[ CAS No. 4595-60-2 ] {[proInfo.proName]}

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Quality Control of [ 4595-60-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4595-60-2 ]

SDS Specification

Alternatived Products of [ 4595-60-2 ]

Product Details of [ 4595-60-2 ]

CAS No. :	4595-60-2	MDL No. :	MFCD00014601
Formula :	C₄H₃BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PGFIHORVILKHIA-UHFFFAOYSA-N
M.W :	158.98	Pubchem ID :	78345
Synonyms :

Calculated chemistry of [ 4595-60-2 ] Expand+

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	29.73
TPSA :	25.78 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	0.5
Log Po/w (WLOGP) :	1.24
Log Po/w (MLOGP) :	0.35
Log Po/w (SILICOS-IT) :	1.77
Consensus Log Po/w :	1.08

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.77
Solubility :	2.67 mg/ml ; 0.0168 mol/l
Class :	Very soluble
Log S (Ali) :	-0.61
Solubility :	38.9 mg/ml ; 0.245 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.49
Solubility :	0.512 mg/ml ; 0.00322 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 4595-60-2 ]

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 [ 4595-60-2 ]

* 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 [ 4595-60-2 ]
Downstream synthetic route of [ 4595-60-2 ]

[ 4595-60-2 ] Synthesis Path-Upstream 1~4

1
[ 110-91-8 ]
[ 4595-60-2 ]
[ 57356-66-8 ]

Reference： [1] ChemSusChem, 2013, vol. 6, # 8, p. 1455 - 1460

2
[ 110-91-8 ]
[ 201230-82-2 ]
[ 4595-60-2 ]
[ 562101-40-0 ]
[ 57356-66-8 ]

Reference： [1] Organic Letters, 2014, vol. 16, # 16, p. 4296 - 4299

3
[ 4595-60-2 ]
[ 115-19-5 ]
[ 37972-24-0 ]

Reference： [1] European Journal of Organic Chemistry, 2005, # 3, p. 522 - 531

4
[ 4595-60-2 ]
[ 1066-54-2 ]
[ 37972-24-0 ]

Reference： [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2185 - 2191

[ 4595-60-2 ] Synthesis Path-Downstream 1~12

1
[ 2923-18-4 ]
[ 4595-60-2 ]
[ 116470-67-8 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 2676 - 2699
[2]Journal of the Chemical Society. Perkin transactions I,1988,p. 921 - 926

2
[ 4595-60-2 ]
[ 628692-15-9 ]
2-methoxy-5-(2-pyrimidyl)pyrimidine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 852 - 857

3
[ 4595-60-2 ]
[ 115-19-5 ]
[ 37972-24-0 ]

Reference： [1]European Journal of Organic Chemistry,2005,p. 522 - 531

4
[ 40318-15-8 ]
[ 4595-60-2 ]
4-methyl-1-pyrimidin-2-yl-1H-pyrrole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide; rac-diaminocyclohexane; In 1,4-dioxane; dodecane; at 100℃; for 12h;	333.9 mg (2.4 [MMOL)] 4-methyl-1H-pyrrole-3-carboxylic acid methyl ester, 891.5 mg (4.2 [MMOL)] tri-potassium phosphate, 4 mg (0.02 mmol) Cul, 22 mg (0.2 [MMOL)] 1,2- diaminocyclohexane and 317.9 mg (2 [MMOL)] of 2-bromopyrimidine was suspended in 3 ml of dioxane. After addition of 90 pl of dodecane the mixture was heated in a sealed tube under argon for 12h at 100 [C.] The mixture was cooled to room temperature and then diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with water (twice), dried over anhydrous sodium sulfate. After filtration the solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column flash chromatography (eluent : heptane/dichloromethane/methanol = 25/2/1) to obtain 300 mg of [4-METHYL-] [1-PYRIMIDIN-2-YL-1] H-pyrrole-3-carboxylic acid methyl ester as a white solid. M. p. [107.] [7 C]

Reference： [1]Patent: WO2004/7478,2004,A2 .Location in patent: Page 57-58

5
[ 874219-45-1 ]
[ 4595-60-2 ]
[ 1143024-54-7 ]

Yield	Reaction Conditions	Operation in experiment
42%	palladium diacetate; triphenylphosphine; In tetrahydrofuran; at 65.0℃;	Intermediate 5: Methyl 2-chloro-5-(pyrimidin-2-yl)benzoate; A mixture of 2-bromopyrimidine (2.8 g, 17.63 mmol), <strong>[874219-45-1]4-chloro-3-(methoxycarbonyl)phenylboronic acid</strong> (4.2 g, 19.59 mmol), palladium acetate (0.22 g, 0.98 mmol) and triphenylphosphine (1.028 g, 3.92 mmol) in THF (80 mL) was heated at 65 0C overnight, then the reaction mixture was cooled, filtered through Celite and concentrated in vacuo. The residue was partitioned between EtOAc (200 mL) and saturated brine (200 mL) and the organic phase was dried, concentrated in vacuo, and then the residue was purified by chromatography on silica gel eluting with EtOAc/isohexane (0 - 50%) to give the title compound as a white solid (2.0 g, 42%): MS 249.

Reference： [1]Patent: WO2009/47558,2009,A1 .Location in patent: Page/Page column 138

6
[ 775351-57-0 ]
[ 4595-60-2 ]
[ 1269406-96-3 ]

Yield	Reaction Conditions	Operation in experiment
38%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100.0℃; for 0.5h;Microwave irradiation;	To a mixture of 2-fluoro-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- benzonitrile (100 mg, 0.405 mmol), 2-bromopyrimidine (194 mg, 1.221 mmol), and K2CO3 (168 mg, 1.214 mmol) in 1,4-dioxane (1.5 mL) and water (0.5 mL) was added Pd(Ph3P)4 (47 mg, 0.041 mmol). The vial was capped and the reaction mixture was heated in a Biotage Initiator microwave reactor to 100 0C for 30 min. Water (4 mL) and EtOAc (5 mL) were added to the reaction mixture. The layers were separated, and the aqueous layer was extracted with EtOAc (2 x 3 mL). The combined organic layers were washed with brine (3 x 1 mL) and concentrated under a stream of nitrogen at 50 0C onto Isolute. Purification via flash column chromatography (0-20% EtOAc/hexanes) afforded the title compound (30.6 mg, 38%). LC-MS m/z 200 (M+H)+, 0.88 min (ret time).

Reference： [1]Patent: WO2011/25799,2011,A1 .Location in patent: Page/Page column 52

7
[ 4595-60-2 ]
[ 1066-54-2 ]
[ 37972-24-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2185 - 2191

8
[ 81290-20-2 ]
[ 4595-60-2 ]
[ 116470-67-8 ]

Yield	Reaction Conditions	Operation in experiment
75%		General procedure: To a well stirred mixture of AgF (1.27 g, 10 mmol) in 10 ml of DMF, Me3SiCF3 (1.7 g, 12 mmol) was added at room temperature. The mixture was stirred for 20 min and copper powder (1.0 g, 15 mmol) was added. After stirring for 4 h, the formation of CuCF3 was complete. The corresponding halogen containing compound (9 mmol) (in the case of 2,6-dibromopyridine, 4.5 mmol) was added and the reaction mixture was stirred under conditions surveyed in Table 1. The reaction was terminated unless signals of CuCF3 were no longer detected in the 19F NMR spectra. The mixture was filtered from the solid precipitate and poured into 50 ml of water. The organic layer was extracted with diethyl ether and dried over MgSO4. Ether was evaporated and the remainder was distilled under reduced pressure or crystallized.

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 133,p. 67 - 71

9
[ 77152-08-0 ]
[ 4595-60-2 ]
[ 116470-67-8 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11126 - 11146

10
[ 624741-47-5 ]
[ 4595-60-2 ]
[ 1293285-05-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate; In tetrahydrofuran; water; at 80.0℃; for 5.16667h;Inert atmosphere;	Synthesis of 3-fluoro-2-(pyrimidin-2-yl)benzonitrile (Intermediate in the synthesis of intermediate A-2) To a solution of <strong>[624741-47-5]3-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile</strong> (4.98 g, 19.1 mmol) and 2-bromopyridine (3.85 g, 23 mmol) in THF (96 mL) was added Na2CO3 (6 g, 57.4 mmol) followed by water (43 mL). The reaction mixture was degassed with N2 for 10 minutes. PdCl2(dtbpf) (374 mg, 0.57 mmol) was added and the reaction mixture was stirred at 80 C. for 5 h. The solution was cooled to room temperature and a mixture of EtOAc and water was added. The aqueous was extracted twice with EtOAc and the combined organic layers were dried over MgSO4, filtered and evaporated. The title compound was precipitated by dissolving the residue in a minimum amount of EtOAc and then adding hexanes. The solid was filtered, washed with hexanes and dried to afford the title compound (2.46 g, 64%). MS (ESI) mass calcd. for C11H6FN3, 199.1; m/z found 200.1 [M+H]+. 1H NMR (400 MHz, Chloroform-d) delta 9.02-8.91 (m, 2H), 7.65 (dt, J=7.7, 1.0 Hz, 1H), 7.60-7.52 (m, 1H), 7.51-7.43 (m, 1H), 7.41 (t, J=4.9 Hz, 1H).
64%	With dichloro[1,1?-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P?]palladium; sodium carbonate; In tetrahydrofuran; water; at 80.0℃; for 5.0h;Inert atmosphere;	10286] To a solution of 3-fluoro-2-(4,4,5,5-tetramethyl-1, 3,2-dioxaborolan-2-yl)benzonitrile (4.98 g, 19.1 mmol) and2-bromopyrimidine (3.85 g, 23 mmol) in THF (96 mE) was added Na2CO3 (6 g, 57.4 mmol) followed by water (43 mE). The reaction mixture was degassed with N2 for 10 minutes. PdC12(dtbpf) (374 g, 0.57 mmol) was added and the reaction mixture was stirred at 800 C. for 5 h. The solution was cooled to room temperature and a mixture of EtOAc and water was added. The aqueous was extracted twice with EtOAc and the combined organic layers were dried over Mg504, filtered and evaporated. The title compound was precipitated by dissolving the residue in a minimum amount of EtOAc and then adding hexanes. The solid was filtered, washed with hexanes and dried to afford the title compound (2.46 g, 64%). MS (ESI) mass calcd. for C,,H6FN3, 199.1; mlz found 200.1 [M+H]. ?H NMR (400 MHz, Chloroform-d) oe 9.02-8.91 (m, 2H), 7.65 (dt, J7.7, 1.0 Hz, 1H), 7.60-7.52 (m, 1H), 7.5 1-7.43 (m, 1H), 7.41 (t, J4.9 Hz, 1H).
64%	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate; In tetrahydrofuran; water; at 80.0℃; for 5.0h;	Synthesis of 3-fluoro-2-(pyrimidin-2-yl)benzonitrile (Intermediate in the synthesis of intermediate A-2) To a solution of <strong>[624741-47-5]3-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile</strong> (4.98 g, 19.1 mmol) and 2-bromopyrimidine (3.85 g, 23 mmol) in THF (96 mL) was added Na2CO3 (6 g, 57.4 mmol) followed by water (43 mL). The reaction mixture was degassed with N2 for 10 minutes. PdCl2(dtbpf) (374 mg, 0.57 mmol) was added and the reaction mixture was stirred at 80 C. for 5 h. The solution was cooled to room temperature and a mixture of EtOAc and water was added. The aqueous was extracted twice with EtOAc and the combined organic layers were dried over MgSO4, filtered and evaporated. The title compound was precipitated by dissolving the residue in a minimum amount of EtOAc and then adding hexanes. The solid was filtered, washed with hexanes and dried to afford the title compound (2.46 g, 64%). MS (ESI) mass calcd. for C11H6FN3, 199.1. m/z found 200.1 [M+H]+. 1H NMR (400 MHz, Chloroform-d) delta 9.02-8.91 (m, 2H), 7.65 (dt, J=7.7, 1.0 Hz, 1H), 7.60-7.52 (m, 1H), 7.51-7.43 (m, 1H), 7.41 (t, J=4.9 Hz, 1H).

Reference： [1]Patent: US2014/275118,2014,A1 .Location in patent: Paragraph 0142; 0143
[2]Patent: US2016/46640,2016,A1 .Location in patent: Paragraph 0285; 0286
[3]Patent: US2016/75696,2016,A1 .Location in patent: Paragraph 0216; 0217

11
[ 867044-28-8 ]
[ 4595-60-2 ]
C₃₈H₂₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; toluene; for 7h;Reflux;	Compound 1 (2.7 g, 17 mmol) and compound 2 (8.0 g, 17 mmol)Was added 1,2-dimethoxyethane (200 ml) and toluene (400 ml)In addition, tetrakis (triphenylphosphine) palladium (0)(0.97 g, 0.84 mmol) and a 2 M aqueous sodium carbonate solution (67 ml) were added and the mixture was refluxed for 7 hours. After completion of the reaction,The solvent was distilled off under reduced pressure, and water was added. The obtained solid was filtered, washed with water and methanol, and dried under reduced pressure.The obtained crude product was purified by silica gel column chromatography (toluene), and the resulting solid was washed with methanol,And dried under reduced pressure to obtain Compound 3 (6.0 g, yield 70%) as a yellow solid.

Reference： [1]Patent: KR2015/119431,2015,A .Location in patent: Paragraph 0496; 0498-0499

12
[ 15016-42-9 ]
[ 4595-60-2 ]
2-(2-vinylphenyl)pyrimidine [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 9114 - 9118

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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 ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

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[ 4595-60-2 ]

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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. 4595-60-2 ] {[proInfo.proName]}

Quality Control of [ 4595-60-2 ]

Related Doc. of [ 4595-60-2 ]

Product Details of [ 4595-60-2 ]

Calculated chemistry of [ 4595-60-2 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4595-60-2 ]

Application In Synthesis of [ 4595-60-2 ]

[ 4595-60-2 ] Synthesis Path-Upstream 1~4

[ 4595-60-2 ] Synthesis Path-Downstream 1~12

Technical Information

Related Functional Groups of [ 4595-60-2 ]

Bromides

Related Parent Nucleus of [ 4595-60-2 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 4595-60-2 ]

Related Parent Nucleus of
[ 4595-60-2 ]