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Chemical Structure| 69272-50-0

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Product Details of [ 69272-50-0 ]

CAS No. :69272-50-0
Formula : C6H6Br2N2
M.W : 265.93
SMILES Code : NC1=C(Br)C=CC(Br)=C1N
MDL No. :MFCD19288763
InChI Key :VPMJBJSLTPBZLR-UHFFFAOYSA-N
Pubchem ID :11821532

Safety of [ 69272-50-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 69272-50-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 2.0
Molar Refractivity 50.65
TPSA ?

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

52.04 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.62
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

1.94
Log Po/w (WLOGP)?

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

2.39
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.

2.33
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

1.78
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.01

Water Solubility

Log S (ESOL):?

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

-3.15
Solubility 0.186 mg/ml ; 0.0007 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.

-2.66
Solubility 0.586 mg/ml ; 0.0022 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

-3.38
Solubility 0.11 mg/ml ; 0.000412 mol/l
Class?

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

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

No
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

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.

-6.54 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

1.0 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<0.0
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)

1.75

Application In Synthesis of [ 69272-50-0 ]

* 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 [ 69272-50-0 ]

[ 69272-50-0 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 131543-46-9 ]
  • [ 69272-50-0 ]
  • [ 148231-12-3 ]
YieldReaction ConditionsOperation in experiment
~ 100% In ethanol; water; for 8h; Into a 500 ml three-necked flask, 3,6-dibromo-1,2-diaminobenzene obtained in (3) described above (FW: 287.90; 24.3 mmole; 7.0 g), 300 ml of ethanol as the solvent and 50 ml of a 40% aqueous solution of glyoxal (about 44 mmole; FW: 58.04; d=1.28) were added, and the resultant mixture was stirred for 8 hours. Recrystallization was conducted 5 times using ethanol as the solvent, and the object compound (5,8-dibromoquinoxaline) was obtained in an approximately quantitative amount.
69% With triethylamine; In ethanol; water; at 20℃; In 300ml three-necked flask was added 1,2-diamino-3,6-dibromobenzene 2.40g (9.02mmol) and ethanol 60ml. Here, after dropping a 39% aqueous glyoxal solution 3g (20.2mmol), and the mixture was stirred overnight at room temperature added a few drops of triethylamine. After that, the precipitated solid was collected by filtration, the desired product was obtained by recrystallized in ethanol. The yield 1.79g, 69% yield.
40% In ethanol; at 80℃; for 3h; After the capacitor is equipped with a 250 mL round bottom flask was placed in 3,6-dibromo-benzene-1,2-diamine (compound 1-i) 1.5 g, ethanol 38 mL and then injected all dissolved. Then, glyoxal (40% aq.) And then injecting a 0.825 g slowly, stirred for 3 hours at 80 . After 3 hours, there is produced a yellow solid was obtained by the filter product 5,8-dibromo-quinoxaline (Compound j-1) through which methanol. (Yield: 40%)
22% In ethanol; for 3h;Reflux; 3,6-dibromobenzene- l ,2-diamine ( lb) (250 mg, 0.94 mmol) in ethanol (6 ml), and 40% aqueous solution of glyoxal (0. 17 ml, 1.2 mmol) were mixed together under stirring. The resulting reaction mixture was heated to reflux for 3 hours and thereafter allowed to stir for 18 hours at room temperature. Filtered the said reaction mixture under vacuum to afford (60 mg, 22%) 5,8-dibromoquinoxaline (21a) as a solid.MS (EI) m/z: 288.9 (M+l). iH NMR (400 MHz, DMSO-d6): 8 9. 13 (s, 2H), 8.18 (s, 2H).
In ethanol; water; for 3h;Reflux; A 40% aqueous solution of glyoxal (8.8 M, 6.3 ml_, 55.1 mmol, 1.3 equiv) was added to a suspension of 3,6-dibromo-benzene-1 ,2-diamine (Step 1.6) (1 1.3 g, 42.4 mmol) in EtOH (280 ml_). The reaction mixture was heated to reflux for 3 h and allowed to cool to rt overnight. Vacuum filtration of the reaction mixture afforded 9.7 g of the title compound as a yellow solid: APCI-MS: 286.2 / 288.1 / 290.1 [M-1]"; tR= 4.40 min (System 1 ).
0.63 g With triethylamine; In ethanol; at 20℃; for 12h; In a 100 mL flask was added 3,6-dibromo-1,2-benzenediamine (1.0 g, 3.76 mmol), 30 mL of absolute ethanol, 4mL of glyoxal solution (40%) and 5 drops of triethylamine. The reaction was stirring at room temperature and light shelter for 12 h. The precipitate obtained was filtered and recrystallized from ethanol to give a yellow solid. Yield: 0.63 g (58%). IR (ATR): 3072; 3052; 1873; 1759; 1676; 1584; 1451; 1373; 1024; 879; 821.1H NMR (400 MHz, CDCl3) d ppm: 9,01 (s, 2H); 7,99 (s, 2H). 13C NMR (400 MHz, CDCl3) d ppm: 146,19; 141,76; 133,89; 124,16.

  • 2
  • [ 69272-50-0 ]
  • glyoxal sodium bisulfite [ No CAS ]
  • [ 148231-12-3 ]
  • 3
  • [ 69272-50-0 ]
  • [ 122-51-0 ]
  • [ 148185-66-4 ]
YieldReaction ConditionsOperation in experiment
With aminosulfonic acid; In methanol; Diamine ( lb) (1 g, 3.76 mmol) was dissolved in methanol (20 ml) under stirring. To the resulting solution triethyl orthoformate (0.748 ml, 4.5 mmol) and sulfamic acid ( 18 mg, 0.18 mmol) was added. The resulting reaction mixture was stirred overnight. Solvent was evaporated from the reaction mass to obtain the residue which was rinsed with ether, dried under air to afford (950 mg, 50% yield for 2 steps) 4,7-dibromo- lH-benzo[d]imidazole ( lc) as a yellow solid. MS (EI) m/z: 276.9 (M+l). NMR (400 MHz, DMSO-d6): 5 13.2 (bs, 1H), 8.36 (s, 1H), 7.35 (s, 2H).
  • 4
  • [ 69272-50-0 ]
  • [ 204905-77-1 ]
  • [ 1259532-61-0 ]
  • 5
  • [ 69272-50-0 ]
  • [ 37091-73-9 ]
  • N,N’-(3,6-dibromobenzene-1,2-diyl)bis(1,3-dimethylimidazolidin-2-imine) [ No CAS ]
  • 6
  • [ 69272-50-0 ]
  • [ 149-73-5 ]
  • [ 148185-66-4 ]
  • 7
  • [ 64-18-6 ]
  • [ 69272-50-0 ]
  • [ 148185-66-4 ]
YieldReaction ConditionsOperation in experiment
100% In methanol; at 65℃; for 24h; Preparation Example 1: 3,6-Dibromo-1,2-phenylenediamine (10 mmol, 2.66 g), formic acid (15 mmol, 0.69 g), 50 mL of methanol wasplaced in a 100 mL single-neck round bottom flask, and heated at 65 C for 24 h. The reaction results were followed by TLC, and the solvent was removed under reduced pressure and purified by column chromatography(dichloromethane).Intermediate B was obtained (yield 100%).
 

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