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[ CAS No. 175711-83-8 ] {[proInfo.proName]}

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Chemical Structure| 175711-83-8

Chemical Structure| 175711-83-8

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Quality Control of [ 175711-83-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 175711-83-8 ]

SDS Specification

Alternatived Products of [ 175711-83-8 ]

Product Citations

Product Details of [ 175711-83-8 ]

CAS No. :	175711-83-8	MDL No. :	MFCD04116328
Formula :	C₈H₆ClFO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OIGMDNONQJGUCF-UHFFFAOYSA-N
M.W :	172.58	Pubchem ID :	15030552
Synonyms :		Chemical Name :	4'-Chloro-2'-fluoroacetophenone

Calculated chemistry of [ 175711-83-8 ] Expand+

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 :	41.6
TPSA :	17.07 ?2

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) :	-5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.76
Log Po/w (XLOGP3) :	2.33
Log Po/w (WLOGP) :	3.1
Log Po/w (MLOGP) :	2.79
Log Po/w (SILICOS-IT) :	3.21
Consensus Log Po/w :	2.64

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.72
Solubility :	0.332 mg/ml ; 0.00193 mol/l
Class :	Soluble
Log S (Ali) :	-2.33
Solubility :	0.812 mg/ml ; 0.0047 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.62
Solubility :	0.041 mg/ml ; 0.000238 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Safety of [ 175711-83-8 ]

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

Application In Synthesis of [ 175711-83-8 ]

* 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 [ 175711-83-8 ]
Downstream synthetic route of [ 175711-83-8 ]

[ 175711-83-8 ] Synthesis Path-Upstream 1~1

1
[ 175711-83-8 ]
[ 1229236-86-5 ]

Reference： [1] Organic Process Research and Development, 2012, vol. 16, # 1, p. 70 - 81
[2] Organic Process Research and Development, 2012, vol. 16, # 1, p. 70 - 81

[ 175711-83-8 ] Synthesis Path-Downstream 1~10

1
[ 198967-23-6 ]
[ 75-16-1 ]
[ 175711-83-8 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether; dichloromethane; at 0 - 20℃; for 2h;	Reference Example 8 : 1- (4-chloro-2-fluorophenyl) ethanone To a solution 4-chloro-2-fluorobenzoic acid (leq) in CH2C12 (1.6 M) was added N, O-dimethylhydroxylamine hydrochloride (1. 5 eq), EDCI (1.5 eq) and triethylamine (4 eq). The reaction mixture was stirred at rt for 16 hrs, concentrated and 0. 5M aqueous citric acid was added. The mixture was extracted with 1: 1 EtOAc: Et20. The combined organic layers were washed with brine, dried over MgS04 and concentrated to give 4-chloro-2-fluoro-N-methoxy-N- methylbenzamide, which was used as such for the next step. To a solution of the above benzamide (leq) in CHsClz (0.5 M) at 0C was added 3M/EtzO MeMgBr (1.25 eq). The reaction mixture was slowly warmed to rt over a 2 hrs period, quenched with 0.5 M aqueous citric acid and extracted with Et20. The combined organic layers were washed with brine, dried over MgS04 and concentrated. The residue was purified by flash chromatography on silica gel eluted with 20% EtOAc/hexane to give the title compound.

Reference： [1]Patent: WO2005/56527,2005,A1 .Location in patent: Page/Page column 23

Yield	Reaction Conditions	Operation in experiment
		(3) Anhydrous magnesium chloride (6.7g, 70mmol) and triethylamine (24.2g, 0.24mol) were added to toluene (120ml), and dimethyl malonate (15.8g, 0.12mmol) was added dropwise under cooling with water. After the reaction mixture was stirred at room temperature for 3 hours, a toluene solution of the compound prepared in reference example 6-(2) (about 20g) in toluene (20ml) was added dropwise at about 20 ?C. The resulting mixture was stirred for 14 hours at room temperature. After concentrated hydrochloric acid (20ml) was added to the reaction mixture under cooling with ice, the resulting mixture was added to ice water. The organic layer was separated, and the aqueous layer was further extracted with toluene. The toluene layer was combined with the former organic layer, washed with brine, dried, and then evaporated to give an oil. The oil was added to a mixture of DMSO (80ml) and water (4ml). The mixture was gradually heated, stirred at 140 ?C (the temperature of oil bath) for 2 hours, and further stirred at 180 ?C for 1 hour. After cooling, the reaction mixture was poured into ice water, and extracted with diethyl ether. The extract was washed with brine, dried, and then evaporated. The residue was distilled under reduced pressure to give 4-chloro-2-fluoroacetophenone (14.4g, oil). 1H-NMR(CDCl3) delta 2.63(3H, d, J=5.03Hz), 7.12-7.25(2H, m), 7.84(1H, t, J=9.02Hz). b.p.:100-104 ?C/20mmHg

3
[ 175711-83-8 ]
[ 725743-41-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With 4-(dimethylamino)pyridine tribromide; In acetic acid; at 20℃; for 24h;	A mixture of <strong>[175711-83-8]4'-chloro-2'-fluoroacetophenone</strong> (17.5 g, 100 mmol), 4-(dimethylamino)pyridine tribromide (40.0 g, 110 mmol) and acetic acid (100 mL) was stirred at room temperature for 24 h. Water (150 mL) was added and after stirring for 30 min the precipitated solid was collected by filtration, washed with water, and dried in vacuo to give the desired bromide intermediate as a white solid (24 g, 95%).
95%	With 4-dimethylaminopyridine tribromide; acetic acid; at 20℃; for 24h;	A mixture of 4?-chloro-2?-fluoroacetophenone (17.5 g, 100 mmol), 4- (dimethylamino)pyridine tribromide (40.0 g, 110 mmol) and acetic acid (100 mL) was stirred room temperature for 24 h. Water (150 mL) was added and after stirring for 30 mm the precipitated solid was collected by filtration, washed with water, and dried in vacuo to give the desired bromide intermediate as a white solid (24 g, 95%).
95%	With 4-(dimethylamino)pyridine tribromide; acetic acid; at 20℃; for 24h;	A mixture of 4?-chloro-2?-fluoroacetophenone (17.5 g, 100 mmol), 4-(dimethylamino)pyridine tribromide (40.0 g, 110 mmol) and acetic acid (100 mE) was stirred at room temperature for 24 h. Water (150 mE) was added and after stirring for 30 mm the precipitated solid was collected by filtration, washed with water, and dried in vacuo to give the desired bromide intermediate as a white solid (24 g, 95%).

85.8%

With pyridinium hydrobromide perbromide; In tetrahydrofuran; at 25℃; for 2h;Green chemistry;

As shown in Figure 2, Tetrahydrofuran (400 mL) and <strong>[175711-83-8]2-fluoro-4-chloroacetophenone</strong> (74.2 g, 1.0 eq) were added to the reaction flask at room temperature, stirred and dissolved completely, and the temperature was controlled at 25 C. A solution of pyridinium tribromide (137.5 g, 1.0 eq) in tetrahydrofuran was added dropwise. The reaction system was stirred at 25 C for 2 hours. after filtration, the filter cake was rinsed with a small amount of tetrahydrofuran to give a yellow solid, dried.Recrystallization from n-hexane (900 ml) and ethyl acetate (100 ml). 92.8 g of yellow was obtained in a yield of 85.8%.

Reference： [1]Patent: US2009/48311,2009,A1 .Location in patent: Page/Page column 39
[2]Patent: WO2016/100766,2016,A1 .Location in patent: Paragraph 0399
[3]Patent: US2018/228158,2018,A1 .Location in patent: Paragraph 0311; 0319
[4]Patent: CN109651119,2019,A .Location in patent: Paragraph 0036-0039

4
[ 1160097-36-8 ]
[ 175711-83-8 ]
[ 1159913-05-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2252 - 2257

5
[ 175711-83-8 ]
2-chloro-1-(4-chloro-2-fluorophenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sulfuryl dichloride; In methanol; n-heptane; at 0℃; for 3.5h;Inert atmosphere;Product distribution / selectivity;	PREPARATION 2 2-Chloro-<strong>[175711-83-8]1-(4-chloro-2-fluorophenyl)ethanone</strong> In a 1 L round bottom flask combine <strong>[175711-83-8]4'-chloro-2'-fluoroacetophenone</strong> (40 g, 231.8 mmol), heptane (120 mL), and methanol (16 mL). Cool to 0 C. and place under nitrogen. Dissolve sulfuryl chloride (21.5 mL, 1.15 equiv.) in heptane (120 mL) and charge to an addition funnel Add drop-wise to the reaction over 60 min. Stir for 2.5 h at 0 C.; a white precipitate forms during this time. Charge the addition funnel with 1 M sodium bicarbonate (400 mL) then add to the reaction drop-wise. After all gas evolution stops, filter the biphasic suspension to collect the title compound (38.18 g, 80%) as white needles. 1H NMR (DMSO-d6) delta 5.00 (d, 2H, J=2.5 Hz), 7.43 (m, 1H), 7.63 (m, 1H), 7.89 (t, 1H, J=8.4 Hz).
57%	With sulfuryl dichloride; In methanol; dichloromethane; at 0 - 20℃; for 24h;Inert atmosphere;	Intermediate P6: 2-Chloro- 1 -(4-chloro-2-fluorophenyl)ethanone To the mixture of 1 -(4-chloro-2-fluorophenyl)ethanone (4.00 g, 23.2 mmol), dichloromethane (12 mL) and methanol (1 .6 mL) cooled to 0 C under argon atmosphere sulfuryl chloride (2.35 mL, 29.0 mmol) solution in dichloromethane (5 mL) was added during 10 minutes. The reaction mixture was stirred for 24 hours at room temperature. Then, the reaction mixture was cooled to 0 C and 14% aqueous solution of sodium hydroxide (20 mL) was added. The mixture was extracted with dichloromethane (2 chi 20 mL). Organic layers were combined, washed with brine, dried (Na2S04) and evaporated under reduced pressure. Remaining solid was dissolved in boiling ethyl acetate and heptane was added to crystallize crystals. White crystals were filtered and washed with heptane to obtain title product with the yield of 57% (2.74 g, 13.2 mmol). 1 H NMR (500 MHz, CDCl3) delta 7.93 (t, J=8.1 Hz, 1 H), 7.29 (dd, J=9.0 Hz, 1 .2 Hz, 1 H), 7.23 (dd, J=10.8 Hz, 1 .9 Hz, 1 H), 4.70 (d, J=2.9 Hz, 2H ). 13C NMR ( 125 MHz, CDCl3) delta 188. 1 , 162.6, 141 ,5, 132.2 (d, J=3.7 Hz), 125.6 (d, J=3.2 Hz), 121 .1 , 1 17.3 (d, J=27.2 Hz), 49.8 (d, J=1 1 .5 Hz).

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 70 - 81
[2]Patent: US2010/152181,2010,A1 .Location in patent: Page/Page column 2
[3]Patent: WO2014/20531,2014,A1 .Location in patent: Page/Page column 16
[4]Journal of Medicinal Chemistry,2014,vol. 57,p. 5702 - 5713

6
[ 175711-83-8 ]
[ 1229236-81-0 ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 70 - 81

7
[ 175711-83-8 ]
[ 1229236-81-0 ]
C₃₂H₁₈Cl₂FN₅O₅ [ No CAS ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 70 - 81

8
[ 175711-83-8 ]
C₂₃H₁₃Cl₂FN₄O₃ [ No CAS ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 70 - 81
[2]Organic Process Research and Development,2012,vol. 16,p. 70 - 81

9
[ 175711-83-8 ]
C₁₅H₁₁Cl₂FN₄O*ClH [ No CAS ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 70 - 81
[2]Organic Process Research and Development,2012,vol. 16,p. 70 - 81

10
[ 175711-83-8 ]
C₁₅H₁₃Cl₂FN₄O [ No CAS ]

Reference： [1]Organic Process Research and Development,2012,vol. 16,p. 70 - 81
[2]Organic Process Research and Development,2012,vol. 16,p. 70 - 81

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Technical Information

? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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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

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