[ CAS No. 13721-00-1 ] {[proInfo.proName]}

Name: 13721-00-1|2,3-Dibromoquinoline|98%
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SKU: A102961
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3d Animation Molecule Structure of 13721-00-1

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Quality Control of [ 13721-00-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13721-00-1 ]

SDS Specification

Alternatived Products of [ 13721-00-1 ]

Product Details of [ 13721-00-1 ]

CAS No. :	13721-00-1	MDL No. :	MFCD00234472
Formula :	C₉H₅Br₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KWVPZTJLHQKCKD-UHFFFAOYSA-N
M.W :	286.95	Pubchem ID :	817315
Synonyms :

Calculated chemistry of [ 13721-00-1 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	57.14
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.51
Log Po/w (XLOGP3) :	3.91
Log Po/w (WLOGP) :	3.76
Log Po/w (MLOGP) :	3.26
Log Po/w (SILICOS-IT) :	3.79
Consensus Log Po/w :	3.45

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.7
Solubility :	0.00574 mg/ml ; 0.00002 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.88
Solubility :	0.0379 mg/ml ; 0.000132 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.4
Solubility :	0.00115 mg/ml ; 0.00000399 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.71

Safety of [ 13721-00-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13721-00-1 ]

* 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.

Upstream synthesis route of [ 13721-00-1 ]
Downstream synthetic route of [ 13721-00-1 ]

[ 13721-00-1 ] Synthesis Path-Upstream 1~2

1
[ 5332-24-1 ]
[ 13721-00-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; Inert atmosphere Stage #2: With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; Inert atmosphere	To a stirred solution of 2-bromoquinoline (306 mg, 1.47 mmol) in CH₂Cl₂ (3 ml) at 0 °C was added m-CPBA (358 mg, 85percent max., 1.76 mmol) and the reaction is allowed to stir at room temperature overnight. Extra CH₂Cl₂ (11.6 ml) was added to the reaction mixture. To the resulting solution at 0 °C was added POBr₃ (516 mg, 1.76 mmol) followed by dropwise addition of DMF (57 ul, 0.74 mmol) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for two hours before extra CH₂Cl₂ (10 ml) was added. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH₂Cl₂ thoroughly. The organic phase is combined and washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography (PE:EA=100:1) to afford the title compound (335 mg, 79percent yield) as a white solid.

Reference： [1] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768
[2] Organic Letters, 2007, vol. 9, # 26, p. 5525 - 5528

2
[ 22615-00-5 ]
[ 13721-00-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; for 6 h; Inert atmosphere	General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH₂Cl₂ (0.1 M) at 0 °C is added POBr₃ (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH₂Cl₂ thoroughly. The organic phase is combined and washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.

Reference： [1] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768

[ 13721-00-1 ] Synthesis Path-Downstream 1~24

1
[ 13721-00-1 ]
[ 146140-95-6 ]
[ 250593-13-6 ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 3959 - 3969

3
3-bromo-2-oxy-quinoline [ No CAS ]
[ 13721-00-1 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1892,vol. <2> 45,p. 50

4
[ 5049-61-6 ]
[ 13721-00-1 ]
pyrazino[1',2':1,2]imidazo[4,5-b]quinoline [ No CAS ]