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[ CAS No. 1945-84-2 ] {[proInfo.proName]}

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Chemical Structure| 1945-84-2
Chemical Structure| 1945-84-2
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Product Details of [ 1945-84-2 ]

CAS No. :1945-84-2 MDL No. :MFCD00041598
Formula : C7H5N Boiling Point : -
Linear Structure Formula :- InChI Key :NHUBNHMFXQNNMV-UHFFFAOYSA-N
M.W :103.12 Pubchem ID :137268
Synonyms :

Calculated chemistry of [ 1945-84-2 ]

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 : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 0.99
Log Po/w (WLOGP) : 1.14
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.38

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.66
Solubility : 2.27 mg/ml ; 0.022 mol/l
Class : Very soluble
Log S (Ali) : -0.85
Solubility : 14.6 mg/ml ; 0.142 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.03
Solubility : 0.956 mg/ml ; 0.00927 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.67

Safety of [ 1945-84-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1945-84-2 ]

* 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 [ 1945-84-2 ]
  • Downstream synthetic route of [ 1945-84-2 ]

[ 1945-84-2 ] Synthesis Path-Upstream   1~20

  • 1
  • [ 1945-84-2 ]
  • [ 54781-19-0 ]
  • [ 51035-40-6 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 7, p. 2185 - 2191
  • 2
  • [ 1945-84-2 ]
  • [ 272-67-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 18, p. 2753 - 2758
  • 3
  • [ 86521-05-3 ]
  • [ 1945-84-2 ]
YieldReaction ConditionsOperation in experiment
80% With methanol; potassium hydroxide In dichloromethane at 0℃; for 0.5 h; 2-((Trimethylsilyl)ethynyl)pyridine (175mg, 1.0 mmol) was dissolved in MeOH/Dichloromethane (2mL/lmL). The solution was cooled to 0 °C and KOH (112mg, 2.0 mmol) was added. The reaction mixture stirred for 0.5 h, and then quenched with H2O, extracted with Dichloromethane (2x3 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give 2-ethynylpyridine (80 mg, 80percent yield).
75%
Stage #1: With potassium hydroxide In methanol at 20℃; for 1 h;
Stage #2: With hydrogenchloride In methanol; water
a)
2-Ethynyl-pyridine
A solution of 2-trimethylsilanylethynyl-pyridine (3.05 g, 14 mmol) in MeOH (8.5 mL) was added dropwise to potassium hydroxide solution (1 N, 14 mL) and the reaction mixture was stirred at room temperature for 1 h and then acidified with HCl (3 N, 8.5 mL) and the mixture concentrated.
The residue was then diluted with water and make alkaline with solid sodium carbonate, extracted with diethyl ether and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated.
Purification by chromatography (silica, diethylether) afforded the title compound (1.3 g, 75percent) as a brown liquid. MS: m/e=176.0 [M+H]+.
75%
Stage #1: With potassium hydroxide In methanol at 20℃; for 1 h;
Stage #2: With hydrogenchloride In methanol; water
Stage #3: With sodium carbonate In water
2-Ethynyl-pyridineA solution of 2-trimethylsilanylethynyl-pyridine (3.05 g, 14 mmol) in MeOH (8.5 mL) was added dropwise to potassium hydroxide solution (1 N, 14 mL) and the reaction mixture was stirred at room temperature for 1 h and then acidified with HC1 (3 N, 8.5 mL) and the mixture concentrated. The residue was then diluted with water and make alkaline with solid sodium carbonate, extracted with diethyl ether and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (1.3 g, 75percent) as a brown liquid. MS: m/e = 176.0[M+H]+.
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 27, p. 7949 - 7953[2] Angew. Chem., 2015, vol. 127, # 27, p. 8060 - 8064,5
[3] Canadian Journal of Chemistry, 2005, vol. 83, # 6-7, p. 716 - 727
[4] Dalton Transactions, 2016, vol. 45, # 25, p. 10209 - 10221
[5] Phosphorus, Sulfur and Silicon and Related Elements, 2002, vol. 177, # 5, p. 1041 - 1045
[6] Synthetic Communications, 2003, vol. 33, # 14, p. 2447 - 2461
[7] Journal of Organometallic Chemistry, 2001, vol. 629, # 1-2, p. 131 - 144
[8] Patent: WO2014/124560, 2014, A1, . Location in patent: Page/Page column 35
[9] Chemistry Letters, 2011, vol. 40, # 9, p. 925 - 927
[10] Patent: US2012/115844, 2012, A1, . Location in patent: Page/Page column 20
[11] Patent: WO2012/62687, 2012, A1, . Location in patent: Page/Page column 45
[12] Research on Chemical Intermediates, 2013, vol. 39, # 1, p. 359 - 370
[13] Synthesis, 1983, # 4, p. 312 - 314
[14] Tetrahedron Letters, 2003, vol. 44, # 41, p. 7611 - 7612
[15] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
[16] Chemical Communications, 2008, # 19, p. 2203 - 2205
[17] Journal of Organometallic Chemistry, 2009, vol. 694, # 9-10, p. 1317 - 1324
[18] Chemical Communications, 2012, vol. 48, # 15, p. 2080 - 2082
[19] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 3033 - 3047
[20] Synlett, 2013, vol. 24, # 9, p. 1101 - 1104
[21] RSC Advances, 2015, vol. 5, # 92, p. 75263 - 75267
[22] Organic and Biomolecular Chemistry, 2016, vol. 14, # 6, p. 2127 - 2133
[23] Tetrahedron, 2016, vol. 72, # 39, p. 5831 - 5842
  • 4
  • [ 1121-60-4 ]
  • [ 90965-06-3 ]
  • [ 1945-84-2 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate In methanol at 20℃; for 1.5 h; Example 104-Methyl-2-[(E)-2-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-vinyl]-thiazole-5-carboxylic acid isopropylamide a) 2-Ethynyl-pyridine; To a mixture of 2-pyridinecarbaldehyde (0.96 mL, 10 mmol) in MeOH (43 mL) was added potassium carbonate (2.76 g, 20 mmol) followed by a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (2.14 g, 11 mmol) in MeOH (14 mL) at room temperature and the resulting mixture stirred for 1.5 h. The mixture was then poured into sodium carbonate solution (1 M) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (728 mg, 71percent) as a yellow liquid. MS: m/e=103.0 [M]+.
71% With potassium carbonate In methanol at 20℃; for 1.5 h; To a mixture of 2-pyridinecarbaldehyde (0.96 mL, 10 mmol) in MeOH (43 mL) was added potassium carbonate (2.76 g, 20 mmol) followed by a solution of (l-diazo-2-oxo-propyl)- phosphonic acid dimethyl ester (2.14 g, 11 mmol) in MeOH (14 mL) at room temperature and the resulting mixture stirred for 1.5 h. The mixture was then poured into sodium carbonate solution (1 M) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (728 mg, 71percent) as a yellow liquid. MS: m/e = 103.0 [M]+.
Reference: [1] Patent: US2012/115868, 2012, A1, . Location in patent: Page/Page column 15
[2] Patent: WO2012/62623, 2012, A1, . Location in patent: Page/Page column 32
  • 5
  • [ 29767-97-3 ]
  • [ 1945-84-2 ]
Reference: [1] Synthesis, 1981, # 5, p. 364 - 365
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 5, p. 709 - 714
[3] Synthesis, 1996, # 5, p. 589 - 590
[4] Journal of Physical Chemistry A, 1998, vol. 102, # 6, p. 904 - 908
[5] Molecular Crystals and Liquid Crystals, 2012, vol. 568, # 1, p. 93 - 97,5
[6] Molecular Crystals and Liquid Crystals, 2012, vol. 568, # 1, p. 93 - 97
  • 6
  • [ 109-04-6 ]
  • [ 1945-84-2 ]
Reference: [1] Canadian Journal of Chemistry, 2005, vol. 83, # 6-7, p. 716 - 727
[2] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134
[3] Journal of Organometallic Chemistry, 2001, vol. 629, # 1-2, p. 131 - 144
[4] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 5, p. 709 - 714
[5] Synthesis, 1996, # 5, p. 589 - 590
[6] Synthesis, 1981, # 5, p. 364 - 365
[7] Synthesis, 1983, # 4, p. 312 - 314
[8] Chemistry Letters, 2011, vol. 40, # 9, p. 925 - 927
[9] Molecular Crystals and Liquid Crystals, 2012, vol. 568, # 1, p. 93 - 97,5
[10] Molecular Crystals and Liquid Crystals, 2012, vol. 568, # 1, p. 93 - 97
[11] Synlett, 2013, vol. 24, # 9, p. 1101 - 1104
[12] Patent: WO2014/124560, 2014, A1,
[13] Angewandte Chemie - International Edition, 2015, vol. 54, # 27, p. 7949 - 7953[14] Angew. Chem., 2015, vol. 127, # 27, p. 8060 - 8064,5
[15] Dalton Transactions, 2016, vol. 45, # 25, p. 10209 - 10221
  • 7
  • [ 1092543-20-8 ]
  • [ 1945-84-2 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 48, p. 6794 - 6796
  • 8
  • [ 1122-62-9 ]
  • [ 1945-84-2 ]
Reference: [1] Synlett, 2009, # 4, p. 558 - 561
  • 9
  • [ 189350-72-9 ]
  • [ 1945-84-2 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 5, p. 709 - 714
  • 10
  • [ 189350-81-0 ]
  • [ 1945-84-2 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 5, p. 709 - 714
  • 11
  • [ 5029-67-4 ]
  • [ 1945-84-2 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 15, p. 2080 - 2082
[2] Synlett, 2013, vol. 24, # 9, p. 1101 - 1104
[3] RSC Advances, 2015, vol. 5, # 92, p. 75263 - 75267
[4] Organic and Biomolecular Chemistry, 2016, vol. 14, # 6, p. 2127 - 2133
  • 12
  • [ 109-09-1 ]
  • [ 1945-84-2 ]
Reference: [1] Synthesis, 1983, # 4, p. 312 - 314
[2] Chemistry Letters, 2011, vol. 40, # 9, p. 925 - 927
[3] Research on Chemical Intermediates, 2013, vol. 39, # 1, p. 359 - 370
  • 13
  • [ 5029-67-4 ]
  • [ 4301-14-8 ]
  • [ 1945-84-2 ]
Reference: [1] Heterocycles, 1997, vol. 46, # 1, p. 209 - 214
  • 14
  • [ 109-04-6 ]
  • [ 74-86-2 ]
  • [ 1945-84-2 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 7, p. 1395 - 1398
  • 15
  • [ 109-04-6 ]
  • [ 4301-14-8 ]
  • [ 1945-84-2 ]
  • [ 28790-65-0 ]
Reference: [1] Heterocycles, 1997, vol. 46, # 1, p. 209 - 214
  • 16
  • [ 109-04-6 ]
  • [ 1066-54-2 ]
  • [ 1945-84-2 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 10, p. 3518 - 3521
  • 17
  • [ 1121-60-4 ]
  • [ 1945-84-2 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 5, p. 709 - 714
[2] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 5, p. 709 - 714
  • 18
  • [ 67-56-1 ]
  • [ 86521-05-3 ]
  • [ 1945-84-2 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 41, p. 7611 - 7612
  • 19
  • [ 109-04-6 ]
  • [ 1066-26-8 ]
  • [ 1945-84-2 ]
Reference: [1] Liebigs Annales, 1996, # 12, p. 2107 - 2113
  • 20
  • [ 1945-84-2 ]
  • [ 81290-20-2 ]
  • [ 86521-05-3 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 91, p. 49775 - 49779
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