[ CAS No. 27063-93-0 ] {[proInfo.proName]}

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Quality Control of [ 27063-93-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 27063-93-0 ]

SDS Specification

Alternatived Products of [ 27063-93-0 ]

Product Details of [ 27063-93-0 ]

CAS No. :	27063-93-0	MDL No. :	MFCD09842453
Formula :	C₇H₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HWSUJPQZGWOXFZ-UHFFFAOYSA-N
M.W :	186.05	Pubchem ID :	14003064
Synonyms :

Calculated chemistry of [ 27063-93-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.87
TPSA :	12.89 ?2

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) :	-5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	2.31
Log Po/w (WLOGP) :	2.46
Log Po/w (MLOGP) :	1.91
Log Po/w (SILICOS-IT) :	2.94
Consensus Log Po/w :	2.34

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.94
Solubility :	0.213 mg/ml ; 0.00114 mol/l
Class :	Soluble
Log S (Ali) :	-2.22
Solubility :	1.12 mg/ml ; 0.00604 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.65
Solubility :	0.0415 mg/ml ; 0.000223 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.35

Safety of [ 27063-93-0 ]

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 [ 27063-93-0 ]

* 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 [ 27063-93-0 ]

[ 27063-93-0 ] Synthesis Path-Downstream 1~12

1
[ 108-47-4 ]
[ 27063-92-9 ]
[ 29976-20-3 ]
[ 27063-93-0 ]

Yield	Reaction Conditions	Operation in experiment
22%; 12%; 35%		Bromination of 2,4-lutidineTo 2,4-lutidine (5.39 mL, 46.7 mmol, 1 eq.) was added oleum (50 mL, containing 20percent free SO3) carefully under stirring at 0 0C. The reaction flask was fitted with a high-efficiency reflux condenser and heated to 165 °C in an oil bath. Bromine (4.3O mL, 83.4 mmol, 0.9 eq.) was added in portions of 0.5 mL over 5 h, and stirring was continued at 155-175 °C for 20 h. The solution was cooled to room temperature, poured on crushed ice (200 g) and stirred for 1 h. The resulting orange solution was neutralised by careful addition of solid Na2CO3, diluted with water and extracted with EtOAc (2 x 250 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by automated flash column chromatography (Biotage KP-Sil.(TM). SNAP 340 g cartridge, 0-15percent EtOAc/hexane) and dried in vacuo to furnish bromolutidines 8, 9 and 10.3,5-Dibromo-2,4-dimethylpyridine 8White solid (1.48 g, 12percent); mp 28-30 °C; 1H NMR deltaH (400 MHz; CDCl3) 2.54 (s, 3H, CH3), 2.61 (s, 3Eta, CH3), 8.41 (s, 1Eta, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 23.8 (CH3), 25.7 (CH3), 120.3 (ArQ, 124.4 (ArQ, 146.4 (ArQ, 148.5 (ArCH), 156.5 (ArQ; IR vmax (filmVcm"1 3045, 2998, 2956, 2921, 1558, 1433, 1376, 1349, 1232, 1049, 993, 928, 783; HRMS (ESI+) for C7H8Br2N requires 263.9018, found (M+H+) 263.9027;5-Bromo-2,4-dimethylpyridine 9Colourless oil (1.89 g, 22percent); 1K NMR deltaH (400 MHz; CDCl3) 2.32 (s, 3H, CH3), 2.44 (s, 3Eta, CH3), 7.00 (s, 1Eta, pyHortho), 8.47 (s, 1Eta, pyHmeta); 13C NMR deltac (100 MHz; CDCl3) 22.1 (CH3), 23.6 (CH3), 120.4 (ArQ, 125.5 (ArCH), 146.7 (ArQ, 150.5 (ArCH), 157.0 (ArQ; IR vmax (filmycm"1 2985, 2957, 2924, 2854, 1592, 1461, 1377, 1353, 1289, 1177, 1032; HRMS (ESI+) for C7H9BrN requires 185.9913, found (M+H+) 185.9918;3-Bromo-2,4-dimethyIpyridine 10Colourless oil (3.04 g, 35percent); 1U NMR deltaH (400 MHz; CDCl3) 2.33 (s, 3H, CH3), 2.61 (s, 3Eta, CH3), 6.91 (d, J=5.0 Hz, IH, pyHmeta), 8.18 (d, J=5.0 Hz, IH, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 23.2 (CH3), 25.7 (CH3), 123.4 (ArCH), 124.3 (ArQ, 146.7 (ArCH), 147.3 (ArQ, 157.4 (ArQ; IR vmax (filn^/cm-1 3050, 2995, 2958, 2922, 1585, 1437, 1389, 1123, 1024, 916, 825; HRMS (ESI+) for C7H9BrN requires 185.9913, found (M+H+) 185.9917;

Reference： [1]Zeitschrift fur Chemie,1988,vol. 28,p. 59 - 60
[2]Zeitschrift fur Chemie,1988,vol. 28,p. 59 - 60
[3]Patent: WO2010/43866,2010,A2 .Location in patent: Page/Page column 48; 87-88
[4]Organic and Biomolecular Chemistry,2011,vol. 9,p. 127 - 135

3
[ 108-47-4 ]
[ 27063-92-9 ]
[ 27063-93-0 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine;	Example 1 Preparation of 5-bromo-2,4-dimethylpyridine STR13 150 ml of 65percent strength oleum are added dropwise to 28.9 ml of 2,4-dimethylpyridine, while cooling with ice and stirring, such that the temperature does not rise above 35° C. When the solution has become homogeneous, 6.42 ml of bromine are slowly added dropwise, with stirring. The mixture is stirred at 80° C. for 31/2 hours. After cooling, it is carefully added dropwise to 1 kg of ice, neutralized with solid Na2 CO3 and extracted 3 times with 300 ml of ether each time. The organic layer is separated off and dried over magnesium sulfate. After removal of the solvent by distillation in vacuo, 34.6 g of a pale yellow oil consisting of the isomers 5-bromo-2,4-dimethylpyridine and 3-bromo-2,4-dimethylpyridine are obtained.

Reference： [1]Patent: US5004748,1991,A

4
[ 27063-93-0 ]
[ 27063-92-9 ]

Yield	Reaction Conditions	Operation in experiment
		The isomers are separated by column chromatography on silicon dioxide gel to give 10 g of 5-bromo-2,4-dimethylpyridine as a colorless liquid (13.0 g of <strong>[27063-93-0]3-bromo-2,4-dimethylpyridine</strong>). Yield: 22percent.

Reference： [1]Patent: US5004748,1991,A

5
[ 108-47-4 ]
iron(II) sulfate [ No CAS ]
[ 27063-92-9 ]
[ 27063-93-0 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine;	(a) Oleum (65percent, 600 ml) was carefully added to cold 2,4-dimethylpyridine (107.4 g). Bromine (80 g) was added and the mixture was heated for 20 hours at 55°, allowed to cool and poured on to ice. The mixture was neutralised with aqueous sodium hydroxide and extracted with ether. The ether extracts were stirred with ferrous sulphate overnight, evaporated and the residue was distilled to give a mixture of 3-bromo-2,4-dimethylpyridine and 5-bromo-2,4-dimethylpyridine (66.6 g, b.p. 88°-90° at 11 mm Hg).

Reference： [1]Patent: US4154834,1979,A

6
[ 27063-93-0 ]
[ 1222184-73-7 ]

Yield	Reaction Conditions	Operation in experiment
		Dimethyl 3-bromopyridine-2,4-dicarboxylate 113-Bromo-2,4-lutidine 10 (7.00 g, 38 mmol, 1 eq.) and water (100 mL) were heated to 100 0C, and a solution of NaOH (1.05 g, 26 mmol, 0.7 eq.) in water (15O mL) was added. KMnO4 (29.7 g, 188 mmol, 5 eq.) was then added in portions over 30 min under vigorous stirring. The resulting dark suspension was stirred under reflux until the colour of KMnO4 had vanished completely (2-3 h, determined in 3 independent experiments). The hot solution was filtered and solids washed with hot water (3 * 50 mL). The filtrate was concentrated to ca. 50 mL in vacuo and neutralised with cone. H2SO4. The solution was concentrated in vacuo, the residue was coevaporated with toluene and suspended in MeOH (200 mL). Cone. H2SO4 (10 mL) was added, the resulting suspension was refluxed overnight and then cooled to room temperature and concentrated in vacuo. The residue was taken up in water, the pH was adjusted to pH 9 by careful addition Of Na2CO3 and the basic solution was extracted with EtOAc (3 x 100 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo. The residue was purified by automated column chromatography (Biotage KP-SIL.(TM). SNAP 100 g cartridge) to afford 11 (4.62 g, 45percent) as a white solid.1H NMR deltaH (400 MHz; CDCl3) 3.98 (s, 3H, OCH3), 4.01 (s, 3Eta, OCH3), 7.60 (d, J=5.0 Hz, IH, pytfortho), 8.64 (d, J=5.0 Hz, IH, pyHmeta); 13C NMR deltac (100 MHz; CDCl3) 53.2 (CH3), 53.3 (CH3), 115.6 (ArC), 125.2 (ArCH), 142.1 (ArC), 148.0 (ArCH), 152.4 (ArC), 164.9 (CO), 165.4 (CO); IR vmax (KBr diskycm"1 3019, 2958, 1743, 1449, 1421, 1279, 1202, 1171; HRMS (ESI+) for C9H8BrNNaO4 requires 295.9529, found (M+Na+) 295.9524; Microanalysis for C9H8BrNO4 requires C 39.44, H 2.94, N 5.11; found C 39.54, H 2.95, N 5.02;

Reference： [1]Patent: WO2010/43866,2010,A2 .Location in patent: Page/Page column 48; 89-90
[2]Organic and Biomolecular Chemistry,2011,vol. 9,p. 127 - 135

7
[ 29976-20-3 ]
[ 27063-92-9 ]
[ 27063-93-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 127 - 135

8
[ 73183-34-3 ]
[ 27063-93-0 ]
[ 1421252-89-2 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 95℃; for 16.0h;	Example 22,4-Dimethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine.To a solution of 3-bronio-2,4-diniethylpyridine (476 nig, 2.56 mmol) in DMSO (14 mL) was added bis(pinocolato) diboron (3.25 g, 12.8 mmol), potassium acetate (1.26 g, 12.8 mmol) andPdCl2(dppf)-CH2Cl2 adduct (209 mg, 0.256 mmol). Reaction was heated at 95°C for 16 h. Water was added and the aqueous phase was extracted with EtOAc (3x). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduce pressure. The residue was purified via FCC (40-70percent EtOAc/heptane) to give the title compound. lH NMR (400 MHz, CDC13) delta ppm 8.35 (d, J=5.1 Hz, 1 H), 6.91 (d, J=5.1 Hz, 1 H), 2.64 (s, 3 H), 2.42 (s, 3 H); 1.43 (s, 12 H); MS (ESI+) m/z 234 A (M+H)+.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 5.0h;Inert atmosphere;	A mixture of <strong>[27063-93-0]3-bromo-2,4-dimethyl-pyridine</strong> (500 mg, 2.69 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (1023 mg, 4.03 mmol), Pd(dppf)Cl2 (219 mg, 0.27 mmol), and potassium acetate (526 mg, 5.37 mmol) in 1,4-dioxane (15 mL) was stirred at 110° C. under N2 for 5 hours. The mixture was used in the next step directly without any purification. LCMS (ESI): [M+H]+=234.1.

Reference： [1]Patent: WO2013/16197,2013,A1 .Location in patent: Page/Page column 77-78
[2]Patent: US2018/282328,2018,A1 .Location in patent: Paragraph 1006; 1007

9
4-(2-cyclopropyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-5-yl)-3,5-dimethylisoxazole [ No CAS ]
[ 76-05-1 ]
[ 27063-93-0 ]
4-(2-cyclopropyl-7-(2,4-dimethylpyridin-3-yl)-1H-benzo[d]imidazol-5-yl)-3,5-dimethylisoxazole trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34 mg		Crude 4-(2-cyclopropyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-5-yl)-3,5-dimethylisoxazole (280 mg crude mixture, 0.2 mmol) from the previous step was added to a 0.5 to 2 mL Smith process vial equipped with a stir bar. To the reaction vessel was added <strong>[27063-93-0]3-bromo-2,4-dimethylpyridine</strong> (112 mg, 0.6 mmol), potassium carbonate (276 mg, 2 mmol), PEPPSI-IPr catalyst (13.6 mg, 0.02 mmol), 1,4-dioxane (0.8 mL) and water (0.2 mL). The reaction mixture was heated in a microwave reactor for 45 minutes at 135° C., then the organic layer was removed by syringe, filtered, and directly injected onto preparative reverse phase high performance liquid chromatography (Phenomenex Gemini C18 column, 5percent to 50percent gradient acetonitrile in water with 0.1percent TFA) to give 4-(2-cyclopropyl-7-(2,4-dimethylpyridin-3-yl)-1H-benzo[d]imidazol-5-yl)-3,5-dimethylisoxazole (34 mg) as a TFA salt. C22H22N4O. 359.2 (M+1). 1H NMR (400 MHz, CD3OD) delta 8.69 (d, J=6.2 Hz, 1H), 7.94 (d, J=6.2 Hz, 1H), 7.79 (d, J=1.4 Hz, 1H), 7.44 (d, J=1.4 Hz, 1H), 2.50 (s, 3H), 2.49-2.40 (m, 4H), 2.36 (s, 3H), 2.30 (s, 3H), 1.57-1.46 (m, 2H), 1.46-1.37 (m, 2H)

Reference： [1]Patent: US2014/336190,2014,A1 .Location in patent: Paragraph 0459; 0461; 0462

10
[ 27063-93-0 ]
(+/-)-cis-N-[8-amino-6-(2,4-dimethyl-3-pyridyl)-2,7-naphthyridin-3-yl]-2-fluorocyclopropanecarboxamide [ No CAS ]

Reference： [1]Patent: US2018/282328,2018,A1

11
[ 27063-93-0 ]
3-bromo-4-methyl-2-(((1-methyl-1H-pyrazol-4-yl)oxy)methyl)pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 5855 - 5862

12
[ 27063-93-0 ]
1,9-dimethyl-1,5-dihydropyrazolo[3′,4′:5,6]pyrano[3,4-b]pyridine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 5855 - 5862

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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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. 27063-93-0 ] {[proInfo.proName]}

Quality Control of [ 27063-93-0 ]

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Product Details of [ 27063-93-0 ]

Calculated chemistry of [ 27063-93-0 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 27063-93-0 ]

Application In Synthesis of [ 27063-93-0 ]

[ 27063-93-0 ] Synthesis Path-Downstream 1~12

Technical Information

Related Functional Groups of [ 27063-93-0 ]

Bromides

Related Parent Nucleus of [ 27063-93-0 ]

Pyridines

Precautionary Statements-General

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Physical hazards

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[ 27063-93-0 ]

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[ 27063-93-0 ]