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Chemical Structure| 503821-94-1 Chemical Structure| 503821-94-1

Structure of 503821-94-1

Chemical Structure| 503821-94-1

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Product Details of [ 503821-94-1 ]

CAS No. :503821-94-1
Formula : C7H4BrIO2
M.W : 326.91
SMILES Code : O=C(O)C1=CC=CC(Br)=C1I
MDL No. :MFCD15527220
Boiling Point : No data available
InChI Key :RBFCXOXAEIWXRW-UHFFFAOYSA-N
Pubchem ID :11232662

Safety of [ 503821-94-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Computational Chemistry of [ 503821-94-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 53.82
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.58
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.

2.75
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.

3.24
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

2.86
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.64

Water Solubility

Log S (ESOL):?

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

-3.96
Solubility 0.0357 mg/ml ; 0.000109 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.

-3.23
Solubility 0.193 mg/ml ; 0.000589 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

-3.55
Solubility 0.0926 mg/ml ; 0.000283 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

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.

-6.31 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.

0.56

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)

1.9

Application In Synthesis of [ 503821-94-1 ]

* 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 [ 503821-94-1 ]

[ 503821-94-1 ] Synthesis Path-Downstream   1~10

  • 2
  • [ 585-76-2 ]
  • [ 503821-94-1 ]
  • 3
  • [ 503821-94-1 ]
  • 7-bromo-8-iodo-1,2,3,4-tetrahydroisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
By the same procedure, using <strong>[503821-94-1]3-bromo-2-iodobenzoic acid</strong> as the starting material, 7-bromo-8-iodo-1,2,3,4-tetrahydroisoquinoline is prepared.
By the same procedure, using <strong>[503821-94-1]3-bromo-2-iodo-benzoic acid</strong> as the starting material, 7-bromo-8-iodo-1,2,3,4-tetrahydroisoquinoline is prepared.
  • 4
  • sodium 2-bromoanilide [ No CAS ]
  • [ 503821-94-1 ]
  • [ 126158-03-0 ]
  • [ 12775-96-1 ]
  • [ 615-36-1 ]
  • 3-bromo-2-(2-bromophenylamino)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; a) 3-Bromo-2-(2-bromophenylamino)benzoic acid (XXII) 3-Bromo-2-iodobenzoic acid (XX) was prepared as described in D. Twiss and R. V. Heinzelmann, J. Org. Chem. 15 (1950) 496. A mixture of 16.0 g (46 mmol) of sodium 3-bromo-2-iodobenzoate [prepared from 15.0 g (46 mmol) of <strong>[503821-94-1]3-bromo-2-iodobenzoic acid</strong> (XX) and 1.1 g (46 mmol) of sodium hydride], 19.5 g (100 mmol) of sodium 2-bromoanilide [prepared from 17.3 g (100 mmol) of 2-bromoaniline (XXI) and 2.4 g (100 mmol) of sodium hydride] and a spatula-tipfull of copper powder in 100 ml of tetrahydrofuran was heated to reflux for 9 h. The solvent was distilled off, the residue extracted with 0.5 M aqueous sodium hydroxide, and the resulting suspension subjected to centrifugation. The centrifugate was acidified with diluted hydrochloric acid, the precipitated solid was filtered off and dried under high vacuum. Fractional sublimation under high vacuum yielded 6.3 g (37% of theory) of 3-bromo-2-(2-bromophenylamino)benzoic acid (XXII) as a yellow powder with a melting point of 181-182 C.
  • 5
  • [ 503821-94-1 ]
  • 3-bromo-2-iodo benzoic acid potassium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In water; at 100℃; <strong>[503821-94-1]3-bromo-2-iodo benzoic acid</strong> (11) (2.56 g, 7.83 mmol) was dissolved in a KOH solution (KOH 536 mg, 9.6 mmol; H2O 5 mL). The mixture was condensed under vacuum at 100C and the resultant solid was heated under vacuum at 100C for 12 h to yield a dried potassium salt. Metallic sodium (200 mg, 8.35 mmol) was dissolved in 100 mL of MeOH, and 2,3-dimethylphenol (1.09 g, 8.35 mmol) was added. The mixture was condensed and heated under vacuum at 100C for 12 h to yield a dried sodium salt. The sodium salt was dissolved in 15 mL of anhydrous dimethyl sulphoxide, and then tris (2-(2- methoxyethoxy) ethyl)amine (TDA-1, 1.0 mL) was added. The mixture was stirred to reach homogeneity at room temperature under anhydrous conditions, and then CuCl (350 mg) and potassium salt powders of the compound 11 were added. The resultant mixture was stirred at 85C for 4 h, cooled down to room temperature, washed with a NaOH solution (NaOH 200 mg, water 100 mL), filtered with diatomite, and acidified with 1 N HCl to pH value at 2-3. A semisolid precipitate was collected, washed with water, and dried to yield a crude product of 3-bromo-2-(2,3-dimethylphenol)-benzoic acid (12) (2.36g, 7.35 mmol, 75%). The crude product can be used for next reaction directly without purification.
With potassium hydroxide; In water; at 100℃; for 12.0h; Preparation of 3-bromo-2-(2,3-dimethylphenol)benzoic acid (12)<strong>[503821-94-1]3-bromo-2-iodo benzoic acid</strong> (11) (2.56 g, 7.83 mmol) was dissolved in a KOH solution (KOH 536 mg, 9.6 mmol; H2O 5 mL). The mixture was condensed under vacuum at 100 C. and the resultant solid was heated under vacuum at 100 C. for 12 h to yield a dried potassium salt. Metallic sodium (200 mg, 8.35 mmol) was dissolved in 100 mL of MeOH, and 2,3-dimethylphenol (1.09 g, 8.35 mmol) was added. The mixture was condensed and heated under vacuum at 100 C. for 12 h to yield a dried sodium salt. The sodium salt was dissolved in 15 mL of anhydrous dimethyl sulphoxide, and then tris(2-(2-methoxyethoxy)ethyl)amine (TDA-1, 1.0 mL) was added. The mixture was stirred to reach homogeneity at room temperature under anhydrous conditions, and then CuCl (350 mg) and potassium salt powders of the compound 11 were added. The resultant mixture was stirred at 85 C. for 4 h, cooled down to room temperature, washed with a NaOH solution (NaOH 200 mg, water 100 mL), filtered with diatomite, and acidified with 1 N HCl to pH value at 2-3. A semisolid precipitate was collected, washed with water, and dried to yield a crude product of 3-bromo-2-(2,3-dimethylphenol)-benzoic acid (12) (2.36 g, 7.35 mmol, 75%). The crude product can be used for next reaction directly without purification.
  • 6
  • [ 503821-94-1 ]
  • [ 1035912-43-6 ]
  • 7
  • [ 503821-94-1 ]
  • [ 1035912-41-4 ]
  • 8
  • [ 503821-94-1 ]
  • [ 1415114-04-3 ]
  • 9
  • [ 503821-94-1 ]
  • [ 117570-53-3 ]
  • 10
  • [ 503821-94-1 ]
  • [ 129095-08-5 ]
 

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