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[ CAS No. 105515-20-6 ] {[proInfo.proName]}

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Chemical Structure| 105515-20-6

Chemical Structure| 105515-20-6

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Quality Control of [ 105515-20-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 105515-20-6 ]

CAS No. :	105515-20-6	MDL No. :	MFCD11847746
Formula :	C₈H₆BrFO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MZDXPUDHZBCYGS-UHFFFAOYSA-N
M.W :	217.04	Pubchem ID :	13730359
Synonyms :

Calculated chemistry of [ 105515-20-6 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.29
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	2.4
Log Po/w (WLOGP) :	3.21
Log Po/w (MLOGP) :	2.94
Log Po/w (SILICOS-IT) :	3.25
Consensus Log Po/w :	2.77

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.04
Solubility :	0.2 mg/ml ; 0.000922 mol/l
Class :	Soluble
Log S (Ali) :	-2.4
Solubility :	0.864 mg/ml ; 0.00398 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.87
Solubility :	0.0291 mg/ml ; 0.000134 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.51

Safety of [ 105515-20-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H317-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 105515-20-6 ]

* 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 [ 105515-20-6 ]
Downstream synthetic route of [ 105515-20-6 ]

[ 105515-20-6 ] Synthesis Path-Upstream 1~3

1
[ 176548-70-2 ]
[ 105515-20-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: With methyllithium In diethyl ether at -78 - -10℃; Stage #2: With ammonium chloride In diethyl ether	1-(3-Bromo-5-fluorophenyl)-ethanone Methyllithium (1.3 M in diethyl ether, 35 mL) was added dropwise to 3-bromo-5-fluorobenzoic acid (5 g) in diethyl ether at -78° C. keeping the temperature below -60° C. The reaction was then left to warm to -10° C. and was stirred for 1 h before being carefully quenched with saturated ammonium chloride (100 mL) until pH=3. The product was extracted with diethyl ether (2*100 mL), dried over sodium sulfate and the solvent removed by evaporation to yield 1-(3-bromo-5-fluorophenyl)ethanone as an off-white solid (4.67 g, 94percent). ¹H NMR (CDCl₃): 2.59 (3H, s, ArCOCH₃), 7.44 (1H, dd, Ar), 7.59 (1H, dd, Ar), 7.87 (1H, s, Ar).

Reference： [1] Patent: US2009/209529, 2009, A1, . Location in patent: Page/Page column 35

2
[ 1435-51-4 ]
[ 78191-00-1 ]
[ 105515-20-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: With n-butyllithium In di-isopropyl ether at -78℃; for 0.5 h; Inert atmosphere Stage #2: at -78 - 30℃; for 0.5 h;	1,3-Dibromo-5-fluoro-benzene (20 g, 78.77 mmol, 1 eq) was dissolved in i-Pr2O (200 mL) in a dried flask under nitrogen. The reaction mixture was cooled to -78 °C and stirred under nitrogen atmosphere. n-BuLi (2.5 M, 31.5 mL, 1 eq) was added drop wise to the above solution and the reaction mixture was stirred at -78 °C for 30 min. After complete addition of n-BuLi, N-methoxy-N-methyl-acetamide (9.75 g, 94.5 mmol, 10.05 mL, 1.2 eq) dropped to the above reaction mixture, while keeping the reaction mixture below -78 °C. After addition, the reaction mixture was warmed slowly to 30 °C for 30 min. The reaction mixture was poured into water (150 mL) and the reaction mixture was stirred for 15 min. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (150 mL), combined organic phase, dried over anhydrous Na2SO4, filtered and evaporated in vacuum to give residue (16 g crude). The residue was purified by flash silica gel chromatography (ISCO®; 120 g CombiFlash® Silica Flash Column, Eluent of 0~10percent Ethyl acetate/Petroleum ether gradient 85 mL/min). Compound was obtained as off-white solid (11.3 g, yield 66percent).¹H NMR (400 MHz, CDCl3) δ ppm 7.91 - 7.84 (m, 1H), 7.63 - 7.54 (m, 1H), 7.45 (td, J=2.0, 7.8 Hz, 1H), 2.63 - 2.55 (m, 3H).

Reference： [1] Patent: WO2018/132268, 2018, A1, . Location in patent: Page/Page column 97

3
[ 627527-04-2 ]
[ 105515-20-6 ]

Yield	Reaction Conditions	Operation in experiment
45%	With dipyridinium dichromate In dichloromethane at 20℃; for 4 h;	To a solution of 1-(3-bromo-5-fluoro-phenyl)-ethanol (2.9 g, 13.2 mmol) in methylene chloride (150 ml) was added at room temperature pyridinium dichromate (3.98 g). The reaction mixture was stirred for 4 hours at room temperature and the solvent was removed in the presence of silica gel. The crude product was purified by chromatography over silica gel to provide 1-(3-bromo-5-fluoro-phenyl)-ethanone (1.39 g, 45percent) as a light yellow solid, MS: m/e=216.1 (M+).

Reference： [1] Patent: US2003/229096, 2003, A1, . Location in patent: Page 21

[ 105515-20-6 ] Synthesis Path-Downstream 1~13

1
[ 627527-04-2 ]
[ 105515-20-6 ]

Yield	Reaction Conditions	Operation in experiment
45%	With dipyridinium dichromate; In dichloromethane; at 20℃; for 4h;	To a solution of 1-(3-bromo-5-fluoro-phenyl)-ethanol (2.9 g, 13.2 mmol) in methylene chloride (150 ml) was added at room temperature pyridinium dichromate (3.98 g). The reaction mixture was stirred for 4 hours at room temperature and the solvent was removed in the presence of silica gel. The crude product was purified by chromatography over silica gel to provide 1-(3-bromo-5-fluoro-phenyl)-ethanone (1.39 g, 45%) as a light yellow solid, MS: m/e=216.1 (M+).

Reference： [1]Patent: US2003/229096,2003,A1 .Location in patent: Page 21

3
[ 176548-70-2 ]
[ 105515-20-6 ]

Yield	Reaction Conditions	Operation in experiment
94%		1-(3-Bromo-5-fluorophenyl)-ethanone Methyllithium (1.3 M in diethyl ether, 35 mL) was added dropwise to <strong>[176548-70-2]3-bromo-5-fluorobenzoic acid</strong> (5 g) in diethyl ether at -78 C. keeping the temperature below -60 C. The reaction was then left to warm to -10 C. and was stirred for 1 h before being carefully quenched with saturated ammonium chloride (100 mL) until pH=3. The product was extracted with diethyl ether (2*100 mL), dried over sodium sulfate and the solvent removed by evaporation to yield 1-(3-bromo-5-fluorophenyl)ethanone as an off-white solid (4.67 g, 94%). 1H NMR (CDCl3): 2.59 (3H, s, ArCOCH3), 7.44 (1H, dd, Ar), 7.59 (1H, dd, Ar), 7.87 (1H, s, Ar).

Reference： [1]Patent: US2009/209529,2009,A1 .Location in patent: Page/Page column 35

4
[ 105515-20-6 ]
[ 14804-31-0 ]
[ 1180016-23-2 ]

Yield	Reaction Conditions	Operation in experiment
60%		(RS)-1-(3-Bromo-5-fluorophenyl)-1-(4-methoxy-3-methylphenyl)-ethanol Magnesium turnings (627 mg) and a crystal of iodine were suspended in tetrahydrofuran (10 mL) at room temperature. To this was added ~5 mL of a solution of 4-bromo-2-methylanisole (4.54 g) in tetrahydrofuran (50 mL). The mixture was then heated to reflux until initiation (colour change from brown to colourless ~15-30 min) after which time the heat was removed. The remaining 4-bromo-2-methylanisole solution was added dropwise to maintain a gentle reflux and then heated at reflux for 2 h. Upon cooling to room temperature, a solution of <strong>[105515-20-6]1-(3-bromo-5-fluorophenyl)-ethanone</strong> (4.67 g) in tetrahydrofuran (50 mL) was added dropwise, again maintaining a gentle reflux. This was then heated at reflux for 2 h before being allowed to cool to room temperature, poured onto ice-water (400 mL), and the solvent removed by evaporation. The product was extracted with ethyl acetate (3*100 mL), dried over sodium sulfate and the solvent removed by evaporation to yield a yellow oil. Purification by flash chromatography on silica (20:1-5:1 hexane/ethyl acetate) yielded the alcohol as a yellow oil (4.4 g, 60%). 1H NMR (CDCl3): 1.88 (3H, s, ArCH3), 2.19 (3H, s, ArCH3), 3.81 (3H, s, ArOCH3), 6.76 (1H, d, Ar), 7.00-7.20 (4H, m, Ar), 7.34 (1H, t, Ar).

Reference： [1]Patent: US2009/209529,2009,A1 .Location in patent: Page/Page column 35

5
[ 105515-20-6 ]
2-(3-bromo-5-fluorophenyl)-1,1,1-trifluoropropan-2-yl methanesulfonate [ No CAS ]

Reference： [1]Patent: WO2018/132268,2018,A1

6
[ 105515-20-6 ]
1-bromo-3-fluoro-5-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene [ No CAS ]

Reference： [1]Patent: WO2018/132268,2018,A1

7
[ 105515-20-6 ]
3-fluoro-5-(1,1,1-trifluoro-2-methylpropan-2-yl)benzaldehyde [ No CAS ]

Reference： [1]Patent: WO2018/132268,2018,A1

8
[ 105515-20-6 ]
[ 81290-20-2 ]
2-(3-bromo-5-fluorophenyl)-1,1,1-trifluoropropan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 0 - 30℃; for 4h;	To a stirred solution of 1-(3-bromo-5-fluoro-phenyl)ethanone (11.2 g, 51.60 mmol, 1 eq) and TMSCF3 (14.68 g, 103.2 mmol, 2 eq) in DMF (100 mL) was added Cs2CO3 (33.63 g, 103.2 mmol, 2 eq) portion wise at 0C resulting in a brown suspension. The reaction mixture was then stirred at 30C for 4 hr. The reaction mixture was quenched by water (100 mL) and separated and extracted with Ethyl acetate (200 mL2), the organic layer was washed with water (200 mL2), and brine (200 mL). The mixture reaction dried over anhydrous Na2SO4, filtered and evaporated in vacuum to give residue. The residue was purified by flash silica gel chromatography (ISCO; 220 g CombiFlash Silica Flash Column, Eluent of 0~30% Ethyl acetate/Petroleum ether gradient 100mL/min). Compoud was obtained as black brown liquid (18.4 g, crude). 1H NMR (400 MHz, CDCl3) delta ppm 7.37 (s, 1H), 7.16 - 7.03 (m, 2H), 1.60 (s, 3H).

Reference： [1]Patent: WO2018/132268,2018,A1 .Location in patent: Page/Page column 97-98

9
[ 1435-51-4 ]
[ 78191-00-1 ]
[ 105515-20-6 ]

Yield	Reaction Conditions	Operation in experiment
66%		1,3-Dibromo-5-fluoro-benzene (20 g, 78.77 mmol, 1 eq) was dissolved in i-Pr2O (200 mL) in a dried flask under nitrogen. The reaction mixture was cooled to -78 C and stirred under nitrogen atmosphere. n-BuLi (2.5 M, 31.5 mL, 1 eq) was added drop wise to the above solution and the reaction mixture was stirred at -78 C for 30 min. After complete addition of n-BuLi, N-methoxy-N-methyl-acetamide (9.75 g, 94.5 mmol, 10.05 mL, 1.2 eq) dropped to the above reaction mixture, while keeping the reaction mixture below -78 C. After addition, the reaction mixture was warmed slowly to 30 C for 30 min. The reaction mixture was poured into water (150 mL) and the reaction mixture was stirred for 15 min. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (150 mL), combined organic phase, dried over anhydrous Na2SO4, filtered and evaporated in vacuum to give residue (16 g crude). The residue was purified by flash silica gel chromatography (ISCO; 120 g CombiFlash Silica Flash Column, Eluent of 0~10% Ethyl acetate/Petroleum ether gradient 85 mL/min). Compound was obtained as off-white solid (11.3 g, yield 66%).1H NMR (400 MHz, CDCl3) delta ppm 7.91 - 7.84 (m, 1H), 7.63 - 7.54 (m, 1H), 7.45 (td, J=2.0, 7.8 Hz, 1H), 2.63 - 2.55 (m, 3H).

Reference： [1]Patent: WO2018/132268,2018,A1 .Location in patent: Page/Page column 97

10
[ 105515-20-6 ]
4-(trifluoromethyl)-2,3-dihydro-1H-isoindol-1-one [ No CAS ]
2-(3-acetyl-5-fluoro-phenyl)-4-(trifluoromethyl)isoindolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100 - 120℃; for 4h;Sealed tube;	To a stirring solution of Xantphos (0.06 g, 0.10 mmol,), l-(3-bromo-5-fluorophenyl)ethanone (0.22 g, 0.99 mmol,), 4-(trifluoromethyl)isoindolin-l-one (200 mg, 0.99 mmol), and cesium carbonate (0.66 g, 1.99 mmol) in dioxane (15 mL) was added palladium(II) acetate (10 mg, 0.05 mmol). The mixture was allowed to stir at 100-120 C for about 4 h in a sealed vial and then cooled to rt. The reaction was diluted with water or 1 M hydrochloric acid. General Work-up Procedure 1 was followed. The crude was purified using flash column chromatography to yield the title compound (214 mg, 64% yield) as a colorless solid.

Reference： [1]Patent: WO2019/148005,2019,A1 .Location in patent: Paragraph 1768

11
[ 105515-20-6 ]
2-(5-fluoro-3-(1-hydroxyethyl)phenyl)-4-(trifluoromethyl)isoindolin-1-one [ No CAS ]

Reference： [1]Patent: WO2019/148005,2019,A1

12
[ 105515-20-6 ]
2-[3-fluoro-5-[(1S)-1-[(4-methyl-1,2,4-triazol-3-yl)sulfanyl]ethyl]phenyl]-4-(trifluoromethyl)isoindolin-1-one [ No CAS ]
2-[3-fluoro-5-[(1R)-1-[(4-methyl-1,2,4-triazol-3-yl)sulfanyl]ethyl]phenyl]-4-(trifluoromethyl)isoindolin-1-one [ No CAS ]

Reference： [1]Patent: WO2019/148005,2019,A1

13
1-(3-bromo-5-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)phenyl)ethan-1-one [ No CAS ]
[ 105515-20-6 ]

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 1759 - 1762

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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.
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P222	Do not allow contact with air.
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Code	Phrase
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P321
P322
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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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.
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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.
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
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P401
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Ghs Hazard Statements

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