[ CAS No. 1125828-26-3 ]

Name: 1-(2-Bromo-5-chlorophenyl)-3-methyl-1H-pyrazole
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SKU: A101758
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Quality Control of [ 1125828-26-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1125828-26-3 ]

SDS

Alternatived Products of [ 1125828-26-3 ]

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 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 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 1~1

1
[ 383-63-1 ]
[ 1125828-26-3 ]
[ 1125828-28-5 ]
[ 1125828-30-9 ]
[ 1125828-32-1 ]

Yield	Reaction Conditions	Operation in experiment
62%		The above THF solution was transferred to a jacketed 3L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet. After diluting with THF (800 mL), the water content in the solution was checked by KF (0.053%). To the above solution was added a solution of i-PrMgCl in THF (Aldrich 2 M, 286 mL, 0.572 mol) at 0-10 C. over 1 hours. The resulting solution was stirred for 30 minutes at 10 C. (GC showed the completion of magnesium-bromine exchange reaction). Ethyl trifluoroacetate (74 mL, 0.620 mol) was then added to the Grignard solution between -20 and -10 C. over 45 minutes, slowly warmed to 0 C., and stirred for 30 minutes at the same temperature. The reaction mixture was poured into 2 N HCl (300 mL) at 0 C., and stirred for 30 minutes at room temperature. The organic layer was diluted with MTBE (500 mL), and washed with brine (250 mL) followed by water (250 mL). Solution assay of organic layer was carried out using GC (Compound 5: 67% solution yield, the corresponding regioisomer 6 was present at about 20% relative to 5). The solution was then concentrated under vacuum to 2× solution. To remove water, THF (500 mL) was added, and evaporated to 2× solution. THF addition-concentration was repeated to give a 2× solution. Heptane (500 mL) was added, concentrated to 2× solution to exchange the solvent for recrystallization. Heptane (500 mL) was again added, concentrated to 3.5× solution.The 3.5× heptane solution was then transferred to a 1L 3-neck jacketed round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet. The solution was heated at 60 C., and the resulting homogeneous solution was slowly (1-2 h) cooled to room temperature with stirring, further cooled to 0 C. and stirred for 30 minutes at the same temperature. The crystals were collected and washed with ice-cold heptane (200 mL), dried under vacuum at 50 C. to afford a pale yellow solid (Compound 5, 85.7 g, 99% pure by GC, 62% yield from fluoride 1). M.p.: 83 C. (DSC onset temperature) 1H NMR (400 MHz, CDCl3) delta 7.85 (1H, d, J=2.5 Hz), 7.48 (1H, d, J=1.7 Hz), 7.38 (1H, d, J=8.3 Hz), 7.31 (1H, dd, J=8.1, 1.8 Hz), 6.33 (1H, d, J=2.5 Hz), 2.30 (3H, s); 13C NMR (100 MHz, CDCl3) delta 184.2 (q, JC-F=36.6 Hz), 151.7, 138.7, 138.5, 130.7, 126.4, 125.7, 124.5, 116.8, 116.1 (q, JC-F=289.8 Hz), 109.7, 13.0; 19F NMR (376 MHz, CDCl3) delta=-76.8 (s).
		The above THF solution was transferred to a jacketed 3 L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet. After diluted with THF (800 mL), the water content in the solution was checked by KF (0.053%). To the above solution was added a solution of i-PrMgCl in THF (Aldrich 2 M, 286 mL, 0.572 mol) at 0-10 C. over 1 hours. The resulting solution was stirred for 30 min at 10 C. (GC showed the completion of magnesium-bromine exchange reaction). Ethyl trifluoroacetate (74 mL, 0.620 mol) was then added to the Grignard solution between -20 and -10 C. over 45 minutes, slowly warmed to 0 C., and stirred for 30 min at the same temperature. The reaction mixture was poured into 2 N HCl (300 mL) at 0 C., and stirred for 30 minutes at room temperature. The organic layer was diluted with MTBE (500 mL), and washed with brine (250 mL) followed by water (250 mL). Solution assay of organic layer was carried out using GC (Compound 5: 67% solution yield, the corresponding regioisomer 6 was present at about 20% relative to 5). The solution was then concentrated under vacuum to 2× solution. To remove water, THF (500 mL) was added, and evaporated to 2× solution. THF addition-concentration was repeated to give a 2× solution. Heptane (500 mL) was added, concentrated to 2× solution to exchange the solvent for recrystallization. Heptane (500 mL) was again added, concentrated to 3.5× solution.The 3.5× heptane solution was then transferred to a 1 L 3-neck jacketed round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet. The solution was heated at 60 C., and the resulting homogeneous solution was slowly (1-2 hours) cooled to room temperature with stirring, further cooled to 0 C. and stirred for 30 min at the same temperature. The crystals were collected and washed with ice-cold heptane (200 mL), dried under vacuum at 50 C. to afford a pale yellow solid (Compound 5, 85.7 g, 99% pure by GC, 62% yield from fluoride 1). 1H NMR (400 MHz, CDCl3) delta 7.85 (1H, d, J=2.5 Hz), 7.48 (1H, d, J=1.7 Hz), 7.38 (1H, d, J=8.3 Hz), 7.31 (1H, dd, J=8.1, 1.8 Hz), 6.33 (1H, d, J=2.5 Hz), 2.30 (3H, s); 13C NMR (100 MHz, CDCl3) delta 184.2 (q, JC-F=36.6 Hz), 151.7, 138.7, 138.5, 130.7, 126.4, 125.7, 124.5, 116.8, 116.1 (q, JC-F=289.8 Hz), 109.7, 13.0; 19F NMR (376 MHz, CDCl3) delta=-76.8 (s).

Reference： [1]Patent: US2009/62540,2009,A1 .Location in patent: Page/Page column 7
[2]Patent: US2009/88447,2009,A1 .Location in patent: Page/Page column 4

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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. 1125828-26-3 ]

Quality Control of [ 1125828-26-3 ]

Related Doc. of [ 1125828-26-3 ]

Product Details of [ 1125828-26-3 ]

Computed Properties of [ 1125828-26-3 ]

Safety of [ 1125828-26-3 ]

Application In Synthesis of [ 1125828-26-3 ]

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

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

Related Functional Groups of [ 1125828-26-3 ]

Chlorides

Bromides

Aryls

Related Parent Nucleus of [ 1125828-26-3 ]

Pyrazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1125828-26-3 ]

Related Parent Nucleus of
[ 1125828-26-3 ]