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Chemical Structure| 2510-23-8 Chemical Structure| 2510-23-8

Structure of 3-Ethynylpyridine
CAS No.: 2510-23-8

Chemical Structure| 2510-23-8

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Product Citations

Product Citations

Krzysztof Kuciński ; Grzegorz Hreczycho ;

Abstract: Commercially available and inexpensive potassium bis(trimethylsilyl)amide (KHMDS) serves as an efficient transition metal-free catalyst for the catalytic sp C−H silylation of several terminal alkynes including two pharmaceuticals. Overall, the presented system allows the synthesis of various attractive silylacetylenes under mild conditions, making this approach an environmentally benign and sustainable alternative to existing synthetic solutions.

Alternative Products

Product Details of [ 2510-23-8 ]

CAS No. :2510-23-8
Formula : C7H5N
M.W : 103.12
SMILES Code : C#CC1=CC=CN=C1
MDL No. :MFCD02177459
InChI Key :CLRPXACRDTXENY-UHFFFAOYSA-N
Pubchem ID :186003

Safety of [ 2510-23-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H228-H315-H319
Precautionary Statements:P210-P240-P241-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
Class:4.1
UN#:1325
Packing Group:

Computational Chemistry of [ 2510-23-8 ] 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 1.0
Num. H-bond donors 0.0
Molar Refractivity 32.17
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.

1.67
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

1.08
Log Po/w (WLOGP)?

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

1.14
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.

1.05
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

2.01
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.39

Water Solubility

Log S (ESOL):?

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

-1.71
Solubility 1.99 mg/ml ; 0.0193 mol/l
Class?

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

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.94
Solubility 11.8 mg/ml ; 0.114 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

-2.03
Solubility 0.956 mg/ml ; 0.00927 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.

-6.16 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)

1.58

Application In Synthesis of [ 2510-23-8 ]

* 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 [ 2510-23-8 ]

[ 2510-23-8 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 2510-23-8 ]
  • [ 145691-59-4 ]
  • [ 752224-60-5 ]
  • 3
  • [ 216393-67-8 ]
  • [ 2510-23-8 ]
  • [ 1202551-89-0 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; for 1h;Reflux; To a mixture of 3-ethynylpyridine (1.13 g, 11 mmol) and 2-fluoro^-chloro-6-iodoaniline (2.71 g, 10 mmol) in triethylamine (100 mL) is added PdCI2(PPh3)2 (175 mg, 0.25 mmol) and CuI (95 mg, 0.50 mmol) and the mixture is refluxed for 1 h. The solvent is removed in vacuo and the residue is purified by silica gel flash chromatography (dichloromethane- methanol, 1 :0 to 24:1 ) to give 4-chloro-2-fluoro-6-pyridin-3-ylethynyl-phenylamine. MS (ESI) m/z 247 (M+H)+.
  • 4
  • [ 2510-23-8 ]
  • [ 5572-94-1 ]
  • [ 1244016-73-6 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine;bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 60℃; for 2h;Inert atmosphere; B. 3-((4-(5,5-dimethyl-l,3,2-dioxaborinan-2-yl)phenyl)ethynyl)pyridine; In an oven dried round bottom flask, a solution of <strong>[5572-94-1]2-(4-iodophenyl)-5,5-dimethyl-1,3,2-dioxaborinane</strong> (21 g, 66.47 mmol) and triethylamine (27.8 mL, 199.40 mmol) in acetonitrile (305 mL) was degassed with a stream of N2 for 5 minutes. After this time, 3- ethynylpyridine (7.20 g, 69.79 mmol), Pd(PPh3)2Cl2 (3.5 g, 4.99 mmol) and copper(I) iodide (0.633 g, 3.32 mmol) were added. The flask was then placed in a 60 0C oil bath and was stirred for 2 h, until TLC indicated formation of a new product. The reaction was allowed to cool to room temperature and was then concentrated in vacuo. The resulting brown solid was dissolved in DCM and then impregnated on silica gel. The crude material was purified by silica gel chromatography (5-50% Ethyl Acetate in Hexanes) to afford the desired product as a yellow solid (16.2 g, 83%). 1U NMR (300 MHz, DMSO-d6) δ: ppm 8.77 (s, IH); 8.61 (d, IH); 7.98 (d, IH); 7.76 (d, 2H); 7.58 (d, 2H); 7.48 (dd, IH), 3.78 (s, 4H); 0.97 (s, 6H).
  • 5
  • [ 2510-23-8 ]
  • [ 160893-07-2 ]
  • [ 1423778-41-9 ]
YieldReaction ConditionsOperation in experiment
57% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 80℃; for 24h;Inert atmosphere; General procedure: To a solution of 2-chloroquinoline (29.7 mg, 0.182 mmole) in THF (1.5 mL) was added PdCl2(PPh3)2 (2.6 mg, 0.0037 mmole), CuI (1.5 mg, 0.0063 mmol). The reaction mixture was stirred for 5 min and triethylamine (0.15 mL) and phenylacetylene (0.03 mL, 0.27 mmol) were added. After the resulting mixture was stirred at 80 C for 24 h, it was allowed to cool to room temperature and filtered through a pad of Celite by the aid of EtOAc. The filtrate was treated with water and extracted with EtOAc (3 x 10 mL). The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The crude oil was purified by column chromatography on silica gel (EtOAc/hexane = 1:10) to give 2-(phenylethynyl)quinoline 5a (25 mg, 60%)
  • 6
  • [ 2510-23-8 ]
  • [ 4181-20-8 ]
  • N,N-bis(4-iodophenyl)-4'-(3-pyridylethynyl)phenylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
46.6% In a 50 mL three-neck round bottom flask equipped with magnetic stirrer, condenser and nitrogen inlet-outlet were introduced3-ethynylpyridine (0.165 g, 1.6 mmol), PdCl2*2PPh3 (0.056 g,0.08 mmol), CuI (0.03 g, 0.16 mmol), PPh3 (0.04 g, 0.16 mmol), triethylamine (15 mL) and tetrahydrofuran (5 mL). The mixture was stirred in nitrogen atmosphere at 50-60 °C for an hour after that 4,4',4''-trisiodotriphenylamine (1 g, 1.6 mmol) dissolved in a mixture of TEA (5 mL) and THF (5 mL) was added. Then the mixture was stirred at 80 °C when the solution color turned out in time from yellow to red and some solids are deposited on the flask's walls. After 24 h the mixture was precipitated in water, filtrated and dried. The pure orange compound 3 was obtained by silica gel chromatography using ethyl acetate/hexane (1:4 vol/vol) as eluent.Yield: 46.6percent. Mp 80 °C. ESI-MS 599.2 (M H). IR (KBr, cm-1): 3032, 2212, 1647, 1599, 1575, 1504, 1479, 1404, 1314, 1284, 1265, 1179, 1142, 1001, 818, 803, 700. 1H NMR (CDCl3, ppm): 8.75 (1H,pyridyl), 8.54 (1H, d, H, pyridyl), 7.81 (1H, d, pyridyl, J 8.0 Hz), 7.57(4H, d, J 8.8 Hz), 7.41 (2H, d, J 8.4 Hz), 7.28 (1H, t, pyridyl), 7.01(2H, d, J 8.4 Hz), 6.85 (4H, d, J 8.8 Hz).
  • 7
  • [ 2510-23-8 ]
  • [ 827-08-7 ]
  • 3-[(2-bromo-3,4,5,6-tetrafluorophenyl)ethynyl]pyridine [ No CAS ]
 

Historical Records

Technical Information

Categories

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[ 2510-23-8 ]

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[ 2510-23-8 ]

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