[ CAS No. 1125828-26-3 ]

Name: 1-(2-Bromo-5-chlorophenyl)-3-methyl-1H-pyrazole
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Quality Control of [ 1125828-26-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1125828-26-3 ]

CAS No. :	1125828-26-3	MDL No. :	MFCD14706004
Formula :	C₁₀H₈BrClN₂	Boiling Point :	344.8±37.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	271.54	Pubchem ID :	25212417
Synonyms :

Computed Properties of [ 1125828-26-3 ]

TPSA :Topological Polar Surface Area	17.8	H-Bond Acceptor Count :	1
XLogP3 :	3.6	H-Bond Donor Count :	0
SP3 :	0.10	Rotatable Bond Count :	1

Safety of [ 1125828-26-3 ]

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 [ 1125828-26-3 ]

Upstream synthesis route of [ 1125828-26-3 ]
Downstream synthetic route of [ 1125828-26-3 ]

[ 1125828-26-3 ] Synthesis Path-Upstream 1~1

1
[ 1453-58-3 ]
[ 1996-29-8 ]
[ 1125828-26-3 ]
[ 1125828-28-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 0.25 h; Stage #2: at 50℃; for 5.00 h;	A 3L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged with potassium tert-butoxide (Aldrich 95percent, 84.6 g, 0.716 mol) and DMSO (400 mL, 4.x.) at room temperature and stirred for 15 minutes. To this solution was added pyrazole 2 (59 g, 0.719 mol) followed by a DMSO rinse (50 mL, 0.5.x.). The resulting orange turbid solution was stirred for 15 minutes and fluoride 1 (100 g, 0.477 mol) was added followed by a DMSO rinse (50 mL, 0.5.x.). This mixture was then heated to 50° C. and held for 5 hours at this temperature. After cooling to room temperature, the reaction mixture was diluted with MTBE (750 mL), and water (500 mL) was added to give a brown turbid mixture. After 15 minutes stirring, the organic layer was separated and sequentially washed with 1 N HCl (250 mL), brine (250 mL), and water (250 mL). Solution assay of organic layer was carried out using GC (conversion >99percent, solution yields of 3 and its regioisomer 4 were 83percent and 17percent, respectively). The MTBE solution was then concentrated under vacuum to a total volume of about 200 mL (KF showed 0.737percent water). THF (500 mL) was added, and concentrated to 2.x. solution (KF=0.158percent). THF addition-concentration sequence was repeated to give a 2.x. solution (KF=0.023percent), which used directly in the next step.Analytical samples of compounds 3 and 4 were purified by column chromatography and characterized: Compound 3: white crystals; M.p.: 76° C. (DSC onset temperature). ¹H NMR (400 MHz, CDCl₃) δ 7.80 (1H, d, J=2.3 Hz), 7.61 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=2.5 Hz), 7.22 (1H, dd, J=8.6, 2.6 Hz), 6.27 (1H, d, J=2.5 Hz), 2.38 (3H, s); ¹³C NMR (100 MHz, CDCl₃) δ 150.8, 140.6, 134.6, 134.1, 132.0, 129.0, 128.2, 115.4, 107.0, 13.6. Compound 4: white crystals; ¹H NMR (400 MHz, CDCl₃) δ 7.65 (1H, d, J=8.6 Hz), 7.62 (1H, d, J=1.5 Hz), 7.43 (1H, d, J=2.5 Hz), 7.35 (1H, dd, J=8.6, 2.2 Hz), 6.21 (1H, s), 2.19 (3H, s); ¹³C NMR (100 MHz, CDCl₃) δ 140.6, 140.2, 140.0, 134.1, 133.9, 130.8, 130.2, 120.7, 105.9, 11.4.
83 %Chromat.	Stage #1: With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 0.25 h; Stage #2: at 50℃; for 5.00 h;	.1. Preparation of 1-(4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone A 3 L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged with potassium tert-butoxide (Aldrich 95percent, 84.6 g, 0.716 mol) and DMSO (400 mL, 4.x.) at room temperature and stirred for 15 minutes. To this solution was added pyrazole 2 (59 g, 0.719 mol) followed by a DMSO rinse (50 mL, 0.5.x.). The resulting orange turbid solution was stirred for 15 min and fluoride 1 (100 g, 0.477 mol) was added followed by a DMSO rinse (50 mL, 0.5.x.). This mixture was then heated to 50° C. and held for 5 hours at this temperature. After cooling to room temperature, the reaction mixture was diluted with MTBE (750 mL), and water (500 mL) was added to give a brown turbid mixture. After 15 min stirring, the organic layer was separated and sequentially washed with 1 N HCl (250 mL), brine (250 mL), and water (250 mL). Solution assay of organic layer was carried out using GC (conversion >99percent, solution yields of 3 and its regioisomer 4 were 83percent and 17percent, respectively). The MTBE solution was then concentrated under vacuum to a total volume of about 200 mL (KF showed 0.737percent water). THF (500 mL) was added, concentrated to 2.x. solution (KF=0.158percent). THF addition-concentration sequence was repeated to give a 2.x. solution (KF=0.023percent) which used directly in the next step.Analytical samples of compounds 3 and 4 were purified by column chromatography and characterized: Compound 3: white crystals; ¹H NMR (400 MHz, CDCl₃) δ 7.80 (1H, d, J=2.3 Hz), 7.61 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=2.5 Hz), 7.22 (1H, dd, J=8.6, 2.6 Hz), 6.27 (1H, d, J=2.5 Hz), 2.38 (3H, s); ¹³C NMR (100 MHz, CDCl₃) δ 150.8, 140.6, 134.6, 134.1, 132.0, 129.0, 128.2, 115.4, 107.0, 13.6. Compound 4: white crystals; ¹H NMR (400 MHz, CDCl₃) δ 7.65 (1H, d, J=8.6 Hz), 7.62 (1H, d, J=1.5 Hz), 7.43 (1H, d, J=2.5 Hz), 7.35 (1H, dd, J=8.6, 2.2 Hz), 6.21 (1H, s), 2.19 (3H, s); ¹³C NMR (100 MHz, CDCl₃) δ 140.6, 140.2, 140.0, 134.1, 133.9, 130.8, 130.2, 120.7, 105.9, 11.4.

Reference： [1] Patent: US2009/62540, 2009, A1. Location in patent: Page/Page column 6-7
[2] Patent: US2009/88447, 2009, A1. Location in patent: Page/Page column 4
[3] Patent: WO2015/35113, 2015, A1. Location in patent: Page/Page column 71

[ 1125828-26-3 ] Synthesis Path-Downstream 1~2

1
[ 75-90-1 ]
[ 1125828-26-3 ]
[ 1033805-26-3 ]

Yield	Reaction Conditions	Operation in experiment
91.2%		Preparation of compound (1)Under nitrogen conditions,To a 5L four-necked round-bottomed flask, 1L of anhydrous toluene and 50mL of anhydrous tetrahydrofuran were added.Then CuBr-SMe2 2g (0.01 mol) was added,Chiral ligand 11g (0.02 mol) and compound (4) 118 g(1.2 mol),The reaction temperature is -20C.Slowly adding all the compounds prepared in one step (3),The TLC monitored the reaction after the addition was complete.The reaction will end after 3 hours,After the end of the reaction, 1 L of saturated aqueous ammonium chloride was added to quench the reaction.Raise to room temperature and separate liquidThe aqueous phase was extracted with ethyl acetate and extracted 3 times each time.Combine the organic phase,The organic phase was concentrated under reduced pressure to give crude compound (1).The crude product was recrystallized from ethyl acetate/petroleum ether to obtain 264.5 g of the compound (1).The yield is 91.2% (two steps).Purity by HPLC: 98.14%.;_Under nitrogen protection,To a 5 L four-neck round bottom flask was added 271 g (1 mol) of compound (2).First add 1 L of anhydrous toluene to a four-necked round bottom flask.1.05 L of anhydrous toluene solution containing 1 M i-PrMgBr was added slowly.The control temperature is around 0C.After the dropwise addition, 100 mL of dry tetrahydrofuran was added to obtain a crude product of the compound (3) which was used directly in the next step.

Reference： [1]Patent: CN107382865,2017,A.Location in patent: Paragraph 0020; 0021; 0022

2
[ 1453-58-3 ]
[ 1996-29-8 ]
[ 1125828-26-3 ]
[ 1125828-28-5 ]

Yield	Reaction Conditions	Operation in experiment
83%; 17%		A 3L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged with potassium tert-butoxide (Aldrich 95%, 84.6 g, 0.716 mol) and DMSO (400 mL, 4×) at room temperature and stirred for 15 minutes. To this solution was added pyrazole 2 (59 g, 0.719 mol) followed by a DMSO rinse (50 mL, 0.5×). The resulting orange turbid solution was stirred for 15 minutes and fluoride 1 (100 g, 0.477 mol) was added followed by a DMSO rinse (50 mL, 0.5×). This mixture was then heated to 50 C. and held for 5 hours at this temperature. After cooling to room temperature, the reaction mixture was diluted with MTBE (750 mL), and water (500 mL) was added to give a brown turbid mixture. After 15 minutes stirring, the organic layer was separated and sequentially washed with 1 N HCl (250 mL), brine (250 mL), and water (250 mL). Solution assay of organic layer was carried out using GC (conversion >99%, solution yields of 3 and its regioisomer 4 were 83% and 17%, respectively). The MTBE solution was then concentrated under vacuum to a total volume of about 200 mL (KF showed 0.737% water). THF (500 mL) was added, and concentrated to 2× solution (KF=0.158%). THF addition-concentration sequence was repeated to give a 2× solution (KF=0.023%), which used directly in the next step.Analytical samples of compounds 3 and 4 were purified by column chromatography and characterized: Compound 3: white crystals; M.p.: 76 C. (DSC onset temperature). 1H NMR (400 MHz, CDCl3) delta 7.80 (1H, d, J=2.3 Hz), 7.61 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=2.5 Hz), 7.22 (1H, dd, J=8.6, 2.6 Hz), 6.27 (1H, d, J=2.5 Hz), 2.38 (3H, s); 13C NMR (100 MHz, CDCl3) delta 150.8, 140.6, 134.6, 134.1, 132.0, 129.0, 128.2, 115.4, 107.0, 13.6. Compound 4: white crystals; 1H NMR (400 MHz, CDCl3) delta 7.65 (1H, d, J=8.6 Hz), 7.62 (1H, d, J=1.5 Hz), 7.43 (1H, d, J=2.5 Hz), 7.35 (1H, dd, J=8.6, 2.2 Hz), 6.21 (1H, s), 2.19 (3H, s); 13C NMR (100 MHz, CDCl3) delta 140.6, 140.2, 140.0, 134.1, 133.9, 130.8, 130.2, 120.7, 105.9, 11.4.
83%Chromat.; 17%Chromat.		.1. Preparation of 1-(4-Chloro-2-(3-methyl-1H-pyrazol-1-yl)phenyl)-2,2,2-trifluoroethanone A 3 L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged with potassium tert-butoxide (Aldrich 95%, 84.6 g, 0.716 mol) and DMSO (400 mL, 4×) at room temperature and stirred for 15 minutes. To this solution was added pyrazole 2 (59 g, 0.719 mol) followed by a DMSO rinse (50 mL, 0.5×). The resulting orange turbid solution was stirred for 15 min and fluoride 1 (100 g, 0.477 mol) was added followed by a DMSO rinse (50 mL, 0.5×). This mixture was then heated to 50 C. and held for 5 hours at this temperature. After cooling to room temperature, the reaction mixture was diluted with MTBE (750 mL), and water (500 mL) was added to give a brown turbid mixture. After 15 min stirring, the organic layer was separated and sequentially washed with 1 N HCl (250 mL), brine (250 mL), and water (250 mL). Solution assay of organic layer was carried out using GC (conversion >99%, solution yields of 3 and its regioisomer 4 were 83% and 17%, respectively). The MTBE solution was then concentrated under vacuum to a total volume of about 200 mL (KF showed 0.737% water). THF (500 mL) was added, concentrated to 2× solution (KF=0.158%). THF addition-concentration sequence was repeated to give a 2× solution (KF=0.023%) which used directly in the next step.Analytical samples of compounds 3 and 4 were purified by column chromatography and characterized: Compound 3: white crystals; 1H NMR (400 MHz, CDCl3) delta 7.80 (1H, d, J=2.3 Hz), 7.61 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=2.5 Hz), 7.22 (1H, dd, J=8.6, 2.6 Hz), 6.27 (1H, d, J=2.5 Hz), 2.38 (3H, s); 13C NMR (100 MHz, CDCl3) delta 150.8, 140.6, 134.6, 134.1, 132.0, 129.0, 128.2, 115.4, 107.0, 13.6. Compound 4: white crystals; 1H NMR (400 MHz, CDCl3) delta 7.65 (1H, d, J=8.6 Hz), 7.62 (1H, d, J=1.5 Hz), 7.43 (1H, d, J=2.5 Hz), 7.35 (1H, dd, J=8.6, 2.2 Hz), 6.21 (1H, s), 2.19 (3H, s); 13C NMR (100 MHz, CDCl3) delta 140.6, 140.2, 140.0, 134.1, 133.9, 130.8, 130.2, 120.7, 105.9, 11.4.
		Potassium /-butoxide (3.9 g, 0.33 mmol) was dissolved in DMSO (25 mL). To this solution was added 3 -methyl pyrazole (2.7 g, 0.33 mmol) and the reaction was heated at 50 C for 30 min. l-Bromo-4-chloro-2-fluorobenzene (4.6 g, 0.22 mmol) was then added and the reaction was stirred at 50 C for 16 h. The reaction was cooled to RT and extracted with water and EtOAc, washed with brine, and dried over Na2S04) filtered and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtO Ac/heptane) provided l-(2- bromo-5-chlorophenyl)-3-methyl-lH-pyrazole and l-(2-bromo-5-chloroplienyl)-5-methyl-lH- pyrazole as a 4: 1 mixture that was used in the next step directly,

Potassium t-butoxide (3.9 g, 0.33 mmol) was dissolved in DMSO (25 mL). Tothis solution was added 3-methyl pyrazole (2.7 g, 0.33 mmol) and the reactionwas heated at 50 C for 30 min. 1-Bromo-4-chloro-2-fluorobenzene (4.6 g, 0.22mmol) was then added and the reaction was stirred at 50 C for 16 h. The reaction was cooled to RT and extractedwith water and ethyl acetate, washed with brine, and dried over Na2SO4,filtered and concentrated in vacuo. Purification by normal phase silica gelcolumn chromatography (ethyl acetate/heptane) provided <strong>[1125828-26-3]1-(2-bromo-5-chlorophenyl)-3-methyl-1H-pyrazole</strong>and 1-(2-bromo-5-chlorophenyl)-5-methyl-1H-pyrazole as a 4:1 mixture (41 & 42) that was used in the nextstep directly (5.4 g).

Reference： [1]Patent: US2009/62540,2009,A1.Location in patent: Page/Page column 6-7
[2]Patent: US2009/88447,2009,A1.Location in patent: Page/Page column 4
[3]Patent: WO2015/35113,2015,A1.Location in patent: Page/Page column 71
[4]Bioorganic and medicinal chemistry letters,2016,vol. 26,p. 1124 - 1129

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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. 1125828-26-3 ]

Quality Control of [ 1125828-26-3 ]

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Product Details of [ 1125828-26-3 ]

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Application In Synthesis of [ 1125828-26-3 ]

[ 1125828-26-3 ] Synthesis Path-Upstream 1~1

[ 1125828-26-3 ] Synthesis Path-Downstream 1~2

Related Functional Groups of [ 1125828-26-3 ]

Chlorides

Bromides

Aryls

Related Parent Nucleus of [ 1125828-26-3 ]

Pyrazoles

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Related Functional Groups of
[ 1125828-26-3 ]

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[ 1125828-26-3 ]