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Chemical Structure| 5469-19-2 Chemical Structure| 5469-19-2

Structure of 5469-19-2

Chemical Structure| 5469-19-2

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Product Details of [ 5469-19-2 ]

CAS No. :5469-19-2
Formula : C9H11Br
M.W : 199.09
SMILES Code : CC1=C(C)C=C(C)C(Br)=C1
MDL No. :MFCD00000072
InChI Key :SCZXFZRJDVZMJI-UHFFFAOYSA-N
Pubchem ID :79610

Safety of [ 5469-19-2 ]

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

Computational Chemistry of [ 5469-19-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.33
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 49.04
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.

2.63
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

3.64
Log Po/w (WLOGP)?

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

3.37
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.

3.98
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

3.9
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.5

Water Solubility

Log S (ESOL):?

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

-3.81
Solubility 0.0307 mg/ml ; 0.000154 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.

-3.33
Solubility 0.0935 mg/ml ; 0.000469 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

-4.42
Solubility 0.00766 mg/ml ; 0.0000385 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

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

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.

-4.93 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

2.0
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<2.0
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)

1.39

Application In Synthesis of [ 5469-19-2 ]

* 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 [ 5469-19-2 ]

[ 5469-19-2 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 64-67-5 ]
  • [ 5469-19-2 ]
  • [ 17851-27-3 ]
  • 2
  • [ 95-63-6 ]
  • [ 5469-19-2 ]
YieldReaction ConditionsOperation in experiment
97.3% With sulfuric acid; dihydrogen peroxide; iodine; iron(II) sulfate; sodium bromide; In dichloromethane; water; at 0℃; Weigh three toluene 0.1mol,0.15 mol of sodium bromide,30% sulfuric acid solution 0.08mol in three-necked flask,Then, 50 g of dichloromethane was added as a solvent,Add catalyst 0.8g ferrous sulfate,0.05g of iodine,The three-necked flask placed 0 low temperature tank, mixing, fully dissolved.A solution of 10% aqueous hydrogen peroxide (H2O, 20.08 mol) was added dropwise at 0 C over 3-5 hours,And incubated for 6 hours.The reaction is over, standing stratification,The organic phase was washed with 100 mL of water, repeated three times, and then the aqueous solution was extracted with 30 mL of dichloromethane, repeated three times. The organic phase solutions were combined,The methylene chloride was recovered under reduced pressure to give a crude solid product, which was recrystallized from twice the mass of gasoline to give white crystals,Is trimethylbenzene, about 19.4 g, yield 97.3%.
  • 4
  • [ 5469-19-2 ]
  • [ 90326-72-0 ]
  • [ 82940-81-6 ]
  • 5
  • [ 5469-19-2 ]
  • [ 41381-36-6 ]
  • 7
  • [ 5469-19-2 ]
  • [ 842136-27-0 ]
  • 8
  • [ 5469-19-2 ]
  • [ 842136-27-0 ]
  • [ 276677-03-3 ]
  • 9
  • [ 5469-19-2 ]
  • 1-bromo-2,4,5-trimethyl-3-nitro-benzene [ No CAS ]
  • 10
  • [ 5469-19-2 ]
  • 2-bromo-3,5,6-trimethyl-benzenesulfonic acid [ No CAS ]
  • 11
  • [ 5469-19-2 ]
  • [ 133833-71-3 ]
  • 12
  • [ 5469-19-2 ]
  • nitric acid-(3-bromo-4,6-dimethyl-2,5-dinitro-benzyl ester) [ No CAS ]
  • nitric acid-(4-bromo-2,5-dimethyl-3,6-dinitro-benzyl ester) [ No CAS ]
  • 13
  • [ 5469-19-2 ]
  • trimesityl-arsine [ No CAS ]
  • 14
  • [ 5469-19-2 ]
  • [ 56457-45-5 ]
  • 15
  • [ 137-17-7 ]
  • [ 5469-19-2 ]
  • 18
  • [ 56403-26-0 ]
  • [ 5469-19-2 ]
  • 19
  • [ 5469-19-2 ]
  • [ 75-03-6 ]
  • [ 17851-27-3 ]
  • 20
  • [ 5469-19-2 ]
  • [ 74-88-4 ]
  • [ 95-93-2 ]
  • 21
  • [ 5469-19-2 ]
  • [ 41381-45-7 ]
  • 22
  • [ 5469-19-2 ]
  • [ 41381-44-6 ]
  • 23
  • [ 5469-19-2 ]
  • [ 13124-84-0 ]
YieldReaction ConditionsOperation in experiment
With potassium permanganate; water; sodium carbonate; for 60h;Reflux; Preparation 1 d: 2-tert-Butyl 5-methyl 6-hromo-2,3-dibydro-1H-isoiiidole-2,5-dicarboxylateStep A: S-Brornobenzene-1,2,4-tricarboxylic acidBromotrimethyl benzene (40.7 g, 205 mmol) was added to a mixture of water (3.25 L), potassium permanganate (232 g, 1.468 mol) and sodium carbonate (28.5 g, 206 mmol). The mixture was stirred at reflux for 60 h. Ethanol (820 mE) was added dropwise, and theresultant mixture was filtered hot through celite, then allowed to cool to ambient temperature. The filtrate was acidified with concentrated aqueous HCI, and the organic solvent was removed in vacuo, The solid product was isolated by filtration.
  • 25
  • [ 92-66-0 ]
  • [ 5469-19-2 ]
  • 2,4,5-Trimethyl-[1,1';4',1'']terphenyl [ No CAS ]
  • 26
  • [ 5469-19-2 ]
  • [ 154152-57-5 ]
YieldReaction ConditionsOperation in experiment
19% With sulfuric acid; nitric acid; for 5h;Cooling with ice; <strong>[5469-19-2]2-bromo-1,4,5-trimethylbenzene</strong> (10g, 50mmol) was dissolved in concentrated sulfuric acid (20mL) inThen in the ice water bath,Concentrated nitric acid (3.5 g, 1.1 eq) was slowly added.After 5 hours of reaction,The reaction mixture was poured into ice-water, filtered,The yellow solid was collected, washed with water, and then column chromatographed (petroleum ether / ethyl acetate = 50/1) to afford the product (2.3 g, 19% yield)
  • 27
  • [ 5469-19-2 ]
  • 2,4,5-trimethyl 1-deuterio benzene [ No CAS ]
  • 28
  • [ 5469-19-2 ]
  • [ 68-12-2 ]
  • [ 5779-72-6 ]
YieldReaction ConditionsOperation in experiment
85% Bromo-2,4,5-trimethyl-benzene (1) (10.00 g, 50.23 mmol) was added into a two-necked flask. The reaction vessel was degassed and refilled with nitrogen three times and then 120 mL of distilled THF was added. The flask was cooled to -78 C and n-butyllithium (25.00 mL, 2.40 M in hexane) was added dropwise. After stirring at -78 C for 2 h, 7.80 mL of dimethyl formamide was added dropwise. The mixture was allowed to react for another 6 h at -78 C and was then warmed to room temperature.Saturated NH4C1 aqueous solution was added to quench the reaction. The mixture was extracted with dichloromethane (DCM). The organic layer was separated, washed with deionized water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated under reduced pressure and the crude product was purified by silica gel column chromatography using hexanelDCM (5/1, v/v) as eluent. 6.30 g of 2,4,5-trimethyl-benzenaldehyde (2) was obtained as white powder in 85.0% yield. 2 (2.00 g, 13.50 mmol) and zinc dust (2.65 g, 40.50 mmol) were added into a two-necked flask with a reflux condenser. The reaction vessel was degassed and refilled with nitrogen three times and then 100 mL of THF was added into the flask. The mixture was cooled to -78 C and TiC14 (2.23 mL, 20.25 mmol) was added dropwise by syringe. The mixture was slowly warmed to room temperature. After stifling for 1 h, the mixture was refluxed for another 24 h. The reaction was quenched with 4% aqueous HC1 solution and filtered. The mixture was extracted with DCM. The organic layer was collected, washed with deionized water and brine, and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated under reduced pressure and the crude product was purified by silica gel column chromatography using hexane/DCM (5/1, v/v) as eluent. 1.43 g of DPE-TM was obtained as white powder in 80.3% yield.
  • 29
  • [ 5469-19-2 ]
  • [ 4330-21-6 ]
  • [ 159277-49-3 ]
  • 31
  • [ 95-63-6 ]
  • [ 7726-95-6 ]
  • [ 5469-19-2 ]
  • 32
  • [ 95-63-6 ]
  • [ 7726-95-6 ]
  • [ 7697-37-2 ]
  • SO2 [ No CAS ]
  • [ 5469-19-2 ]
  • [ 90326-72-0 ]
  • [ 41381-36-6 ]
  • [ 116496-13-0 ]
 

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