Home Cart Sign in  
Chemical Structure| 54286-63-4 Chemical Structure| 54286-63-4

Structure of 54286-63-4

Chemical Structure| 54286-63-4

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 54286-63-4 ]

CAS No. :54286-63-4
Formula : C6H2Br2N2O
M.W : 277.90
SMILES Code : BrC1=CC=C(Br)C2=NON=C12
MDL No. :MFCD02114623
InChI Key :ZUGAIWASFADONS-UHFFFAOYSA-N
Pubchem ID :179636

Safety of [ 54286-63-4 ]

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

Computational Chemistry of [ 54286-63-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 47.2
TPSA ?

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

38.92 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.33
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

2.56
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.

2.51
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

2.79
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.59

Water Solubility

Log S (ESOL):?

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

-3.78
Solubility 0.046 mg/ml ; 0.000165 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.

-3.03
Solubility 0.262 mg/ml ; 0.000944 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

-4.24
Solubility 0.0158 mg/ml ; 0.000057 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

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.

-6.18 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

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<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)

2.45

Application In Synthesis of [ 54286-63-4 ]

* 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.

  • Upstream synthesis route of [ 54286-63-4 ]

[ 54286-63-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 273-09-6 ]
  • [ 54286-63-4 ]
YieldReaction ConditionsOperation in experiment
25% at 90℃; for 2 h; Reflux Benzo[c][l,2,5]oxadiazole (2.5 g, 21 mmol) was heated to 90 0C with iron powder (0.23 g, 4.2 mmol). The molten liquid was then treated with bromine (3.2 ml, 62 mmol) and refluxed for 2 h. The resultant solution was poured onto ice and the precipitate filtered. The precipitate was then mixed with aq. NaHCO3, stirred for 15 min and filtered. Flash chromatography (n-hexane/EtOAc 9:1) afforded the title compound as an orange solid (1.5 g, 25 percent); m.p. 88 - 92 0C; vmax(thin film) 1514, 1344, 1201, 1026, 954, 871, 841 cm-1; δH(500 MHz, CDCl3) 7.51 (2H, s, Ar-H); δC (126 MHz, CDCl3) 149.6 (C=N), 134.4 (Ar-Q, 108.9 (ipso-Ai-Q; m/z (EI) 280([81'81Br]M+, 6percent), 278 ([81^9Br]M+, 8percent), 276 ([79^9Br]M+, 6percent), 250 (5percent), 248 (10percent), 246 (7percent), 197 (5percent); all data agree with those reported in the literature.
References: [1] Journal of Materials Chemistry C, 2015, vol. 3, # 5, p. 973 - 976.
[2] New Journal of Chemistry, 2012, vol. 36, # 3, p. 550 - 553.
[3] Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 732 - 742.
[4] Journal of Materials Chemistry C, 2015, vol. 3, # 35, p. 9145 - 9153.
[5] Patent: WO2009/34396, 2009, A2, . Location in patent: Page/Page column 91-92.
[6] Journal of the Chemical Society, 1931, p. 3308.
[7] Dyes and Pigments, 2012, vol. 95, # 2, p. 229 - 235.
[8] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 19, p. 3996 - 4003.
[9] Synthetic Communications, 2016, vol. 46, # 12, p. 1052 - 1061.
[10] RSC Advances, 2017, vol. 7, # 33, p. 20440 - 20450.
  • 2
  • [ 35036-93-2 ]
  • [ 54286-63-4 ]
References: [1] Chemical Communications, 2005, # 14, p. 1848 - 1850.
  • 3
  • [ 4050-81-1 ]
  • [ 54286-63-4 ]
References: [1] Synthetic Communications, 2016, vol. 46, # 12, p. 1052 - 1061.
[2] Journal of the Chemical Society, 1931, p. 3308.
  • 4
  • [ 480-96-6 ]
  • [ 54286-63-4 ]
References: [1] Journal of the Chemical Society, 1931, p. 3308.
[2] Journal of the Chemical Society, 1931, p. 3308.
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 19, p. 3996 - 4003.
[4] Journal of Materials Chemistry C, 2015, vol. 3, # 35, p. 9145 - 9153.
[5] Synthetic Communications, 2016, vol. 46, # 12, p. 1052 - 1061.
  • 5
  • [ 4609-97-6 ]
  • [ 54286-63-4 ]
References: [1] Journal of the Chemical Society, 1931, p. 3308.
[2] Journal of Organic Chemistry, 1964, vol. 29, p. 3722 - 3723.
  • 6
  • [ 776-12-5 ]
  • [ 54286-63-4 ]
References: [1] Journal of Organic Chemistry, 1964, vol. 29, p. 3722 - 3723.
  • 7
  • [ 71173-22-3 ]
  • [ 54286-63-4 ]
References: [1] Journal of Organic Chemistry, 1964, vol. 29, p. 3722 - 3723.
  • 8
  • [ 88-72-2 ]
  • [ 54286-63-4 ]
References: [1] Dyes and Pigments, 2012, vol. 95, # 2, p. 229 - 235.
  • 9
  • [ 88-74-4 ]
  • [ 54286-63-4 ]
References: [1] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 19, p. 3996 - 4003.
[2] Synthetic Communications, 2016, vol. 46, # 12, p. 1052 - 1061.
  • 10
  • [ 1516-58-1 ]
  • [ 54286-63-4 ]
References: [1] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 19, p. 3996 - 4003.
  • 11
  • [ 830-47-7 ]
  • [ 54286-63-4 ]
References: [1] Journal of the Chemical Society, 1931, p. 3308.
 

Historical Records

Technical Information

Categories