After the addition was complete, the mixture was heated at reflux for 3.5 hours.
The reaction mixture was then cooled to room temperature, and the layers separated.
The aqueous layer was extracted with chloroform (3*250 ml).
Organic layers were combined, dried over magnesium sulfate, filtered, and the filtrate concentrated to give the title compound 162a (9.58 g, 25 percent). 1H NMR (CDCl3, 300 MHz): δ7.54 (d, 1H, J=8.8 Hz), 6.83 (d, 1H, J=1.9 Hz), 6.75 (dd, 1H, J=8.4, 1.8 Hz), 2.54 (s, 3H) ppm.
25% With hydrogenchloride; boron trichloride In toluene; acetonitrile Step 1
Preparation of 1-(2-amino-4-bromophenyl)ethanone
Under an argon atmosphere a solution of 3-bromoaniline (31.3 g, 181.8 mmol) and acetonitrile (75 g, 1.818 mol) in anhydrous toluene (120 ml) was added dropwise over 2.5 hours to a stirred solution of boron trichloride (23.4 g, 200 mmol) in (200 ml) hexanes cooled in an ice bath.
After the addition was completed, aluminum chloride (26.6 g, 200 mmol) was added portion wise over 30 minutes.
The mixture was allowed to warm to ambient temperature and then heated at reflux for 16 hours with stirring.
The reaction mixture was then cooled to 10° C. and 100 ml of a 3N HCl solution was added dropwise with continued stirring.
After the addition was complete, the mixture was heated at reflux for 3.5 hours, then cooled to room temperature, and the layers separated.
The aqueous layer was extracted with chloroform (3*250 ml).
Organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to give the title compound (9.58 g, 25percent).
1H NMR (CDCl3, 300 MHz): δ 7.54 (d, 1H, J=8.8 Hz), 6.83 (d, 1H, J=1.9 Hz), 6.75 (dd, 1H, J=8.4, 1.8 Hz), 2.54 (s, 3H) ppm.
25% With hydrogenchloride; boron trichloride In toluene; acetonitrile Step A
Preparation of 1-(2-Amino-4-bromophenyl)ethanone (162a)
Under an argon atmosphere a solution of 3-bromoaniline (31.3 g, 181.8 mmol) and acetonitrile (75 g, 1.818 mol) in anhydrous toluene (120 ml) was added dropwise to boron trichloride (23.4 g, 200 mmol) in (200 ml) hexanes under cooling in an ice bath and stirring over 2.5 hours.
After the addition was completed, aluminum chloride (26.6g, 200 mmol) was added portion wise over 30 minutes.
The mixture was allowed to warm to ambient temperature and then heated at reflux for 16 hours with stirring.
A 3N HCl solution (100 ml) was added dropwise to the reaction mixture under stirring at 10 ° C.
After the addition was complete, the mixture was heated at reflux for 3.5 hours.
The reaction mixture was then cooled to room temperature, and the layers separated.
The aqueous layer was extracted with chloroform (3*250 ml).
Organic layers were combined, dried over magnesium sulfate, filtered, and the filtrate concentrated to give the title compound 162a (9.58 g, 25percent).
1H NMR (CDCl3, 300 MHz): δ 7.54 (d, 1H, J=8.8 Hz), 6.83 (d, 1H, J=1.9 Hz), 6.75 (dd, 1H, J=8.4, 1.8 Hz), 2.54 (s, 3H) ppm.

Reference: [1] Patent: US2003/166636, 2003, A1
[2] Patent: US2002/52360, 2002, A1
[3] Patent: US2002/137737, 2002, A1
[4] Patent: US6503902, 2003, B2
[5] Patent: US5061800, 1991, A
  • 2
  • [ 90004-94-7 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
85% at 90℃; for 1.00 h; Iron powder (5.69 g, 102.0 mmol) was added to a solution of l-(4-bromo-2- nitropheny ethanone (62, 4.16 g, 17.0 mmol) in 30 mL of acetic acid and the resulting suspension was heated to 90 °C for 1 hour. After cooling to room temperature the reaction mixture was diluted with brine and EtOAc and adjusted to pH 10 by the addition of 3N aqueous NaOH. The mixture was filtered and the filtrate was extracted 3x with EtOAc. The combined organic phases were dried with Na2S04, filtered and the filtrate concentrated under vacuum to give of 1 -(2-amino-4- bromophenyl)ethanone (63, 3.1 g, 14.4 mmol, 85percent). MS: 214.0 m/z (M+H)+.
Reference: [1] Liebigs Annalen der Chemie, 1990, # 2, p. 205 - 206
[2] Patent: WO2012/162254, 2012, A1. Location in patent: Page/Page column 152
  • 3
  • [ 30186-18-6 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
56% With ammonia In N,N-dimethyl-formamide at 60℃; for 9.00 h; Inert atmosphere 2-Acetyl-5-bromophenol (322 mg, 1.5 mmol) was dissolved in N, N-dimethylformamide (3 mL)Ammonia (1.7 mL, 45 mmol) was added dropwise thereto, reacted at 60 ° C under nitrogen for 9 hours, and allowed to cool to room temperature. The reaction solution was poured into 16 mL of water and extracted with dichloromethane (3 x 5 mL). The organic phase was washed with saturated brine (2 x 5 mL), dried over anhydrous sodium sulfate, filtered, sonicated and purified by flash column chromatography The product was dichloromethane: methanol = 50: 1 V / V)2-acetyl-5-bromoaniline as a yellow oil in a yield of 56percent.
Reference: [1] Patent: CN106631820, 2017, A. Location in patent: Paragraph 0143; 0144; 0145; 0146
  • 4
  • [ 75-05-8 ]
  • [ 591-19-5 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
4 g
Stage #1: With aluminum (III) chloride; boron trichloride In dichloromethane; toluene at 0 - 90℃; for 5.00 h;
Stage #2: With hydrogenchloride; water In dichloromethane; toluene at 50℃; for 1.00 h;
Acetonitrile (23.7 g, 580 mmol) was added to 3-Bromoaniline (10 g, 58 mmol) in toluene (70 mL). The mixture was cooled to 0°C and BC13 (1 M in CH2C12, 64 mL, 64 mmol) was added drop wise, while keeping the temperature below 10°C. Next, A1C13 (11.6 g, 87 mmol) was added in small portions at 0°C. The reaction mixture was heated to 90°C for 5 hours. The reaction mixture was cooled to room temperature and quenched with aqueous HCl (2N, 100 mL). The mixture was heated to 50°C for 1 hour, cooled to room temperature and separated. The organic layer was separated and washed with water and brine. The organic layer was collected, dried and concentrated, resulting in l-(2-amino-4-bromophenyl)ethanone (4 g). Method A2; Rt: 0.98 min. m/z=: 215.7 (M+H)+ Exact mass: 215.0
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[2] Patent: WO2012/13643, 2012, A1. Location in patent: Page/Page column 86
[3] Patent: WO2013/98313, 2013, A1. Location in patent: Page/Page column 41
[4] Patent: WO2014/152738, 2014, A1. Location in patent: Page/Page column 72; 73
  • 5
  • [ 20776-50-5 ]
  • [ 917-54-4 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
33% at -78℃; for 1.00 h; To a -78 °C solution of 2-amino-4-bromobenzoic acid (2.16 g, 10 mmol) in THF (20 mL) was added MeLi (13.3 mL, 3M, 0.04 mmol). The resulting reaction was allowed to stir at -78 °C for 1 hour, then was quenched with water and extracted with EtOAc. The organic extract was dried over anhydrous Na2S04, filtered and concentrated in vacuo and the resulting residue was purified using flash chromatography on silica gel to provide Int-21 (700 mg, 33 percent). 1H NM (CDC13): δ 7.51 - 7.58 (m, 1 H), 6.72 - 6.84 (m, 2 H), 6.37 (s, 2 H), 7.73 (s, 2 H). MS (ESI) m/e (M+H*): 214.
Reference: [1] Patent: WO2012/50848, 2012, A1. Location in patent: Page/Page column 121
  • 6
  • [ 1438400-32-8 ]
  • [ 123858-51-5 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 45, p. 5225 - 5227
  • 7
  • [ 591-19-5 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
25% With hydrogenchloride; boron trichloride In toluene; acetonitrile Step A
Preparation of 1-(2-amino-4-bromophenyl)ethanone (162a)
Under an argon atmosphere a solution of 3-bromoaniline (31.3 g, 181.8 mmol) and acetonitrile (75 g, 1.818 mol) in anhydrous toluene (120 ml) was added dropwise to boron trichloride (23.4 g, 200 mmol) in (200 ml) hexanes under cooling in an ice bath and stirring over 2.5 hours.
After the addition was completed, aluminum chloride (26.6 g, 200 mmol) was added portion wise over 30 minutes.
The mixture was allowed to warm to ambient temperature and then heated at reflux for 16 hours with stirring.
A 3N HCl solution (100 ml) was added dropwise to the reaction mixture under stirring at 10° C.
After the addition was complete, the mixture was heated at reflux for 3.5 hours.
The reaction mixture was then cooled to room temperature, and the layers separated.
The aqueous layer was extracted with chloroform (3*250 ml).
Organic layers were combined, dried over magnesium sulfate, filtered, and the filtrate concentrated to give the title compound 162a (9.58 g, 25percent).
1H NMR (CDCl3, 300 MHz): δ 7.54 (d, 1H, J=8.8 Hz), 6.83 (d, 1H, J=1.9 Hz), 6.75 (dd, 1H, J=8.4, 1.8 Hz), 2.54 (s, 3H) ppm.
25% With hydrogenchloride; boron trichloride In toluene; acetonitrile Step A
Preparation of 1-(2-amino-4-bromophenyl)ethanone (162a)
Under an argon atmosphere a solution of 3-bromoaniline (31.3 g, 181.8 mmol) and acetonitrile (75 g, 1.818 mol) in anhydrous toluene (120 ml) was added dropwise to boron trichloride (23.4 g, 200 mmol) in (200 ml) hexanes under cooling in an ice bath and stirring over 2.5 hours.
After the addition was completed, aluminum chloride (26.6 g, 200 mmol) was added portion wise over 30 minutes.
The mixture was allowed to warm to ambient temperature and then heated at reflux for 16 hours with stirring.
A 3N HCl solution (100 ml) was added dropwise to the reaction mixture under stirring at 10° C.
After the addition was complete, the mixture was heated at reflux for 3.5 hours.
The reaction mixture was then cooled to room temperature, and the layers separated.
The aqueous layer was extracted with chloroform (3*250 ml).
Organic layers were combined, dried over magnesium sulfate, filtered, and the filtrate concentrated to give the title compound 162a (9.58 g, 25 percent). 1H NMR (CDCl3, 300 MHz): δ7.54 (d, 1H, J=8.8 Hz), 6.83 (d, 1H, J=1.9 Hz), 6.75 (dd, 1H, J=8.4, 1.8 Hz), 2.54 (s, 3H) ppm.
25% With hydrogenchloride; boron trichloride In toluene; acetonitrile Step 1
Preparation of 1-(2-amino-4-bromophenyl)ethanone
Under an argon atmosphere a solution of 3-bromoaniline (31.3 g, 181.8 mmol) and acetonitrile (75 g, 1.818 mol) in anhydrous toluene (120 ml) was added dropwise over 2.5 hours to a stirred solution of boron trichloride (23.4 g, 200 mmol) in (200 ml) hexanes cooled in an ice bath.
After the addition was completed, aluminum chloride (26.6 g, 200 mmol) was added portion wise over 30 minutes.
The mixture was allowed to warm to ambient temperature and then heated at reflux for 16 hours with stirring.
The reaction mixture was then cooled to 10° C. and 100 ml of a 3N HCl solution was added dropwise with continued stirring.
After the addition was complete, the mixture was heated at reflux for 3.5 hours, then cooled to room temperature, and the layers separated.
The aqueous layer was extracted with chloroform (3*250 ml).
Organic layers were combined, dried over magnesium sulfate, filtered, and concentrated to give the title compound (9.58 g, 25percent).
1H NMR (CDCl3, 300 MHz): δ 7.54 (d, 1H, J=8.8 Hz), 6.83 (d, 1H, J=1.9 Hz), 6.75 (dd, 1H, J=8.4, 1.8 Hz), 2.54 (s, 3H) ppm.
25% With hydrogenchloride; boron trichloride In toluene; acetonitrile Step A
Preparation of 1-(2-Amino-4-bromophenyl)ethanone (162a)
Under an argon atmosphere a solution of 3-bromoaniline (31.3 g, 181.8 mmol) and acetonitrile (75 g, 1.818 mol) in anhydrous toluene (120 ml) was added dropwise to boron trichloride (23.4 g, 200 mmol) in (200 ml) hexanes under cooling in an ice bath and stirring over 2.5 hours.
After the addition was completed, aluminum chloride (26.6g, 200 mmol) was added portion wise over 30 minutes.
The mixture was allowed to warm to ambient temperature and then heated at reflux for 16 hours with stirring.
A 3N HCl solution (100 ml) was added dropwise to the reaction mixture under stirring at 10 ° C.
After the addition was complete, the mixture was heated at reflux for 3.5 hours.
The reaction mixture was then cooled to room temperature, and the layers separated.
The aqueous layer was extracted with chloroform (3*250 ml).
Organic layers were combined, dried over magnesium sulfate, filtered, and the filtrate concentrated to give the title compound 162a (9.58 g, 25percent).
1H NMR (CDCl3, 300 MHz): δ 7.54 (d, 1H, J=8.8 Hz), 6.83 (d, 1H, J=1.9 Hz), 6.75 (dd, 1H, J=8.4, 1.8 Hz), 2.54 (s, 3H) ppm.

Reference: [1] Patent: US2003/166636, 2003, A1
[2] Patent: US2002/52360, 2002, A1
[3] Patent: US2002/137737, 2002, A1
[4] Patent: US6503902, 2003, B2
[5] Patent: US5061800, 1991, A
  • 8
  • [ 90004-94-7 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
85% at 90℃; for 1.00 h; Iron powder (5.69 g, 102.0 mmol) was added to a solution of l-(4-bromo-2- nitropheny ethanone (62, 4.16 g, 17.0 mmol) in 30 mL of acetic acid and the resulting suspension was heated to 90 °C for 1 hour. After cooling to room temperature the reaction mixture was diluted with brine and EtOAc and adjusted to pH 10 by the addition of 3N aqueous NaOH. The mixture was filtered and the filtrate was extracted 3x with EtOAc. The combined organic phases were dried with Na2S04, filtered and the filtrate concentrated under vacuum to give of 1 -(2-amino-4- bromophenyl)ethanone (63, 3.1 g, 14.4 mmol, 85percent). MS: 214.0 m/z (M+H)+.
Reference: [1] Liebigs Annalen der Chemie, 1990, # 2, p. 205 - 206
[2] Patent: WO2012/162254, 2012, A1. Location in patent: Page/Page column 152
  • 9
  • [ 30186-18-6 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
56% With ammonia In N,N-dimethyl-formamide at 60℃; for 9.00 h; Inert atmosphere 2-Acetyl-5-bromophenol (322 mg, 1.5 mmol) was dissolved in N, N-dimethylformamide (3 mL)Ammonia (1.7 mL, 45 mmol) was added dropwise thereto, reacted at 60 ° C under nitrogen for 9 hours, and allowed to cool to room temperature. The reaction solution was poured into 16 mL of water and extracted with dichloromethane (3 x 5 mL). The organic phase was washed with saturated brine (2 x 5 mL), dried over anhydrous sodium sulfate, filtered, sonicated and purified by flash column chromatography The product was dichloromethane: methanol = 50: 1 V / V)2-acetyl-5-bromoaniline as a yellow oil in a yield of 56percent.
Reference: [1] Patent: CN106631820, 2017, A. Location in patent: Paragraph 0143; 0144; 0145; 0146
  • 10
  • [ 75-05-8 ]
  • [ 591-19-5 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
4 g
Stage #1: With aluminum (III) chloride; boron trichloride In dichloromethane; toluene at 0 - 90℃; for 5.00 h;
Stage #2: With hydrogenchloride; water In dichloromethane; toluene at 50℃; for 1.00 h;
Acetonitrile (23.7 g, 580 mmol) was added to 3-Bromoaniline (10 g, 58 mmol) in toluene (70 mL). The mixture was cooled to 0°C and BC13 (1 M in CH2C12, 64 mL, 64 mmol) was added drop wise, while keeping the temperature below 10°C. Next, A1C13 (11.6 g, 87 mmol) was added in small portions at 0°C. The reaction mixture was heated to 90°C for 5 hours. The reaction mixture was cooled to room temperature and quenched with aqueous HCl (2N, 100 mL). The mixture was heated to 50°C for 1 hour, cooled to room temperature and separated. The organic layer was separated and washed with water and brine. The organic layer was collected, dried and concentrated, resulting in l-(2-amino-4-bromophenyl)ethanone (4 g). Method A2; Rt: 0.98 min. m/z=: 215.7 (M+H)+ Exact mass: 215.0
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[2] Patent: WO2012/13643, 2012, A1. Location in patent: Page/Page column 86
[3] Patent: WO2013/98313, 2013, A1. Location in patent: Page/Page column 41
[4] Patent: WO2014/152738, 2014, A1. Location in patent: Page/Page column 72; 73
  • 11
  • [ 20776-50-5 ]
  • [ 917-54-4 ]
  • [ 123858-51-5 ]
YieldReaction ConditionsOperation in experiment
33% at -78℃; for 1.00 h; To a -78 °C solution of 2-amino-4-bromobenzoic acid (2.16 g, 10 mmol) in THF (20 mL) was added MeLi (13.3 mL, 3M, 0.04 mmol). The resulting reaction was allowed to stir at -78 °C for 1 hour, then was quenched with water and extracted with EtOAc. The organic extract was dried over anhydrous Na2S04, filtered and concentrated in vacuo and the resulting residue was purified using flash chromatography on silica gel to provide Int-21 (700 mg, 33 percent). 1H NM (CDC13): δ 7.51 - 7.58 (m, 1 H), 6.72 - 6.84 (m, 2 H), 6.37 (s, 2 H), 7.73 (s, 2 H). MS (ESI) m/e (M+H*): 214.
Reference: [1] Patent: WO2012/50848, 2012, A1. Location in patent: Page/Page column 121
  • 12
  • [ 1438400-32-8 ]
  • [ 123858-51-5 ]
Reference: [1] Chemical Communications, 2013, vol. 49, # 45, p. 5225 - 5227
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