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[ CAS No. 1918-79-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1918-79-2
Chemical Structure| 1918-79-2
Chemical Structure| 1918-79-2
Structure of 1918-79-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1918-79-2 ]

CAS No. :1918-79-2 MDL No. :MFCD00005439
Formula : C6H6O2S Boiling Point : -
Linear Structure Formula :CH3C4H2SCOOH InChI Key :VCNGNQLPFHVODE-UHFFFAOYSA-N
M.W : 142.18 Pubchem ID :74713
Synonyms :

Calculated chemistry of [ 1918-79-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.24
TPSA : 65.54 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) : -5.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.35
Log Po/w (XLOGP3) : 1.86
Log Po/w (WLOGP) : 1.75
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 2.34
Consensus Log Po/w : 1.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.24
Solubility : 0.821 mg/ml ; 0.00578 mol/l
Class : Soluble
Log S (Ali) : -2.86
Solubility : 0.197 mg/ml ; 0.00139 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.4
Solubility : 5.63 mg/ml ; 0.0396 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 1918-79-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1918-79-2 ]

* 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 [ 1918-79-2 ]
  • Downstream synthetic route of [ 1918-79-2 ]

[ 1918-79-2 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 554-14-3 ]
  • [ 124-38-9 ]
  • [ 1918-79-2 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2576 - 2579
[2] Bulletin of the Chemical Society of Japan, 2012, vol. 85, # 3, p. 369 - 371
[3] RSC Advances, 2014, vol. 4, # 26, p. 13430 - 13433
[4] Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 193, p. 167 - 170
  • 2
  • [ 13679-74-8 ]
  • [ 1918-79-2 ]
YieldReaction ConditionsOperation in experiment
70% With Oxone; trifluoroacetic acid In 1,4-dioxane for 10 h; Reflux; Green chemistry General procedure: To a mixture of acetophenone (100 mg, 1 equiv) or phenylacetylene (1 equiv) in dioxane (5 mL), Oxone (2 equiv) and TFA (2 equiv) were added. The mixture was then heated to reflux for 10 h and then cooled to r.t. H2O (10 mL) was added and the mixture was extracted with EtOAc (2 × 20 mL). The combined organic layers were treated with sat. NaHCO3 solution and the aqueous layer was poured onto crushed ice and treated with 2 M HCl; a colorless solid precipitated out. The precipitate was filtered off and dried in vacuo to give benzoic acid (3a) after column chromatography (silica gel; EtOAc–hexane, 1:9) as a white crystalline solid; yield: 0.096 g (95percent) from 1a; mp 122–123 °C.
Reference: [1] Synthesis (Germany), 2015, vol. 47, # 20, p. 3161 - 3168
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 3096
[3] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 5,29
  • 3
  • [ 765-58-2 ]
  • [ 201230-82-2 ]
  • [ 1918-79-2 ]
  • [ 19432-69-0 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 26, p. 8336 - 8340
  • 4
  • [ 1430823-64-5 ]
  • [ 1918-79-2 ]
Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 32, p. 5377 - 5385
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 29, p. 7973 - 7978
  • 5
  • [ 765-58-2 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 1918-79-2 ]
  • [ 19432-69-0 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 26, p. 8336 - 8340
  • 6
  • [ 554-14-3 ]
  • [ 1918-79-2 ]
Reference: [1] Chemistry Letters, 1983, p. 127 - 128
[2] Journal of the American Chemical Society, 1948, vol. 70, p. 1646
[3] Journal of the American Chemical Society, 1934, vol. 56, p. 1127
[4] Journal of Organic Chemistry, 1948, vol. 13, p. 635,637
[5] Journal of the American Chemical Society, 1950, vol. 72, p. 3695,3696, 3697
[6] Journal of the American Chemical Society, 1950, vol. 72, p. 3695,3696, 3697
  • 7
  • [ 63273-26-7 ]
  • [ 123-56-8 ]
  • [ 1918-79-2 ]
Reference: [1] Patent: US5773411, 1998, A,
  • 8
  • [ 13679-70-4 ]
  • [ 1918-79-2 ]
Reference: [1] Journal of Organic Chemistry, 1948, vol. 13, p. 635,637
[2] Green Chemistry, 2018, vol. 20, # 17, p. 3931 - 3943
  • 9
  • [ 554-14-3 ]
  • [ 108-24-7 ]
  • [ 1918-79-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 1221 - 1230
  • 10
  • [ 59303-13-8 ]
  • [ 1918-79-2 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 3695,3696, 3697
  • 11
  • [ 79852-26-9 ]
  • [ 1918-79-2 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 3695,3696, 3697
  • 12
  • [ 16494-36-3 ]
  • [ 67-66-3 ]
  • [ 1918-79-2 ]
Reference: [1] Dalton Transactions, 2004, # 1, p. 157 - 165
  • 13
  • [ 527-72-0 ]
  • [ 1918-79-2 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, # 52, p. 5051 - 5054
  • 14
  • [ 86786-68-7 ]
  • [ 74-88-4 ]
  • [ 1918-79-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, p. 791 - 794
  • 15
  • [ 638-02-8 ]
  • [ 1918-79-2 ]
Reference: [1] Chemische Berichte, 1885, vol. 18, p. 2252
  • 16
  • [ 16494-36-3 ]
  • [ 1918-79-2 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1933, vol. 52, p. 538,547
  • 17
  • [ 110-13-4 ]
  • [ 1918-79-2 ]
Reference: [1] Chemische Berichte, 1885, vol. 18, p. 2252
  • 18
  • [ 13679-74-8 ]
  • [ 1918-79-2 ]
  • [ 4282-31-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1932, vol. 51, p. 1134,1141
  • 19
  • [ 527-72-0 ]
  • [ 74-88-4 ]
  • [ 1918-79-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, p. 791 - 794
  • 20
  • [ 59753-16-1 ]
  • [ 74-88-4 ]
  • [ 1918-79-2 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, # 52, p. 5051 - 5054
[2] Tetrahedron Letters, 1980, vol. 21, # 52, p. 5051 - 5054
  • 21
  • [ 1918-79-2 ]
  • [ 29421-99-6 ]
YieldReaction ConditionsOperation in experiment
100% With iron(III) chloride; bromine In acetic acid at 25℃; for 5 h; A solution of bromine (725 uL, 14.1 mmol) in AcOH (2.8 ml.) was added dropwise to δ-methyl^-thiophenecarboxylic acid (2 g, 14.1 mmol) and FeCI3 (456 mg, 2.81 mmol) in AcOH (28 ml.) at 25 0C. After 5h, the solution was poured onto ice and the precipitate was filtered and washed with water affording the title compound (3 g, quant.) as a yellow powder: LCMS (ES) m/z 222 (M+H)+.
Reference: [1] Patent: WO2008/98104, 2008, A1, . Location in patent: Page/Page column 81
[2] Patent: WO2010/93885, 2010, A1, . Location in patent: Page/Page column 36-37
[3] Patent: WO2017/176961, 2017, A1, . Location in patent: Paragraph 00768
  • 22
  • [ 1918-79-2 ]
  • [ 75-03-6 ]
  • [ 5751-81-5 ]
YieldReaction ConditionsOperation in experiment
34% With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 2 h; To a solution of commercially available 5-methylthiophene-2-carboxylic acid (SI-13) (1.0g, 7.04 mmol) and K2CO3 (1.94 g, 14.08 mmol) in DMF (10 mL), CH3CH2I (1.65 g, 10.56mmol) was added dropwise and the reaction mixture was stirred at room temperature for 2hours. Then, the reaction was quenched with water and extracted with EtOAc. The organiclayer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated togive compound SI-14 (400 mg, 34percent) as a pale yellow oil. ESI-MS m/z 171 [M+H]+ calc.for C8H10O2S. This intermediate was used in the next step without further purification orcharacterization.
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 506 - 524
[2] Patent: WO2014/131855, 2014, A1, . Location in patent: Page/Page column 63; 64
[3] Patent: WO2016/20307, 2016, A1, . Location in patent: Page/Page column 45
  • 23
  • [ 1918-79-2 ]
  • [ 5751-81-5 ]
YieldReaction ConditionsOperation in experiment
85% With sulfuric acid In ethanol Part 1
5-methyl-thiophene-2-carboxylic acid ethyl ester
A solution of 5-methyl-thiophene-2-carboxylic acid (25.2 g, 177 mmol) in EtOH (500 mL) is treated with conc. H2SO4 (15 mL) and heated to a gentle reflux for 72 h.
The solution is partially concentrated and poured into water (500 mL) and extracted with Et2O (3*).
The combined extracts are washed with aq Na2CO3, water, dried over Na2SO4, filtered and concentrated in vacuo.
Vacuum distillation of the residue afforded 5-methyl-thiophene-2-carboxylic acid ethyl ester (25.6 g, 85percent): bp 98-99° C./9-10 mbar; 1H NMR (CDCl3, 300 MHz) δ7.6 (s, 1 H), 6.78 (s, 1 H), 4.30 (q, J=6.0 Hz, 2 H), 2.50 (s, 3 H), 1.34 (t, J=6.0 Hz, 3 H).
Reference: [1] Patent: US2003/166668, 2003, A1,
  • 24
  • [ 1918-79-2 ]
  • [ 64-17-5 ]
  • [ 5751-81-5 ]
YieldReaction ConditionsOperation in experiment
67% for 72 h; Reflux δ-Methyl-thiophene^-carboxylic acid (30.5 mmol) is dissolved in Ethanol (53 ml), H2SO4 (0.5 eq) is added and the reaction is heated to reflux for 3 days. The solvent is removed in vacuo and the remaining material dissolved in Dichloromethane. The organic layer is extracted with saturated NaHCO3 and washed with brine. The organic layer is dried over IS^SO4 and the solvent removed in vacuo. 5-Methyl- thiophene-2-carboxylic acid ethyl ester is obtained as brown oil in a yield of 67 percent. HPLC (Method A): 3.36 min, LCMS (Method A): 2.20 min, 171.2 m/z (MH+)
Reference: [1] Patent: WO2009/106203, 2009, A1, . Location in patent: Page/Page column 63
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 3258
  • 25
  • [ 1918-79-2 ]
  • [ 75-03-6 ]
  • [ 19432-66-7 ]
Reference: [1] Patent: US5840917, 1998, A,
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