Home Cart Sign in  
Chemical Structure| 4269-17-4 Chemical Structure| 4269-17-4

Structure of 4269-17-4

Chemical Structure| 4269-17-4

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 4269-17-4 ]

CAS No. :4269-17-4
Formula : C13H7BrO
M.W : 259.10
SMILES Code : O=C1C2=C(C3=C1C=CC=C3)C(Br)=CC=C2
MDL No. :MFCD22988837
InChI Key :YWYZCXNQMZOYHM-UHFFFAOYSA-N
Pubchem ID :255651

Safety of [ 4269-17-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 4269-17-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 63.01
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.39
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.75
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.66
Log Po/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.

3.27
Log Po/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

4.31
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.47

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-4.4
Solubility 0.0103 mg/ml ; 0.0000397 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.8
Solubility 0.041 mg/ml ; 0.000158 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

-5.93
Solubility 0.000304 mg/ml ; 0.00000117 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

Yes
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.

-5.22 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

1.0
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)

2.44

Application In Synthesis of [ 4269-17-4 ]

* 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 [ 4269-17-4 ]

[ 4269-17-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 583-55-1 ]
  • [ 172732-52-4 ]
  • [ 4269-17-4 ]
  • 2
  • [ 902518-11-0 ]
  • [ 4269-17-4 ]
  • C31H20BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% 9- (2-bromo-phenyl) -9H- carbazole (9- (2-bromophenyl) -9H-carbazole, 3-1) was dissolved 9.4g (29mmol) in 80mL of anhydrous tetrahydrofuran cooled to -78 It was. Normal to the cooled solution - and then put the semi-butyl lithium (2.5M) 13mL (32mmol) slowly and stirred for 30 minutes at the same temperature. 4-bromo--9H- fluorene-9-one (4-bromo-9H-fluoren-9-one) To a mixture of the cold put 7.5g (29mmol, 3-2). When the reaction is complete, the mixture gives the temperature up to room temperature and stirred was added a saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate and treated with anhydrous magnesium sulfate and concentrated after filtration. It was added to an excess of hexane and a small amount of ethyl acetate to the compound of the concentrated state after stirring was filtered to give 10.6g of the desired compound 3-3 (72%) of white solid.
  • 3
  • [ 902518-11-0 ]
  • [ 4269-17-4 ]
  • C31H18BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% A solution of the intermediate a (6.96 g) in purified THF (300 ml) was cooled to -78 C. A 2.5 M hexane solution of n-butyllithium (8.64 ml) was gradually added dropwise. After stirring at the same temperature for 30 min, 4-bromo-9-fluorenone (6.08 g) was added. After stirring at the same temperature for 40 min and further stirring at ordinary temperature for 3 h, the reaction was terminated by adding an aqueous solution of ammonium chloride. After extracting the organic substances with ethyl ether, the extract was dried over anhydrous magnesium sulfate, and then the ethyl ether was removed. The obtained solid was dispersed in ethanol and the dispersion was stirred for one day. The solid collected by filtration was vacuum-dried to obtain an intermediate (10.12 g, 97% yield), which was then dispersed in 10 ml of acetic acid. After adding 10 drops of concentrated sulfuric acid, the dispersion was refluxed for 4 h. The precipitated solid was collected by filtration, washed with ethanol, and vacuum-dried to obtain the intermediate B (9.49 g, 97% yield). MS: [M+H]+=563
97% A solution of the intermediate a (6.96 g) in purified THF (300 ml) was cooled to -78 C. A 2.5 M hexane solution of n-butyllithium (8.64 ml) was gradually added dropwise. After stirring at the same temperature for 30 min, 4-bromo-9-fluorenone (6.08 g) was added. After stirring at the same temperature for 40 min and further stirring at ordinary temperature for 3 h, the reaction was terminated by adding an aqueous solution of ammonium chloride. After extracting the organic substances with ethyl ether, the extract was dried over anhydrous magnesium sulfate, and then the ethyl ether was removed. The obtained solid was dispersed in ethanol and the dispersion was stirred for one day. The solid collected by filtration was vacuum-dried to obtain an intermediate (10.12 g, 97% yield), which was then dispersed in 10 ml of acetic acid. After adding 10 drops of concentrated sulfuric acid, the dispersion was refluxed for 4 h. The precipitated solid was collected by filtration, washed with ethanol, and vacuum-dried to obtain the intermediate B (9.49 g, 97% yield). MS: [M+H]+=563
97% Intermediate a (6.96 g) was dissolved in purified THF (300 ml) and then cooled to -78 C. A 2.5 M solution of n-butyllithium in hexane (8.64 ml) was slowly added dropwise. After stirring at the same temperature for 30 minutes, 4-bromo-9-fluorenone, (6.08 g) was added. After stirring at the same temperature for 40 minutes, the temperature was raised to room temperature and further stirred for 3 hours, and then an aqueous solution of ammonium chloride was added to terminate the reaction. After extracting organic matter with ethyl ether, the extract was dried over anhydrous magnesium sulfate, then ethyl ether was removed. The resulting solid was dispersed in ethanol and stirred for 1 day. The solid filtered off was dried under vacuum to obtain 10.12 g (97% yield) of intermediate. The obtained intermediate was dispersed in 10 ml of acetic acid, 10 drops of concentrated sulfuric acid was added thereto, and the mixture was refluxed for 4 hours. The obtained solid was filtered off, washed with ethanol and then dried under vacuum to obtain 9.49 g (97% yield) of Intermediate B.
65% 9-(2-Bromophenyl)carbazole (12.81 g, 40 mmol)Add in a three-necked flask,Stir and dissolve with 200 mL of anhydrous tetrahydrofuran.Nitrogen protection,Cool down to -78 C,Then slowly add dropwise 16 mL of 2.5 M butyl lithium solution.Stir for half an hour after adding.Next 4-bromo-l-ketone (10.36 g, 40 mmol)a tetrahydrofuran solution is dropped into the reaction solution,After the drop, rise to room temperature,Stir the reaction for 2 hours,Quenched by adding saturated ammonium chloride solution,Add water,Concentrated organic phase,Get a yellow oil,Add this oilA mixture of 100 mL of HAc and 20 mL of HCl was stirred and refluxed for 12 hours.Cool, then add saturated brine,And extracted with dichloromethane,The organic phase is obtained.Wash the organic phase three times with water,Evaporate to remove the solvent,The residue was recrystallized from DCM/PE.The compound 5-1 (12.56 g, yield 65%) was obtained as a white solid.

 

Historical Records

Technical Information

Categories