189807-21-4|4-Fluoro-2-(trifluoromethyl)benzoyl chloride| Ambeed

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Quality Control of [ 189807-21-4 ] Purity: 97% SDS Specification

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Product Details of [ 189807-21-4 ]

CAS No. :	189807-21-4
Formula :	C₈H₃ClF₄O
M.W :	226.56
SMILES Code :	O=C(Cl)C1=CC=C(F)C=C1C(F)(F)F
MDL No. :	MFCD00061158
InChI Key :	OEYHURRIOWWRMD-UHFFFAOYSA-N
Pubchem ID :	605680

Safety of [ 189807-21-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	8
UN#:	3265
Packing Group:	Ⅱ

Application In Synthesis of [ 189807-21-4 ]

* 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 [ 189807-21-4 ]
Downstream synthetic route of [ 189807-21-4 ]

[ 189807-21-4 ] Synthesis Path-Upstream 1~1

1
[ 1258861-50-5 ]
[ 189807-21-4 ]
[ 1258861-20-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine In dichloromethane at 20℃; for 3 h;	EXAMPLE 14-Fluoro-N-methyl-N-(1-(4-(1-methyl-1H-pyrazol-5-yl)phthalazin-1-yl)piperidin-4-yl)-2-(trifluoromethyl)benzamideTreat a solution of N-methyl-1-(4-(1-methyl-1H-pyrazol-5-yl)phthalazin-1-yl)piperidin-4-amine (2.8 g, 8.68 mmol) and triethylamine (3.36 mL, 26 1 mmol) in CH₂Cl₂(30 mL) with 4-fluoro-2-(trifluoromethyl)benzoyl chloride (2.14 mL, 10.42 mmol). Stir for 3 h at ambient temperature. Concentrate the reaction mixture under reduced pressure. Purify the resulting residue by flash silica gel chromatography (hexane:ethyl acetate:2 M NH₃in MeOH=20:5:1) to provide the free base as a yellow foam (3.83 g, 86percent). ES/MS m/z 513.0 (M+1).

References: [1] Patent: US2010/324048, 2010, A1, . Location in patent: Page/Page column 6.

[ 189807-21-4 ] Synthesis Path-Downstream 1~3

1
[ 141179-72-8 ]
[ 189807-21-4 ]

Yield	Reaction Conditions	Operation in experiment
91.3%	With oxalyl dichloride; In dichloromethane; at 0 - 25℃; for 0.5h;	General procedure: The purchased acids (14.40 mmol) was added into 5 mL DCM andcooled to 0 C. After the oxalyl chloride (1.50 mL, 17.30 mmol) was added drop wise, the mixture was removed to room temperature and stirred for 30 min. The solvent was evaporated for use.To a cooled solution of 5 (3.70 g, 17.30 mmol) in 20 mL DCM wasadded Et3N (3.00 mL, 21.60 mmol) then the prepared chloride wasadded drop wise. The mixture was stirred at room temperature for 1 h.The solvent was evaporated under reduced pressure and the residuewas purification by column chromatography with dichloromethane/methanol as eluent on silica gel to give the derivatives7a-7h.4.1.3.1. Tert-butyl-4-(4-fluoro-N-methyl-2-(trifluoromethyl) benzamido)piperidine-1-carboxylate (7a). Colorless oil, yield: 91.3%. Majorrotamer: 1H NMR (300 MHz, CDCl3) delta (ppm): 7.44-7.39 (m, 1H,ArH), 7.32-7.29 (m, 2H, ArH), 4.73 (m, 1H, CH3NCH), 4.25 (m, 2H,BocNCH2), 2.88-2.82 (m, 2H, BocNCH2), 2.63 (s, 3H, NCH3), 1.79-1.63(m, 4H, CH3N(CH2)2), 1.46 (s, 9H, Boc-H). Minor rotamer: 1H NMR(300 MHz, CDCl3) delta (ppm): 7.44-7.39 (m, 1H, ArH), 7.32-7.29 (m, 2H,ArH), 4.15-4.11 (m, 2H, BocNCH2), 3.23 (s, 1H, CH3NCH), 2.98 (s, 3H,NCH3), 2.51-2.35 (m, 2H, BocNCH2), 1.79-1.63 (m, 4H, CH3N(CH2)2),1.43 (s, 9H, Boc-H).
	With thionyl chloride; for 2h;Heating / reflux;	4-Fluoro-2- (trifluoromethyl) benzoic acid (2. 0G) was dissolved in thionyl chloride (20ML) and heated at reflux for 2h. The reaction was then cooled and evaporated (co- evaporated with DCM x 3) and then dissolved in DCM (50ML). This solution was added slowly to 1-tert-butoxy-carbonylpiperazine (1.62g), and TEA (2. 54ML), dissolved in DCM (50ML). The reaction was then stirred at rt for 2h before being washed with 1 N HCI (2X100M1), saturated sodium hydrogen carbonate (2X100ML) and brine (50ML). The organic layer was dried (MgSO4) and evaporated to give the title compound (D23) (3. 09G).
	With oxalyl dichloride; N,N-dimethyl-formamide; In hexane; dichloromethane; at 20℃; for 18h;	REFERENCE EXAMPLE 1 (4-Fluoro-2-trifluoromethyl-phenyl)-(5H,11H-pyrrolo[2,1-c] [1,4]benzodiazepin-10-yl)-methanone oxalyl chloride (2.0 g) was added to a suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (2.0 g) in dichloromethane (25 ml).. Two drops of dimethylformamide were added and the mixture was stirred for 18 hours at room temperature.. The resultant solution was evaporated to dryness to give the crude acid chloride.. This was redissolved in dichloromethane and filtered.. Evaporation of this material gave a liquid which was then redissolved in hexane, filtered, and evaporated to yield the acid chloride as a pale yellow viscous liquid, which was used without further purification. The acid chloride (2.26 g) in dichloromethane (25 ml) was added portionwise to a mixture of 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (1.66 g), dichloromethane (10 ml), and diisopropylethylamine (1.30 g), cooled in an ice bath.. After remaining at room temperature for 18 hours, the reaction mixture was washed with water and saturated aqueous sodium bicarbonate.. The dichloromethane solution was dried over anhydrous sodium sulfate and filtered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane.. The combined organic phase was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred.. After cooling, the crystals were collected by filtration to yield 2.57 g of the title compound, m.p. 154-155 C.

	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane;Heating / reflux;	A suspension of <strong>[141179-72-8]2-trifluoromethyl-4-fluorobenzoic acid</strong> (16.85 g, 81 mmol) in dichloromethane (150 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (8.5 mL, 97.4 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 10 minutes, and then evaporated to dryness in vacuo. The crude acid chloride was used as such in the next step
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 18h;	Oxalyl chloride (2.0 g) was added to a suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (2.0 g) in dichloromethane (25 ml). Two drops of dimethylformamide were added and the mixture was stirred for 18 hours at room temperature. The resultant solution was evaporated to dryness to give the crude acid chloride. This was redissolved in dichloromethane and filtered. Evaporation of this material gave a liquid which was then redissolved in hexane, filtered, and evaporated to yield the acid chloride as a pale yellow viscous liquid, which was used without further purification.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h;	Preparation Example 11 DMF (3 drops) and oxalyl chloride (2.55 ml) were added to a mixture of <strong>[141179-72-8]4-fluoro-2-(trifluoromethyl)benzoic acid</strong> (5.50 g) and dichloromethane (50 ml), followed by stirring at room temperature for 3 hours. The reaction solution was added dropwise to a 2M methylamine-THF solution (17.3 ml) and a solution of triethylamine (5.55 ml) in dichloromethane (50 ml) under ice cooling, followed by stirring for 30 minutes and concentration under reduced pressure, addition of water and extraction with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium bicarbonate solution and then saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with diisopropylether to obtain 4-fluoro-N-methyl-2-(trifluoromethyl)benzamide (4.37 g) as a white solid.
	With thionyl chloride; N,N-dimethyl-formamide; In ethyl acetate; at 70℃; for 3h;	4-Fluoro-2-(trifluoromethyl)benzoic acid (150 g), ethyl acetate (1200 mL), N,N-dimethylformamide (2.78 mL), and thionyl chloride (78.9 mL) were mixed, followed by stirring at 70 C for 3 hours. The solvent of this reaction mixture was evaporated under reduced pressure to obtain a residue containing 4-fluoro-2-(trifluoromethyl)benzoyl chloride. To the obtained residue were added acetonitrile (450 mL) and pyridine (291 mL), and 2-propanol (450 mL) was added dropwise thereto, followed by stirring at room temperature for 30 minutes. This mixture was subjected to a liquid separation operation by addition of toluene (600 mL) and water (600 mL), followed by extraction by addition of toluene (600 mL) to the aqueous layer. The obtained organic layers were combined, washed with 3 M hydrochloric acid (1200 mL), and then further washed with a solution of sodium chloride (150 g) and water (900 mL), and the solvent was evaporated therefrom under reduced pressure to obtain isopropyl 4-fluoro-2-(trifluoromethyl)benzoate (165 g) in a yield of 91.5%. 1H-NMR (CDCl3): 1.37 (6H, d, J = 6.0 Hz), 5.20-5.30 (1H, m), 7.28-7.31 (1H, m), 7.44 (1H, dd, J = 2.4, 9.2 Hz), 7.82 (1H, dd, J = 5.6, 8.8 Hz)
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 0.5h;	2-Trifluoromethyl-4-fluorobenzoic acid (VII-1) (3.00 g, 14.40 mmol) was dissolved in dichloromethane (5.00 mL).Add 2 drops of DMF and cool to 0 C.Add oxalyl chloride (1.50 ml, 17.30 mmol),Displaced at room temperature for 30 min,The dichloromethane was spun dry to give the acid chloride.

References: [1]Bioorganic and medicinal chemistry,2020,vol. 28.
[2]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 818 - 829.
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 954 - 959.
[4]Patent: WO2004/37800,2004,A1 .Location in patent: Page 24.
[5]Patent: EP1000062,2004,B1 .Location in patent: Page 31.
[6]Patent: EP1000059,2004,B1 .Location in patent: Page 30.
[7]Patent: US6831079,2004,B1 .Location in patent: Page/Page column 36.
[8]Patent: EP2298747,2011,A1 .Location in patent: Page/Page column 25.
[9]Patent: EP2860175,2015,A1 .Location in patent: Paragraph 0121;0122.
[10]Patent: CN109734700,2019,A .Location in patent: Paragraph 0072; 0080; 0081.

2
[ 79-37-8 ]
[ 5129-72-6 ]
[ 141179-72-8 ]
[ 189807-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	Step A. 2-Trifluoromethyl-4-fluorobenzoyl chloride A suspension of <strong>[141179-72-8]2-trifluoromethyl-4-fluorobenzoic acid</strong> (16.85 g, 81 mmol) in dichloromethane (150 mL) containing a few drops of diethylformamide was treated dropwise under nitrogen with oxalyl chloride (8.5 mL, 97.4 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 10 minutes, and then evaporated to dryness in vacuo. The crude acid chloride was used as such in the next step.

References: [1]Patent: US6090803,2000,A .

3
[ 79-37-8 ]
[ 141179-72-8 ]
[ 189807-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; dichloromethane;	Step A. 2-Trifluoromethyl-4-fluorobenzoyl chloride A suspension of <strong>[141179-72-8]2-trifluoromethyl-4-fluorobenzoic acid</strong> (16.85 g, 81 mmol) in dichloromethane (150 mL) containing a few drops of dimethylformamide was treated dropwisc under nitrogen with oxalyl chloride (8.5 mL, 97.4 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 10 minutes, and then evaporated to dryness in vacuo. The crude acid chloride was used as such in the next step.
	In dichloromethane;	Step A. 2-Trifluoromethyl-4-fluorobenzoyl chloride A suspension of <strong>[141179-72-8]2-trifluoromethyl-4-fluorobenzoic acid</strong> (16.85 g, 81 mmol) in dichloromethane (150 mL) containing a few drops of dimethylforrnamide was treated dropwise under nitrogen with oxalyl chloride (8.5 mL, 97.4 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 10 minutes, and then evaporated to dryness in vacuo. The crude acid chloride was used as such in the next step.
	In N-methyl-acetamide; dichloromethane;	Step A. 2-Trifluoromethyl-4-fluorobenzoyl chloride A suspension of <strong>[141179-72-8]2-trifluoromethyl-4-fluorobenzoic acid</strong> (16.85 g, 81 mmol) in dichloromethane (150 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (8.5 mL, 97.4 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 10 minutes, and then evaporated to dryness in vacuo. The crude acid chloride was used as such in the next step.

References: [1]Patent: EP1149096,2002,B1 .
[2]Patent: US6194407,2001,B1 .
[3]Patent: US6235900,2001,B1 .

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • 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 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 • Rosenmund Reduction • 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 • Wittig Reaction • Wolff-Kishner Reduction

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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

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CAS No.: 189807-21-4

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