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Chemical Structure| 1074-24-4 Chemical Structure| 1074-24-4

Structure of 1074-24-4

Chemical Structure| 1074-24-4

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Product Details of [ 1074-24-4 ]

CAS No. :1074-24-4
Formula : C8H8Br2
M.W : 263.96
SMILES Code : CC1=CC(Br)=C(C)C=C1Br
MDL No. :MFCD00000091
InChI Key :QENIALCDPFDFHX-UHFFFAOYSA-N
Pubchem ID :66175

Safety of [ 1074-24-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 1074-24-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 51.77
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.76
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

4.03
Log Po/w (WLOGP)?

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

3.83
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.

4.39
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

4.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.82

Water Solubility

Log S (ESOL):?

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

-4.46
Solubility 0.00916 mg/ml ; 0.0000347 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.

-3.73
Solubility 0.0488 mg/ml ; 0.000185 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

-4.88
Solubility 0.0035 mg/ml ; 0.0000132 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

Low
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

Yes
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

Yes
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.

-5.05 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

1.0
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)

1.49

Application In Synthesis of [ 1074-24-4 ]

* 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 [ 1074-24-4 ]

[ 1074-24-4 ] Synthesis Path-Downstream   1~10

  • 2
  • [ 1074-24-4 ]
  • [ 544-92-3 ]
  • [ 39095-25-5 ]
  • [ 292037-85-5 ]
  • 3
  • [ 1074-24-4 ]
  • [ 13321-74-9 ]
  • 4,2',5',4''-tetramethyl-2,5,2'',5''-tetramethoxy-1,1':4',1''-terphenyl [ No CAS ]
  • 4
  • [ 1074-24-4 ]
  • [ 33513-42-7 ]
  • [ 7044-92-0 ]
YieldReaction ConditionsOperation in experiment
82% Weigh 5g of raw materials (19mmol) and 0.17g, 0.95mmol of hexamethylphosphoric triamide (HMPA), put them into a 500mL three-necked flask with a built-in thermometer, and after 3 times of vacuum ventilation,Place it in a dry ice ethanol bath, control the temperature at -78C, add 2.1 equiv tert-butyl lithium (39.9 mmol, 30.69 mL, 1.3 M/L) dropwise, and the addition is completed in 1 hour. Slowly rise to room temperature, and continue stirring at room temperature for 20 min. Then the reaction system was reset in a dry ice ethanol bath, kept at -78C, and 13.89g of DMF was slowly added dropwise to the system. After the addition was completed, the dry ice ethanol bath was removed, and the mixture was stirred at room temperature for 50 minutes. Under ice bath, 40mL saturated aqueous ammonium chloride solution was added dropwise to the reaction system and quenched; ethyl acetate was extracted twice, the organic phase was washed twice with saturated brine, the organic phase was dried, concentrated under reduced pressure, evaporated to dryness, and the crude product was subjected to Purified by column chromatography, 2.54 g of white solid was obtained with a yield of 82%.
  • 6
  • [ 1074-24-4 ]
  • [ 24067-17-2 ]
  • [ 152219-88-0 ]
  • 8
  • [ 628-36-4 ]
  • [ 1074-24-4 ]
  • C12H10Br2N6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% at 150℃; for 24h; The magneton, of the reflux condenser and a thermometer 50 ml round-bottom flask three port respectively added in 1,4-dibromo -2,5-dimethyl (1mmol) and double-carbohydrazide (4mmol), are started to stir the 150oC, reaction 24 hours. After the reaction, the reaction liquid to room temperature, will be precipitated by adding 100 ml hot methanol, after stirring to dissolve, filtered, filtrate slowly volatilized to obtain white solid, yield 85percent
85% at 150℃; for 24h; The molar ratio of 1,4-dibromo-2,5-dimethylbenzene: bisformylhydrazide was 1: 4A 50 mL three-neck round bottom flask equipped with a magnetron, a reflux condenser and a thermometer was charged with 1,4-dibromo-2,5-diMethylbenzene (1 mmol) and bisformylhydrazide (4 mmol) were added and the mixture was stirred at 150 ° C for 24 hours. After completion of the reaction,The solution was cooled to room temperature and the resulting precipitate was added to 100 mL of hot methanol. After stirring, the solution was filtered and the filtrate was slowly evaporated to obtain whiteColor solid, yield 85percent.
85% at 150℃; for 24h; The molar ratio of 1,4-dibromo-2,5-dimethylbenzene: bisformylhydrazide was 1: 4A 50 mL three-necked round bottom flask equipped with a magnetic stirrer, a reflux condenser and a thermometer was charged with 1,4-dibromo-2,5-diMethylbenzene (1 mmol) and bisformylhydrazide (4 mmol) were added and the mixture was stirred at 150 ° C for 24 hours. After completion of the reaction,The solution was cooled to room temperature and the resulting precipitate was added to 100 mL of hot methanol. After stirring, the solution was filtered and the filtrate was slowly evaporated to obtain whiteColor solid, yield 85percent. Analysis for C12N6H1QBr2: Theory: C, 36.21; H, 2.53; N, 21.11. Found: C,The molar ratio of 1,4-dibromo-2,5-dimethylbenzene: bisformylhydrazine is 1: 4, the reaction temperature is 150 ° C, the reaction time is 24 hours, the reaction time is 24 hours, hour. Dibromo-2,5-dimethylbenzene and bisformylhydrazine were prepared under heating using a "one-pot" process4-yl) methyl) -2,5-dibromomethyl) -new-1,2,4-triazole (1).
85% at 150℃; for 24h; Equipped with a magnetic,Reflux condenserAnd a thermometer 50 mL three-necked round bottom flask were added1,4-dibromo-2,5-dimethylbenzene (1 mmol) and formyl hydrazine bis (4 mmol),Start stirring at 150 oC,Reaction for 24 hours.After the reaction,The reaction solution was cooled to room temperature,The resulting precipitate was added to 100 mL of hot methanol,After stirring to dissolve,filter,Slow evaporation of the filtrate gave a white solid,Yield 85percent.

  • 9
  • [ 890042-13-4 ]
  • [ 1074-24-4 ]
  • 2-(4-bromo-2,5-dimethylphenyl)triphenylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 90℃; for 12h;Inert atmosphere; Synthesis of 2-(4-bromo-2,5-dimethylphenyl)triphenylene A mixture of 52.8 g (200 mmol) of 1,4-dibromo-2,5-dimethyl benzene, 70.9 g (200 mmol) of <strong>[890042-13-4]4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane</strong>, 2.3 g (2 mmol) of tetrakis(triphenylphosphine)palladium, 400 ml of 2M Na2CO3, 400 ml of EtOH and 800 ml toluene was degassed and placed under nitrogen, and then heated at 90 C. for 12 hours. After the reaction finish, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica gel (hexane-dichloromethane) to give product 60.1 g (146 mmol, 73%) as a white solid.
  • 10
  • copper(I) cyanide [ No CAS ]
  • [ 1074-24-4 ]
  • [ 39095-25-5 ]
YieldReaction ConditionsOperation in experiment
87.4% In N,N-dimethyl-formamide; at 155℃; for 48h; 2,5-dibromo-p-xylene (30 mmol) and CuCN (8.1 g, 90 mmol) were refluxed in 100 mL of DMF at 155 C for 48 h.After cooling, the mixture is poured into 500 mL of w(NH3·H2O)=15% ammonia water.The precipitate was collected by filtration and washed with 500 mL of w(NH 3 ·H 2 O)=15% aqueous ammonia and 500 mL of water, respectively.The solid was dried in a vacuum oven and dissolved in 100 mL of chloroform.Then it is eluted with a short silica gel column with chloroform.The solvent is removed to obtain solid crude product.Recrystallize with 300mL ethanol,White needle crystals were obtained with a yield of 87.4% (4.09 g),
 

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