[ CAS No. 7745-93-9 ] {[proInfo.proName]}

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Quality Control of [ 7745-93-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7745-93-9 ]

SDS Specification

Alternatived Products of [ 7745-93-9 ]

Product Details of [ 7745-93-9 ]

CAS No. :	7745-93-9	MDL No. :	MFCD00007195
Formula :	C₇H₆BrNO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	XFZFJQHXWJIBQV-UHFFFAOYSA-N
M.W :	216.03	Pubchem ID :	82189
Synonyms :

Calculated chemistry of [ 7745-93-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
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 :	47.93
TPSA :	45.82 ?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) :	-5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	3.24
Log Po/w (WLOGP) :	2.67
Log Po/w (MLOGP) :	2.77
Log Po/w (SILICOS-IT) :	0.8
Consensus Log Po/w :	2.27

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.56
Solubility :	0.0597 mg/ml ; 0.000277 mol/l
Class :	Soluble
Log S (Ali) :	-3.88
Solubility :	0.0288 mg/ml ; 0.000133 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.02
Solubility :	0.204 mg/ml ; 0.000946 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.9

Safety of [ 7745-93-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7745-93-9 ]

* 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 [ 7745-93-9 ]
Downstream synthetic route of [ 7745-93-9 ]

[ 7745-93-9 ] Synthesis Path-Upstream 1~2

1
[ 7745-93-9 ]
[ 1008-95-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 12, p. 2059 - 2063

2
[ 7745-93-9 ]
[ 26670-89-3 ]

Reference： [1] Chemische Berichte, 1896, vol. 29, p. 1410

[ 7745-93-9 ] Synthesis Path-Downstream 1~9

1
[ 7745-93-9 ]
[ 27139-97-5 ]

Reference： [1]Tetrahedron,1988,vol. 44,p. 6525 - 6536

2
[ 7745-93-9 ]
[ 102169-44-8 ]

Reference： [1]Journal of the Chemical Society,1953,p. 2816,2819

3
[ 7745-93-9 ]
[ 458532-98-4 ]
[ 611225-98-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethylene glycol dimethyl ether; water; at 90℃; for 16.5h;	Step 1.Synthesis of 3-chloro-4-(2-methyl-5-nitrophenyl)pyridine nitrogen was bubbled through a solution of 2-bromo-1-methyl-4-nitrobenzene (1 eq) in dimethoxyethane and water (3:1) for 0.5 h. bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by 3-chloro-4-pyridine boronic acid hydrate (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to 90 C. for 16 h under nitrogen.The reaction mixture was concentrated and partitioned between ethyl acetate and water.The organic layer was washed with brine and dried with sodium sulfate and concentrated.Purification on silica gel gave 3-chloro-4-(2-methyl-5-nitrophenyl)pyridine. MS: MH+=248.

Reference： [1]Patent: US2004/122237,2004,A1 .Location in patent: Page 201

4
[ 7745-93-9 ]
[ 557-21-1 ]
[ 939-83-3 ]

Yield	Reaction Conditions	Operation in experiment
42%	tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; for 24.0h;	A mixture of compound 1 (250.0 g, 1.16 mol), Zn(CN)2 (135.0 g, 1.16 mol) and Pd(PPh3)4 (25 g, 0.02 mol) in dry DMF (1500 mL) was stirred at 80 C for 24 hours under N2. TLC (petroleum ether: ethyl acetate = 10:1) showed the reaction was complete, then the mixture was poured into toluene (1500 mL) and washed with 2 N NH3 H2O (800 mLx2). The aqueous layer was extracted with toluene (800 mLx2). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give crude product, which was purified by column chromatography (first petroleum ether, then petroleum ether: ethyl acetate 10:1) to afford compound 2 (25.5 g, yield: 42%) as a grey solid and recover compound 1 (170 g) as yellow solid.1H NMR (300 MHz, CDCI3): delta 8.46-8.47 (d, J = 3.0 Hz, 1 H), 8.31-8.34 (dd, J = 9.0 Hz, 1 H), 7.53-7.56 (d, J = 9.0 Hz, 1 H), 2.68 (s, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6273 - 6278
[2]Patent: WO2006/117669,2006,A1 .Location in patent: Page/Page column 41; 113

5
[ 7745-93-9 ]
[ 66521-66-2 ]
[ 152460-09-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	With copper(l) iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 120℃; for 0.5h;Microwave irradiation;	The mixture of 4-(Pyridin-3-yl) pyrimidin-2- amine (0.378 g,2.2 mmol), copper iodide (0.5 mmol) and anhydrous K2CO3(4 mmol), Dioxane (5 mL), 2-bromo-1-methyl-4- nitrobenzene(2 mmol), and DMEDA (0.5 mmol) was irradiated in the microwave synthesizer and heated at 120 C for 30 min. After completion of the reaction, ammonium hydroxide and brine solution was added andthen extracted with ethyl acetate. The organic layer was dried overanhydrous sodium sulphate, the solvent was evaporated in buchirotary evaporator and the resulting solid was dried under vacuum.The crude was purified by using silica gel column chromatographyusing ethyl acetate: chloroform (50:50) to yield 0.498 g (79.0percent) ofthe imatinib intermediate compound as yellowish powder. Melting point194-196 °C. ES-MS (M1) found (m/z): 308.1. 1H NMR (DMSOd6):2.49(S, 3H); 7.32-7.37 (m, 1H); 7.40-7.48 (m, 1H); 7.49e7.51(m, 1H); 7.85-7.88 (m, 1H); 8.02 (m, 1H); 8.48-8.51 (m, 1H);8.57-8.59 (m, 1H); 9.20(S, 1H); 9.29 (S, 1H).
60%	With copper(l) iodide; potassium carbonate; potassium iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 110℃; for 24h;Inert atmosphere; Schlenk technique;	4-(Pyridine-3-yl) pyridine-2-amine (8.60 g, 0.05 mol), CuI (2.39 g, 0.0125 mmol), anhydrous K2CO3 (14.0 g, 0.1 mol), KI (2.08 g, 0.0125 mol) were added to a Schlenk-type three-neck flask fitted with a thermometer, magnetic stirbar, and septum. The flask was evacuated and back filled with N2 three times. Dioxane (250 mL) and 2-bromo-4-nitrotoluene (9.82 g, 0.045 mol) were added to the flask. Finally, N,N'-dimethylethylenediamine (1.10 g, 0.0125 mol) was added by syringe at room temperature with stirring. The reaction mixture was stirred at 110° C. under N2 for 24 hours and then cooled to room temperature. Ammonia (30percent, 100 mL) and saturated NaCl (400 mL), were added to the reaction mixture which was then extracted with ethyl acetate (500 mL*3). The organic phase was dried over Na2SO4 and a yellow solid was obtained after the solvent was removed under reduced pressure. The crude product was purified by column chromatography (biotage: DMC/Methanol, 1-8percent, 20 CV). The desired product was obtained as a yellow solid (8.3 g, yield: 60percent); 1H NMR (500 MHz, CDCl3) delta 2.49 (s, 3H), 7.36 (m, 1H), 7.15 (br., 1H), 7.35 (d, 1H), 7.38 (d, 1H), 7.52 (m, 1H), 7.88 (d, 1H), 8.55 (d, 1H), 8.60 (d, 1H), 8.76 (d, 1H), 9.28 (s, 1H), 9.50 (s, 1H). LC-MS (m/z) calculated, 307.3, found, 308.3 [M+H]+.
	With potassium tert-butylate; In dimethyl sulfoxide; at 120℃; for 12h;	2-bromo-1-methyl-4-nitrobenzene(0.63 g, 2.9 mmol), <strong>[66521-66-2]4-(pyridin-3-yl)pyrimidin-2-amine</strong> (1) (0.60 g, 3.5 mmol), and KOtBu(0.49 g, 4.40 mmol) was added flask containing PS-CuO (57.5 mg, 20 wtpercent of CuOin PS, 0.145 mmol based on Cu) in 15 mL DMSO. The resulting mixture was heatedto 120oC and stirred for 12 h. Aftercooling, the mixture was poured into EtOAc (20.0 mL) and washed with water (2 × 10.0 mL).The organic layer was separated and dried over MgSO4, and thenevaporated under reduced pressure. The resulting mixture was reacted with stannouschloride (1.64 g, 8.70 mmol) and 1.64 mL of Con. HCl in MeOH (10 mL) at at 50 oCfor 8 h. After completion the reaction mixture was poured into crushed ice followedby basification with sodium bicarbonate. The layer was separated and dried overanhydrous MgSO4, evaporated under reduced pressure to afford the crudeproduct which was purified by using column chromatography(hexane : EtOAc = 4:1) obtainedas yellow solid 67percent (0.54 g, 1.95 mmol).1HNMR (300 MHz, CDCl3) delta 9.25 (dd, J= 1.5 Hz, 1H), 8.71 (dd, J1= 3.3 Hz, J2 = 1.5 Hz,1H), 8.48 (d, J = 5.1 Hz, 1H), 8.35-8.31(m, 1H), 7.59 (d, J = 2.1 Hz,? 1H), 7.43 ? 7.38 (m, 1H), 7.12 (d, J = 5.4Hz,1H) 7.03(bs, 1H), 6.98 (d, J = 8.1 Hz, 1H), 6.41 (dd, , J1 = 5.7 Hz, J2= 2.4 Hz, 1H), 3.59(bs, 2H), 2.24(s, 3H). 13C NMR (75 MHz, CDCl3): delta 162.5, 160.7, 159.0, 151.4, 148.5, 145.1,137.9, 134.4, 132.7, 131.0, 123.5, 118.1, 110.6, 108.4, 108.0 HRMS(ESI) calcd. for C16H16N5 [M+H]+ 278.1406, found 278.1400.

Reference： [1]RSC Advances,2015,vol. 5,p. 20516 - 20520
[2]Organic and Biomolecular Chemistry,2009,vol. 7,p. 5129 - 5136
[3]Chemical Communications,2010,vol. 46,p. 1118 - 1120
[4]Angewandte Chemie - International Edition,2013,vol. 52,p. 8551 - 8556
    Angew. Chem.,2013,vol. 125,p. 8713 - 8718,6
[5]European Journal of Organic Chemistry,2007,p. 6084 - 6088
[6]Organic Process Research and Development,2008,vol. 12,p. 490 - 495
[7]Angewandte Chemie - International Edition,2015,vol. 54,p. 179 - 183
    Angew. Chem.,2015,vol. 127,p. 181 - 185,5
    Angewandte Chemie,2015,vol. 127,p. 181 - 185,5
[8]Journal of Molecular Structure,2018,vol. 1171,p. 541 - 550
[9]Patent: US9095622,2015,B2 .Location in patent: Page/Page column 32
[10]Archiv der Pharmazie,2017,vol. 350
[11]ChemMedChem,2011,vol. 6,p. 2009 - 2018
[12]Tetrahedron Letters,2012,vol. 53,p. 6657 - 6661

6
[ 7745-93-9 ]
[ 98545-64-3 ]

Reference： [1]Chinese Chemical Letters,2011,vol. 22,p. 1411 - 1414
[2]European Journal of Medicinal Chemistry,2014,vol. 81,p. 59 - 75

7
[ 7745-93-9 ]
[ 105-56-6 ]
[ 939-83-3 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3644 - 3647

8
[ 7745-93-9 ]
[ 404844-11-7 ]

Reference： [1]Organic Process Research and Development,2008,vol. 12,p. 490 - 495

9
[ 7745-93-9 ]
[ 66521-66-2 ]
[ 152460-10-1 ]

Yield	Reaction Conditions	Operation in experiment
83%		In a dried schlenk flask (25mL in volume) equipped with a stirring bar were placed with 2-bromo-4-nitrotoluene (54.0mg, 0.25mmol, 1.0 eq.), and <strong>[66521-66-2]4-(3-pyridinyl)-2-pyrimidine amine</strong> (43.0 mg, 0.25mmol, 1.0 eq.), Pd2(dba)3 (11.5mg, 0.0125mmol, 5molpercent), BINAP (18.7mg, 0.03mmol, 12molpercent), Cs2CO3 (163.0mg, 0.5mmol, 2.0 eq.). After evacuation and refill with dry nitrogen for three times, dioxane (3.0mL) was added with syringes under a stream of nitrogen. The resulting mixture was allowed to stir at 100°C for 24h, and dioxane was removed. Then, B2pin2 (1.0mmol, 4.0 eq.) and KOt-Bu (0.5mmol, 2.0 eq.) in 1.0mL iPrOH was added and the mixture was then stirred in the preheated oil bath at 110°C for 4h. Purification by flash chromatography on silica gel using dichloromethane: methanol=50: 1.8 was obtained as yellow solid (57.5mg, isolated yield 83percent). When expanded to 1.0mmol, 0.208g product can be obtained, yield 75percent. Melting point (°C): 133.0?135.0; 1H NMR (400MHz, DMSO?d6) delta 9.27 (dd, J=2.0, 0.4Hz, 1H), 8.73?8.68 (m, 2H), 8.48 (d, J=4.8Hz, 1H), 8.44?8.39 (m, 1H), 7.54 (ddd, J=0.8, 4.8, 5.6Hz, 1H), 7.37 (d, J=4.8Hz, 1H), 6.89 (d, J=8.0Hz, 1H), 6.82 (d, J=2.4Hz, 1H), 6.36 (dd, J=8.0, 2.4Hz, 1H), 4.87 (s, 2H), 2.08 (s, 3H); 13C NMR (101MHz, DMSO?d6) delta 161.96, 161.78, 159.82, 151.79, 148.60, 147.24, 138.42, 134.73, 132.77, 130.80, 124.28, 119.78, 111.58, 111.39, 107.54, 17.70; HRMS (ESI) m/z calcd for C16H16N5+ (M+H)+ 278.14002, found 278.14035; IR (cm?1): 3434, 3346, 3214, 2360, 2343, 1592, 1323, 1151, 767, 676.

Reference： [1]Tetrahedron,2019,vol. 75,p. 721 - 731

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Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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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. 7745-93-9 ] {[proInfo.proName]}

Quality Control of [ 7745-93-9 ]

Related Doc. of [ 7745-93-9 ]

Product Details of [ 7745-93-9 ]

Calculated chemistry of [ 7745-93-9 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 7745-93-9 ]

Application In Synthesis of [ 7745-93-9 ]

[ 7745-93-9 ] Synthesis Path-Upstream 1~2

[ 7745-93-9 ] Synthesis Path-Downstream 1~9

Technical Information

Related Functional Groups of [ 7745-93-9 ]

Aryls

Bromides

Nitroes

Precautionary Statements-General

Prevention

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Storage

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Physical hazards

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[ 7745-93-9 ]