[ CAS No. 886364-94-9 ]

Name: 886364-94-9|5-Bromo-4-methylpicolinaldehyde|97%
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3d Animation Molecule Structure of 886364-94-9

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Quality Control of [ 886364-94-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 886364-94-9 ]

SDS Specification

Alternatived Products of [ 886364-94-9 ]

Product Details of [ 886364-94-9 ]

CAS No. :	886364-94-9	MDL No. :	MFCD07375095
Formula :	C₇H₆BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PKKXSXWOKVKYOW-UHFFFAOYSA-N
M.W :	200.03	Pubchem ID :	59474500
Synonyms :

Calculated chemistry of [ 886364-94-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.29
TPSA :	29.96 Å²

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) :	-6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.36
Log Po/w (XLOGP3) :	1.7
Log Po/w (WLOGP) :	1.96
Log Po/w (MLOGP) :	0.89
Log Po/w (SILICOS-IT) :	2.62
Consensus Log Po/w :	1.71

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.53
Solubility :	0.591 mg/ml ; 0.00296 mol/l
Class :	Soluble
Log S (Ali) :	-1.94
Solubility :	2.27 mg/ml ; 0.0114 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.22
Solubility :	0.121 mg/ml ; 0.000605 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 886364-94-9 ]

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 [ 886364-94-9 ]

* 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 [ 886364-94-9 ]
Downstream synthetic route of [ 886364-94-9 ]

[ 886364-94-9 ] Synthesis Path-Upstream 1~2

1
[ 941294-57-1 ]
[ 68-12-2 ]
[ 886364-94-9 ]

Reference： [1] Patent: WO2011/67272, 2011, A1, . Location in patent: Page/Page column 77
[2] Patent: US2012/238517, 2012, A1, . Location in patent: Page/Page column 36

2
[ 3430-26-0 ]
[ 886364-94-9 ]

Reference： [1] Patent: WO2011/67272, 2011, A1,
[2] Patent: US2012/238517, 2012, A1,

[ 886364-94-9 ] Synthesis Path-Downstream 1~14

2
[ 941294-57-1 ]
[ 68-12-2 ]
[ 886364-94-9 ]

Yield	Reaction Conditions	Operation in experiment
		In an oven-dried flask the compound obtained in Step A (4.67 g) was dissolved in tetrahydrofuran (22 ml). The solution was cooled to -15°C, then isopropyl magnesium bromide (17.2 ml, 15percent solution in THF) was added dropwise at a rate to keep the internal temperature between -15°C to -10°C. The reaction was stirred at this temperature for 1 hour, then anhydrous dimethylformamide (1.8 ml) was added at a rate to keep the internal temperature below 0°C. The reaction was stirred at this temperature for 1 hour, then poured into water and extracted with diethyl ether. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude title aldehyde product (2.4 g, brown solid) was used as such in the next step.
		Step B:5-Bromo-4-methyl-pyridine-2-carbaldehydeIn an oven-dried flask the compound obtained in Step A (4.67 g) was dissolved in tetrahydrofuran (22 ml).The solution was cooled to -15° C., then isopropyl magnesium bromide (17.2 ml, 15percent solution in THF) was added dropwise at a rate to keep the internal temperature between -15° C. to -10° C.The reaction was stirred at this temperature for 1 hour, then anhydrous dimethylformamide (1.8 ml) was added at a rate to keep the internal temperature below 0° C.The reaction was stirred at this temperature for 1 hour, then poured into water and extracted with diethyl ether.The organic layer was dried over sodium sulfate and concentrated in vacuo.The crude title aldehyde product (2.4 g, brown solid) was used as such in the next step.

Reference： [1]Patent: WO2011/67272,2011,A1 .Location in patent: Page/Page column 77
[2]Patent: US2012/238517,2012,A1 .Location in patent: Page/Page column 36

3
[ 3430-26-0 ]
[ 886364-94-9 ]

Reference： [1]Patent: WO2011/67272,2011,A1

4
[ 886364-94-9 ]
[ 1309959-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; at 20℃; for 0.25h;	To a solution of the compound obtained in Step B (3.1 g) in EtOH (47.5 ml) and water (23 ml) were added hydroxylamine hydrochloride (1.4g) and sodium acetate (1.9 g). The reaction was stirred for 15 min at room temperature. The white solid was filtered off and the solution concentrated in vacuo to afford the crude title product (2.2 g, white solid), which was used directly for the next step. LCMS (Method F) 2.09 min, M+H 564/566.
	With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; at 20℃; for 0.25h;	Step C:<strong>[886364-94-9]5-Bromo-4-methyl-pyridine-2-carbaldehyde</strong> oximeTo a solution of the compound obtained in Step B (3.1 g) in EtOH (47.5 ml) and water (23 ml) were added hydroxylamine hydrochloride (1.4 g) and sodium acetate (1.9 g).The reaction was stirred for 15 min at room temperature.The white solid was filtered off and the solution concentrated in vacuo to afford the crude title product (2.2 g, white solid), which was used directly for the next step. LCMS (Method F) 2.09 min, M+H 564/566.

Reference： [1]Patent: WO2011/67272,2011,A1 .Location in patent: Page/Page column 77
[2]Patent: US2012/238517,2012,A1 .Location in patent: Page/Page column 36

5
[ 886364-94-9 ]
[ 1309959-26-9 ]

Reference： [1]Patent: WO2011/67272,2011,A1

6
[ 886364-94-9 ]
[ 1309959-28-1 ]

Reference： [1]Patent: US2012/238517,2012,A1
[2]Patent: WO2011/67272,2011,A1

7
[ 886364-94-9 ]
[ 1309959-27-0 ]

Reference： [1]Patent: US2012/238517,2012,A1
[2]Patent: WO2011/67272,2011,A1

8
[ 24424-99-5 ]
[ 886364-94-9 ]
[ 74-89-5 ]
tert-butyl (5-bromo-4-methylpyridin-2-yl)methyl(methyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		To a solution of <strong>[886364-94-9]5-bromo-4-methylpicolinaldehyde</strong> (1.044 g, 5.22 mmol) in MeOH (20.0 ml) was added 2.0 M methylamine in MeOH (8.0 ml, 16.00 mmol) followed by sodium cyanoborohydride (1.313 g, 20.89 mmol) and acetic acid (1.00 ml, 17.47 mmol). After stirring at room temperature for 90 mins, the reaction was quenched with HCl (6.0 N in water) (25.0 ml, 150 mmol). The mixture was stirred at room temperature for 30 mins, and treated with NaOH (4 N in water) until pH reached 10. The mixture was extracted with Et2O. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was dissolved in CH2Cl2 (30 mL), and treated with Boc-anhydride (1.198 g, 5.49 mmol). After stirring at room temperature for 30 mins, the reaction was concentrated. The residue was purified on silica gel (40 g, 0-100percent EtOAc in hexanes) to give the desired product as a yellow oil (1.101 g, 67percent). LCMS calculated for C13H20BrN2O2 (M+H)+ m/z=315.1; found 315.0.

Reference： [1]Patent: US2018/72741,2018,A1 .Location in patent: Paragraph 0801-0802

9
[ 886364-94-9 ]
N-methyl-1-(4-methyl-5-(3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)pyridin-2-yl)methanamine [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1

10
[ 24424-99-5 ]
[ 886364-94-9 ]
tert-butyl methyl((4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)methyl)carbamate [ No CAS ]

Reference： [1]Patent: US2018/72741,2018,A1

11
[ 886364-94-9 ]
5-bromo-2-(difluoromethyl)-4-methylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20℃;Inert atmosphere;	To the solution of 5-bromo-4-methyl-pyridine-2-carbaldehyde (200 mg, l,00mmol) in DCM (7.7 niL) at -78°C (diethylamino)sulfurtrifluoride (242 mg, 0.198 mL, 1.50 mmol) was added under nitrogen atmosphere. The reaction mixture was allowed to warm up to RT over 4h and stirred at RT overnight. The reaction mixture was quenched with 2 M aq. NaOH and extracted with DCM (3x). The combined organic layers were washed with brine, dried over Na2S04(s) and concentrated at 100 mbar. The resulting crude product (220 mg) was used directly in the next step.

Reference： [1]Patent: WO2019/12037,2019,A1 .Location in patent: Paragraph 0218; 0219; 0220

12
[ 886364-94-9 ]
[ 107-21-1 ]
5-bromo-2-(1,3-dioxolan-2-yl)-4-methylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49.6%	With toluene-4-sulfonic acid; In toluene; at 110℃; for 12h;	To a solution of ethylene glycol (310 mg, 5.00 mmol, 280 pL, 2.00 equiv), 5-bromo-4- methyl-pyridine-2-carbaldehyde (500 mg, 2.50 mmol, 1.00 equiv) in toluene (20.0 mL) was added / oluenesul fonic acid (47.6 mg, 250 pmol, 0.10 equiv). The mixture was stirred at 110 C for 12 h and was subsequently concentrated in vacuo to give a residue. The residue was purified by column chromatography (Si02, petroleum ether/ethyl acetate = 1/0 to 5: 1) to afford 5-bromo- 2-(l, 3-dioxolan-2-yl)-4-methylpyridine (320 mg, 1.24 mmol, 49.6% yield) as a colorless oil. 1H NMR (400MHz, CDCI3) d = 8.64 (s, 1H), 7.42 (s, 1H), 5.80 (s, 1H), 4.19 - 4.14 (m, 2H), 4.10 - 4.05 (m, 2H), 2.42 (s, 3H).

Reference： [1]Patent: WO2019/152419,2019,A1 .Location in patent: Paragraph 0329-0330

13
[ 886364-94-9 ]
2-(1,3-dioxolan-2-yl)-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine [ No CAS ]

Reference： [1]Patent: WO2019/152419,2019,A1

14
[ 886364-94-9 ]
5-(((5-fluoro-2,3-dihydrobenzofuran-4-yl)methyl)amino)-8-(6-formyl-4-methylpyridin-3-yl)imidazo[1,2-c]pyrimidine-2-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2019/152419,2019,A1

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[ 886364-94-9 ]

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P234	Keep only in original container.
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Code	Phrase
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P314	Get medical advice/attention if you feel unwell.
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P321
P322
P330	Rinse mouth.
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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.
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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.
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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.
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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. 886364-94-9 ]

Quality Control of [ 886364-94-9 ]

Related Doc. of [ 886364-94-9 ]

Product Details of [ 886364-94-9 ]

Calculated chemistry of [ 886364-94-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 886364-94-9 ]

Application In Synthesis of [ 886364-94-9 ]

[ 886364-94-9 ] Synthesis Path-Upstream 1~2

[ 886364-94-9 ] Synthesis Path-Downstream 1~14

Related Functional Groups of [ 886364-94-9 ]

Bromides

Aldehydes

Related Parent Nucleus of [ 886364-94-9 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

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[ 886364-94-9 ]

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[ 886364-94-9 ]