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[ CAS No. 67808-64-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 67808-64-4
Chemical Structure| 67808-64-4
Chemical Structure| 67808-64-4
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Product Details of [ 67808-64-4 ]

CAS No. :67808-64-4 MDL No. :MFCD01859942
Formula : C7H6O3S Boiling Point : -
Linear Structure Formula :- InChI Key :APNKWEPRZUSZCJ-UHFFFAOYSA-N
M.W : 170.19 Pubchem ID :818924
Synonyms :

Calculated chemistry of [ 67808-64-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.14
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.99
TPSA : 71.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.57
Log Po/w (XLOGP3) : 1.58
Log Po/w (WLOGP) : 1.35
Log Po/w (MLOGP) : 0.28
Log Po/w (SILICOS-IT) : 2.51
Consensus Log Po/w : 1.46

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.03
Solubility : 1.59 mg/ml ; 0.00936 mol/l
Class : Soluble
Log S (Ali) : -2.69
Solubility : 0.344 mg/ml ; 0.00202 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.69
Solubility : 3.51 mg/ml ; 0.0206 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.32

Safety of [ 67808-64-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67808-64-4 ]

* 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 [ 67808-64-4 ]
  • Downstream synthetic route of [ 67808-64-4 ]

[ 67808-64-4 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 67808-64-4 ]
  • [ 50340-79-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 1, p. 17 - 28
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2265 - 2279
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5982 - 5986
[4] Patent: WO2017/31176, 2017, A1, . Location in patent: Page/Page column 85
  • 2
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  • [ 50340-79-9 ]
Reference: [1] Patent: US5047554, 1991, A,
  • 3
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  • [ 4565-31-5 ]
YieldReaction ConditionsOperation in experiment
59% With potassium hydroxide; water In tetrahydrofuran The compound 25 (2 g, 12.8 mmol) was dissolved in 200 ml of mixture solvent (THF: H20=1 : 1) and HYDROLYZATION was conducted by adding KOH (1.1 g, 19.2 MMOL). After the completion of the reaction, THF was removed under reduced pressure.
The water layer was titrated with 1N HC1 solution in pH 1-2 and then extracted with ethyl acetate (200 ml X 5) to obtain the desirable compound 25 (1.2 g, yield 59percent).
1H NMR (300MHZ, CDC13) 10.00 (s, 1H), 7.93-7. 92 (d, J=3.92Hz, 1H), 7.78-7. 77 (d, J=3.9Hz, 1H). I3C NMR (300MHZ, CDC13) 182. 2, 163. 70, 141. 57, 139. 70, 133. 79, 132. 79.
Reference: [1] Patent: WO2004/37808, 2004, A1, . Location in patent: Page 14-15; 93
  • 4
  • [ 4565-31-5 ]
  • [ 74-88-4 ]
  • [ 67808-64-4 ]
YieldReaction ConditionsOperation in experiment
62% With sodium carbonate In N,N-dimethyl-formamide at 25℃; for 20 h; Step 1. Methyl 5-formyl-2-thiophenecarboxylateA mixture of 5-formyl-2-thiophene carboxylic acid (2.34 g, 15 mmol) and sodium carbonate (5.57 g, 52.5 mmol) in DMF (25 ml) at 25 0C was treated with iodomethane (1.15 ml, 18 mmol) and the mixture was stirred for 20 h before being quenched with the addition of water and saturated aqueous NH4Cl. The resulting solid precipitate was collected by filtration to give methyl 5-formyl-2- thiophenecarboxylate as a solid. The filtrate was extracted with EtOAc (3 x 30 ml) and the combined organic extracts were washed with water and brine, dried (Na2SO4), concentrated under reduced pressure, and subjected to flash chromatography to give solid material that was combined with the solid collected by precipitation to give methyl 5-formyl-2-thiophenecarboxylate as a white solid (1.60 g, 62percent): ESI-MS (m/z): 171.2 (M+H+).
Reference: [1] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 1, p. 17 - 28
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 12, p. 5982 - 5986
[3] Patent: WO2008/124582, 2008, A1, . Location in patent: Page/Page column 130
[4] Patent: US5047554, 1991, A,
[5] Patent: US2006/293343, 2006, A1, . Location in patent: Page/Page column 89
[6] Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2265 - 2279
[7] Patent: WO2005/79791, 2005, A1, . Location in patent: Page/Page column 125-126
[8] Patent: WO2006/123639, 2006, A1, . Location in patent: Page/Page column 135-136
  • 5
  • [ 108499-32-7 ]
  • [ 67808-64-4 ]
YieldReaction ConditionsOperation in experiment
70% With 4-methylmorpholine N-oxide In acetonitrile at 25℃; for 12 h; Molecular sieve To a solution of 4-methylmorpholine N-oxide (0.449 g, 3.83 mmol) in MeCN (5 mL) at 0 °C, in presence of molecular sieves 3Å, compound 13 in MeCN (0.300 g, 1.28 mmol) was added. Reaction mixture was kept stirring at 25 °C for 12 h and then filtered and purified by column chromatography on silica gel (EtOAc/n-hexane 1:20) to obtain the title compound (yield 70percent);
Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 127 - 138
  • 6
  • [ 530145-16-5 ]
  • [ 67808-64-4 ]
YieldReaction ConditionsOperation in experiment
75% With manganese(IV) oxide In acetone for 48 h; The compound 24 (3 g, 17.4 mmol) was dissolved in acetone and an excess of MN02 was added thereto. After 2days of the reaction time, the reaction solution was filtered under reduced pressure with Celite545 and then an exraction process was conducted with acetone sufficiently. The filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate= 2: 1) to obtain the compound 25 (2.2 g, yield 75percent) 1H NMR (300MHZ, CDC13) 9.98 (s, 1H), 7.85-7. 84 (d, J=3.9Hz, 1H), 7.76-7. 75 (d, J=3.9Hz, 1H). 13C NMR (300MHZ, CDC13) 183.02, 160.99, 139.75, 136.36, 135.09, 132.28, 51.96.
Reference: [1] Patent: WO2004/37808, 2004, A1, . Location in patent: Page 14-15; 93
  • 7
  • [ 52157-62-7 ]
  • [ 79-22-1 ]
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Reference: [1] Patent: WO2004/13130, 2004, A1, . Location in patent: Page 203
  • 8
  • [ 67-56-1 ]
  • [ 4565-31-5 ]
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YieldReaction ConditionsOperation in experiment
0.45 g With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 5 - 20℃; for 1 h; In a reaction vessel,5-formylthiophene-2-carboxylic acid (0.50 g),4-dimethylaminopyridine (0.11 g), methanol (0.87 g) and chloroform (12 mL) were added,It was cooled to 5 ° C.To this was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.74 g).After stirring at room temperature for 1 hour,3 mol / L hydrochloric acid (8 mL) was added.The reaction solution was extracted with chloroform,The organic layer was washed with saturated brine.The organic phase was dried over anhydrous sodium sulfate,The solvent was distilled off to obtain a crude product.This was purified with a silica gel column (chloroform)To give a yellow product (5-formylthiophene-2-carboxylic acid methyl ester, 0.45 g).
Reference: [1] Patent: JP2015/86268, 2015, A, . Location in patent: Paragraph 0125-0127
  • 9
  • [ 7732-18-5 ]
  • [ 154935-51-0 ]
  • [ 67808-64-4 ]
Reference: [1] Patent: US5260296, 1993, A,
  • 10
  • [ 1001200-44-7 ]
  • [ 67808-64-4 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 4, p. 688 - 695
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