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Quality Control of [ 142404-82-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 142404-82-8 ]

SDS Specification

Alternatived Products of [ 142404-82-8 ]

Product Details of [ 142404-82-8 ]

CAS No. :	142404-82-8	MDL No. :	MFCD06798092
Formula :	C₈H₉BrN₂O	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	WVJCOPBDWMWUNP-UHFFFAOYSA-N
M.W :	229.07	Pubchem ID :	15179563
Synonyms :

Safety of [ 142404-82-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 142404-82-8 ]

* 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.

Downstream synthetic route of [ 142404-82-8 ]

[ 142404-82-8 ] Synthesis Path-Downstream 1~15

1
[ 98198-48-2 ]
[ 108-24-7 ]
[ 142404-82-8 ]

Yield	Reaction Conditions	Operation in experiment
		5-bromo-4-methylpyridin-2-amine (0.578 mmol) was dissolved in acetic anhydride (5.78 mmol) and heated at 1 10 C for 30 minutes. The reaction was quenched with ice. The aqueous reaction mixture neutralized with sodium hydroxide solution was extracted with ethyl acetate. The ethyl acetate layer was separated and dried over sodium sulfate. The organic layer was evaporated to dryness. The crude material was purified (silica column, MeOH/CHCL). 1HNMR (300MHz, DMSO-d6): 10.53 (s, 1H), 8.34 (s, 1H), 8.06 (s, 1H), 2.30 (s, 3H), 2.05 (s, 3H); MS (m/z): 231 (M+2)+.

Reference： [1]Advanced Synthesis and Catalysis,1996,vol. 338,p. 663 - 666
[2]Patent: WO2012/7926,2012,A1 .Location in patent: Page/Page column 79

2
[ 5327-32-2 ]
2-acetamido-4-methylpyridinium hydrobromide perbromide [ No CAS ]
[ 142404-82-8 ]

Yield	Reaction Conditions	Operation in experiment
88%; 83.1%	With bromine; In dichloromethane;	Into a 100 ml three-neck flask, 5.0 g (0.033 mol) of Ia was introduced. Then, 15 ml of dichloromethane was added thereto so as to dissolve Ia. Thereafter, 5.34 g (0.33 mol) of bromine was added dropwise thereto. An orange-colored slurry was formed. After being stirred overnight at room temperature, the slurry was filtered under reduced pressure. When the cake obtained by the filtration was dried, 5.5 g (yield: 88%) of IIIa was obtained. After the pH of the mother liquor after the filtration under reduced temperature was adjusted to 9-10 with 5% sodium hydroxide aqueous solution, an organic layer was separated therefrom. When the solvent was evaporated away, 3.14 g (yield: 83.1%) of IIa was obtained as a slightly brown crystal.
88%; 83.1%	With bromine; In dichloromethane;	Into a 100ml three-neck flask, 5.0g (0.033mol) of Ia was introduced. Then, 15ml of dichloromethane was added thereto so as to dissolve Ia. Thereafter, 5.34g (0.33mol) of bromine was added dropwise thereto. An orange-colored slurry was formed. After being stirred overnight at room temperature, the slurry was filtered under reduced pressure. When the cake obtained by the filtration was dried, 5.5g (yield: 88%) of IIIa was obtained. After the pH of the mother liquor after the filtration under reduced temperature was adjusted to 9-10 with 5% sodium hydroxide aqueous solution, an organic layer was separated therefrom. When the solvent was evaporated away, 3.14g (yield: 83.1%) of IIa was obtained as a slightly brown crystal.

Reference： [1]Patent: US5290943,1994,A
[2]Patent: EP530524,1993,A1

3
[ 5327-32-2 ]
[ 142404-82-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0℃; for 0.5h;	(2); N-Bromosuccinimide (6.8 mmol, 1.2 g) was added to a N'N- dimethylformamide solution (20 ml) of 2-(acetylamino)-4-picoline (6.7 mmol, 1 g) at 0C, followed by stirring at the same temperature for 30 minutes. Water (20 ml) was added to the resulting reaction mixture on ice to stop the reaction, and an aqueous layer was extracted with diethyl ether five times. An organic layer was dried over anhydrous sodium sulfate, and filtered, followed by distilling away a solvent under reduced pressure. The resulting crude product was purified with column chromatography to obtain 1.25 g of 2-(acetylamino)-5-bromo-4-picoline (yield 82%). 1H NMR δ ppm (300 MHz, CDCl3) data of this compound are 8.27 (s, IH), 8.13 (s, IH), 7.85 (brs, IH), 2.41 (s, 3H), 2.20 (s, 3H).
	With bromine; In CH3 CO2 Na; water;	Example 9 Single step synthesis of 2-acetamido-4-methyl-5-bromopyridine (IIa) by bromination of 2-acetamido-4-methylpyridine (Ia) in aqueous solution of sodium acetate (CH3 CO2 Na) Into a 300 ml three-neck flask, 155 ml of water was introduced and then a solution in which 12.3 g (0.15 mol) of CH3 CO2 Na has been dissolved in 25 ml of water was added thereto. The pH at this moment was 8.8. Then, 9.0 g (0.06 mol) of 2-acetamido-4-methylpyridine (Ia) was added thereto and dispersed therein. Thereafter, 9.6 g (0.06 mol) of bromine was added dropwise thereto for 12 minutes at 19-24 C. After being stirred overnight, the mixture was filtered under reduced pressure. The cake obtained by the filtration was washed with water.

Reference： [1]Patent: WO2009/88103,2009,A1 .Location in patent: Page/Page column 15
[2]Patent: US5290943,1994,A
[3]Organic Process Research and Development,2017,vol. 21,p. 1095 - 1109

4
2-acetamido-4-methylpyridinium hydrobromide perbromide [ No CAS ]
[ 142404-82-8 ]
[ 5327-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	In water;	While being stirred at room temperature, 97.1g of the above-obtained mixture of IIa and IIIa was added thereto. After being heated on a hot water bath and reacted for two hours at 38C, the reaction mixture was further reacted overnight at room temperature and then reacted for two hours on a hot bath at 45C. The color of the slurry gradually changed from orange to yellow. After being cooled to room temperature, the pH of the slurry was adjusted to 4.96 with 5% NaOH aqueous solution. Then, it was filtered under reduced pressure. The cake obtained by the filtration was washed with 40ml of water. When the washed cake was dried, 62.4g of IIa was obtained as pale brown powder.

Reference： [1]Patent: EP530524,1993,A1

5
[ 17997-47-6 ]
[ 142404-82-8 ]
[ 1058728-83-8 ]

Reference： [1]Chemical Communications,2008,p. 3558 - 3560

6
[ 142404-82-8 ]
[ 1111637-72-9 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of 6-acetamido-4-methylpyridin-3-ylboronic acid (73)To a stirred solution of the 2-acetylamino-5-bromo-4-methylpyridine (1.858g, 8.11 mmol) and boron isopropoxide (7.5ml, 32.4mmol) in THF cooled to -780C was added n-butyl lithium (4.1 ml, 41mmol of 10 M soln in hexanes). After 1 hour at -780C, the reaction was quenched with water and warmed to room temperature. THF was removed under reduced pressure. Added 2N HCI until a precipitate developed. Filtered and washed with a minimal amount of water and dried under vacuum. 1 H NMR (400 MHz, DMSO-d6) d ppm 2.07 (s, 3 H) 2.39 (s, 3 H) 7.84 (s, 1 H) 8.09 (s, 2 H) 8.33 (s, 1 H) 10.36 (s, 1 H).

Reference： [1]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 52

7
[ 123324-71-0 ]
[ 142404-82-8 ]
[ 1171975-45-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; at 20 - 90℃;	(3); 4-t-Butylphenyl boronic acid (7.21 mmol, 1.28 g),Tris(dibenzylideneacetone)dipalladium(0) (0.20 mmol, 180 mg), tricyclohexylphosphine (1.31 mmol, 368 mg) and cesium carbonate (19.66 mmol, 6.41 g) were successively added to a dioxane solution (30 ml) of 2-(acetylamino)-amino-5- bromo-4-picoline (6.55 mmol, 1.5 g) at room temperature, and the temperature was elevated to 90C, followed by stirring for 9.5 hours. Water (30 ml) was added to the resulting reaction mixture on ice to stop the reaction, and an aqueous layer was extracted with ethyl acetate. An organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and filtered, followed by distilling away a solvent under reduced pressure. The resulting crude product was purified with column chromatography to obtain 1.58 g of 2-(acetylamino)-amino-5-(4-t-butylphenyl)-4- picoline (yield 85%). 1H NMR δ ppm (300 MHz, CDCl3) data of this compound are 8.10 (s, IH), 8.09 (s, IH), 7.98 (brs, IH), 7.45 (d, 2H, J=8.4Hz), 7.23 (d, 2H, J=8.7 Hz), <n="17"/>2.33 (s, 3H), 2.22 (s, 3H), 1.36 (s, 9H).

Reference： [1]Patent: WO2009/88103,2009,A1 .Location in patent: Page/Page column 15-16

8
[ 1356035-56-7 ]
[ 142404-82-8 ]
[ 1356035-34-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 111℃; for 0.13333299999999998h;Microwave irradiation;	To the stirred solution 2-(cyanoimino)-l-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-2,3- dihydro-lH-imidazo[4,5-c]quinolin-8-ylboronic acid (0.390 mmol) in dry DMF (5 mL) was added <strong>[142404-82-8]N-(5-bromo-4-methylpyridin-2-yl)acetamide</strong> (0.390 mmol) followed by catalyst palladium dichlorobis triphenylphosphine (0.039 mmol). Saturated solution of sodium carbonate (0.780 mmol) was added to it and the resulting solution was heated to 1 1 1 C for 8 minutes in microwave. Solvent was evaporated and the crude material was extracted in EtOAc, washed with brine several times and dried over anhydrous Na2S04. The solvent was evaporated and the crude solid was purified (silica gel column, CHC?/MeOH as eluent) to obtain the title compound. .H NMR (300 MHz, DMSO-d6): δ 10.46 (s, 1H), 9.26 (s, 1H), 9.02 (d, J=2.4 Hz, 1H), 8.35 (dd, J= 2.4, 8.4 Hz, 1H), 8.17 (d, J=8.7 Hz, 1H), 7.91 (m, 3H), 7.70 (dd, J=1.8, 8.7 Hz, 1H), 6.60 (s, 1H), 3.90 (s, 3H), 2.08 (s, 3H), 2.00 (s, 3H), 1.70 (s, 6H); MS (m/z): 516 (M+l)+.

Reference： [1]Patent: WO2012/7926,2012,A1 .Location in patent: Page/Page column 79; 80

9
[ 142404-82-8 ]
[ 100367-40-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid;	Next, this compound is reacted with nitric acid and sulfuric acid to produce

Reference： [1]Patent: WO2012/106189,2012,A1 .Location in patent: Page/Page column 13-14
[2]Organic Process Research and Development,2017,vol. 21,p. 1095 - 1109

10
[ 142404-82-8 ]
[ 676491-46-6 ]

Reference： [1]Patent: WO2012/106189,2012,A1

11
[ 142404-82-8 ]
[ 701214-00-8 ]

12
[ 142404-82-8 ]
[ 452296-79-6 ]

Reference： [1]Patent: WO2012/106189,2012,A1

13
[ 142404-82-8 ]
(3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl di-tert-butyl phosphate [ No CAS ]

Reference： [1]Patent: WO2012/106189,2012,A1
[2]Organic Process Research and Development,2017,vol. 21,p. 1095 - 1109
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14
[ 142404-82-8 ]
1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl hydrogen phosphate [ No CAS ]

15
[ 142404-82-8 ]
[ 884495-14-1 ]

Reference： [1]Patent: WO2012/106189,2012,A1
[2]Organic Process Research and Development,2017,vol. 21,p. 1095 - 1109

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Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? Mannich Reaction ? Petasis Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Ugi Reaction

Historical Records

Related Functional Groups of
[ 142404-82-8 ]

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P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
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.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
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.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
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. 142404-82-8 ] {[proInfo.proName]}

Quality Control of [ 142404-82-8 ]

Related Doc. of [ 142404-82-8 ]

Product Details of [ 142404-82-8 ]

Safety of [ 142404-82-8 ]

Application In Synthesis of [ 142404-82-8 ]

[ 142404-82-8 ] Synthesis Path-Downstream 1~15

Technical Information

Related Functional Groups of [ 142404-82-8 ]

Bromides

Amides

Amines

Related Parent Nucleus of [ 142404-82-8 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 142404-82-8 ]

Related Parent Nucleus of
[ 142404-82-8 ]