[ CAS No. 105884-19-3 ] {[proInfo.proName]}

Name: 105884-19-3|1-(5-Bromo-2-chlorophenyl)ethanone|98%
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Quality Control of [ 105884-19-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 105884-19-3 ]

SDS Specification

Alternatived Products of [ 105884-19-3 ]

Product Details of [ 105884-19-3 ]

CAS No. :	105884-19-3	MDL No. :	MFCD02683851
Formula :	C₈H₆BrClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FVJMYXDLWAEIKP-UHFFFAOYSA-N
M.W :	233.49	Pubchem ID :	13628145
Synonyms :

Calculated chemistry of [ 105884-19-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.35
TPSA :	17.07 Å²

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) :	-5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.05
Log Po/w (XLOGP3) :	2.92
Log Po/w (WLOGP) :	3.31
Log Po/w (MLOGP) :	3.08
Log Po/w (SILICOS-IT) :	3.46
Consensus Log Po/w :	2.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.46
Solubility :	0.0801 mg/ml ; 0.000343 mol/l
Class :	Soluble
Log S (Ali) :	-2.94
Solubility :	0.268 mg/ml ; 0.00115 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.21
Solubility :	0.0145 mg/ml ; 0.0000619 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.59

Safety of [ 105884-19-3 ]

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

Application In Synthesis of [ 105884-19-3 ]

* 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 [ 105884-19-3 ]
Downstream synthetic route of [ 105884-19-3 ]

[ 105884-19-3 ] Synthesis Path-Upstream 1~1

1
[ 749932-77-2 ]
[ 105884-19-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: With dipyridinium dichromate In dichloromethane for 39 h; Stage #2: With Celite In dichloromethane for 0.333333 h;	Pyridinium dichromate (2.6g, 6.94 mmol) was added to a solution of 1- (5-BROMO-2-CHLORO- phenyl)-ethanol (1.09 g, 4.6 mmol) in CH2CI2 (20 mL). The reaction was stirred for 15 hours and then more pyridinium dichromate (2.6g, 6.94 mmol) was added. After another 24 hours celite was added and the mixture was stirred for 20 mins. The reaction mixture was filtered through a pad of celite washing with ether. The filtrate was concentrated to a brown oil. The residue was purified by flash silica gel chromatography (0percent to 10percent EtOAc in hexanes) to give the title compound as a clear oil (0.92 G, 85percent). 1H NMR (400 MHz, CDC13) : 6 2.64 (s, 3H), 7.29 (d, J=8.6 Hz, 1 H), 7.51 (dd, J=8.6, 2.3 Hz, 1 H), 7.66 (d, J=2.3 Hz, 1 H).
85%	With pyridinium dichromate In dichloromethane for 39 h;	Pyridinium dichromate (2.6 g, 6.94 mmol) was added to a solution of 1-(5-bromo-2-chloro-phenyl)-ethanol (1.09 g, 4.6 mmol) in CH₂Cl₂(20 mL). The reaction was stirred for 15 hours and then more pyridinium dichromate (2.6 g, 6.94 mmol) was added. After another 24 hours celite was added and the mixture was stirred for 20 mins. The reaction mixture was filtered through a pad of celite washing with ether. The filtrate was concentrated to a brown oil. The residue was purified by flash silica gel chromatography (0percent to 10percent EtOAc in hexanes) to give the title compound as a clear oil (0.92 g, 85percent). ¹H NMR (400 MHz, CDCl₃): δ 2.64 (s, 3H), 7.29 (d, J=8.6 Hz, 1H), 7.51 (dd, J=8.6, 2.3 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H).

Reference： [1] Patent: WO2004/74270, 2004, A2, . Location in patent: Page 363-364
[2] Patent: US2005/176701, 2005, A1, . Location in patent: Page/Page column 177

[ 105884-19-3 ] Synthesis Path-Downstream 1~33

1
[ 105884-19-3 ]
[ 289039-22-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium hydroxide; hydrazine; In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; at 170℃; for 24h;	Sodium hydroxide (0.39g, 9. 6MMOL) and hydrazine monohydrate (0.56mL, 11.5 mmol) were added to a solution of 1- (5-BROMO-2-CHLORO-PHENYL)-ETHANONE (0.9g, 3.85 mmol) dissolved in triethylene glycol (5mL). The reaction mixture was heated to 170 C for 24 hours and then partitioned between 1N HCI and EtOAc. The organic layer was washed with brine, dried over NA2SO4AND concentrated. The residue was purified by flash silica gel chromatography (0% to 5% EtOAc in hexanes) to give the title compound (0.52 G, 62%). 1H NMR (400 MHz, CDCI3) : 6 1.23 (t, J=7.6 Hz, 3 H), 2.72 (q, J=7.6 Hz, 2 H), 7.19 (d, J=8.6 Hz, 1 H), 7.25 (dd, J=8.3, 2.3 Hz, 1 H), 7. 36 (d, J=2.5 Hz, 1 H).
62%	With sodium hydroxide; hydrazine; In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; at 170℃; for 24h;	Sodium hydroxide (0.39 g, 9.6 mmol) and hydrazine monohydrate (0.56 mL, 11.5 mmol) were added to a solution of <strong>[105884-19-3]1-(5-Bromo-2-chloro-phenyl)-ethanone</strong> (0.9 g, 3.85 mmol) dissolved in triethylene glycol (5 mL). The reaction mixture was heated to 170 C. for 24 hours and then partitioned between 1N HCl and EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash silica gel chromatography (0% to 5% EtOAc in hexanes) to give the title compound (0.52 g, 62%). 1H NMR (400 MHz, CDCl3): delta 1.23 (t, J=7.6 Hz, 3H), 2.72 (q, J=7.6 Hz, 2H), 7.19 (d, J=8.6 Hz, 1H), 7.25 (dd, J=8.3, 2.3 Hz, 1H), 7.36 (d, J=2.5 Hz, 1H).

Reference： [1]Patent: WO2004/74270,2004,A2 .Location in patent: Page 363
[2]Patent: US2005/176701,2005,A1 .Location in patent: Page/Page column 177

2
[ 749932-77-2 ]
[ 105884-19-3 ]

Yield	Reaction Conditions	Operation in experiment
85%		Pyridinium dichromate (2.6g, 6.94 mmol) was added to a solution of 1- (5-BROMO-2-CHLORO- phenyl)-ethanol (1.09 g, 4.6 mmol) in CH2CI2 (20 mL). The reaction was stirred for 15 hours and then more pyridinium dichromate (2.6g, 6.94 mmol) was added. After another 24 hours celite was added and the mixture was stirred for 20 mins. The reaction mixture was filtered through a pad of celite washing with ether. The filtrate was concentrated to a brown oil. The residue was purified by flash silica gel chromatography (0% to 10% EtOAc in hexanes) to give the title compound as a clear oil (0.92 G, 85%). 1H NMR (400 MHz, CDC13) : 6 2.64 (s, 3H), 7.29 (d, J=8.6 Hz, 1 H), 7.51 (dd, J=8.6, 2.3 Hz, 1 H), 7.66 (d, J=2.3 Hz, 1 H).
85%	With pyridinium dichromate; In dichloromethane; for 39h;	Pyridinium dichromate (2.6 g, 6.94 mmol) was added to a solution of 1-(5-bromo-2-chloro-phenyl)-ethanol (1.09 g, 4.6 mmol) in CH2Cl2 (20 mL). The reaction was stirred for 15 hours and then more pyridinium dichromate (2.6 g, 6.94 mmol) was added. After another 24 hours celite was added and the mixture was stirred for 20 mins. The reaction mixture was filtered through a pad of celite washing with ether. The filtrate was concentrated to a brown oil. The residue was purified by flash silica gel chromatography (0% to 10% EtOAc in hexanes) to give the title compound as a clear oil (0.92 g, 85%). 1H NMR (400 MHz, CDCl3): delta 2.64 (s, 3H), 7.29 (d, J=8.6 Hz, 1H), 7.51 (dd, J=8.6, 2.3 Hz, 1H), 7.66 (d, J=2.3 Hz, 1H).

Reference： [1]Patent: WO2004/74270,2004,A2 .Location in patent: Page 363-364
[2]Patent: US2005/176701,2005,A1 .Location in patent: Page/Page column 177

4
[ 105884-19-3 ]
[ 749932-77-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium tetrahydroborate; In methanol; at 0 - 20℃; for 2h;	Sodium borohydride (1.182 g, 51.4 mmol) was added to a stirred solution of <strong>[105884-19-3]1-(5-bromo-2-chlorophenyl)ethanone</strong> (10 g, 42.8 mmol) in methanol at 0 C. The resulting bubbling white mixture was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was quenched with acetone (50 mL) and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (10 g, 99% yield) as a white solid: 1H NMR (CDCl3) delta 7.75 (d, 1H), 7.32 (m, 1H), 7.19 (m, 1H), 5.23 (q, 1H), 1.95 (d, 1H), 1.48 (d, 3H).
99%	With sodium tetrahydroborate; In methanol; at 0 - 20℃;	4. Preparation of 1-(5-Bromo-2-chlorophenyl)-ethanol Sodium borohydride (1.182 g, 51.4 mmol) was added to a stirred solution of <strong>[105884-19-3]1-(5-bromo-2-chlorophenyl)ethanone</strong> (10 g, 42.8 mmol) in methanol at 0 C., The resulting bubbling white mixture was allowed to warm to room temperature and stirred for 2 h. The reaction mixture was quenched with acetone (50 mL) and concentrated by rotary evaporation. The residue was partitioned between ethyl acetate and water. The organic phase was dried and concentrated to yield the title compound (10 g, 42.5 mmol, 99% yield) as a white solid: 1H NMR (CDCl3): delta 7.75 (d, 1H), 7.32 (m, 1H), 7.19 (m, 1H), 5.23 (q, 1H), 1.95 (d, 1H), 1.48 (d, 3H).

Reference： [1]Patent: US2009/88322,2009,A1 .Location in patent: Page/Page column 8
[2]Patent: US2009/62125,2009,A1 .Location in patent: Page/Page column 9

5
[ 105884-19-3 ]
[ 1380796-81-5 ]

Reference： [1]Patent: EP2468726,2012,A1
[2]Patent: WO2012/76413,2012,A1
[3]Patent: WO2012/76413,2012,A1
[4]Organic Process Research and Development,2012,vol. 16,p. 1739 - 1745
[5]Organic Process Research and Development,2012,vol. 16,p. 1739 - 1745

6
[ 105884-19-3 ]
[ 1380796-86-0 ]

7
[ 110-86-1 ]
[ 105884-19-3 ]
[ 1380796-82-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With iodine; In Isopropyl acetate; at 10℃; for 18h;Reflux;	-r2-(5-Bromo-2-chloro-phenyl)-2-oxo-ethyll-pyridinium iodideMethod 2-Step a-To a suspension of iodine (277 g, 1. 1 mol) in iPrOAc (400 mL) in a 5 L 4-neck round bottom flask, cooled at 10C, pyridine (433 mL, 5.35 mol) was added via dropping funnel in 5 min (DeltaTau= +5C).After complete addition a solution of l-(5-Bromo-2-chloro-phenyl)- ethanone (250 g, 1.07 mol) in iPrOAc (600 mL) was via dropping funnel added at once (no exotherm observed). Further 300 mL of iPrOAc were added to wash the glassware and give the final reaction volume to 5 vol. The resulting mixture was heated at reflux until complete conversion of the acetophenone (18h from HPLC analysis).The reaction mixture was then cooled to 15C using an ice bath, filtered and the formed solid was washed with H2O (1 L) and EtOH (450 mL). After filtration and drying until constant weight, 330 g of a yellow solid were obtained. Yield: 70%.1H-NMR (400 MHz DMSO-d6): delta 6.41 (2H, s), 7.64-7.66 ( 1H, m), 7.90-7.92 (1H, m), 8.28-8. 13 (3H, m), 8.73-8.77 ( 1H, m), 8.98-8.99 (2H, m)./// z 3 1 3 (M+H)+; retention time = 0.85/3 (HPLC).
70%		1-[2-(5-Bromo-2-chloro-phenyl)-2-oxo-ethyl]-pyridinium iodide Method 2-Step a-To a suspension of iodine (277 g, 1.1 mol) in iPrOAc (400 mL) in a 5 L 4-neck round bottom flask, cooled at 10C, pyridine (433 mL, 5.35 mol) was added via dropping funnel in 5 min (DeltaT= +5C). After complete addition a solution of <strong>[105884-19-3]1-(5-Bromo-2-chloro-phenyl)-ethanone</strong> (250 g, 1.07 mol) in iPrOAc (600 mL) was via dropping funnel added at once (no exotherm observed). Further 300 mL of iPrOAc were added to wash the glassware and give the final reaction volume to 5 vol. The resulting mixture was heated at reflux until complete conversion of the acetophenone (18h from HPLC analysis). The reaction mixture was then cooled to 15C using an ice bath, filtered and the formed solid was washed with H2O (1 L) and EtOH (450 mL). After filtration and drying until constant weight, 330 g of a yellow solid were obtained. Yield: 70%. 1H-NMR (400 MHz DMSO-d6): delta 6.41 (2H, s), 7.64-7.66 (1H, m), 7.90-7.92 (1H, m), 8.28-8.13 (3H, m), 8.73-8.77 (1H, m), 8.98-8.99 (2H, m). m/z 313 (M+H)+; retention time = 0.85/3 (HPLC).

Reference： [1]Patent: WO2012/76413,2012,A1 .Location in patent: Page/Page column 13-14
[2]Patent: EP2468726,2012,A1 .Location in patent: Page/Page column 7
[3]Organic Process Research and Development,2012,vol. 16,p. 1739 - 1745

8
[ 105884-19-3 ]
[ 1380796-87-1 ]

9
[ 105884-19-3 ]
[ 1380796-77-9 ]

10
[ 105884-19-3 ]
[ 1261775-99-8 ]

Yield	Reaction Conditions	Operation in experiment
76.6%	With bromine; In dichloromethane; acetic acid; at 0 - 20℃; for 3h;Inert atmosphere; Industry scale;	Method 3-Step a2-Bromo-l-(2-chloro-5-methyl-phenyl)-ethanonel-Cl-5-Br-acetophenone (1.345 Kg, 5.7 mol, 1 eq) was charged in a 10L reactor under nitrogen flux: 2.5L of DCM were added followed by AcOH and by other 2.5L of DCM. The mixture was stirred 20 minutes at +5C.A solution of Br2 (458.8 g, 6 mol, 1.05 eq) in 5L of DCM was added dropwise in 2h keeping the temperature between 0C and 5C: at the end of the addition, the mixture was stirred lh at 20C until HPLC check indicate complete conversion.Workup: DCM was partially removed by distillation at reduced pressure (4L, 600 mbar, T=70C), the resulting mixture was washed with thiosulphate (2% wt solution, 0.5 vol), water (2x0.5 vol), NaOH 0.2M solution (0.5 vol) and water (2x0.5 vol).1L of DCM was removed under vacuum then 2.5L of cyclohexane were added: the remaining DCM was distilled under reduced pressure (35C, 400 mbar) to give a clear yellow solution.The yellow solution was cooled at 0C and stirred lh until the formation of a white precipitate was observed: the filtration of the white suspension was filtered on Buchner funnel to give 1.224 Kg of a white crystalline solid (HPLC purity>90%@254 nm), that was dried under vacuum overnight at rt.Mother liquor were concentrated under vacuum, the residue was cooled at 0C, filtered on Buchner and dried on filter overnight: a second crop of desired product was collected (140g, pale yellow crystalline solid.. 1364g (4.37 mol) of desired product were obtained. Yield: 76.6%.HPLC purity > 99% 1H-NMR (400 MHz CDC13): delta 4.42(s, 2H); delta 7.25 (d, 1H, 3J= 9Hz); delta 7,49 (dd, 1H, 3J= 9 Hz, 4J= 3 Hz); delta 7.61 (d, 1H, 4J= 3 Hz).

Reference： [1]Patent: WO2012/76413,2012,A1 .Location in patent: Page/Page column 15-16
[2]Organic Process Research and Development,2012,vol. 16,p. 1739 - 1745

11
[ 105884-19-3 ]
[ 1381927-39-4 ]

Reference： [1]Patent: WO2012/76413,2012,A1
[2]Organic Process Research and Development,2012,vol. 16,p. 1739 - 1745

12
[ 105884-19-3 ]
C₂₀H₂₄N₂O₂ [ No CAS ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 1739 - 1745
[2]Organic Process Research and Development,2012,vol. 16,p. 1739 - 1745

13
[ 105884-19-3 ]
C₈H₄BrClO₂ [ No CAS ]