[ CAS No. 220513-46-2 ] {[proInfo.proName]}

Name: 220513-46-2|6-Bromo-8-fluoroquinoline|97%
Brand: Ambeed
SKU: A137549
Price: 19.0 USD
Availability: InStock
Rating: 96 (26 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 220513-46-2

Structure of 220513-46-2 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 220513-46-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 220513-46-2 ]

SDS Specification

Alternatived Products of [ 220513-46-2 ]

Product Details of [ 220513-46-2 ]

CAS No. :	220513-46-2	MDL No. :	MFCD11053791
Formula :	C₉H₅BrFN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DDCOYWOYIUEOHQ-UHFFFAOYSA-N
M.W :	226.05	Pubchem ID :	46738885
Synonyms :

Calculated chemistry of [ 220513-46-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.4
TPSA :	12.89 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) :	-5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	2.88
Log Po/w (WLOGP) :	3.56
Log Po/w (MLOGP) :	2.98
Log Po/w (SILICOS-IT) :	3.54
Consensus Log Po/w :	3.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.67
Solubility :	0.048 mg/ml ; 0.000213 mol/l
Class :	Soluble
Log S (Ali) :	-2.81
Solubility :	0.35 mg/ml ; 0.00155 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.84
Solubility :	0.00327 mg/ml ; 0.0000145 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.42

Safety of [ 220513-46-2 ]

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

Application In Synthesis of [ 220513-46-2 ]

* 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 [ 220513-46-2 ]
Downstream synthetic route of [ 220513-46-2 ]

[ 220513-46-2 ] Synthesis Path-Upstream 1~3

1
[ 367-24-8 ]
[ 56-81-5 ]
[ 220513-46-2 ]

Yield	Reaction Conditions	Operation in experiment
96.9%	Stage #1: With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 110℃; Stage #2: at 95 - 140℃; Stage #3: With ammonia In water	A solution of concentrated sulphuric acid (63 ml, 820 mmol) in water (49.4 ml) was treated with sodium 3-nitro-benzenesulfonate (commercially available, for example, from Aldrich) (47.9 g, 213 mmol) and glycerol (commercially available, for example, from Fluka) (52 ml, 720 mmol) to give a thick grey suspension. This was heated to 110 ⁰C. 4-Bromo-2- fluoroaniline (commercially available, for example, from Fluorochem) (38 g, 200 mmol) was added portion wise over 10 min, during which the temperature rose to 95 ⁰C. The reaction was heated to 140 ⁰C and stirred overnight. The reaction mixture was cooled and then poured into water (1000 ml) and basified to pH 7 with aqueous ammonia (0.88 s.g., 190 ml). The brown precipitated that formed was collected by filtration and partially dried. This solid <n="50"/>(63 g) was loaded onto a Silica column (1500 ml) and eluted with EtOAc to give the title compound (43.8 g, 96.9percent) LCMS RT = 2.87 min, ES+ve m/z 226/228 [M+H]⁺.
88%	With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 95 - 140℃;	A solution of concentrated H2504 (0.63 ml, ii .82 mmoi) in H20 (0.48 ml, 26.6 mmoi) was treated with 3-Nitrohenzenesulfonic acid, sodium salt ( 0.48g. 2.132 nrniol) and glycerol (0.516 ml. 706 mmoi) to give a thick grey suspension, the mixture was heated to 110 °C. 4-Bromo2fluoroaniline was added portion wise over 10 mm, during which the temperature rose to 95 °C. The reaction was heated to 140 °C and stirred overnight. The reaction mixture was cooled and then poured into water and basified to pH 7 with aqueous ammonia. The brown precipitated that formed was collected by filtration and partially dried. This solid (0.63 g) was purified by flash column chromatography givethe 6-bromo-8-fluoroquinohne (04 g, 1770 mmoi, 88 percent yield) compound.
81.2%	With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 110 - 140℃;	Glycerol (14.5 g, 158 mmol) And the catalyst sodium 3-nitrobenzenesulfonate (14.2 g, 63 mmol) were added to the sulfuric acid Aqueous solution (20 mL of concentrated sulfuric acid + 15 mL of water), The mixture was heated to 110 ° C and 2-fluoro-4-bromoaniline C-1 (10 g, 52.6 mmol) was added slowly and stirred at 140 ° C overnight. After dropping to room temperature, pour into crushed ice, adjust the pH to about 8 with concentrated aqueous ammonia, extract with ethyl acetate, wash with water, Washed with saturated saline, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude product was purified by column chromatography to obtain 9.65 g of white solid compound C-2, yield 81.2percent

60%

Stage #1: With sulfuric acid; sodium 3-nitrobenzenesulfonate In water at 135℃;
Stage #2: With sodium hydroxide In waterCooling with ice

5.00 g (26.3 mmol) of 4-bromo-2-fluoroaniline, 5.31 g (57.89 mmol) glycerol and 9.89 g (43.94 mmol) of 3-nitrophenylsulfonic acid-sodium salt were prepared and homogenized. Then 25 ml of 70percent sulfuric acid was added dropwise. The mixture was stirred overnight at 135°C. The cooled black reaction mixture was made alkaline, cautiously and with ice cooling, with 50percent sodium hydroxide solution, and then filtered on a large bed of silica gel and kieselguhr. It was washed again with water and ethyl acetate. The phases collected were combined, then the organic phase was separated. The aqueous phase that remained was then extracted with ethyl acetate (2x). Then the organic phases thus obtained and the phase already separated previously were combined. It was dried over magnesium sulfate and the volatile components were removed in a rotary evaporator. The residue was finally purified by MPLC (Puriflash Analogix: 4OM: isohexane / ethyl acetate = 4 / 1). We obtained 3.56 g (60percent of theor.) of the target compound. IH-NMR (400 MHz, DMSO-D₆): δ [ppm] = 7.70 (dd, 2H), 7.89 (dd, IH), 8.17 (s, IH), 8.44 (d, IH), 9.00 (d, IH).

Reference： [1] Patent: WO2009/50204, 2009, A1, . Location in patent: Page/Page column 15; 48-49
[2] Patent: WO2018/116072, 2018, A1, . Location in patent: Page/Page column 97; 98
[3] Patent: CN105968115, 2016, A, . Location in patent: Paragraph 0449-0451
[4] Patent: WO2010/20363, 2010, A1, . Location in patent: Page/Page column 131-132
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 4066 - 4084

2
[ 367-24-8 ]
[ 127-68-4 ]
[ 220513-46-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: With sulfuric acid; glycerol In water at 85 - 133℃;	Intermediate 16-Bromo-8-fluoroquinoline A solution of concentrated sulphuric acid (63 ml, 820 mmol) in water (49.4 ml) was treated with sodium 3-nitro-benzenesulfonate (commercially available, for example, from Aldrich) (47.9 g, 213 mmol) and glycerol (commercially available, for example, from Fluka and/or Aldrich) (52 ml, 720 mmol) to give a thick grey suspension. This was heated to 110° C. (internal temperature was 85° C.). 4-Bromo-2-fluoroaniline (commercially available, for example, from Fluorochem and/or Aldrich) (38 g, 200 mmol) was added over 10 min in portions, during which the internal temperature rose to 95° C. The reaction was heated to 140° C. (internal temperature was 133° C.) and stirred overnight. The reaction mixture was cooled and then poured into water (1000 ml) and basified to pH 7 with aqueous ammonia (0.88 s.g, approximately 190 ml). The brown precipitate that formed was collected by filtration and partially dried. This solid (63 g) was loaded onto a column of silica (1500 ml) and eluted with EtOAc to give the title compound as a light brown solid (43.8 g, 97percent). LCMS RT=2.87 min, ES+ve m/z 226/228 [M+H]⁺.

Reference： [1] Patent: US2009/270355, 2009, A1, . Location in patent: Page/Page column 21

3
[ 367-24-8 ]
[ 107-02-8 ]
[ 220513-46-2 ]

Yield	Reaction Conditions	Operation in experiment
22%	Stage #1: With hydrogenchloride In water; toluene at 100℃; Stage #2: With sodium hydroxide In water	Intermediate 3 6-Bromo-8-fluoroquinoline 4-Bromo-2-fluoroaniline (commercially available, for example, from Aldrich) (5.788 g, 30.46 mmol) was dissolved in hydrochloric acid (5M, 137 ml), toluene (40 ml) and acrolein (6 ml, 91 mmol) were added. The solution was stirred at 100⁰C overnight. The aqueous was separated and 10M sodium hydroxide was added until the solution became basic. The compound which appeared in the shape of a powder was dissolved in dichloromethane, and the organic layer was separated, washed with water and brine. The organic layer was dried with sodium sulphate, filtered and evaporated. The sample was dissolved in dichloromethane and purified by flashmaster (100 g column, 0-100percent ethyl acetate-cyclohexane, 60 min). The pure fractions were combined and evaporated to give the title compound (1.512 g, 22percent). LCMS RT=2.87 min, ES+ve m/z 226/228 (M+H)⁺.

Reference： [1] Patent: WO2010/94643, 2010, A1, . Location in patent: Page/Page column 42-43

[ 220513-46-2 ] Synthesis Path-Downstream 1~5

1
[ 367-24-8 ]
[ 56-81-5 ]
[ 220513-46-2 ]

Yield	Reaction Conditions	Operation in experiment
96.9%	Stage #1: propane-1,2,3-triol With sulfuric acid; m-nitrobenzene sulfonic acid sodium salt In lithium hydroxide monohydrate at 110℃; Stage #2: 4-bromo-2-fluoroaniline In lithium hydroxide monohydrate at 95 - 140℃; Stage #3: With ammonia In lithium hydroxide monohydrate	1 A solution of concentrated sulphuric acid (63 ml, 820 mmol) in water (49.4 ml) was treated with sodium 3-nitro-benzenesulfonate (commercially available, for example, from Aldrich) (47.9 g, 213 mmol) and glycerol (commercially available, for example, from Fluka) (52 ml, 720 mmol) to give a thick grey suspension. This was heated to 110 0C. 4-Bromo-2- fluoroaniline (commercially available, for example, from Fluorochem) (38 g, 200 mmol) was added portion wise over 10 min, during which the temperature rose to 95 0C. The reaction was heated to 140 0C and stirred overnight. The reaction mixture was cooled and then poured into water (1000 ml) and basified to pH 7 with aqueous ammonia (0.88 s.g., 190 ml). The brown precipitated that formed was collected by filtration and partially dried. This solid (63 g) was loaded onto a Silica column (1500 ml) and eluted with EtOAc to give the title compound (43.8 g, 96.9%) LCMS RT = 2.87 min, ES+ve m/z 226/228 [M+H]+.
88%	With sulfuric acid; m-nitrobenzene sulfonic acid sodium salt In lithium hydroxide monohydrate at 95 - 140℃;	32.A Step A: 6-hromo-8-fluoroquinoline A solution of concentrated H2504 (0.63 ml, ii .82 mmoi) in H20 (0.48 ml, 26.6 mmoi) was treated with 3-Nitrohenzenesulfonic acid, sodium salt ( 0.48g. 2.132 nrniol) and glycerol (0.516 ml. 706 mmoi) to give a thick grey suspension, the mixture was heated to 110 °C. 4-Bromo2fluoroaniline was added portion wise over 10 mm, during which the temperature rose to 95 °C. The reaction was heated to 140 °C and stirred overnight. The reaction mixture was cooled and then poured into water and basified to pH 7 with aqueous ammonia. The brown precipitated that formed was collected by filtration and partially dried. This solid (0.63 g) was purified by flash column chromatography givethe 6-bromo-8-fluoroquinohne (04 g, 1770 mmoi, 88 % yield) compound.
81.2%	With sulfuric acid; m-nitrobenzene sulfonic acid sodium salt In lithium hydroxide monohydrate at 110 - 140℃;	1 Synthesis step 1: 8-fluoro-6-bromoquinoline (C-2) Glycerol (14.5 g, 158 mmol) And the catalyst sodium 3-nitrobenzenesulfonate (14.2 g, 63 mmol) were added to the sulfuric acid Aqueous solution (20 mL of concentrated sulfuric acid + 15 mL of water), The mixture was heated to 110 ° C and 2-fluoro-4-bromoaniline C-1 (10 g, 52.6 mmol) was added slowly and stirred at 140 ° C overnight. After dropping to room temperature, pour into crushed ice, adjust the pH to about 8 with concentrated aqueous ammonia, extract with ethyl acetate, wash with water, Washed with saturated saline, dried over anhydrous sodium sulfate, filtered and evaporated to dryness. The crude product was purified by column chromatography to obtain 9.65 g of white solid compound C-2, yield 81.2%

60%	Stage #1: 4-bromo-2-fluoroaniline; propane-1,2,3-triol With sulfuric acid; m-nitrobenzene sulfonic acid sodium salt In lithium hydroxide monohydrate at 135℃; Stage #2: With sodium hydroxide In lithium hydroxide monohydrate Cooling with ice;	114A 5.00 g (26.3 mmol) of 4-bromo-2-fluoroaniline, 5.31 g (57.89 mmol) glycerol and 9.89 g (43.94 mmol) of 3-nitrophenylsulfonic acid-sodium salt were prepared and homogenized. Then 25 ml of 70% sulfuric acid was added dropwise. The mixture was stirred overnight at 135°C. The cooled black reaction mixture was made alkaline, cautiously and with ice cooling, with 50% sodium hydroxide solution, and then filtered on a large bed of silica gel and kieselguhr. It was washed again with water and ethyl acetate. The phases collected were combined, then the organic phase was separated. The aqueous phase that remained was then extracted with ethyl acetate (2x). Then the organic phases thus obtained and the phase already separated previously were combined. It was dried over magnesium sulfate and the volatile components were removed in a rotary evaporator. The residue was finally purified by MPLC (Puriflash Analogix: 4OM: isohexane / ethyl acetate = 4 / 1). We obtained 3.56 g (60% of theor.) of the target compound. IH-NMR (400 MHz, DMSO-D6): δ [ppm] = 7.70 (dd, 2H), 7.89 (dd, IH), 8.17 (s, IH), 8.44 (d, IH), 9.00 (d, IH).
	With sulfuric acid; m-nitrobenzene sulfonic acid sodium salt In lithium hydroxide monohydrate at 150℃;
	With sulfuric acid; p-nitrobenzenesulfonic acid at 135℃; for 16h;	1.118.1 Step 1 To a stirred solution of 4-bromo-2-fluoroaniline (8.00 g, 42.102 mmol, 1.00 eq.) and 4-nitrobenzenesulfonic acid (14.28 g, 70.286 mmol, 1.67 eq.) in glycerol (8.53 g, 0.093 mmol, 2.2 eq.) was added 70% H2SO4 (40.00 mL, 750.423 mmol) drop-wise at ambient temperature under air atmosphere. The resulting mixture was stirred for 16 h at 135 °C under air atmosphere. The mixture was then allowed to cool to ambient temperature, it was basified to pH 10 with 50% NaOH at 0 °C, filtered, and the filter cake was washed with EtOAc. The filtrate was extracted with EtOAc (2 x 100 mL) and the combined organic layers were washed with brine (1x100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product 6-bromo-8- fluoroquinoline (7.5 g, 78.81%) was used in the next step directly without further purification. LCMS (ES) [M+l] + m/z: 226.
	With sulfuric acid; p-nitrobenzenesulfonic acid at 135℃; for 16h;	1.118.1 Step 1 To a stirred solution of 4-bromo-2-fluoroaniline (8.00 g, 42.102 mmol, 1.00 eq.) and 4-nitrobenzenesulfonic acid (14.28 g, 70.286 mmol, 1.67 eq.) in glycerol (8.53 g, 0.093 mmol, 2.2 eq.) was added 70% H2SO4 (40.00 mL, 750.423 mmol) drop-wise at ambient temperature under air atmosphere. The resulting mixture was stirred for 16 h at 135 °C under air atmosphere. The mixture was then allowed to cool to ambient temperature, it was basified to pH 10 with 50% NaOH at 0 °C, filtered, and the filter cake was washed with EtOAc. The filtrate was extracted with EtOAc (2 x 100 mL) and the combined organic layers were washed with brine (1x100 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product 6-bromo-8- fluoroquinoline (7.5 g, 78.81%) was used in the next step directly without further purification. LCMS (ES) [M+l] + m/z: 226.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2009/50204, 2009, A1 Location in patent: Page/Page column 15; 48-49
[2]Current Patent Assignee: PI INDUSTRIES LTD - WO2018/116072, 2018, A1 Location in patent: Page/Page column 97; 98
[3]Current Patent Assignee: SHANGHAI PHARMACEUTICALS HOLDING COMPANY LIMITED - CN105968115, 2016, A Location in patent: Paragraph 0449-0451
[4]Current Patent Assignee: BAYER AG - WO2010/20363, 2010, A1 Location in patent: Page/Page column 131-132
[5]Location in patent: experimental part Childers, Wayne E.; Havran, Lisa M.; Asselin, Magda; Bicksler, James J.; Chong, Dan C.; Grosu, George T.; Shen, Zhongqi; Abou-Gharbia, Magid A.; Bach, Alvin C.; Harrison, Boyd L.; Kagan, Natasha; Kleintop, Teresa; Magolda, Ronald; Marathias, Vasilios; Robichaud, Albert J.; Sabb, Annmarie L.; Zhang, Mei-Yi; Andree, Terrance H.; Aschmies, Susan H.; Beyer, Chad; Comery, Thomas A.; Day, Mark; Grauer, Steven M.; Hughes, Zoe A.; Rosenzweig-Lipson, Sharon; Platt, Brian; Pulicicchio, Claudine; Smith, Deborah E.; Sukoff-Rizzo, Stacy J.; Sullivan, Kelly M.; Adedoyin, Adedayo; Huselton, Christine; Hirst, Warren D. [Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 4066 - 4084]
[6]Current Patent Assignee: GLOBAL BLOOD THERAPEUTICS, INC. - WO2022/31735, 2022, A1 Location in patent: Paragraph 472-474
[7]Current Patent Assignee: GLOBAL BLOOD THERAPEUTICS, INC. - WO2022/31735, 2022, A1 Location in patent: Paragraph 472-474

2
[ 367-24-8 ]
[ 127-68-4 ]
[ 220513-46-2 ]

Yield	Reaction Conditions	Operation in experiment
97%		Intermediate 16-Bromo-8-fluoroquinoline A solution of concentrated sulphuric acid (63 ml, 820 mmol) in water (49.4 ml) was treated with sodium 3-nitro-benzenesulfonate (commercially available, for example, from Aldrich) (47.9 g, 213 mmol) and glycerol (commercially available, for example, from Fluka and/or Aldrich) (52 ml, 720 mmol) to give a thick grey suspension. This was heated to 110 C. (internal temperature was 85 C.). 4-Bromo-2-fluoroaniline (commercially available, for example, from Fluorochem and/or Aldrich) (38 g, 200 mmol) was added over 10 min in portions, during which the internal temperature rose to 95 C. The reaction was heated to 140 C. (internal temperature was 133 C.) and stirred overnight. The reaction mixture was cooled and then poured into water (1000 ml) and basified to pH 7 with aqueous ammonia (0.88 s.g, approximately 190 ml). The brown precipitate that formed was collected by filtration and partially dried. This solid (63 g) was loaded onto a column of silica (1500 ml) and eluted with EtOAc to give the title compound as a light brown solid (43.8 g, 97%). LCMS RT=2.87 min, ES+ve m/z 226/228 [M+H]+.

Reference： [1]Patent: US2009/270355,2009,A1 .Location in patent: Page/Page column 21

3
[ 220513-46-2 ]
[ 73183-34-3 ]
[ 1210048-29-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate In 1,4-dioxane at 130℃; Inert atmosphere;	115A.1 Under an argon atmosphere, 1.00 g (4.42 mmol) of example 114A was dissolved in 20 ml dioxane. Then 1.302 g (13.27 mmol) potassium acetate, 289 mg (0.354 mmol) of 1,1 '-bis-(diphenyl- - 1 3 - phosphino)ferrocene-palladium(II) chloride-dichloromethane complex and 1.69 g (6.64 mmol) of 4,4,4'4'5,5,5'5'-octamethyl-2,2'-bi-l,3,2-dioxaborolan were added. The reaction mixture was stirred overnight at an oil bath temperature of 1300C. After cooling, dichloromethane was added and it was filtered on kieselguhr. Then it was washed again with ethyl acetate. The filtrate was concentrated in a rotary evaporator at reduced pressure and dried under high vacuum. We obtained 2.01 g of 8-fluoroquinolin-6-yl)boric acid [73%, (LC-MS)] as raw product. This was reacted subsequently without further purification.

Reference： [1]Current Patent Assignee: BAYER AG - WO2010/20363, 2010, A1 Location in patent: Page/Page column 132-133

4
[ 220513-46-2 ]
[ 1061650-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II); molybdenum(0) hexacarbonyl; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 1 h / 130 °C / Microwave irradiation 2: sodium hydroxide / tetrahydrofuran; methanesulfonic acid / 16 h
	Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere 2: hydrogenchloride / 2 h / 90 °C
	Multi-step reaction with 2 steps 1: tetrakis-(triphenylphosphine)-palladium / N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere 2: hydrogenchloride / water monomer / 2 h

Reference： [1]Current Patent Assignee: CANCER RESEARCH UK - WO2015/49535, 2015, A1
[2]Current Patent Assignee: COLLABORATIVE MEDICINAL DEV; COLLABORATIVE MEDICINAL DEVELOPMENT - WO2020/185738, 2020, A1
[3]Current Patent Assignee: COLLABORATIVE MEDICINAL DEV - WO2022/20150, 2022, A1

5
[ 220513-46-2 ]
[ 16642-95-8 ]
6-butylsulfonyl-8-fluoroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; In dimethyl sulfoxide; at 120℃; for 18h;	A 100 ml. round bottom flask was charged with 6-bromo-8-fluoroquinoline (250 mg, 1.1 1 mmol), DMSO (5 ml_), Cul (320 mg, 2.21 mmol), sodium butane-1 - sulfinate (319 mg, 2.21 mmol) and the mixture was heated at 120 C for 18 h. The crude material was purified on silica gel using ethyl acetate and hexanes to provide 6- butylsulfonyl-8-fluoroquinoline (260 mg, 87% yield).

Reference： [1]Patent: WO2019/106434,2019,A1 .Location in patent: Paragraph 178

Recommend Products

Same Skeleton Products

Related Products

Isomers

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Convert Haloalkanes into Alcohols by SN2 • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Halogenation of Alkenes • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Methylation of Ammonia • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Williamson Ether Syntheses

Historical Records

Related Functional Groups of
[ 220513-46-2 ]

Fluorinated Building Blocks

[ 1133115-78-2 ]

5-Bromo-8-fluoroquinoline

Similarity: 0.97

[ 927800-38-2 ]

4-Bromo-8-fluoroquinoline

Similarity: 0.92

[ 1432323-09-5 ]

3-Bromo-8-fluoroquinolin-6-amine

Similarity: 0.88

[ 127827-52-5 ]

6-Bromo-7-fluoroquinoline

Similarity: 0.88

[ 917251-99-1 ]

8-Bromo-5-fluoroquinoline

Similarity: 0.86

Bromides

[ 1133115-78-2 ]

5-Bromo-8-fluoroquinoline

Similarity: 0.97

[ 927800-38-2 ]

4-Bromo-8-fluoroquinoline

Similarity: 0.92

[ 1432323-09-5 ]

3-Bromo-8-fluoroquinolin-6-amine

Similarity: 0.88

[ 127827-52-5 ]

6-Bromo-7-fluoroquinoline

Similarity: 0.88

[ 917251-99-1 ]

8-Bromo-5-fluoroquinoline

Similarity: 0.86

Related Parent Nucleus of
[ 220513-46-2 ]

Quinolines

[ 1133115-78-2 ]

5-Bromo-8-fluoroquinoline

Similarity: 0.97

[ 927800-38-2 ]

4-Bromo-8-fluoroquinoline

Similarity: 0.92

[ 1432323-09-5 ]

3-Bromo-8-fluoroquinolin-6-amine

Similarity: 0.88

[ 127827-52-5 ]

6-Bromo-7-fluoroquinoline

Similarity: 0.88

[ 917251-99-1 ]

8-Bromo-5-fluoroquinoline

Similarity: 0.86

Ghs Precautionary Statements

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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

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. 220513-46-2 ] {[proInfo.proName]}

Quality Control of [ 220513-46-2 ]

Related Doc. of [ 220513-46-2 ]

Product Details of [ 220513-46-2 ]

Calculated chemistry of [ 220513-46-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 220513-46-2 ]

Application In Synthesis of [ 220513-46-2 ]

[ 220513-46-2 ] Synthesis Path-Upstream 1~3

[ 220513-46-2 ] Synthesis Path-Downstream 1~5

Technical Information

Related Functional Groups of [ 220513-46-2 ]

Fluorinated Building Blocks

Bromides

Related Parent Nucleus of [ 220513-46-2 ]

Quinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 220513-46-2 ]

Related Parent Nucleus of
[ 220513-46-2 ]