[ CAS No. 50998-17-9 ] {[proInfo.proName]}

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Quality Control of [ 50998-17-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 50998-17-9 ]

SDS Specification

Alternatived Products of [ 50998-17-9 ]

Product Details of [ 50998-17-9 ]

CAS No. :	50998-17-9	MDL No. :	MFCD00837757
Formula :	C₈H₅BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NOYFLUFQGFNMRB-UHFFFAOYSA-N
M.W :	209.04	Pubchem ID :	610939
Synonyms :

Calculated chemistry of [ 50998-17-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.24
TPSA :	25.78 ?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) :	-5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	2.27
Log Po/w (WLOGP) :	2.39
Log Po/w (MLOGP) :	1.61
Log Po/w (SILICOS-IT) :	2.65
Consensus Log Po/w :	2.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.24
Solubility :	0.121 mg/ml ; 0.000577 mol/l
Class :	Soluble
Log S (Ali) :	-2.45
Solubility :	0.745 mg/ml ; 0.00356 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.19
Solubility :	0.0136 mg/ml ; 0.0000652 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.63

Safety of [ 50998-17-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 50998-17-9 ]

* 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 [ 50998-17-9 ]
Downstream synthetic route of [ 50998-17-9 ]

[ 50998-17-9 ] Synthesis Path-Upstream 1~7

1
[ 50998-17-9 ]
[ 97674-02-7 ]
[ 83570-42-7 ]

Reference： [1] Patent: US2005/256309, 2005, A1, . Location in patent: Page/Page column 35
[2] Patent: US2005/272736, 2005, A1, . Location in patent: Page/Page column 35
[3] Patent: WO2016/30443, 2016, A1, . Location in patent: Page/Page column 80
[4] Patent: WO2017/144633, 2017, A1, . Location in patent: Page/Page column 95
[5] Patent: WO2017/144639, 2017, A1, . Location in patent: Page/Page column 80

2
[ 50998-17-9 ]
[ 83570-42-7 ]

Yield	Reaction Conditions	Operation in experiment
45%	With bis-triphenylphosphine-palladium(II) chloride In toluene at 20 - 90℃;	To a degassed stirred solution of 6-bromo quinoxaline (2.0 g, 9.50 mmol) in toluene (20 mL), 1- ethoxy vinyl tributyltin (3.8 g, 10.5 mmol) followed by Pd(PPh₃)₂CI₂ (0.67 g, 0.95 mmol) were added at RT and stirred at 90 °C overnight. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to RT, filtered through celite and the obtained filtrate was evaporated under vacuum. To the resulting crude mixture, 6 N HCI solution (20 mL) was added and the mixture was stirred at RT for 1 h. The solution was neutralized with sat. NaHC0₃ and the aqueous layer was extracted with DCM (2 x 100 mL). The combined organic layer was dried over Na₂S0₄ and concentrated under vacuum. The resulting crude material was purified by flash chromatography (Biotage Isolera, eluent: 30percent EtOAc in hexane) to afford the title compound. Yield: 45percent (800 mg, brown solid). ¹H NMR (400 MHz, DMSO-tf₆): δ 9.06-9.04 (m, 2H), 8.70 (d, J = 2.4 Hz, 1 H), 8.28 (dd, J = 8.8, 2.8 Hz, 1 H), 8.16 (d, J = 8.4 Hz, 1 H), 2.97 (s, 3H). LCMS: (Method A) 173 (M+H), Rt. 2.2 min, 99.1 percent (Max).

Reference： [1] Patent: WO2019/37860, 2019, A1, . Location in patent: Page/Page column 68

3
[ 3476-89-9 ]
[ 91-19-0 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Yield	Reaction Conditions	Operation in experiment
35%	With bromine In acetonitrile for 2.5 h; Reflux; Inert atmosphere	General procedure: Bromine was added dropwise to a magnetically stirred refluxing solution of quinoxaline (1) or tetrahydroquinoxaline 15 or 19 in the relevant solvent. The resulting reaction mixture was heated at reflux temperature. The reaction was monitored by TLC or ¹H NMR spectroscopy. After the desired time, the resulting reaction mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The mixture was diluted with a saturated solution of sodium carbonate (10mL) and the mixture was extracted with ethyl acetate (2×25mL). Combined organic layers were washed with water, dried over Na₂SO₄ and concentrated. The crude was purified appropriate method described in below.

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

4
[ 34413-35-9 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
[2] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

5
[ 2423-66-7 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
[2] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

6
[ 528852-07-5 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

7
[ 91-19-0 ]
[ 50998-17-9 ]
[ 76982-23-5 ]

Reference： [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632

[ 50998-17-9 ] Synthesis Path-Downstream 1~15

1
[ 50998-17-9 ]
[ 7467-91-6 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 5351 - 5358
[2]Journal of the American Chemical Society,2016,vol. 138,p. 13493 - 13496
[3]Organic Letters,2017,vol. 19,p. 3033 - 3036
[4]ChemCatChem,2019

2
[ 34413-35-9 ]
[ 50998-17-9 ]
6,7-dibromoquinoxaline [ No CAS ]
5,7-dibromoquinoxaline [ No CAS ]
[ 148231-12-3 ]

Reference： [1]Tetrahedron,2017,vol. 73,p. 1618 - 1632
[2]Tetrahedron,2017,vol. 73,p. 1618 - 1632

3
[ 34413-35-9 ]
[ 50998-17-9 ]
[ 1131040-38-4 ]
6,7-dibromoquinoxaline [ No CAS ]
5,7-dibromoquinoxaline [ No CAS ]
[ 148231-12-3 ]

Reference： [1]Tetrahedron,2017,vol. 73,p. 1618 - 1632
[2]Tetrahedron,2017,vol. 73,p. 1618 - 1632

4
[ 34413-35-9 ]
[ 50998-17-9 ]
6,7-dibromoquinoxaline [ No CAS ]
[ 148231-12-3 ]

Reference： [1]Tetrahedron,2017,vol. 73,p. 1618 - 1632
[2]Tetrahedron,2017,vol. 73,p. 1618 - 1632

5
[ 528852-07-5 ]
[ 50998-17-9 ]
6,7-dibromoquinoxaline [ No CAS ]
5,7-dibromoquinoxaline [ No CAS ]
[ 148231-12-3 ]