[ CAS No. 149739-65-1 ]

Name: 149739-65-1|3-(3-Bromophenyl)-1H-pyrazole|95%
Brand: Ambeed
SKU: A909444
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Quality Control of [ 149739-65-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 149739-65-1 ]

SDS Specification

Alternatived Products of [ 149739-65-1 ]

Product Details of [ 149739-65-1 ]

CAS No. :	149739-65-1	MDL No. :	MFCD01940433
Formula :	C₉H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NVRXIZHZQPRBKL-UHFFFAOYSA-N
M.W :	223.07	Pubchem ID :	2735613
Synonyms :

Calculated chemistry of [ 149739-65-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.72
TPSA :	28.68 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) :	-5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.65
Log Po/w (XLOGP3) :	2.57
Log Po/w (WLOGP) :	2.84
Log Po/w (MLOGP) :	2.18
Log Po/w (SILICOS-IT) :	3.26
Consensus Log Po/w :	2.5

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.45
Solubility :	0.0783 mg/ml ; 0.000351 mol/l
Class :	Soluble
Log S (Ali) :	-2.82
Solubility :	0.337 mg/ml ; 0.00151 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.61
Solubility :	0.00545 mg/ml ; 0.0000244 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 149739-65-1 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 149739-65-1 ]

* 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 [ 149739-65-1 ]

[ 149739-65-1 ] Synthesis Path-Downstream 1~20

1
[ 492-37-5 ]
[ 149739-65-1 ]
[ 1268613-68-8 ]

Reference： [1]Journal of Molecular Catalysis B: Enzymatic,2010,vol. 66,p. 113 - 119

2
[ 149739-65-1 ]
[ 74-88-4 ]
[ 425379-68-6 ]

Yield	Reaction Conditions	Operation in experiment
99%		3-(3-Bromo-phenyl)-1 H-pyrazole (17 g; 60.97 mmol; 1.00 eq.) dissolved in THF (5 mL)was added dropwise to a suspension of Sodium hydride (2.44 g; 60.97 mmol; 1 .00eq.) in THF (500 mL) maintained at 0C. The reaction mixture was stirred for 30 mmbefore the dropwise addition of lodomethane (8.03 mL; 122 mmol; 2.00 eq.). It wasthen allowed to warm to RT and stirred for another 4h. Ice was added to quench thereaction and the mixture was extracted with ethyl acetate (30 mL x 2). Combinedorganic layers were dried over anhydrous sodium sulfate, filtered and concentrated togive the title compound as a brown liquid (14.5 g, 99%). LC/MS: (max plot) 99 %;(254nm) 99%; Rt 4.1 mm; 239.0 (M+1).
99%		3-(3-Bromo-phenyl)-1H-pyrazole (17 g; 60.97 mmol; 1.00 eq.) dissolved in THF (5 mL) was added dropwise to a suspension of Sodium hydride (2.44 g; 60.97 mmol; 1.00 eq.) in THF (500 mL) maintained at 0C. The reaction mixture was stirred for 30 min before the dropwise addition of lodomethane (8.03 mL; 122 mmol; 2.00 eq.). It was then allowed to warm to RT and stirred for another 4h. Ice was added to quench the reaction and the mixture was extracted with ethyl acetate (30 mL x 2). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound as a brown liquid (14.5 g, 99%). LC/MS: (max plot) 99 %; (254nm) 99 %; Rt 4.1 min; 239.0 (M+1).
70%	With sodium t-butanolate; In N,N-dimethyl-formamide; at 20℃; for 24h;	Synthesis of intermediate compound 4[00107] In a 300 ml eggplant-type flask, 7.00 g (31.4 mmol) of compound 3, 3.30 g (34.5 mmol) of sodium tert-butoxide, and 100 ml of DMF were placed. Then, 2.15 ml (34.5 mmol) of idomethane was added dropwise to the resultant mixture, followed by stirring at room temperature for 24 hours. The loss of the raw materials and production of a new compound were confirmed by TLC (Thin Layer Chromatography) . The reaction solution was concentrated, and an organic phase was recovered by three times of separation with toluene/water. The organic phase was dried over magnesium sulfate,concentrated, and then purified by silica gel columnchromatography (developing solvent toluene : heptane : ethyl acetate = 10:10:1). A target substance was concentrated to produce 5.21 g (22.0 mmol) of compound 4 (yield 70.0%).Nine protons were attributed by 1H-NMR (CDC13: 7.95 (s, 1H) , 7.71 ppm (d, 1H) , 7.42-7.39 ppm (m, 2H) , 7.26 ppm (t, 1H) , 6.53 ppm (d, 1H) , 3.96 ppm (s, 3H) ) . A peak was observed at m/z = 236 in GS-MS (gas chromatography direct-coupled to mass spectrometry) to confirm the target compound.

70%

With sodium t-butanolate; In N,N-dimethyl-formamide; at 20℃; for 24h;

Into 300 ml round-bottomed flask, 7.00 g (31.4 mmol) compound 3, 3.30 g (34.5 mmol) sodium tert-butoxide , and 100 ml DMF were placed. Thereto, 2.15 ml (34.5 mmol) of iodomethane was added dropwise and the mixture was stirred for 24 hours at room temperature. Elimination of the raw materials and generation of a new compound were confirmed by thin layer chromatography (TLC). The reaction solution was concentrated and separated three times with toluene/water to recover the organic phase. The organic phase was dried over magnesium sulfate, concentrated, and purified by silica gel column chromatography (developing solvent:toluene: heptane: ethyl acetate = 10:10:1). The target substance was concentrated to obtain 5.21 g (22.0 mmol) of compound 4 (yield: 70.0%). Nine protons were assigned by 1H- NMR (CDCl3:7.95 (s, 1H) , 7.71 ppm (d, 1H) , 7.42-7.39 ppm (m, 2H), 7.26 ppm (t, 1H) , 6.53 ppm (d, 1H) , 3.96 ppm (s, 3H) ) . When analyzed with a gas chromatograph-mass spectrometer (GS-MS), a peak was observed at m/z = 236. The product was confirmed to be the target substance.

Reference： [1]Patent: WO2015/106058,2015,A1 .Location in patent: Page/Page column 119
[2]Patent: EP3092225,2019,B1 .Location in patent: Paragraph 0377-0378
[3]Patent: WO2011/70992,2011,A1 .Location in patent: Page/Page column 30-32
[4]Patent: WO2011/70989,2011,A1 .Location in patent: Page/Page column 30-31

3
[ 149739-65-1 ]
[ 1311285-11-6 ]

Reference： [1]Patent: WO2011/70989,2011,A1

4
[ 149739-65-1 ]
[ 1311286-89-1 ]

Reference： [1]Patent: WO2011/70989,2011,A1

5
[ 149739-65-1 ]
[ 1311285-12-7 ]

Reference： [1]Patent: WO2011/70992,2011,A1

6
[ 149739-65-1 ]
C₆₆H₈₁IrN₁₂ [ No CAS ]

Reference： [1]Patent: WO2011/70992,2011,A1

7
[ 1817-49-8 ]
[ 149739-65-1 ]
[ 1373254-11-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 3538 - 3555

8
[ 2142-63-4 ]
[ 149739-65-1 ]

Reference： [1]Patent: WO2013/41457,2013,A1
[2]Patent: WO2015/106058,2015,A1
[3]Patent: EP3092225,2019,B1

9
[ 1428581-88-7 ]
[ 149739-65-1 ]

Yield	Reaction Conditions	Operation in experiment
2.5 g	With hydrazine hydrate; In ethanol; for 1h;Reflux;	To a solution of the product obtained in the previous step (3 g, 1 1.8 mmol) in EtOH (50 ml) was added hydrazinehydrate (2.2 g, 35.4 mmol, 85%) at room temperature. The reaction mixture was stirred at reflux temperature for 1 hour. After cooling to ambient temperature, the mixture was concentrated and the residue was dissolved in CH2CI2 (50 ml). The solution was washed with brine, dried over Na2S04 and concentrated under reduced pressure to give 3-(3- bromophenvD-1 H-pyrazole (2.5 g) as yellow solid.

Reference： [1]Patent: WO2013/41457,2013,A1 .Location in patent: Page/Page column 22

10
[ 149739-65-1 ]
[ 1428581-98-9 ]

Reference： [1]Patent: WO2013/41457,2013,A1

11
[ 149739-65-1 ]
[ 73183-34-3 ]
[ 1217340-87-8 ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine; In 1,4-dioxane; for 4h;Reflux;	A mixture of Pd2(dba)3 (183 mg, 0.20 mmol), PCy3 (132 mg, 0.47 mmol) in dioxane was stirred for 30 mins at room temperature under a nitrogen atmosphere. Before the product obrained in the previous step (1 .5 g, 6.73 mmol), bis(pinacolato)diboron (2.56 g, 10.1 mmol) and potassium acetate (1 .32 g, 13.5 mmol) were added. The reaction mixture was stirred at reflux temperature 4 hours. After cooling to room temperature, the mixture was filtered and concentrated under reduced pressure. The residue was purified using normal phasechromatography, eluting with petroleum ether containing 10% ethyl acetate to give the title compound 3-(3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl)-1 H-pyrazole (1 .8 g).MS (ESI) m/z: 271.0 (M+H+).

Reference： [1]Patent: WO2013/41457,2013,A1 .Location in patent: Page/Page column 23

12
1-(3-bromophenyl)-3-dimethylamino-2-propen-1-one [ No CAS ]
[ 149739-65-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydrazine hydrate; In ethanol; at 85℃; for 14h;	A solution of (E)-1 -(3-Bromo-phenyl)-3-dimethylamino-propenone (15 g; 59.03 mmol;1 .00 eq.) and Hydrazine hydrate (5.80 mL; 118.05 mmol; 2.00 eq.) in Ethanol (150.00mL) was refluxed to 85 00 for 14 h. Ethanol was removed under reduced pressureand the residue was diluted in DCM (50 mL) and washed with water, then brine. Theorganic layer was dried over Na2SO4, filtered and concentrated to give the titlecompound as a yellow liquid (1 7g, 99%). 1 H NMR (DMSO; 400 MHz) 6 13.00 (s, 1 H), 7.99-7.97 (m, 1 H), 7.82-7.80 (m, 2H), 7.48-7.41 (m, 1 H), 7.39-7.33 (m, 1 H), 6.79 (d, J = 2.20 Hz, 1 H). LC/MS: 224.9 (M+1).
99%	With hydrazine hydrate; In ethanol; at 85℃; for 14h;Reflux;	A solution of (E)-1-(3-Bromo-phenyl)-3-dimethylamino-propenone (15 g; 59.03 mmol; 1.00 eq.) and Hydrazine hydrate (5.80 mL; 118.05 mmol; 2.00 eq.) in Ethanol (150.00 mL) was refluxed to 85 C for 14 h. Ethanol was removed under reduced pressure and the residue was diluted in DCM (50 mL) and washed with water, then brine. The organic layer was dried over Na2SO4, filtered and concentrated to give the title compound as a yellow liquid (17g, 99%). 1H NMR (DMSO; 400 MHz) delta 13.00 (s, 1H), 7.99-7.97 (m, 1H), 7.82-7.80 (m, 2H), 7.48-7.41 (m, 1H), 7.39-7.33 (m, 1H), 6.79 (d, J = 2.20 Hz, 1H). LC/MS: 224.9 (M+1).

Reference： [1]Patent: WO2015/106058,2015,A1 .Location in patent: Page/Page column 118; 119
[2]Patent: EP3092225,2019,B1 .Location in patent: Paragraph 0375-0376

13
[ 149739-65-1 ]
3-([1,1’-biphenyl]-3-yl)-4-bromo-1H-pyrazole [ No CAS ]