Home Cart Sign in  
Chemical Structure| 55717-45-8 Chemical Structure| 55717-45-8

Structure of 55717-45-8

Chemical Structure| 55717-45-8

*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 [ 55717-45-8 ]

CAS No. :55717-45-8
Formula : C5H4BrNO
M.W : 174.00
SMILES Code : OC1=CN=C(Br)C=C1
MDL No. :MFCD04114184
InChI Key :PTEFNEALEPSHLC-UHFFFAOYSA-N
Pubchem ID :2762865

Safety of [ 55717-45-8 ]

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

Computational Chemistry of [ 55717-45-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 33.96
TPSA ?

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

33.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.31
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

1.52
Log Po/w (WLOGP)?

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

1.55
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.

0.58
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

1.64
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.32

Water Solubility

Log S (ESOL):?

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

-2.43
Solubility 0.644 mg/ml ; 0.0037 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.

-1.82
Solubility 2.61 mg/ml ; 0.015 mol/l
Class?

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

Very 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

-2.3
Solubility 0.876 mg/ml ; 0.00504 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.

-6.28 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

1.0
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<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)

1.69

Application In Synthesis of [ 55717-45-8 ]

* 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.

  • Upstream synthesis route of [ 55717-45-8 ]
  • Downstream synthetic route of [ 55717-45-8 ]

[ 55717-45-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 55717-45-8 ]
  • [ 75-03-6 ]
  • [ 42834-01-5 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5 h;
Stage #2: at 20℃; for 3.5 h;
Reference Example 12 [0441] Step 1 [0442] To a solution of Compound vii-2 (2.0g, 11.49mmol) in DMF (20mL) was added sodium hydride (0.644g, 16.09mmol) at room temperature, and the mixture was stirred for 30 minutes. Iodoethane (1.858mL, 22.99mmol) was added to the mixture and the resulting mixture was stirred for additional 3.5 hours at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed by water and brine, dried over anhydrous magnesium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give Compound vii-3 (2.32g, Yield 100percent). [0443] 1H-NMR (CDCl3) δ: 8.03 (1H, d, J = 2.75 Hz), 7.35 (1H, d, J = 8.69 Hz), 7.07 (1H, dd, J = 8.62, 2.97 Hz), 4.05 (2H, q, J = 6.91 Hz), 1.43 (3H, t, J = 6.94 Hz).
References: [1] Patent: EP2752410, 2014, A1, . Location in patent: Paragraph 0441-0443.
[2] Patent: WO2012/74126, 2012, A1, . Location in patent: Page/Page column 335; 336.
  • 2
  • [ 55717-45-8 ]
  • [ 74-96-4 ]
  • [ 42834-01-5 ]
References: [1] Patent: US2012/214785, 2012, A1, . Location in patent: Page/Page column 46.
[2] Patent: WO2013/92616, 2013, A1, . Location in patent: Page/Page column 92.
[3] Patent: US2013/158004, 2013, A1, . Location in patent: Paragraph 0559; 0560; 0561; 0562; 0563.
  • 3
  • [ 55717-45-8 ]
  • [ 56-23-5 ]
  • [ 888327-36-4 ]
YieldReaction ConditionsOperation in experiment
2.9%
Stage #1: at 150℃; for 8 h;
Stage #2: With potassium hydroxide In water
Step 2; 2-Bromo-5-trifluoromethoxy-pyridine:; Into a 50 mL sealed tube was placed 6-bromopyridin-3-ol (2.5 g, 14.37 mmol), perchloromethane (6.6 g, 42.86 mmol) and antimony pentafloride (101 g, 465.44 mmol). The resulting solution was heated at 1500C for 8 hours. After cooling to room temperature, the reaction mixture was poured into ice water and neutralized with saturated KOH. The resulting solution was extracted with EtOAc (100 ml x 2) and the organic layers combined and dried over MgSO4. The solvent was concentrated to afford O.lg (2.9percent) of 2-bromo-5-(trifluoromethoxy)pyridine.
References: [1] Patent: WO2006/55187, 2006, A1, . Location in patent: Page/Page column 90.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 55717-45-8 ]

Bromides

Chemical Structure| 105170-27-2

A226003 [105170-27-2]

2-Bromo-5-methoxypyridine

Similarity: 0.90

Chemical Structure| 1003711-43-0

A153668 [1003711-43-0]

2-Bromo-5-hydroxy-3-methylpyridine

Similarity: 0.88

Chemical Structure| 42834-01-5

A491913 [42834-01-5]

2-Bromo-5-ethoxypyridine

Similarity: 0.86

Chemical Structure| 36953-40-9

A170223 [36953-40-9]

2-Bromo-4-hydroxypyridine

Similarity: 0.81

Chemical Structure| 845827-14-7

A100832 [845827-14-7]

2-Bromo-5-(difluoromethoxy)pyridine

Similarity: 0.77

Alcohols

Chemical Structure| 1003711-43-0

A153668 [1003711-43-0]

2-Bromo-5-hydroxy-3-methylpyridine

Similarity: 0.88

Chemical Structure| 36953-40-9

A170223 [36953-40-9]

2-Bromo-4-hydroxypyridine

Similarity: 0.81

Chemical Structure| 130284-56-9

A246277 [130284-56-9]

2-Bromo-3-chloro-5-hydroxypyridine

Similarity: 0.74

Chemical Structure| 118289-16-0

A186800 [118289-16-0]

2-Bromopyridine-4-methanol

Similarity: 0.74

Chemical Structure| 74115-13-2

A241929 [74115-13-2]

5-Bromo-3-pyridinol

Similarity: 0.74

Related Parent Nucleus of
[ 55717-45-8 ]

Pyridines

Chemical Structure| 105170-27-2

A226003 [105170-27-2]

2-Bromo-5-methoxypyridine

Similarity: 0.90

Chemical Structure| 1003711-43-0

A153668 [1003711-43-0]

2-Bromo-5-hydroxy-3-methylpyridine

Similarity: 0.88

Chemical Structure| 42834-01-5

A491913 [42834-01-5]

2-Bromo-5-ethoxypyridine

Similarity: 0.86

Chemical Structure| 36953-40-9

A170223 [36953-40-9]

2-Bromo-4-hydroxypyridine

Similarity: 0.81

Chemical Structure| 845827-14-7

A100832 [845827-14-7]

2-Bromo-5-(difluoromethoxy)pyridine

Similarity: 0.77