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Quality Control of [ 42881-66-3 ] Purity: 95% SDS Specification

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Product Details of [ 42881-66-3 ]

CAS No. :	42881-66-3
Formula :	C₁₀H₈BrNO
M.W :	238.08
SMILES Code :	COC1=CC=C2N=CC=C(Br)C2=C1
MDL No. :	MFCD08437074
InChI Key :	HRFFYKLVLCFCQG-UHFFFAOYSA-N
Pubchem ID :	11160747

Safety of [ 42881-66-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 42881-66-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	55.93
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	22.12 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.51
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.85
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.01
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.19
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.73

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.61
Solubility	0.0578 mg/ml ; 0.000243 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.97
Solubility	0.253 mg/ml ; 0.00106 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.69
Solubility	0.00489 mg/ml ; 0.0000206 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.73 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.55

Application In Synthesis of [ 42881-66-3 ]

* 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 [ 42881-66-3 ]

[ 42881-66-3 ] Synthesis Path-Downstream 1~32

1
[ 6279-51-2 ]
[ 42881-66-3 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1930,vol. 128,p. 211,212.

2
[ 42881-66-3 ]
[ 148249-36-9 ]
[ 553635-71-5 ]

References: [1]Heterocycles,2003,vol. 59,p. 473 - 476.

3
[ 42881-66-3 ]
[ 159590-02-0 ]
4-[1-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-6-methoxy-quinoline [ No CAS ]

References: [1]Heterocycles,2003,vol. 59,p. 473 - 476.

4
[ 42881-66-3 ]
[ 208655-73-6 ]
[ 553635-71-5 ]

References: [1]Heterocycles,2003,vol. 59,p. 473 - 476.

5
[ 42881-66-3 ]
(4R)-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)allyl]-(3R)-vinylpiperidine-1-carboxylic acid benzyl ester [ No CAS ]
(4R)-[3-(6-methoxyquinolin-4-yl)allyl]-(3R)-vinylpiperidine-1-carboxylic acid benzyl ester [ No CAS ]
(4R)-[3-(6-methoxyquinolin-4-yl)allyl]-(3R)-vinylpiperidine-1-carboxylic acid benzyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 706 - 707.

6
[ 13788-72-2 ]
[ 42881-66-3 ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 706 - 707.
[2]Tetrahedron Letters,2010,vol. 51,p. 2685 - 2689.

7
[ 42881-66-3 ]
[ 76167-58-3 ]
(1-benzo[1,3]dioxol-5-ylmethyl-piperidin-4-yl)-(6-methoxy-quinolin-4-yl)-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2339 - 2352.

8
[ 42881-66-3 ]
[ 140-80-7 ]
[ 32571-37-2 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 2232 - 2235.

9
[ 23432-39-5 ]
[ 42881-66-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With phosphorus tribromide; In water; N,N-dimethyl-formamide; at 0℃;	To a solution of 6-(methyloxy)-4-quinolinol (23.6 g, 135 mmol) in DNF (100 mL) was added PBr3 (16 mL, 169 mmol) in portions. The flask was filled with a bubbler. When bubbling ceased, the suspension was dumped into icy water with stirring. The resulting mixture was diluted with a large volume of water (-600 mL). The percipitate was filtered, washed with water and dried under vaccume line to afford the title compound as an off-white solid (31.4 g, 97%): LC/MS (ES) m/e 239 (M+H)+
95%	With phosphorus tribromide; sodium hydroxide; In water; N,N-dimethyl-formamide; at 75℃;	A three-necked round bottom flask vented to a 1M NaOH (aq) gas trap was charged with 4-hydroxy-6-methoxyquinoline (12.07 g, 68.90 mmol, 1.0 equiv) and anhydrous N,Ndimethylformamide(75 mL) and stirred magnetically. To the heterogeneous mixture was addedPBr3 (8.0 mL, 85 mmol, 1.2 equiv) drop/portionwise over several minutes by syringe. During theaddition, the internal temperature rose to 75 C, and gas was evolved. A copious precipitate formedtoward the end of the addition. The vent to the gas trap was removed 15 min after the completionof addition, and the reaction was stirred vigorously for an additional 1h 45 min, then quenched bypouring onto 150 g ice in 150 mL water. After brief stirring, Na2CO3 (20 g) was added in smallportions (bubbling), and the mixture was stirred for 15 min, whereupon the pH was approximately7. The taupe-colored product was isolated by vacuum filtration on a Buchner funnel, washingextensively with water. After drying for several days in a vacuum desiccator, the title compoundwas obtained in ca. 95% purity as a light tan, powdery solid (15.58 g, 65.44 mmol, 95%).
95%	With phosphorus tribromide; sodium hydroxide; In N,N-dimethyl-formamide; at 75℃; for 1.75h;	A threenecked round bottom flask vented to a 1MNaOH (aq) gas trap was charged with 14 (12.07 g, 68.9() rnmol, 10 equiv) and anhydious NN-dimethy1forrnainide (75 mL)and stirred magnetically. To the heterogeneous mixture was added PBr3 (8.0 mL, 85 mmol,1.2 equiv) drop/porlionwise over several minutes by syringe. Duiing the addition, the internal temperature rose to 75 C, and gas was evolved. A copious precipitate formed toward the end of the addition. The vent to the gas trap was 15 mm after the completion of addition, and the reaction was stirred vigorously for an additional lh 45 mm, then quenchedby pouring onto 150 g ice in 150 mL water. Aer brief stirring, Na2CO3 (20 g) was added in small portions (bubbling), and the mixture was stirred for 15 mm, whereupon the pH was approximately 7. The taupecoiored product was isolated by vacuum filtration on a Buchner finnel. washing extensively with water. After drying for several days in a vacuum desiccator, the title compound was obtained in ca. 95% purity as a light tan, powdery solid (1558 g, 6544 mmol, 95%). ‘H NMR (300 MHz, DMSOd6) ?: 857 (d, J= 4.7, 1H); 8.00(d, J= 9.2, 111); 7.89 (d. ,J= 4.7, 1H); 7.51 (dd, J= 2.8, ). 2, IH); 7.39 (d, J= 2.8, 1H); 3.96 (S. 3H). (See W02006/0002047, which is incorporated by reference herein in its entirety.)

87%

With phosphorus tribromide; In N,N-dimethyl-formamide; at 20℃; for 2h;

Preparation of 4-ethenyl-6-(methyloxy)quinoline; a) 4-bromo-6-methoxy quinoline; To a stirred solution of 4-hydroxy-6-methoxyquinoline (1.20 g, 70.5 mmole) in DMF (60 ml_) at RT was added PBr3 (8.0 mL, 84.6 mmole) dropwise. After 2h, the reaction contents were poured onto H2O (300 mL) and the product filtered and washed with H2O to give, after drying under high vacuum, the title compound (14.3 g, 87%) as a light yellow solid: LC-MS (ES) m/e 233 (M+H)+.

References: [1]Patent: WO2007/16610,2007,A2 .Location in patent: Page/Page column 31.
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2477 - 2480.
[3]Patent: WO2018/195098,2018,A1 .Location in patent: Page/Page column 44; 45.
[4]Patent: WO2006/2047,2006,A2 .Location in patent: Page/Page column 77.
[5]Journal of Medicinal Chemistry,2009,vol. 52,p. 6966 - 6978.
[6]Organic Letters,2018,vol. 20,p. 1195 - 1199.
[7]European Journal of Medicinal Chemistry,2012,vol. 57,p. 259 - 267.
[8]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2723 - 2727.

10
[ 42881-66-3 ]
[ 49612-21-7 ]

Yield	Reaction Conditions	Operation in experiment
		C. (6-Methoxy-quinolin-4-yl)-hydrazine. To a solution of 4-bromo-6-methoxy-quinoline (5.4 g, 28 mmol) in 1-methyl-2-pyrrolidinone (27 mL) was added hydrazine (1.52 mL, 33.6 mmol). The reaction was heated at 150 C. for 12 h. The reaction was then cooled to RT and added dropwise to an ethereal solution (700 mL) at RT. The white precipitate was collected by filtration, washed with Et2O (80 mL), and dried under reduced pressure. The resulting solid was dissolved in CH2Cl2 (100 mL) and washed with 1 N NaOH (100 mL). The aqueous layer was back-extracted with CH2Cl2 (2*100 mL). The combined organic layers were washed with 1 N NaOH (50 mL), brine (30 mL), dried (MgSO4), filtered and concentrated to afford 4.3 g (82% crude) of a brown solid. HPLC: Rt=4.22 min. MS (ESI): exact mass calculated for C10H11N3O, 189.1; m/z found, 190.4 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.26 (d, J=6.5, 1H), 7.75 (d, J=9.2, 1H), 7.52 (d, J=2.5, 1H), 7.46 (dd, J=9.2, 2.6, 1H), 7.19 (d, J=6.5, 1H), 3.95 (s, 3H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 2723 - 2727.
[2]Patent: US2006/223810,2006,A1 .Location in patent: Page/Page column 20.

11
[ 42881-66-3 ]
(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-[2-(6-methoxy-quinolin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-yl]-amine [ No CAS ]