[ CAS No. 56962-04-0 ] {[proInfo.proName]}

Name: 56962-04-0|3-Bromo-5-chlorophenol|97%
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Quality Control of [ 56962-04-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 56962-04-0 ]

Product Details of [ 56962-04-0 ]

CAS No. :	56962-04-0	MDL No. :	MFCD07780676
Formula :	C₆H₄BrClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GMGWXLPFRHYWAS-UHFFFAOYSA-N
M.W :	207.45	Pubchem ID :	22630180
Synonyms :

Calculated chemistry of [ 56962-04-0 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.18
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.95 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	3.68
Log Po/w (WLOGP) :	2.81
Log Po/w (MLOGP) :	2.84
Log Po/w (SILICOS-IT) :	2.7
Consensus Log Po/w :	2.78

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.94
Solubility :	0.0239 mg/ml ; 0.000115 mol/l
Class :	Soluble
Log S (Ali) :	-3.79
Solubility :	0.0333 mg/ml ; 0.00016 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.3
Solubility :	0.105 mg/ml ; 0.000506 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.72

Safety of [ 56962-04-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362+P364-P403+P233-P501	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 56962-04-0 ]

* 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 [ 56962-04-0 ]
Downstream synthetic route of [ 56962-04-0 ]

[ 56962-04-0 ] Synthesis Path-Upstream 1~9

1
[ 108-37-2 ]
[ 56962-04-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 18 h; Inert atmosphere Stage #2: With Oxone In water; acetone for 0.166667 h;	a. 3-Bromo-5-chloro-phenol (Intermediate 62a) A flask containing (1,5-cyclooctadiene)(methoxy)-iridium(I) dimer (84 mg, 0.13 mmol), 4,4'-di-tert butyl-2-2'-dipyridyl (69 mg, 0.26 mmol) and bis(pinacolato)diboron (1.29 g, 5.11 mmol) was purged with Ar, then hexanes (26 mL) and 1-bromo-3-chlorobenzene (1 mL, 8.51 mmol) were added sequentially. The solution was stirred at RT for 18 h. The reaction mixture was concentrated in vacuo, re-dissolved in acetone (26 mL), then oxone (5.23 g, 8.51 mmol) in water (26 mL) added [Caution: exotherm observed]. After 10 min, the reaction mixture was diluted with DCM. The layers separated, and the aqueous layer extracted with DCM. The combined organics were washed with brine, dried and concentrated in vacuo to give the title compound (1.43 g, 81percent). LCMS (Method 3): Rt 3.74 min, m/z 205, 207 [M-H⁺].
81%	Stage #1: With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; for 18 h; Inert atmosphere Stage #2: With Oxone In water; acetone for 0.166667 h;	A flask containing (l,5-cyclooctadiene)(methoxy)-iridium(I) dimer (84 mg, 0.13 mmol), 4,4'-di-tert butyl-2-2'-dipyridyl (69 mg, 0.26 mmol) and bis(pinacolato)diboron (1.29 g, 5.11 mmol) was purged with Ar, then hexanes (26 mL) and l-bromo-3- chlorobenzene (1 mL, 8.51 mmol) were added sequentially. The solution was stirred at RT for 18 h. The reaction mixture was concentrated in vacuo, re-dissolved in acetone (26 mL), then oxone (5.23 g, 8.51 mmol) in water (26 mL) added [Caution: exotherm observed]. After 10 min, the reaction mixture was diluted with DCM. The layers separated, and the aqueous layer extracted with DCM. The combined organics were washed with brine, dried and concentrated in vacuo to give the title compound (1.43 g, 81percent). LCMS (Method 3): Rt 3.74 min, m/z 205, 207 [M-H⁺].
62%	Stage #1: at 150℃; for 3.5 h; Inert atmosphere Stage #2: With Oxone; water In acetoneCooling with ice	3-Bromo-5-chloro-phenol; Under an atmosphere of dry nitrogen, 103 mg 1 ,5-cyclooctadiene(H5-indenyl)iridium (I) was put in a 25 ml. Pyrex bottle. Subsequently were added 0.04 ml. 1 ,2-bis(dimethylphosphino)ethane, 0.61 ml. 3-bromochlorobenzene and 1.52 ml. pinacolborane. The mixture was stirred at 150°C for 3.5 h. After cooling to room temperature, the borane adduct was taken up in 17 ml. acetone to give a clear solution. This solution was added slowly to 17.41 ml. of a 0.30 M solution of oxone in water cooled in an ice bath. The mixture was stirred vigorously for 15 min. at room <n="47"/>temperature and extracted three times with DCM. The combined organic phases were dried over Na₂SC>₄ and evaporated to dryness. The residue was purified by flash chromatography (DCM) to yield 750 mg (62percent) of a beige solid. ¹H NMR complies with known data (compound (1 ), Maleczka, 2003).

Reference： [1] Patent: US2014/364412, 2014, A1, . Location in patent: Paragraph 0683; 0684
[2] Patent: WO2014/195402, 2014, A1, . Location in patent: Page/Page column 217
[3] Patent: WO2009/115515, 2009, A1, . Location in patent: Page/Page column 44-45
[4] Journal of the American Chemical Society, 2003, vol. 125, # 26, p. 7792 - 7793
[5] Synthesis, 2011, # 6, p. 857 - 859

2
[ 174913-12-3 ]
[ 56962-04-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: With lithium iodide In 2,4,6-trimethyl-pyridine at 170℃; for 4 h; Stage #2: With hydrogenchloride In 2,4,6-trimethyl-pyridine; water at 20℃;	A 250 mL flask was charged with 81b (7.0 g, 41.766 mmol) and 2,4,6-collidine (100 mL). The mixture was heated to 170° C. and LiI (16.76 g, 125.298 mmol) was added and the reaction mixture was heated for 4 h. When 81b was consumed the reaction was cooled to RT and quenched with 10percent aqueous HCl. The resulting mixture was extracted with EtOAc and washed with water and brine. The EtOAc extract was dried over (Na₂SO₄) and filtered. The solvent was removed in vacuo to afford a yellow oil which was purified by silica gel chromatography eluting with EtOAc/hexane (10:90) to afford 6.0 g (94percent) of 81c

Reference： [1] Patent: US2005/239881, 2005, A1, . Location in patent: Page/Page column 41-42
[2] Patent: US2006/25462, 2006, A1, . Location in patent: Page/Page column 16-17
[3] Patent: WO2008/157273, 2008, A1, . Location in patent: Page/Page column 36
[4] Patent: WO2008/157330, 2008, A1, . Location in patent: Page/Page column 34

3
[ 210992-77-1 ]
[ 56962-04-0 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 2, p. 477 - 480

4
[ 33863-76-2 ]
[ 56962-04-0 ]

Reference： [1] Organic Process Research and Development, 2010, vol. 14, # 2, p. 477 - 480
[2] Patent: WO2008/157273, 2008, A1,
[3] Patent: WO2008/157330, 2008, A1,

5
[ 108-43-0 ]
[ 56962-04-0 ]

Reference： [1] Monatshefte fuer Chemie, 1926, vol. 47, p. 376

6
[ 87504-69-6 ]
[ 108-86-1 ]
[ 56962-04-0 ]

Reference： [1] Monatshefte fuer Chemie, 1926, vol. 47, p. 376

7
[ 883195-40-2 ]
[ 56962-04-0 ]

Reference： [1] Journal of the Chemical Society, 1926, p. 2078

8
[ 7446-70-0 ]
[ 87504-69-6 ]
[ 71-43-2 ]
[ 108-86-1 ]
[ 56962-04-0 ]

Reference： [1] Monatshefte fuer Chemie, 1926, vol. 47, p. 376

9
[ 56962-04-0 ]
[ 77-78-1 ]
[ 174913-12-3 ]

Reference： [1] Monatshefte fuer Chemie, 1926, vol. 47, p. 376

[ 56962-04-0 ] Synthesis Path-Downstream 1~88

1
[ 56962-04-0 ]
[ 73183-34-3 ]
[ 960388-56-1 ]

Yield	Reaction Conditions	Operation in experiment
28%	With water; potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; at 150℃; for 0.25h;	<strong>[56962-04-0]3-Bromo-5-chlorophenol</strong> (5 g, 19.9 mmol, described in: Maleczka R. E. et. al. J. Am. Chem. Soc. 2003, 125, 7792-7793), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolane (6.06 g, 23.9 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (487 mg, 0.6 mmol), potassium acetate (5.86 g, 59.7 mmol), 1,2-dimethoxyethane (60 mL) and water (4 mL) were divided into four microwave vials and irradiated in a microwave at 150° C. for 15 min each. When cooled to ambient temperature the mixtures were pooled, diluted with brine and extracted with diethyl ether. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Purified by column chromatography, using a gradient with 0-5percent acetonitrile in dichloromethane as the eluent, to give 1.43 g (28percent yield) of the title compound: 1H NMR (DMSO-d6) delta 9.89 (s, 1H), 7.02 (s, 2H), 6.91 (s, 1H), 1.28 (s, 12H); MS (ES) m/z 253 [M-H]-.
28%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 150℃; for 0.25h;Irradiation in a microwave;	<strong>[56962-04-0]3-Bromo-5-chlorophenol</strong> (5 g, 19.9 mmol, described in: Maleczka R. E. et. al. J. lambda(roe. Chem. Soc. 2003, 725, 7792-7793), 454,4',4',5,5,5l,5I-octamethyl-2,2'-bi-l>3,2- dioxaborolane (6.06 g, 23.9 mmol), [l,r-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (487 mg, 0.6 mmol), potassium acetate (5.86 g, 59.7 mmol), 1,2-dimethoxyethane (60 mL) and water (4 mL) were divided into four microwave vials and irradiated in a microwave at 150 °C for 15 min each. When cooled to room temperature the mixtures were pooled, diluted with brine and extracted with diethyl ether. The combined organics were dried over sodium sulfate and concentrated in vacuo. Purified by column chromatography, using dichloromethane/acetonitrile (95:5) as the eluent, to give 1.43 g (28percent yield) of the title compound: 1H NMR (DMSO-^6) delta 9.89 (s, 1 H) 7.02 (s, 2 H) 6.91 (s, 1 H) 1.28 (s, 12 H); MS (ESI) m/z 253 [M-H]\\
28%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; water; at 150℃; for 0.25h;Microwave irradiation;	Example 5 3-Chloro-5-(4A5,5-tetramethyl-1.3.2-dioxaborolan-2-yl)phenol; <strong>[56962-04-0]3-Bromo-5-chlorophenol</strong> (5 g, 19.9 mmol, described in: Maleczka R. E. et. al. J. Am. Chem. Soc. 2003, 125, 7792-7793), 4,4,4',4',5,5,51,51-octamethyl-2,2'-bi-l,3,2- dioxaborolane (6.06 g, 23.9 mmol), [l,r-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (487 mg, 0.6 mmol), potassium acetate (5.86 g, 59.7 mmol), 1 ,2-dimethoxyethane (60 mL) and water (4 mL) were divided into four microwave <n="50"/>vials and irradiated in a microwave at 150 °C for 15 min each. When cooled to ambient temperature the mixtures were pooled, diluted with brine and extracted with diethyl ether. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Purified by column chromatography, using a gradient with 0-5percent acetonitrile in dichloromethane as the eluent, to give 1.43 g (28percent yield) of the title compound: 1H NMR (DMSOd6) delta 9.89 (s, 1 H), 7.02 (s, 2 H), 6.91 (s, 1 H), 1.28 (s, 12 H); MS (ES) m/z 253 [M-I]-.

28%

With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; at 150℃; for 0.25h;Microwave irradiation;

Example 5; 3-Chloro-5-f4.4.5.5-tetramethvl-1.3.2-dioxaborolan-2-vDphenol/ \\cr ^ OH; <strong>[56962-04-0]3-Bromo-5-chlorophenol</strong> (5 g, 19.9 mmol, described in: Maleczka R. E. et. al. J. Am.Chem. Soc. 2003, 125, 7792-7793), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi~l,3,2- dioxaborolane (6.06 g, 23.9 mmol), [l,r-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (487 mg, 0.6 mmol), potassium acetate (5.86 g, 59.7 mmol), 1,2-dimethoxyethane (60 mL) and water (4 mL) were divided into four microwave vials and irradiated in a microwave at 150 °C for 15 min each. When cooled to ambient temperature the mixtures were pooled, diluted with brine and extracted with diethyl ether.The combined organic phases were dried over sodium sulfate and concentrated in vacuo.Purified by column chromatography, using a gradient with 0-5percent acetonitrile in dichloromethane as the eluent, to give 1.43 g (28percent yield) of the title compound: 1H NMR(DMSO-J6) delta 9.89 (s, 1 H), 7.02 (s, 2 H), 6.91 (s, 1 H), 1.28 (s, 12 H); MS (ES) m/z 253[M-I]-.

Reference： [1]Patent: US2007/299087,2007,A1 .Location in patent: Page/Page column 16
[2]Patent: WO2008/76046,2008,A1 .Location in patent: Page/Page column 114
[3]Patent: WO2007/145568,2007,A1 .Location in patent: Page/Page column 48-49
[4]Patent: WO2007/145569,2007,A1 .Location in patent: Page/Page column 47

2
[ 108-37-2 ]
[ 56962-04-0 ]

Yield	Reaction Conditions	Operation in experiment
81%		a. 3-Bromo-5-chloro-phenol (Intermediate 62a) A flask containing (1,5-cyclooctadiene)(methoxy)-iridium(I) dimer (84 mg, 0.13 mmol), 4,4'-di-tert butyl-2-2'-dipyridyl (69 mg, 0.26 mmol) and bis(pinacolato)diboron (1.29 g, 5.11 mmol) was purged with Ar, then hexanes (26 mL) and 1-bromo-3-chlorobenzene (1 mL, 8.51 mmol) were added sequentially. The solution was stirred at RT for 18 h. The reaction mixture was concentrated in vacuo, re-dissolved in acetone (26 mL), then oxone (5.23 g, 8.51 mmol) in water (26 mL) added [Caution: exotherm observed]. After 10 min, the reaction mixture was diluted with DCM. The layers separated, and the aqueous layer extracted with DCM. The combined organics were washed with brine, dried and concentrated in vacuo to give the title compound (1.43 g, 81percent). LCMS (Method 3): Rt 3.74 min, m/z 205, 207 [M-H+].
81%		A flask containing (l,5-cyclooctadiene)(methoxy)-iridium(I) dimer (84 mg, 0.13 mmol), 4,4'-di-tert butyl-2-2'-dipyridyl (69 mg, 0.26 mmol) and bis(pinacolato)diboron (1.29 g, 5.11 mmol) was purged with Ar, then hexanes (26 mL) and l-bromo-3- chlorobenzene (1 mL, 8.51 mmol) were added sequentially. The solution was stirred at RT for 18 h. The reaction mixture was concentrated in vacuo, re-dissolved in acetone (26 mL), then oxone (5.23 g, 8.51 mmol) in water (26 mL) added [Caution: exotherm observed]. After 10 min, the reaction mixture was diluted with DCM. The layers separated, and the aqueous layer extracted with DCM. The combined organics were washed with brine, dried and concentrated in vacuo to give the title compound (1.43 g, 81percent). LCMS (Method 3): Rt 3.74 min, m/z 205, 207 [M-H+].
62%		3-Bromo-5-chloro-phenol; Under an atmosphere of dry nitrogen, 103 mg 1 ,5-cyclooctadiene(H5-indenyl)iridium (I) was put in a 25 ml. Pyrex bottle. Subsequently were added 0.04 ml. 1 ,2-bis(dimethylphosphino)ethane, 0.61 ml. 3-bromochlorobenzene and 1.52 ml. pinacolborane. The mixture was stirred at 150°C for 3.5 h. After cooling to room temperature, the borane adduct was taken up in 17 ml. acetone to give a clear solution. This solution was added slowly to 17.41 ml. of a 0.30 M solution of oxone in water cooled in an ice bath. The mixture was stirred vigorously for 15 min. at room <n="47"/>temperature and extracted three times with DCM. The combined organic phases were dried over Na2SC>4 and evaporated to dryness. The residue was purified by flash chromatography (DCM) to yield 750 mg (62percent) of a beige solid. 1H NMR complies with known data (compound (1 ), Maleczka, 2003).

Reference： [1]Patent: US2014/364412,2014,A1 .Location in patent: Paragraph 0683; 0684
[2]Patent: WO2014/195402,2014,A1 .Location in patent: Page/Page column 217
[3]Patent: WO2009/115515,2009,A1 .Location in patent: Page/Page column 44-45
[4]Journal of the American Chemical Society,2003,vol. 125,p. 7792 - 7793
[5]Synthesis,2011,p. 857 - 859

3
[ 108-43-0 ]
[ 56962-04-0 ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

4
[ 56962-04-0 ]
[ 174913-46-3 ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

5
[ 56962-04-0 ]
3,4-dibromo-5-chloro-2,6-dinitro-anisole [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

6
[ 56962-04-0 ]
[ 46008-95-1 ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

7
[ 56962-04-0 ]
2-bromo-6-chloro-3,5-diiodo-[1,4]benzoquinone [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

8
[ 56962-04-0 ]
[ 876486-87-2 ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

9
[ 56962-04-0 ]
3,4-dibromo-5-chloro-2,6-diiodo-phenol [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

10
[ 56962-04-0 ]
3-bromo-5-chloro-2,4,6-triiodo-anisole [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

11
[ 56962-04-0 ]
3-bromo-2,4,5,6-tetrachloro-anisole [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

12
[ 56962-04-0 ]
5-bromo-3-chloro-2,4-dinitro-phenol [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

13
[ 56962-04-0 ]
[ 860734-36-7 ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

14
[ 56962-04-0 ]
3-bromo-5-chloro-2,4,6-trinitro-anisole [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1926,vol. 47,p. 376

15
[ 930836-30-9 ]
[ 56962-04-0 ]
[ 1004112-67-7 ]

Reference： [1]Chemical Communications,2007,p. 5149 - 5151

16
[ 3209-22-1 ]
[ 56962-04-0 ]
[ 1034474-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 2h;	EXAMPLE 3AAlternative preparation of 3 -chloro-5- { [5-chloro- 1 -( 1 H-pyrazolo [3 ,4-6]pyridin-3 -ylmethyl)- 1 H- 1 ,2,3 -benzotriazol-4-yl] oxy } benzonitrile Step 1 : 2-(3-bromo-5-chlorophenoxy)-l-chloro-3-nitrobenzene; 2,3-dichloronitrobenzene (764 mg, 3.99 mmol), <strong>[56962-04-0]3-bromo-5-chlorophenol</strong> (1.65 g, 7.98 mmol) and potassium carbonate (661 mg, 4.79 mmol) were suspended in NMP (5mL) and placed in an oil bath at 120°C. After 2 hours, the reaction was allowed to cool to room temperature, saturated aqueous ammonium chloride (1OmL) was added and the mixture was extracted with ethyl acetate (2x5 OmL). The combined organic fractions were washed with dilute brine (4x50 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by automated column chromatography on silica gel (80g), eluting with 0-100percent Ceta2Cl2/hexanes to yield the title compound. lH NMR (CD3CN) delta 8.02(dd, J=8.3Hz, j=1.5 Hz, IH), 7.88 (dd, J=8.2Hz,, J=1.6Hz, IH), 7.52 (dd, J=8.2Hz, J=8.3Hz, IH), 7.38 (m, IH), 7.07 (m, IH), 6.97 (m, IH).

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933
[2]Patent: WO2008/76223,2008,A1 .Location in patent: Page/Page column 39

17
[ 628692-22-8 ]
[ 56962-04-0 ]
[ 1155846-87-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 1h;	To a round bottom flask charged with <strong>[56962-04-0]3-bromo-5-chlorophenol</strong> (5.20 g, 25.1 mmol) and potassium carbonate (3.46 g, 25.1 mmol) was added N-methylpyrrolidinone (25 mL). To this suspension under N2 was added 2-chloro-3-fluoro-4-(trifluoromethyl)pyridine (5.00 g,25.1 mmol) and the reaction mixture was placed in an oil bath at 12O0C. After 60 minutes, the <n="77"/>reaction mixture was allowed to cool to room temperature at which point, water (100 mL) was added. The mixture was extracted with ethyl acetate (2 x 100 mL) and the combined organic fractions were washed with brine (3 x 100 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was adsorbed onto silica gel and purified by column chromatography on a pre-packed silica gel Redi Sep 330 gram column, eluting with 0-75percent CH2CI2 in hexanes to yield the title compound. lH NMR (CDCI3) delta 8.53(d, J= 5.0 Hz, IH), 7.62 (d, J= 5.0Hz, IH)5 7.29-7.27 (m, IH), 6.87-6.84 (m, IH), 6.76-6.73 (m, IH). HRMS (M+ 1) = 385.8957.
	With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 1h;	Step 1(a): 3-(3-bromo-5-chlorophenoxy)-2-chloro-4-(trifluoromethyl)pyridine (1-2) A mixture of the <strong>[56962-04-0]3-bromo-5-chlorophenol</strong> (3.74 g; 18.0 mmol), 2-chloro-3-fluoro-4-(trifluoromethyl)pyridine (3.00 g; 15.0 mmol) and K2CO3 (2.49 g; 18.0 mmol) in NMP (15 mL) was heated to 120° C. for one hour, then cooled to room temperature. The mixture was then diluted with 250 mL EtOAc and washed with 3.x.250 mL 1:1 H2O:brine. The organic extracts were dried (Na2SO4) and concentrated in vacuo. Purification by ISCO CombiFlash (120 g column; load with toluene; 100:0 to 0:100 hexanes:CH2Cl2 over 40 minutes) provided title compound (1-2) as a white solid. Repurification of the mixed fractions provided additional title compound. 1H NMR (400 MHz, CDCl3): delta 8.55 (d, J=5.0 Hz, 1 H); 7.64 (d, J=5.0 Hz, 1 H); 7.30 (s, 1 H); 6.88 (s, 1 H); 6.77 (s, 1 H).

Reference： [1]Patent: WO2009/67166,2009,A2 .Location in patent: Page/Page column 74-75
[2]Patent: US2011/245296,2011,A1 .Location in patent: Page/Page column 18
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 917 - 922

18
[ 312904-99-7 ]
[ 56962-04-0 ]
[ 1034709-16-4 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 70 - 80℃; for 2h;	A mixture of 3-fluoro-4-methylpyridine-2-carbonitrile (11-1; 2.1g, 15.43 mmol). <strong>[56962-04-0]3-bromo-5-chlorophenol</strong> (3.68g, 17.74 mmol) and cesium carbonate (5.03g, 15.43 mmol) in DMF (30 mL) was heated to 70°C for 1 hour and then to 8O0C for 1 hour. After this time, the reaction mixture was partitioned between water (300 mL) and ethyl acetate (2x500 mL). The combined extracts were washed with water (100 mL) and then brine (100 mL), dried overMgSO4, filtered and the solvent removed in vacuo. The residue was chromatographed using a RediSep column (33Og) and eluted with a gradient of 0-10percent EtOAc/CH2Cl2 and the pure fractions combined and concentrated on the rotary evaporator to give the title compound. LRMS(M+1)=324.9.

Reference： [1]Patent: WO2009/67166,2009,A2 .Location in patent: Page/Page column 99
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7344 - 7350

19
[ 1155847-43-0 ]
[ 56962-04-0 ]
[ 1155847-61-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 55℃; for 0.166667h;	To a solution of 4-chloro-3-fluoropyridine-2-carbonitrile (2.18g, 9.03 mmol) in DMF (10 mL) was added <strong>[56962-04-0]3-bromo-5-chlorophenol</strong> (1.96g, 9.48 mmol) and potassium carbonate (1.25g, 9.03 mmol) and the mixture was heated to 55C for 10 minutes. The mixture was cooled to room temperature and partitioned between water (200 mL) and ethyl acetate (2x100 mL). The combined organic extracts were dried over MgStheta4, filtered, and the solvent evaporated in vacuo to provide the title compound. LRMS (M+l): 344.8

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7344 - 7350
[2]Patent: WO2009/67166,2009,A2 .Location in patent: Page/Page column 115

20
[ 56962-04-0 ]
[ 100-39-0 ]
[ 1187966-48-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tetra-(n-butyl)ammonium iodide; potassium carbonate; In acetone; for 2h;Reflux;	1-Benzyloxy-3-bromo-5-chloro-benzene; 2.54 g 3-Bromo-5-chloro-phenol was dissolved in 50 ml. acetone. Subsequently were added 8.04 g potassium carbonate, 1.52 ml. benzyl bromide and 0.86 g tetrabutylammonium iodide. The mixture was refluxed for 2 h., cooled to room temperature and filtrated, and the filtrate was concentrated to dryness. The residue was chromatographed over a short column of silica, eluting with DCM/PA 1 :4, and the pink color of the product fractions (at the front) was removed with active carbon. After filtration and evaporation, 3.11 g (90percent) of a pale yellow oil was obtained. 1H NMR (400 MHz, CDCI3) delta 5.03 (s, 2H), 6.92 (t, J=2 Hz, 1 H), 7.03 (t, J=2 Hz, 1 H), 7.12 (t, J=1.5 Hz, 1 H), 7.31-7.45 (m, 5H).

Reference： [1]Patent: WO2009/115515,2009,A1 .Location in patent: Page/Page column 45

21
[ 317356-84-6 ]
[ 56962-04-0 ]
[ 874974-96-6 ]

Yield	Reaction Conditions	Operation in experiment
		step 3-To a solution of sodium tert-butoxide (4.2 g, 43.7 mmol) and THF (180 mL) maintained under an Ar atmosphere at RT was added a solution of <strong>[56962-04-0]3-bromo-5-chloro-phenol</strong> (42c, 9.5 g, 45.7 mmol) and THF (35 mL). The resulting solution was aged at RT for 15 min. The solution was cooled to 0° C., and solution of 22b (10.2 g, 41.6 mmol) and THF (20 mL) was added over 3 min. The purple mixture was stirred at RT for 3 h, and then added to an aqueous solution of NH4Cl (150 mL) and extracted with Et2O (3.x.200 mL). The combined organic extracts were washed with 0.5 M aqueous NaOH (2.x.50 mL) and brine (100 mL), dried (MgSO4), filtered and the volatiles were evaporated to afford 16.2 g of [3-(3-bromo-5-chloro-phenoxy)-2-fluoro-4-nitro-phenyl]-acetic acid ethyl ester (44a) as a tan solid.

Reference： [1]Patent: US2006/25462,2006,A1 .Location in patent: Page/Page column 16-17

22
[ 1210835-76-9 ]
[ 56962-04-0 ]
[ 1210835-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 50 - 80℃; for 15h;	To a solution of 4-chloro-6-methoxy-5-nitro-nicotinic acid ethyl esterpyridine (1.61 g, 6.18 mmol) in dry DMF (14 mL) was added powdered potassium carbonate (1.71 g, 13.6 mmol) followed by <strong>[56962-04-0]3-bromo-5-chloro-phenol</strong> (1.41 g, 6.8 mmol). The mixture was heated to 50° C. for 6 hours and then at 80° C. for 5 hours. Additional <strong>[56962-04-0]3-bromo-5-chloro-phenol</strong> (220 mg) was added as well as K2CO3 (270 mg) and heating at 80° C. was continued for 4 hours. The material was cooled to ambient and concentrated (rotary evaporator/high vacuum pump). The remainder was taken up in ethyl acetate (60 ml) and water (60 ml). Agitate and collect the EtOAc phase. Back extract with EtOAc (2.x.40 ml), combine the organic phases and dry over magnesium sulfate. Chromatography (SiO2 [60 g], 2-14percent EtOAc/Hexanes) gave the title compound as a light yellow-brown solid (1.92 g).

Reference： [1]Patent: US2010/56535,2010,A1 .Location in patent: Page/Page column 32

23
[ 210992-77-1 ]
[ 56962-04-0 ]

Reference： [1]Organic Process Research and Development,2010,vol. 14,p. 477 - 480

24
[ 33863-76-2 ]
[ 56962-04-0 ]

Reference： [1]Organic Process Research and Development,2010,vol. 14,p. 477 - 480
[2]Patent: WO2008/157273,2008,A1

25
methanolic sodium methoxide [ No CAS ]
reverse transcriptase [ No CAS ]
glacial HOAc [ No CAS ]
ethyl 2,3-difluoro-4-nitro-phenyl acetate [ No CAS ]
[ 33863-76-2 ]
[ 56962-04-0 ]
[ 874974-96-6 ]

Yield	Reaction Conditions	Operation in experiment
	With aqueous HBr; ammonium chloride; sodium t-butanolate; In tetrahydrofuran; diethyl ether; hexane;	Example 3Succinic acid mono-{3-[4-chloro-3-(3-chloro-5-cyano-phenoxy)-2-fluoro-benzyl]-4-methyl-5-oxo-4,5-dihydro-[1,2,4]triazol-1-ylmethyl}ester (I-2)steps 1 and 2-A solution of 1-bromo-3-chloro-5-fluoro-benzene (42a, 55 g, 263 mmol) was cooled to 0° C. and treated with a 25percent methanolic sodium methoxide solution (68 mL, 315 mmol) and heated to 40° C. for 3 h.The solution was cooled and partitioned between water (1 L) and a 1:1 mixture of hexane/diethyl ether (3200 mL).The combined extracts were washed with brine (60 mL), dried (Na2SO4), filtered and the solvents evaporated in vacuo to afford 42b as an oil (57.3 g, 92percent pure, 238 mmol).The ether 42b (43 g, 173 mmol) was treated with glacial HOAc (150 mL) and 48percent aqueous HBr (100 mL) and heated to 120° C.After 40 h, the volatiles were removed while heated to 80° C. and then cooled to RT.The residue was partitioned between water (100 mL) and DCM (3250 mL).The combined extracts were washed with H2O (50 mL), aqueous NaHCO3 solution (250 mL), brine (50 mL), and (MgSO4).The solvents were removed to afford 23.3 g of 42c as a grey solid.step 3-To a solution of sodium tert-butoxide (4.2 g, 43.7 mmol) and THF (180 mL) maintained under an Ar atmosphere at RT was added a solution of <strong>[56962-04-0]3-bromo-5-chloro-phenol</strong> (42c, 9.5 g, 45.7 mmol) and THF (35 mL).The resulting solution was aged at RT for 15 min.The solution was cooled to 0° C., and solution of 22b (10.2 g, 41.6 mmol) and THF (20 mL) was added over 3 min.The purple mixture was stirred at RT for 3 h, and then added to an aqueous solution of NH4Cl (150 mL) and extracted with Et2O (3200 mL).The combined organic extracts were washed with 0.5 M aqueous NaOH (2*50 mL) and brine (100 mL), dried (MgSO4), filtered and the volatiles were evaporated to afford 16.2 g of [3-(3-bromo-5-chloro-phenoxy)-2-fluoro-4-nitro-phenyl]-acetic acid ethyl ester (44a) as a tan solid.

Reference： [1]Patent: US2011/207688,2011,A1

26
[ 56962-04-0 ]
[ 1155847-48-5 ]

Reference： [1]Patent: US2011/245296,2011,A1

27
[ 56962-04-0 ]
[ 1338225-97-0 ]

Reference： [1]Patent: US2011/245296,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 917 - 922

28
[ 56962-04-0 ]
[ 1155846-86-8 ]

Reference： [1]Patent: US2011/245296,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 917 - 922

29
[ 56962-04-0 ]
[ 1338226-05-3 ]

Reference： [1]Patent: US2011/245296,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 917 - 922

30
[ 56962-04-0 ]
[ 1155846-88-0 ]

Reference： [1]Patent: US2011/245296,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 917 - 922

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[ 56962-04-0 ]
[ 1338226-09-7 ]

Reference： [1]Patent: US2011/245296,2011,A1

32
[ 56962-04-0 ]
[ 1338226-10-0 ]

Reference： [1]Patent: US2011/245296,2011,A1

33
[ 56962-04-0 ]
[ 1338226-19-9 ]

Reference： [1]Patent: US2011/245296,2011,A1

34
[ 56962-04-0 ]
[ 101664-56-6 ]
[ 1338226-08-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 5h;	Step 3(a): 3-(3-bromo-5-chlorophenoxy)-2-chloro-4-nitropyridine 1-oxide (3-2) A suspension of <strong>[56962-04-0]3-bromo-5-chlorophenol</strong> (1.32 g; 6.35 mmol), 2-chloro-3-fluoro-4-nitropyridone-N-oxide (1.11 g; 5.78 mmol) and K2CO3 (0.798 g; 5.78 mmol) in 3:1 THF:DMF (23 mL) was stirred at room temperature for 5 hours. THF was removed in vacuo, and then the mixture was diluted with saturated aqueous NaHCO3 and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was triturated with Et2O to provide the title compound as a brown solid of sufficient purity to be used directly. 1H NMR (400 MHz, MeOD): delta 8.57 (d, J=7.5 Hz, 1 H); 8.21 (d, J=7.5 Hz, 1 H); 7.43 (s, 1 H); 7.26 (s, 1 H); 7.16 (s, 1 H).

Reference： [1]Patent: US2011/245296,2011,A1 .Location in patent: Page/Page column 21

35
[ 1345336-82-4 ]
[ 56962-04-0 ]
[ 1345336-85-7 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

36
[ 3209-22-1 ]
[ 56962-04-0 ]
[ 1034474-42-4 ]
[ 1345336-62-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

37
[ 56962-04-0 ]
[ 1345337-24-7 ]
3-chloro-5-[5-chloro-2-({2-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-2H-pyrazolo[3,4-b]pyridine-3-yl}methyl)-2H-1,2,3-benzotriazol-4-yl]-oxy}benzonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

38
[ 56962-04-0 ]
[ 1345337-40-7 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

39
[ 56962-04-0 ]
C₂₆H₂₀Cl₂N₆O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

40
[ 56962-04-0 ]
[ 1345336-22-2 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

41
[ 56962-04-0 ]
C₂₆H₂₀Cl₂N₆O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

42
[ 56962-04-0 ]
C₂₇H₂₂Cl₂N₆O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

43
[ 56962-04-0 ]
C₂₄H₂₀BrCl₂N₅O₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

44
[ 56962-04-0 ]
[ 1345337-31-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

45
[ 56962-04-0 ]
3-chloro-5-[5-chloro-1-(1H-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1H-benzimidazol-4-yl]oxy}benzonitrile dihydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

46
[ 56962-04-0 ]
[ 1345336-27-7 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

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[ 56962-04-0 ]
[ 1345336-31-3 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

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[ 56962-04-0 ]
[ 1345336-38-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

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[ 56962-04-0 ]
[ 1345336-41-5 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

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[ 56962-04-0 ]
[ 1345336-45-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

51
[ 56962-04-0 ]
[ 1034474-42-4 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933
[2]Patent: WO2008/76223,2008,A1

52
[ 56962-04-0 ]
[ 1034474-43-5 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933
[2]Patent: WO2008/76223,2008,A1

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[ 56962-04-0 ]
[ 1034474-44-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933
[2]Patent: WO2008/76223,2008,A1

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[ 56962-04-0 ]
[ 1034708-81-0 ]

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55
[ 56962-04-0 ]
[ 1345336-68-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

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[ 56962-04-0 ]
[ 1345336-71-1 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

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[ 56962-04-0 ]
[ 1034474-39-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933
[2]Patent: WO2008/76223,2008,A1

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[ 56962-04-0 ]
[ 1034708-82-1 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

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[ 56962-04-0 ]
[ 1345336-76-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

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[ 56962-04-0 ]
[ 1345336-78-8 ]

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61
[ 56962-04-0 ]
[ 1345336-88-0 ]

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62
[ 56962-04-0 ]
[ 1345336-91-5 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933

63
[ 56962-04-0 ]
[ 1034474-21-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933
[2]Patent: WO2008/76223,2008,A1

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[ 56962-04-0 ]
[ 1034474-40-2 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7920 - 7933
[2]Patent: WO2008/76223,2008,A1

65
[ 771-69-7 ]
[ 56962-04-0 ]
[ 1093267-98-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of sodium f-butoxide in THF (600 mL) was added 3-bromo-5- chlorophenol (34.4 g, 166 mmol) at 0 °C, and the mixture stirred at rt for 15 min. The mixture was cooled to 0 °C and 1 ,2,3-trifluoro-4-nitrobenzene (28.0 g, 158 mmol) was added dropwise. The mixture was stirred for 3 h at rt and concentrated to dryness. The residue was dissolved in ethyl acetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated to give 51.4 g of the title compound. 1H <n="38"/>NMR (DMSO-d6) .sect. 8.07 - 8.19 (m, 1 H), 7.64 - 7.75 (m, 1 H), 7.45 - 7.51 (m, 1 H), 7.35 - 7.41 (m, 1 H), 7.30 (s, 1 H).
	With sodium t-butanolate; In tetrahydrofuran; at 0 - 20℃; for 0.25h;	To a suspension of sodium f-butoxide in THF (600 ml.) was added 3-bromo-5- chlorophenol (34.4 g, 166 mmol) at 0 0C, and the mixture stirred at rt for 15 min. The <n="36"/>mixture was cooled to 0 0C and 1 ,2,3-trifluoro-4-nitrobenzene (28.0 g, 158 mmol) was added dropwise. The mixture was stirred for 3 h at rt and concentrated to dryness. The residue was dissolved in ethyl acetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated to give 51.4 g of the title compound. 1H NMR (DMSOd6) delta 8.07 - 8.19 (m, 1 H), 7.64 - 7.75 (m, 1 H), 7.45 - 7.51 (m, 1 H), 7.35 - 7.41 (m, 1 H), 7.30 (s, 1 H).

Reference： [1]Patent: WO2008/157273,2008,A1 .Location in patent: Page/Page column 36-37
[2]Patent: WO2008/157330,2008,A1 .Location in patent: Page/Page column 34-35

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[ 56962-04-0 ]
[ 874974-96-6 ]

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[2]Patent: WO2008/157273,2008,A1

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[ 56962-04-0 ]
[ 874974-97-7 ]

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[2]Patent: WO2008/157273,2008,A1

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[ 56962-04-0 ]
[ 874974-98-8 ]

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[2]Patent: WO2008/157273,2008,A1

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[ 56962-04-0 ]
[ 874974-99-9 ]

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[2]Patent: WO2008/157273,2008,A1

70
[ 56962-04-0 ]
[ 1094347-65-5 ]

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71
[ 56962-04-0 ]
2-({4-chloro-3-[(3-chloro-5-ethenylphenyl)oxy]-2-fluorophenyl}methyl)-5-(3,5-dimethyl-4-isoxazolyl)-1,3,4-oxadiazole [ No CAS ]

Reference： [1]Patent: WO2008/157273,2008,A1

72
[ 56962-04-0 ]
[ 1094347-67-7 ]

Reference： [1]Patent: WO2008/157273,2008,A1

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[ 56962-04-0 ]
[ 1094345-37-5 ]

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[ 56962-04-0 ]
[ 1094345-66-0 ]

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[ 56962-04-0 ]
[ 1094341-69-1 ]

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[ 56962-04-0 ]
[ 1094345-69-3 ]

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[ 56962-04-0 ]
[ 1094341-70-4 ]

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[ 56962-04-0 ]
[ 1093987-88-2 ]

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[2]Patent: WO2008/157273,2008,A1

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[ 56962-04-0 ]
[ 1093987-91-7 ]

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[ 56962-04-0 ]
[ 1093987-90-6 ]

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[ 56962-04-0 ]
[ 1093987-92-8 ]

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[ 56962-04-0 ]
[ 1093987-93-9 ]

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[ 56962-04-0 ]
[ 1093987-95-1 ]

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[ 56962-04-0 ]
[ 1093987-94-0 ]

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[ 56962-04-0 ]
[ 1093987-96-2 ]

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[ 1093987-97-3 ]

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[ 1093987-99-5 ]

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[ 56962-04-0 ]
[ 1093988-00-1 ]

Reference： [1]Patent: WO2008/157330,2008,A1

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 56962-04-0 ] {[proInfo.proName]}

Quality Control of [ 56962-04-0 ]

Related Doc. of [ 56962-04-0 ]

Product Details of [ 56962-04-0 ]

Calculated chemistry of [ 56962-04-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 56962-04-0 ]

Application In Synthesis of [ 56962-04-0 ]

[ 56962-04-0 ] Synthesis Path-Upstream 1~9

[ 56962-04-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 56962-04-0 ]

Aryls

Bromides

Chlorides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 56962-04-0 ]