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[ CAS No. 10602-00-3 ] {[proInfo.proName]}

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Chemical Structure| 10602-00-3
Chemical Structure| 10602-00-3
Structure of 10602-00-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 10602-00-3 ]

CAS No. :10602-00-3 MDL No. :MFCD00168819
Formula : C9H6O2 Boiling Point : -
Linear Structure Formula :- InChI Key :SJXHLZCPDZPBPW-UHFFFAOYSA-N
M.W : 146.14 Pubchem ID :589706
Synonyms :

Calculated chemistry of [ 10602-00-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.34
TPSA : 37.3 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) : -5.66 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 2.15
Log Po/w (WLOGP) : 1.45
Log Po/w (MLOGP) : 2.16
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.85

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.533 mg/ml ; 0.00365 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.397 mg/ml ; 0.00272 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.83
Solubility : 2.15 mg/ml ; 0.0147 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.48

Safety of [ 10602-00-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10602-00-3 ]

* 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 [ 10602-00-3 ]
  • Downstream synthetic route of [ 10602-00-3 ]

[ 10602-00-3 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 10602-00-3 ]
  • [ 556-08-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 22, p. 3968 - 3976
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 30, p. 7850 - 7854[3] Angew. Chem., 2013, vol. 125, # 30, p. 8004 - 8008
  • 2
  • [ 619-58-9 ]
  • [ 10602-00-3 ]
  • [ 16819-43-5 ]
  • [ 116075-75-3 ]
Reference: [1] Tetrahedron, 1995, vol. 51, # 8, p. 2325 - 2330
  • 3
  • [ 75867-41-3 ]
  • [ 10602-00-3 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride In methanol Synthesis of 4-ethynylbenzoic acid
4-(Trimethylsilyl)ethynyl-benzoic acid methyl ester (714 mg, 3.07 mmol) was dissolved in 4percent KOH:MeOH (w:v, 30 mL) and allowed to reflux overnight.
The reaction was quenched with 6N HCl to pH 2-3 (as indicated by pH paper) and extracted 2* with EtOAc.
The combined organic layers were dried over anhydrous Na2SO4 and evaporated to afford 4-ethynylbenzoic acid (427 mg, 2.92 mmol, 95percent) as a brown solid. 1H-NMR (d6-acetone, 500 MHz) δ (ppm): 7.62 (d, J=16.2 Hz, 2H); 8.03 (d, J=16.3 Hz, 2H).
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 30, p. 10692 - 10700
[2] Patent: US2013/65248, 2013, A1, . Location in patent: Page/Page column
[3] Patent: US9290791, 2016, B2,
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4851 - 4856
[5] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575
[6] Organic and Biomolecular Chemistry, 2010, vol. 8, # 14, p. 3272 - 3280
[7] Journal of Materials Chemistry, 2011, vol. 21, # 36, p. 14041 - 14047
[8] Chinese Chemical Letters, 2015, vol. 26, # 6, p. 763 - 767
[9] Synthesis, 1980, # 8, p. 627 - 630
[10] Inorganic Chemistry, 2011, vol. 50, # 18, p. 9097 - 9105
[11] Patent: WO2013/170030, 2013, A1,
[12] Patent: WO2014/82286, 2014, A1,
[13] Patent: US2015/51242, 2015, A1,
  • 4
  • [ 3034-86-4 ]
  • [ 10602-00-3 ]
YieldReaction ConditionsOperation in experiment
77% With lithium hydroxide In methanol; water for 2 h; To a solution of 2 ( 0.5 g, 3.13 mmol) in MeOH (10 ml) was added LiOH (0.312 g. 12.52mmol) in water (10 ml). The mixture was stirred for 2 h then quenched by HCI solution (2N) extracted with EtOAc (30 ml x 3). The combined organic was dried over anhydrous Na2SO4 concentrated to give the desired intermediate 3 (0.35 g, 77percent) as yellow solid.
77% With lithium hydroxide In methanol; water for 2 h; To a solution of 2 (0.5 g, 3.13 mmol) in MeOH (10 mL) was added LiOH (0.312 g, 12.52 mmol) in water (10 mL). The mixture was stirred for 2 h, then quenched by HCl solution (2N), extracted with EtOAc (30 mL*3). The combined organic was dried over anhydrous Na2SO4, concentrated to gie the desired intermediate 3 (0.35 g, 77percent) as yellow solid.
Reference: [1] Patent: WO2014/82286, 2014, A1, . Location in patent: Paragraph 67
[2] Patent: US2015/51242, 2015, A1, . Location in patent: Paragraph 0112
[3] Inorganic Chemistry, 2011, vol. 50, # 18, p. 9097 - 9105
[4] Patent: WO2013/170030, 2013, A1, . Location in patent: Page/Page column 98
[5] ACS Infectious Diseases, 2017, vol. 3, # 9, p. 634 - 644
  • 5
  • [ 33577-98-9 ]
  • [ 10602-00-3 ]
Reference: [1] Macromolecules, 2005, vol. 38, # 17, p. 7205 - 7206
[2] Journal of Organic Chemistry, 1992, vol. 57, # 25, p. 6998 - 6999
[3] Macromolecules, 2010, vol. 43, # 14, p. 6014 - 6023
[4] Journal of Materials Chemistry B, 2015, vol. 3, # 3, p. 491 - 497
[5] Revue Roumaine de Chimie, 2010, vol. 55, # 11-12, p. 989 - 994
[6] Patent: CN107043352, 2017, A, . Location in patent: Paragraph 0017; 0018
[7] Patent: CN107082762, 2017, A, . Location in patent: Paragraph 0017; 0018
[8] Patent: CN107417618, 2017, A, . Location in patent: Paragraph 0017; 0018
  • 6
  • [ 150969-54-3 ]
  • [ 10602-00-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 47, p. 14852 - 14857[2] Angew. Chem., 2016, vol. 128, # 47, p. 15074 - 15079,6
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7186 - 7194
[4] Journal of the American Chemical Society, 1997, vol. 119, # 27, p. 6345 - 6359
[5] Angewandte Chemie - International Edition, 2010, vol. 49, # 8, p. 1430 - 1433
[6] Angewandte Chemie - International Edition, 2012, vol. 51, # 33, p. 8334 - 8338
  • 7
  • [ 16116-80-6 ]
  • [ 10602-00-3 ]
Reference: [1] Chemical Communications, 2006, # 13, p. 1430 - 1432
[2] Chemistry - A European Journal, 2014, vol. 20, # 7, p. 2016 - 2021
  • 8
  • [ 51934-41-9 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of the American Chemical Society, 1997, vol. 119, # 27, p. 6345 - 6359
[2] Bulletin of the Chemical Society of Japan, 2016, vol. 89, # 1, p. 27 - 32
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 47, p. 14852 - 14857[4] Angew. Chem., 2016, vol. 128, # 47, p. 15074 - 15079,6
  • 9
  • [ 619-42-1 ]
  • [ 10602-00-3 ]
Reference: [1] Macromolecules, 2005, vol. 38, # 17, p. 7205 - 7206
[2] Journal of Organic Chemistry, 1992, vol. 57, # 25, p. 6998 - 6999
[3] Synthesis, 1980, # 8, p. 627 - 630
[4] Macromolecules, 2010, vol. 43, # 14, p. 6014 - 6023
[5] Revue Roumaine de Chimie, 2010, vol. 55, # 11-12, p. 989 - 994
[6] Patent: US2013/65248, 2013, A1,
[7] Patent: WO2013/170030, 2013, A1,
[8] Patent: WO2014/82286, 2014, A1,
[9] Patent: US2015/51242, 2015, A1,
[10] Journal of Materials Chemistry B, 2015, vol. 3, # 3, p. 491 - 497
[11] Patent: US9290791, 2016, B2,
[12] Patent: CN107043352, 2017, A,
[13] Patent: CN107082762, 2017, A,
[14] Patent: CN107417618, 2017, A,
  • 10
  • [ 51934-41-9 ]
  • [ 115-19-5 ]
  • [ 10602-00-3 ]
Reference: [1] Synthesis, 2008, # 4, p. 605 - 609
  • 11
  • [ 10602-03-6 ]
  • [ 10602-00-3 ]
Reference: [1] Dalton Transactions, 2009, # 44, p. 9794 - 9799
[2] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
  • 12
  • [ 5798-75-4 ]
  • [ 10602-00-3 ]
Reference: [1] Macromolecules, 2005, vol. 38, # 18, p. 7645 - 7652
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7186 - 7194
  • 13
  • [ 619-44-3 ]
  • [ 10602-00-3 ]
Reference: [1] Inorganic Chemistry, 2011, vol. 50, # 18, p. 9097 - 9105
[2] Journal of Materials Chemistry, 2011, vol. 21, # 36, p. 14041 - 14047
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575
[4] Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4851 - 4856
[5] Chinese Chemical Letters, 2015, vol. 26, # 6, p. 763 - 767
  • 14
  • [ 10602-02-5 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organometallic Chemistry, 1986, vol. 311, p. C35 - C38
[2] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
  • 15
  • [ 111291-97-5 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3618 - 3624
  • 16
  • [ 586-76-5 ]
  • [ 10602-00-3 ]
Reference: [1] Revue Roumaine de Chimie, 2010, vol. 55, # 11-12, p. 989 - 994
[2] Patent: US2013/65248, 2013, A1,
[3] Journal of Materials Chemistry B, 2015, vol. 3, # 3, p. 491 - 497
[4] Patent: US9290791, 2016, B2,
  • 17
  • [ 59247-47-1 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3618 - 3624
  • 18
  • [ 111291-96-4 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3618 - 3624
  • 19
  • [ 586-75-4 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3618 - 3624
  • 20
  • [ 10602-01-4 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
  • 21
  • [ 93611-64-4 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
  • 22
  • [ 19675-63-9 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
  • 23
  • [ 619-66-9 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
  • 24
  • [ 619-58-9 ]
  • [ 10602-00-3 ]
Reference: [1] Chemical Communications, 2006, # 13, p. 1430 - 1432
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9562 - 9575
  • 25
  • [ 766-96-1 ]
  • [ 10602-00-3 ]
Reference: [1] Journal of Organometallic Chemistry, 1986, vol. 311, p. C35 - C38
  • 26
  • [ 10602-00-3 ]
  • [ 50446-44-1 ]
Reference: [1] Macromolecules, 2005, vol. 38, # 18, p. 7645 - 7652
  • 27
  • [ 110-91-8 ]
  • [ 10602-00-3 ]
  • [ 851895-20-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6142 - 6146
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