[ CAS No. 22960-18-5 ] {[proInfo.proName]}

Name: 22960-18-5|8-Bromo-6-fluoroquinoline|97%
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Quality Control of [ 22960-18-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 22960-18-5 ]

Product Details of [ 22960-18-5 ]

CAS No. :	22960-18-5	MDL No. :	MFCD09907837
Formula :	C₉H₅BrFN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DOINWPRJXLNEBB-UHFFFAOYSA-N
M.W :	226.05	Pubchem ID :	21271249
Synonyms :

Calculated chemistry of [ 22960-18-5 ]

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) :	-5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.15
Log Po/w (XLOGP3) :	2.86
Log Po/w (WLOGP) :	3.56
Log Po/w (MLOGP) :	2.98
Log Po/w (SILICOS-IT) :	3.54
Consensus Log Po/w :	3.02

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.66
Solubility :	0.0495 mg/ml ; 0.000219 mol/l
Class :	Soluble
Log S (Ali) :	-2.79
Solubility :	0.367 mg/ml ; 0.00162 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 :	1.52

Safety of [ 22960-18-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 22960-18-5 ]

* 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.

Downstream synthetic route of [ 22960-18-5 ]

[ 22960-18-5 ] Synthesis Path-Downstream 1~17

1
[ 1003-98-1 ]
[ 56-81-5 ]
[ 22960-18-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sulfuric acid; sodium 3-nitrobenzenesulfonate; at 150℃; for 20h;	Step 1: 8-bromo-6-fluoroquinoline[004541 To a mixture of <strong>[1003-98-1]2-bromo-4-fluoroaniline</strong> (7.00 g, 36.84 mmol), glycerinum (7.00 g, 76.00 mmol) and sodium 3-nitrobenzenesulfonate (12.44 g, 55.30 mmol) was added 70% sulfuric acid (26 mL) slowly. After addition, the reaction mixture was heated to 150C for 20 hours. Then the reaction mixture was cooled to rt, and poured into water, and then adjusted to pH 7 with aqueous sodium hydroxide solution. The resulting mixture was filtered and the filter cake was dissolved in EtOAc. The mixture was stirred at it for a while and filtered. The filtrate was concentrated in vacuo. The crude was purified by silica column chromatography (PE/EtOAc (v/v) = 15/1) to give the title compound as a white solid (8.08 g, 97.0 %). The compound was characterized by the following spectroscopic data:MS(ESI, pos.ion)m/z: 226.0 (M+1), 228.0(M+3); exact mass of C9H5BrFN: 224.96.
43%	With ferrous(II) sulfate heptahydrate; sodium 3-nitrobenzenesulfonate; In methanesulfonic acid; at 125℃; for 24h;	General procedure: General procedure for synthesis of substituted 8-bromoquinoline (Scheme 3): to a 50 mL roundbottom flask was added 4-substituted 2-bromoaniline, glycerol (17.0 equiv), m-nitrobenzenesulfonatesodium (1.2 equiv), FeSO4?7H2O (0.05 equiv), and MsOH. The reaction mixture was heated at 125 Cfor 24 h. After cooling to room temperature, aqueous NaOH solution (2.5 M) was added to thereaction mixture to adjust pH to 12. Then EtOH was added to form a black solution, which wasextracted with EA or DCM (3 × 100 mL). The combined organic phase was washed with H2O (100mL), brine (100 mL), and dried with anhydrous Na2SO4. After removing the solvents, the residue waspurified by silica gel chromatography.
		Example 2 Intermediate 2-6-fluoro-8-bromo-quinoline To a mixture of 7.0 g of <strong>[1003-98-1]2-bromo-4-fluoro-aniline</strong>, 7.0 g of glycerol and 13.0 g of m-nitrobenzene sulfonic acid sodium salt, 20 ml of 70% sulfuric acid was added drop by drop. The reaction temperature was raised to 150 C. for 4 hr. The mixture was cooled, poured on water neutralized with NaOH and the formed precipitate was filtered to yield 34.7 g of 6-fluoro-8-bromo-quinoline. MS (ES) m/z (relative intensity): 227 (M++H, 100).

	With sulfuric acid; sodium 3-nitrobenzenesulfonate; In water; at 150℃; for 4h;	To a mixture of 7.0 g of <strong>[1003-98-1]2-bromo-4-fluoro-aniline</strong>, 7.0 g of glycerol and 13.0 g of m- nitrobenzene sulfonic. acid sodium salt, 20 ml of 70% sulfuric acid was added drop by drop. The reaction temperature was raised to 150 C for 4 hr. The mixture was cooled, poured on water neutralized with NAOH and the formed precipitate was filtered to yield 34.7 g of 6- FLUORO-8-BROMO-QUINOLINE. MS (ES) m/z (relative intensity): 227 (M++H, 100).
		To a mixture of <strong>[1003-98-1]2-bromo-4-fluoroaniline</strong> (commercially available, 7.0 g), glycerol (7.0 g) and m-nitrobenzene sulfonic acid sodium salt (13.0 g) was added 20 ml of 70% sulfuric acid dropwise. The reaction temperature was raised to 150 C. for 4 hr. The mixture then was cooled to room temperature, poured on ice water and filtered through celite. The filtrate was neutralized with NaOH and the resulting precipitate was collected by vacuum filtration to yield 3.47 g of the title compound as a light yellow solid; MP=75-78 C.; MS (ES) m/z (relative intensity): 227 (M+H)+ (100).

Reference： [1]Patent: WO2015/90232,2015,A1 .Location in patent: Paragraph 00454
[2]Molecules,2020,vol. 25
[3]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000
[4]Patent: US2009/54454,2009,A1 .Location in patent: Page/Page column 13-14
[5]Patent: WO2004/99191,2004,A2 .Location in patent: Page 30
[6]Journal of Medicinal Chemistry,2010,vol. 53,p. 4066 - 4084
[7]Patent: US2007/27160,2007,A1 .Location in patent: Page/Page column 45

2
[ 22960-18-5 ]
[ 57260-71-6 ]
[ 796851-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; for 3h;Heating / reflux;	Example 3 Intermediate 3-6-fluoro-8-(t-Boc)-piperazino-quinoline To a mixture of 2.2 g of 6-fluoro-8-bromo-quinoline in THF, was added 0.045 g of Pd2(dba)3, 1.3 g of NaOt-Bu, 0.044 g of binap, 0.052 g of tetrakis(triphenylphosphine) palladium (0) and 2.2 g of t-Boc piperazine. The mixture was refluxed for 3 hours. The reaction mixture was then cooled to room temperature, diluted with ether, filtered through celite and concentrated in vacuo. The crude material was then purified by flash chromatography to give 3.0 g of 6-fluoro-8(t-Boc)-piperazino-quinoline. MS (ES) m/z (relative intensity): 332 (M++H, 100).
	With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; for 3h;Heating / reflux;	To a mixture of 2.2 g OF 6-FLUORO-8-BROMO-QUINOLINE in THF, was added 0.045 g of Pd2 (dba) 3,1. 3 g of NaOt-Bu, 0.044 g of binap, 0.052 g of tetralcis (triphenylphosphine) palladium (0) and 2.2 g of t-Boc piperazine. The mixture was refluxed for 3 hours. The reaction mixture was then cooled to room temperature, diluted with ether, filtered through celite and concentrated in vacuo. The crude material was then purified by flash chromatography to give 3.0 g of 6-FLUORO-8 (t-Boc) -piperazino-quinoline. MS (ES) M/Z (relative intensity): 332 (M++H, 100).
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; for 3h;Heating / reflux;	To a mixture of 6-fluoro-8-bromoquinoline (Step 1, 2.2 g) in anhydrous tetrahydrofuran, was added tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 0.045 g) sodium tert-butoxide (1.3 g), 2,2'-bis(diphenylphosphino)-1,1'-binapthyl (BINAP, 0.044 g), 0.052 g tetrakis(triphenylphosphine)-palladium (0) (0.052 g) and tert-butoxycarbonyl-piperazine (2.2 g). The mixture was refluxed for 3 hours under a nitrogen atmosphere. The reaction was then cooled to room temperature, diluted with ether, filtered through celite and concentrated on a rotary evaporator. The crude material was purified by flash chromatography using 100% CH2Cl2 to give 3.0 g of the desired product as a brown oil; MS (ES) m/z (relative intensity): 332 (M+H)+ (100).

Reference： [1]Patent: US2009/54454,2009,A1 .Location in patent: Page/Page column 14
[2]Patent: WO2004/99191,2004,A2 .Location in patent: Page 30-31
[3]Patent: US2007/27160,2007,A1 .Location in patent: Page/Page column 45

3
[ 22960-18-5 ]
[ 177-11-7 ]
[ 1227293-44-8 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4066 - 4084

4
[ 108-86-1 ]
[ 22960-18-5 ]
[ 1315322-76-9 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 6394 - 6400

5
[ 22960-18-5 ]
[ 111-34-2 ]
[ 1346817-49-9 ]

Yield	Reaction Conditions	Operation in experiment
71%		-(6-Fluoro- uinolin-8-yl)-ethanoneTo a solution of 6-fluoro-8-bromo-quinoline (1.53 g, 6.8 mmol) in acetonitrile (35 ml_) was added palladium(ll) acetate (0.31 g, 1.36 mmol, 0.2 eq.), butyl vinyl ether (2.04 g, 20 mmol, 3.0 eq.), and 1 ,3-bis(diphenylphosphino)propane (0.70 g, 1.7 mmol, 0.25 eq) was added triethylamine (1.1 g, 11 mmol, 1.6 eq). The resulting mixture was heated to 90 C for 17 hr and then evaporated under reduced pressure. The residue was dissolved in aqueous hydrochloric acid (2M, 15 ml_) and stirred, at room temperature, for 1.5 hr. This mixture was then diluted with water (35 ml_) and the pH adjusted with solid sodium hydrogen carbonate until neutral. The mixture was then extracted with ethyl acetate (100 ml_); the organic phase was dried over over magnesium sulphate. The resulting mixture was filtered and concentrated under reduced pressure to give a brown oil. This crude product was purified by chromatography on silica gel eluting with 10% ethyl acetate in pentane (by volume) to produce the title compound as a pale yellow solid (0.91 g, 71 %).1H NMR (400 MHz, CDCI3): δ ppm 2.96 (s, 3H), 7.48 (dd, 1 H), 7.56 (dd, H), 7.74 (dd, 1 H), 8.16 (dd, 1 H), 8.95 (dd, 1 H)

Reference： [1]Patent: WO2011/138751,2011,A2 .Location in patent: Page/Page column 71

6
[ 3054-95-3 ]
[ 1003-98-1 ]
[ 22960-18-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With hydrogenchloride; In water; at 111℃; for 24h;	General procedure: A 1N HCl solution (82.5 mL) was added to the aniline (~1 mmol) in a round bottom flask. To this was added acrolein diethyl acetal (2.5 mmol). The resulting solution was refluxed at 111 C for 24 hours. After cooling to room temperature, the solution was neutralized (pH 7-8) by addition of solid Na2CO3. The product was then extracted into dichloromethane (3 x 100 mL), and the combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The crude residue was then purified by column chromatography (elution mixture of hexane with ethyl acetate or 15% ethyl acetate/cyclohexane with methanol) to give the desired quinoline product.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6436 - 6439

7
[ 22960-18-5 ]
2,4,6-tribromo-3-(6-fluoroquinolin-8-yl)phenol [ No CAS ]
2,4,6-tribromo-3-(6-fluoroquinolin-8-yl)phenol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000

8
[ 22960-18-5 ]
2,4,6-tribromo-3-(6-fluoroquinolin-8-yl)phenol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000

9
[ 22960-18-5 ]
[ 87199-18-6 ]
3-(6-fluoroquinolin-8-yl)phenol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 9996 - 10000

10
[ 22960-18-5 ]
N-(tert-butyl)-6-fluoro-5-tosylquinolin-8-amine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 7564 - 7568

11
[ 22960-18-5 ]
[ 75-64-9 ]
N-(tert-butyl)-6-fluoroquinolin-8-amine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 7564 - 7568

12
[ 22960-18-5 ]
[ 20439-47-8 ]
(1R,2R)‐N¹,N²‐bis(6‐fluoroquinolin‐8‐yl)cyclohexane‐1,2‐diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 85℃;Schlenk technique; Inert atmosphere;	General procedure: To an oven-dried Schlenk flask were added diamine 3 (1.0 equiv),Pd2(dba)3 (5 mol%), rac-BINAP (10 mol%), NaOtBu (3.0 equiv), and toluene under Ar atmosphere.Then 8-haloqunoline 4 (2.2 equiv) was added directly. The flask was sealed, and the reaction wasstirred at 85 C until the complete consumption of the starting material 3. The mixture was cooled toroom temperature, filtered through a silica plug, and the plug was washed with EA. The combinedfiltrates were concentrated under reduced pressure, and the residue was purified by silica gelchromatography to give the desired product Ln.

Reference： [1]Molecules,2020,vol. 25

13
[ 22960-18-5 ]
6-fluoro-1,2,3,4-tetrahydroquinoline-8-carbonitril [ No CAS ]

Reference： [1]Patent: WO2021/188769,2021,A1

14
[ 22960-18-5 ]
1-(2-chloro-3-cyano-4-trifluoromethanesulfonylphenyl)-6-fluoro-1,2,3,4-tetrahydroquinoline-8-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2021/188769,2021,A1

15
[ 22960-18-5 ]
1-[5-cyano-6-(trifluoromethyl)pyridin-3-yl]-6-fluoro-1,2,3,4-tetrahydroquinoline-8-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2021/188769,2021,A1

16
[ 22960-18-5 ]
C₁₆H₁₀F₅N₃ [ No CAS ]

Reference： [1]Patent: WO2021/188769,2021,A1

17
[ 557-21-1 ]
[ 22960-18-5 ]
6-fluoroquinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃;	The mixture of <strong>[22960-18-5]8-bromo-6-fluoroquinoline</strong> (15.7 g, 69.5 mmol), Zn(CN)2 (4.9 g, 41.7 mmol, 0.8 equiv.) and Pd(PPh3)4 (8 g, 6.9 mmol, 10 % mol) in anhydrous DMF (100 mL) was stirred at 100 C for overnight. Then reaction was cooled to room temperature and diluted with H2O (500 mL). Yellow solid was filtered off, washed with H2O and dried under vacuum. Crude product was used in the next step without further purification.
	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃;	The mixture of <strong>[22960-18-5]8-bromo-6-fluoroquinoline</strong> (15.7 g, 69.5 mmol), Zn(CN)2 (4.9 g, 41.7 mmol, 0.8 equiv.) and Pd(PPh3)4 (8 g, 6.9 mmol, 10 % mol) in anhydrous DMF (100 mL) was stirred at 100 C for overnight. Then reaction was cooled to room temperature and diluted with H2O (500 mL). Yellow solid was filtered off, washed with H2O and dried under vacuum. Crude product was used in the next step without further purification.

Reference： [1]Patent: WO2021/188769,2021,A1 .Location in patent: Paragraph 0243; 0248
[2]Patent: WO2021/188769,2021,A1 .Location in patent: Paragraph 0243; 0248

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Code	Phrase
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P378
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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
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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. 22960-18-5 ] {[proInfo.proName]}

Quality Control of [ 22960-18-5 ]

Related Doc. of [ 22960-18-5 ]

Product Details of [ 22960-18-5 ]

Calculated chemistry of [ 22960-18-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 22960-18-5 ]

Application In Synthesis of [ 22960-18-5 ]

[ 22960-18-5 ] Synthesis Path-Downstream 1~17

Related Functional Groups of [ 22960-18-5 ]

Fluorinated Building Blocks

Bromides

Related Parent Nucleus of [ 22960-18-5 ]

Quinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 22960-18-5 ]

Related Parent Nucleus of
[ 22960-18-5 ]