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[ CAS No. 498-62-4 ] {[proInfo.proName]}

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Chemical Structure| 498-62-4
Chemical Structure| 498-62-4
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Product Details of [ 498-62-4 ]

CAS No. :498-62-4 MDL No. :MFCD00005466
Formula : C5H4OS Boiling Point : -
Linear Structure Formula :- InChI Key :RBIGKSZIQCTIJF-UHFFFAOYSA-N
M.W : 112.15 Pubchem ID :68135
Synonyms :

Calculated chemistry of [ 498-62-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 29.71
TPSA : 45.31 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) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 1.01
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 2.73
Consensus Log Po/w : 1.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.63
Solubility : 2.6 mg/ml ; 0.0232 mol/l
Class : Very soluble
Log S (Ali) : -1.55
Solubility : 3.16 mg/ml ; 0.0281 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.55
Solubility : 3.12 mg/ml ; 0.0279 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 498-62-4 ]

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

Application In Synthesis of [ 498-62-4 ]

* 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 [ 498-62-4 ]
  • Downstream synthetic route of [ 498-62-4 ]

[ 498-62-4 ] Synthesis Path-Upstream   1~30

  • 1
  • [ 498-62-4 ]
  • [ 21047-57-4 ]
  • [ 67237-53-0 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 16, p. 4070 - 4073
  • 2
  • [ 498-62-4 ]
  • [ 67237-53-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 47, p. 9979 - 9982
  • 3
  • [ 498-62-4 ]
  • [ 71637-34-8 ]
YieldReaction ConditionsOperation in experiment
95% With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 3 h; To a solution of thiophene-3-carbaldehyde (10 g, 89.3 mmol) in THF (200 mL) at 0 °C was added NaBH4 (1.7 g, 45.0 mmol) in portions. After stirring at 0 °C for 3 h, The reaction was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, and dried over anhydrous Na2S04. After filtration and concentration, the crude product was purified by column chromatography to give the title compound (9.7 g, 95percent).
70% With sodium tetrahydroborate In ethanol; benzene at 0 - 20℃; for 4 h; A solution of 3-thiophenecarboxaldehyde 11 (10 g, 89.3 mmol) in 20 mL of benzene and 20 mL of absolute ethyl alcohol was cooled to 0°C and then sodium borohydride (4.39 g, 116 mmol) was added in three portions to the solution over an hour. After the addition, the reaction mixture was warmed up to room temperature and stirred for anther 3 hours and quenched with 3 mL of water. The solvent was evaporated and the residue was taken by 300 mL of dichloromethane and washed with 2x100 mL of water. The organic layer was dried over NA2S04 and concentrated via rotary evaporation. The crude product was purified via a flash chromatography on silica gel with an eluent of dichloromethane/hexanes (1/1) to give 7.1 of pure product (70percent).APOS;H NMR (CDCL3) 8 7.28-7. 32 (m, 1H), 7.20-7. 22 (brm, 1H), 7.08 (dd, 4.4 Hz, 1.2 Hz, 1H), 4.68 (s, 2H), 1.74 (brm, 1H). Anal. CSH60S requires C, 52.60 ; H, 5.30. Found C, 53.89 ; H, 5.61.
61 %Chromat. With formaldehyd; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; water; sodium carbonate In dimethyl sulfoxide at 120℃; for 24 h; Inert atmosphere; Sealed tube General procedure: Knölker iron complex 2a (3 mol percent,12.6 mg), paraformaldehyde (300 mg, 10 mmol), and Na2CO3 (106 mg, 1 mmol,1.0 equiv) and a stirring bar were charged in a pressure tube and flushed withargon. DMSO (1.0 mL), degassed water (1.0 mL), and benzaldehyde (1 mmol)were added under an argon atmosphere to the pressure tube with a syringe.The pressure tube was placed in oil and heated at 120 C for 24 h, then cooledto room temperature. The reaction mixture was neutralized with HCl (1M) andstirred for 30 min. After extraction with EtOAc for 3 times, the combinedorganic layers were dried over MgSO4. The crude product was purified bycolumn chromatography (Heptane/EtOAc: 70:30). The reaction was cooled toroom temperature and hexadecane (100 lL) was added as a GC internalstandard.
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 26, p. 5695 - 5699
[2] Journal of the Chemical Society, Chemical Communications, 1984, # 3, p. 163 - 164
[3] Tetrahedron, 1996, vol. 52, # 43, p. 13615 - 13622
[4] Patent: WO2011/69063, 2011, A2, . Location in patent: Page/Page column 94
[5] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
[6] Magnetic Resonance in Chemistry, 1988, vol. 26, p. 129 - 133
[7] Macromolecules, 2013, vol. 46, # 3, p. 708 - 717
[8] Patent: WO2004/65384, 2004, A1, . Location in patent: Page 35-36; 16/19
[9] Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 189, # 1, p. 155 - 168
[10] Chemistry - A European Journal, 2006, vol. 12, # 10, p. 2739 - 2744
[11] Electrochimica Acta, 2012, vol. 59, p. 270 - 278
[12] Chemistry - A European Journal, 2012, vol. 18, # 50, p. 15935 - 15939
[13] Chemistry - A European Journal, 2013, vol. 19, # 45, p. 15210 - 15218
[14] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
[15] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1118 - 1121
[16] European Journal of Organic Chemistry, 2016, vol. 2016, # 12, p. 2207 - 2211
[17] Inorganic Chemistry, 2017, vol. 56, # 18, p. 11282 - 11298
  • 4
  • [ 498-62-4 ]
  • [ 17715-69-4 ]
  • [ 71637-34-8 ]
  • [ 1285144-58-2 ]
Reference: [1] Patent: US2014/50683, 2014, A1, . Location in patent: Paragraph 0084 - 0086
  • 5
  • [ 498-62-4 ]
  • [ 1192-58-1 ]
  • [ 71637-34-8 ]
  • [ 173276-64-7 ]
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 2, p. 394 - 399
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 21, p. 2669 - 2672
  • 6
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  • [ 71637-34-8 ]
  • [ 173276-64-7 ]
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 2, p. 394 - 399
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 21, p. 2669 - 2672
  • 7
  • [ 498-62-4 ]
  • [ 557-20-0 ]
  • [ 71637-34-8 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 13, p. 2133 - 2136
  • 8
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  • [ 59311-67-0 ]
Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 4466
  • 9
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  • [ 1641-09-4 ]
YieldReaction ConditionsOperation in experiment
89% With hydroxylamine hydrochloride In methanol; water at 20℃; for 18 h; Irradiation General procedure: A round bottom flask was charged with a mixture of benzaldehyde 1(1.0 mmol), NH2OH.HCl 2 (1.5 mmol), Cog-C3N4 (20 mg) in H2O/MeOH (1:1, 5 mL) and stirred under the visible light condition at roomtemperature for 14–20 h. After completion of the reaction (monitored by TLC), the catalyst was filtered and added EtOAc (10 mL). Remaining organic layer was washed with brine (2×5 mL) and distilled water(1×10 mL) and dried over anhydrous sodium sulfate. Solvent was evaporated under reduced pressure to afford the crude residue, which was further purified by flash chromatography, EtOAc/n-hexane: 10:90 to obtain the analytically pure product 3
86% With hydroxylamine hydrochloride; zinc trifluoromethanesulfonate In toluene at 100℃; for 24 h; General procedure for the synthesis of nitriles: A pressure tube was charged with an appropriate amount of Zn(OTf)2 (0.036 mmol, 5.0 mol percent), the corresponding aldehyde (0.72 mmol) and hydroxylamine hydrochloride (1.2 equiv, 0.86 mmol). After the addition of toluene (2.0 mL) the reaction mixture was stirred in a preheated oil bath at 100 °C for 24 h. The mixture was cooled in an ice bath and biphenyl (internal standard) was added. The solution was diluted with dichloromethane and an aliquot was taken for GC-analysis (30 m Rxi-5 ms column, 40-300 °C). The solvent was carefully removed and the residue was purified by column chromatography (n-hexane/ethyl acetate). The analytical properties of the corresponding nitriles are in agreement with the literature.
Reference: [1] Organic Letters, 2017, vol. 19, # 11, p. 3005 - 3008
[2] Catalysis Communications, 2019, p. 76 - 81
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 8, p. 1055 - 1058
[4] Tetrahedron Letters, 2012, vol. 53, # 7, p. 882 - 885
[5] Chemical Communications, 2013, vol. 49, # 54, p. 6030 - 6032
[6] Organic and Biomolecular Chemistry, 2013, vol. 11, # 20, p. 3349 - 3354
[7] Organic and Biomolecular Chemistry, 2015, vol. 13, # 39, p. 9948 - 9952
  • 10
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  • [ 1641-09-4 ]
Reference: [1] Angewandte Chemie, International Edition, 2009, vol. 48, # 34, p. 6286 - 6288[2] Angewandte Chemie, 2009, vol. 121, # 34, p. 6404 - 6406
  • 11
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  • [ 38622-91-2 ]
  • [ 13781-53-8 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 85, # 1-4, p. 23 - 30
  • 12
  • [ 498-62-4 ]
  • [ 26421-44-3 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 1, p. 104 - 109
[2] Journal of Organic Chemistry, 1987, vol. 52, # 1, p. 104 - 109
  • 13
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  • [ 74-88-4 ]
  • [ 26421-44-3 ]
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  • [ 84815-20-3 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 1, p. 104 - 109
  • 14
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  • [ 272-14-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 1, p. 289 - 290
[2] Patent: US2004/14755, 2004, A1,
  • 15
  • [ 498-62-4 ]
  • [ 67-56-1 ]
  • [ 22913-26-4 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 17, p. 5172 - 5176
  • 16
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  • [ 100523-84-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
  • 17
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  • [ 7311-70-8 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
  • 18
  • [ 498-62-4 ]
  • [ 38150-49-1 ]
Reference: [1] Bl. Univ. Osaka Prefect., 1958, vol. <A> 6, p. 127,133[2] Chem.Abstr., 1959, p. 4248
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 8049 - 8065
  • 19
  • [ 498-62-4 ]
  • [ 389-58-2 ]
Reference: [1] Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 42, p. 63 - 72
[2] Macromolecules, 2010, vol. 43, # 2, p. 697 - 708
[3] Journal of the American Chemical Society, 2012, vol. 134, # 1, p. 539 - 547
[4] Synlett, 2014, vol. 25, # 10, p. 1466 - 1472
[5] Chemistry - A European Journal, 2018, vol. 24, # 43, p. 11082 - 11093
  • 20
  • [ 498-62-4 ]
  • [ 25796-77-4 ]
Reference: [1] Synthesis, 2002, # 8, p. 1053 - 1056
[2] Macromolecules, 2010, vol. 43, # 2, p. 697 - 708
[3] Synlett, 2014, vol. 25, # 10, p. 1466 - 1472
[4] Patent: CN105439976, 2016, A,
[5] Patent: CN105601662, 2016, A,
  • 21
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  • [ 74-88-4 ]
  • [ 29421-72-5 ]
  • [ 84815-20-3 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 1, p. 104 - 109
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  • [ 74-88-4 ]
  • [ 26421-44-3 ]
  • [ 29421-72-5 ]
  • [ 84815-20-3 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 1, p. 104 - 109
  • 23
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  • [ 5650-52-2 ]
Reference: [1] Patent: WO2015/101928, 2015, A1,
[2] Patent: WO2016/44770, 2016, A1,
  • 24
  • [ 498-62-4 ]
  • [ 73540-75-7 ]
  • [ 32281-36-0 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 4, p. 1457 - 1460
  • 25
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  • [ 18791-79-2 ]
YieldReaction ConditionsOperation in experiment
88% With aluminum (III) chloride; bromine In dichloromethane for 12.17 h; Thiophene-3-carbaldehyde (6.5 g, 0.06 mol) was dissolved in 200 mL of dichloromethane (dry), and 14 g of aluminum chloride was added. The dark solution was stirred for 10 min and solution of bromine (10 g, 0.066 mol) in 10 mL of dichloromethane was added dropwise over 10 min period. The mixture was stirred for 12 h and poured onto crush-ice. The organic layer was separated and extracted with 2 N HCl, washed by water. The organic phase was dried over anhydrous MgSO4 and reduced solvent. The white liquid product was purified by vacuum distillation, with yield of 88percent (10 g).
88%
Stage #1: With aluminum (III) chloride In dichloromethane at 0℃; for 2 h;
Stage #2: With bromine In dichloromethane at 0 - 40℃;
Anhydrous aluminum chloride (5.9 g, 44.5 mmol) was added in small portions over a period of 2 h to a solution of thiophene-3-carbaldehyde (2.0 g, 17.8 mmol) in CH2Cl2 (100 mL) maintaining the temperature at 0 °C. Bromine (2.56 g, 16.0 mmol) in CH2Cl2 (50 mL) was then added dropwise to the reaction mixture at 0 °C.
The reaction mixture was refluxed at 40 °C for 1 h, quenched with water, and extracted with CH2Cl2.
The combined extracts were dried over anhydrous Na2SO4, and concentrated under reduced pressure.
The crude product was purified by column chromatography (silica 60-120 mesh, eluant 10percent EtOAc in petroleum ether) to give 5-bromothiophene-3-carbaldehyde (3.0 g, yield 88percent).
64% With aluminum (III) chloride; bromine In dichloromethane at 20℃; for 6 h; Heating / reflux AlCl3 (15g, 0.112 mol) was added in portions over 2 h to a solution of thiophene- 3-carboxaldehyde (5g, 0.044 mol) in CH2Cl2 (150 mL) at rt. Br2 (2.13 mL, 0.041 mol) in CH2Cl2 (20 mL) was added drop wise. The mixture was heated at reflux for 6 h, cooled, poured into H2O (250 mL) and extracted with CH2Cl2. The combined extracts were washed with brine, dried (MgSO4), concentrated and distilled to yield the sub-title compound 5.4 g (64percent).
Reference: [1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1170 - 1174
[2] Patent: EP2533783, 2015, B1, . Location in patent: Paragraph 1044-1045
[3] Patent: WO2006/77412, 2006, A1, . Location in patent: Page/Page column 85
[4] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 10, p. 1393 - 1403
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 5, p. 1190 - 1194
[6] Revue Roumaine de Chimie, 2012, vol. 57, # 4-5, p. 345 - 351
[7] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
[8] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 15, p. 2011 - 2014
[9] Patent: US5597832, 1997, A,
[10] Patent: US2006/293343, 2006, A1, . Location in patent: Page/Page column 91
[11] Patent: US2009/143372, 2009, A1,
[12] Patent: US6740647, 2004, B1, . Location in patent: Page column 31-32
[13] Patent: WO2004/94430, 2004, A1, . Location in patent: Page 23
[14] Patent: WO2006/123639, 2006, A1, . Location in patent: Page/Page column 138
[15] Doklady Chemistry, 2014, vol. 454, # 2, p. 25 - 31[16] Dokl. Akad. Nauk, 2014, vol. 454, # 4, p. 417 - 423,7
[17] Patent: WO2007/131764, 2007, A2, . Location in patent: Page/Page column 135; 7/8
  • 26
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  • [ 27757-86-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 8, p. 1512 - 1522
[2] Patent: EP2511283, 2012, A1,
[3] Patent: US2013/45942, 2013, A1,
[4] Patent: JP2015/172077, 2015, A,
  • 27
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  • [ 36155-85-8 ]
YieldReaction ConditionsOperation in experiment
31% With N-chloro-succinimide In acetic acid at 110℃; for 4 h; To a solution of thiophene-3-carbaldehyde (20.0 g, 178.3 mmol) and N-chlorosuccinimide (23.8 g, 178.3 mmol) in AcOH (180 mL) was stirred at 110 °C for 4 hours. After the completion of reaction, the solution was cooled to room temperature, and then was diluted with EtOAc (120 mL), washed with H20 (100 mL x 3), saturated NaHC03 (50 mL x 2), brine, dried over anhydrous Na2S04 and concentrated to afford 5-chlorothiophene-3-carboxylic acid (8.0 g, 54.6 mmol, 31percent yield) as yellow solid, which was used directly in the next step without further purification.
Reference: [1] Patent: WO2015/140133, 2015, A1, . Location in patent: Page/Page column 110
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 8, p. 2568 - 2578
[3] Patent: WO2015/142903, 2015, A2, . Location in patent: Page/Page column 98
  • 28
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  • [ 3685-51-6 ]
Reference: [1] Tetrahedron: Asymmetry, 1997, vol. 8, # 4, p. 527 - 536
  • 29
  • [ 498-62-4 ]
  • [ 474416-61-0 ]
Reference: [1] Synthesis, 2002, # 8, p. 1053 - 1056
[2] Macromolecules, 2010, vol. 43, # 2, p. 697 - 708
[3] Synlett, 2014, vol. 25, # 10, p. 1466 - 1472
[4] Patent: CN105439976, 2016, A,
[5] Patent: CN105601662, 2016, A,
  • 30
  • [ 498-62-4 ]
  • [ 365547-20-2 ]
Reference: [1] Macromolecules, 2010, vol. 43, # 2, p. 697 - 708
[2] Journal of the American Chemical Society, 2012, vol. 134, # 1, p. 539 - 547
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