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Chemical Structure| 3430-17-9 Chemical Structure| 3430-17-9
Chemical Structure| 3430-17-9

*Storage: Inert atmosphere,Room Temperature.

2-Bromo-3-methylpyridine

CAS No.: 3430-17-9

Synonyms: 2-Bromo-3-picoline

4.5 *For Research Use Only !

Cat. No.: A179455 Purity: 98%

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Product Details of [ 3430-17-9 ]

CAS No. :3430-17-9
Formula : C6H6BrN
M.W : 172.02
SMILES Code : CC1=CC=CN=C1Br
Synonyms :
2-Bromo-3-picoline
MDL No. :MFCD00239380
InChI Key :PZSISEFPCYMBDL-UHFFFAOYSA-N
Pubchem ID :220832

Safety of [ 3430-17-9 ]

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

Calculated chemistry of [ 3430-17-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 36.9
TPSA ?

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

12.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.85
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

2.24
Log Po/w (WLOGP)?

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

2.15
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.

1.58
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

2.54
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.07

Water Solubility

Log S (ESOL):?

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

-2.87
Solubility 0.231 mg/ml ; 0.00134 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.

-2.15
Solubility 1.23 mg/ml ; 0.00714 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

-3.26
Solubility 0.0948 mg/ml ; 0.000551 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.

-5.76 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

2.0
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)

1.56

Application In Synthesis [ 3430-17-9 ]

* 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 [ 3430-17-9 ]

[ 3430-17-9 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 3430-17-9 ]
  • [ 39974-94-2 ]
  • [ 118812-92-3 ]
  • 2
  • [ 3430-17-9 ]
  • [ 626-44-8 ]
  • [ 1066-45-1 ]
  • [ 252358-83-1 ]
  • 3
  • [ 3430-17-9 ]
  • [ 68-12-2 ]
  • [ 55589-47-4 ]
  • 4
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  • [ 85279-30-7 ]
  • 6
  • [ 3430-17-9 ]
  • [ 59718-84-2 ]
  • 7
  • [ 3430-17-9 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 59718-84-2 ]
YieldReaction ConditionsOperation in experiment
93.6% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine; at 80℃; under 2585.81 Torr; for 16h; A mixture of 2-bromo-3-methylpyridine (5.0 g, 29.0 mmol), Pd(dppf)C12 (2.1 g, 2.9 mmol), and triethylamine (8.8 g, 87 mmol) in methanol (250 mL) was stirred at 80 C under CO atmosphere (50 psi) for 16 h. The mixture was filtered and the filtrate concentrated in vacuo, then purified by column chromatography on Si02 to give the desired product (4.1 g, 93.6%). LCMS (mlz): 152.0 (M+1).
  • 8
  • [ 3430-17-9 ]
  • [ 116986-09-5 ]
  • 9
  • [ 850568-54-6 ]
  • [ 3430-17-9 ]
  • tert-butyl 4-(3-methylpyridin-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃; Example 83A tert-butyl 4-(3-methylpyridin-2-yl)benzoate A mixture of 2-bromo-3-methylpyridine (0.688 g, 4 mmol), <strong>[850568-54-6](4-(tert-butoxycarbonyl)phenyl)boronic acid</strong> (0.888 g, 4 mmol), potassium carbonate (1.16 g, 8.40 mmol), and PdCl2dppf (0.146 g, 0.2 mmol) in dimethoxyethane (8.5 mL) and water (4.7 mL) was heated at 80° C. overnight. The mixture was diluted with 50 mL of ether and was then washed with a solution of methanesulfonic acid (0.25 mL) in water (12 mL) and with brine sequentially. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (0 to 50percent EtOAc-heptanes, eluent) to afford the title compound as a yellow oil (0.560 g, 52percent). 1H NMR (400 MHz, CDCl3) delta 8.55 (m, 1H), 8.07 (d, J=8.3 Hz, 2H), 7.65-7.52 (m, 3H), 7.21 (dd, J=7.8, 4.8 Hz, 1H), 2.34 (s, 3H), 1.58 (s, 9H). MS (DCI+) m/z 270.0 (M+H).
  • 10
  • [ 3430-17-9 ]
  • [ 15016-42-9 ]
  • 1,7-dimethyl-6H-pyrido[2,1-a]isoquinolin-6-one [ No CAS ]
  • 11
  • [ 3430-17-9 ]
  • [ 15016-42-9 ]
  • 3-methyl-2-(2-vinylphenyl)pyridine [ No CAS ]
  • 12
  • [ 3430-17-9 ]
  • [ 15754-51-5 ]
  • bis(4-methoxyphenyl)(3-methylpyridin-2-yl)phosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With bis(triphenylphosphine)nickel(II) chloride; potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 24h;Schlenk technique; Inert atmosphere; Add bis(p-methoxy)phenylphosphorus oxide (0.952g, 5mmol), 2-bromo-3-methylpyridine (0.60mL, 6mmol), K2CO3 (1.38) to 100mL Schlenk reaction flask under nitrogen atmosphere. g, 10mmol). Ni(PPh3)Cl2 (159.25mg, 0.25mmol), DMF (5mL), and stirred at 90C for 24h. After the reaction, the mixture was diluted with water and extracted three times with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, the mixture was chromatographed on silica gel column, eluted with petroleum ether/ethyl acetate=2:1, and drained to obtain a white solid (0.88g, 2.5mmol). The rate is 50%.
 

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