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Chemical Structure| 52414-97-8 Chemical Structure| 52414-97-8

Structure of 52414-97-8

Chemical Structure| 52414-97-8

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Product Details of [ 52414-97-8 ]

CAS No. :52414-97-8
Formula : C7H6BrNO2
M.W : 216.03
SMILES Code : O=[N+](C1=C(C)C=CC=C1Br)[O-]
MDL No. :MFCD02673631
Boiling Point : No data available
InChI Key :XDKMDDOCVPNVMB-UHFFFAOYSA-N
Pubchem ID :142929

Safety of [ 52414-97-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 52414-97-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 47.93
TPSA ?

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

45.82 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.78
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

2.79
Log Po/w (WLOGP)?

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

2.67
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.

2.77
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

0.8
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.16

Water Solubility

Log S (ESOL):?

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

-3.27
Solubility 0.115 mg/ml ; 0.000531 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.

-3.41
Solubility 0.0843 mg/ml ; 0.00039 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

-3.02
Solubility 0.204 mg/ml ; 0.000946 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

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.

-5.64 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

2.0 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)

1.8

Application In Synthesis of [ 52414-97-8 ]

* 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 [ 52414-97-8 ]

[ 52414-97-8 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 52414-97-8 ]
  • [ 53848-17-2 ]
YieldReaction ConditionsOperation in experiment
42% A mixture of tellurium (21.6 g, 169.4 mmol) and NaBH4 (15.0 g, 396 mmol) in 575 mL of absolute EtOH was heated at reflux under an atmosphere of N2 for 1 hr, then allowed to cool to rt. A solution of 3-bromo-2-nitrotoluene (1c; 7.32 g, 33.8 mmol) in 25 mL EtOH was added all at once and the mixture stirred at room temp for 2 hrs. The reaction mixture was filtered through a CELITE pad and the filtrate evaporated under reduced pressure. The residue was taken up in Et2O (about 200 mL), washed with brine then dried over MgSO4. Evaporation of the solvent afforded 2.66 g (42%) of 2a as a dark liquid.
42% step 2 2-BROMO-6-METHYLANILINE (2a) -A mixture of tellurium (21.6 g, 169.4 mmol) and NaBH4 (15.0 g, 396 mmol) in 575 mL of absolute ETOH was heated at reflux under an atmosphere of N2 for 1 hr, then allowed to cool to rt. A solution of 3-bromo-2- nitrotoluene (LC ; 7.32g, 33.8 mmol) in 25 mL ETOH was added all at once and the mixture allowed to stir at room temperature for 2 hrs. The reaction mixture was filtered through a CELITE (D pad and the filtrate evaporated under reduced pressure. The residue was taken up in ET20 (about 200 mL), washed with brine then dried over MGS04. Evaporation of the solvent afforded 2.66g (42%) of 2a as a dark liquid.
  • 2
  • [ 591-17-3 ]
  • [ 7697-37-2 ]
  • [ 108-39-4 ]
  • [ 52414-98-9 ]
  • [ 52414-97-8 ]
  • [ 40385-54-4 ]
  • 3
  • [ 591-17-3 ]
  • [ 7697-37-2 ]
  • [ 52414-98-9 ]
  • [ 52414-97-8 ]
  • [ 40385-54-4 ]
  • [ 5411-53-0 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 4 2-Bromo-6-methylbenzenamine A mixture of mercuric acetate (100 g, 0.31 mol) and 4-nitrotoluene (500 g, 3.6 mol) is heated at 150 C. for 4 hr. A small amount of precipitate is filtered off and a saturated salt solution is added. The reaction is steam distilled to remove unreacted 4-nitrotoluene (about 350 ml). A gold colored precipitate is filtered off (100 g), crushed to a fine powder and added portionwise to bromine (50 g) in a cold saturated solution of potassium bromide (80 g). This is stirred for 1 hr and chloroform and water is added. A solid by-product is filtered off. The aqueous phase is extracted with chloroform. The combined chloroform extracts are dried and evaporated to afford 90 g of semisolid. Chromatography on silica gel using 80% acetone in toluene gives 46 g of 3-bromo-2-nitrotoluene: nmr (CDCl3) delta 2.5 (s, 3H) and 7.8 (m, 3H).
  • 5
  • [ 52414-97-8 ]
  • [ 845751-59-9 ]
 

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