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[ CAS No. 71637-34-8 ] {[proInfo.proName]}

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Chemical Structure| 71637-34-8
Chemical Structure| 71637-34-8
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Product Details of [ 71637-34-8 ]

CAS No. :71637-34-8 MDL No. :MFCD00014534
Formula : C5H6OS Boiling Point : -
Linear Structure Formula :- InChI Key :BOWIFWCBNWWZOG-UHFFFAOYSA-N
M.W :114.17 Pubchem ID :123570
Synonyms :

Calculated chemistry of [ 71637-34-8 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 30.45
TPSA : 48.47 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) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 0.72
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 0.46
Log Po/w (SILICOS-IT) : 2.42
Consensus Log Po/w : 1.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.46
Solubility : 3.92 mg/ml ; 0.0344 mol/l
Class : Very soluble
Log S (Ali) : -1.32
Solubility : 5.51 mg/ml ; 0.0483 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.44
Solubility : 4.15 mg/ml ; 0.0364 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.01

Safety of [ 71637-34-8 ]

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 [ 71637-34-8 ]

* 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 [ 71637-34-8 ]
  • Downstream synthetic route of [ 71637-34-8 ]

[ 71637-34-8 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 18791-78-1 ]
  • [ 71637-34-8 ]
YieldReaction ConditionsOperation in experiment
50% With hydrogen; sodium acetate; palladium dichloride In methanol at 35℃; for 12 h; Typical procedures: 6-bromonicotinaldehyde (930 mg, 5.0 mmol), NaOAc (820 mg, 10.0 mmol), MeOH (30 mL), and PdCl2 (45 mg) were mixed in a glass bottle capped with a balloon filled with hydrogen. After stirred at 35 °C for 4 h, the mixture was filtered and washed with MeOH. The solvent was removed and the residue was dissolved in water, neutralized with solid NaHCO3, and extracted with ethyl acetate. The organic phase was dried over anhyd Na2SO4, and then filtered. The solvent was removed and the residue was subjected to chromatography to yield pyridin-3-ylmethanol (428 mg, 78percent).
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 29, p. 3798 - 3801
  • 2
  • [ 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
  • 3
  • [ 85719-70-6 ]
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Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 12, p. 2120 - 2122
  • 4
  • [ 117657-52-0 ]
  • [ 71637-34-8 ]
  • [ 1432266-59-5 ]
  • [ 1447913-95-2 ]
Reference: [1] Patent: WO2013/105676, 2013, A1, . Location in patent: Page/Page column 272; 273
  • 5
  • [ 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
  • 6
  • [ 88-13-1 ]
  • [ 71637-34-8 ]
Reference: [1] Synthetic Communications, 1984, vol. 14, # 1, p. 1 - 10
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 2445
[3] Journal of the American Chemical Society, 1954, vol. 76, p. 2445
[4] Journal of the American Chemical Society, 1954, vol. 76, p. 2445
  • 7
  • [ 872-31-1 ]
  • [ 71637-34-8 ]
Reference: [1] Patent: US2005/23507, 2005, A1,
  • 8
  • [ 117657-59-7 ]
  • [ 71637-34-8 ]
  • [ 117657-70-2 ]
  • [ 117657-74-6 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 48, p. 5965 - 5968
[2] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
  • 9
  • [ 117657-61-1 ]
  • [ 71637-34-8 ]
  • [ 117657-72-4 ]
  • [ 117657-76-8 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 48, p. 5965 - 5968
[2] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
  • 10
  • [ 117657-63-3 ]
  • [ 71637-34-8 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 48, p. 5965 - 5968
[2] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8741 - 8749
  • 11
  • [ 498-62-4 ]
  • [ 1192-58-1 ]
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  • [ 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
  • 12
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  • [ 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
  • 13
  • [ 498-62-4 ]
  • [ 557-20-0 ]
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Reference: [1] Organic Letters, 2002, vol. 4, # 13, p. 2133 - 2136
  • 14
  • [ 100523-84-0 ]
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Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 2445
  • 15
  • [ 98277-70-4 ]
  • [ 71637-34-8 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 3800,3803
  • 16
  • [ 36157-41-2 ]
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Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 2445
  • 17
  • [ 36157-42-3 ]
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Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 2445
  • 18
  • [ 53935-71-0 ]
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Reference: [1] Journal of the American Chemical Society, 1954, vol. 76, p. 2445
  • 19
  • [ 616-44-4 ]
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Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 3800,3803
  • 20
  • [ 34846-44-1 ]
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Reference: [1] Canadian Journal of Chemistry, 1989, vol. 67, p. 1071 - 1076
  • 21
  • [ 17303-83-2 ]
  • [ 71637-34-8 ]
  • [ 222840-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 2227 - 2238
  • 22
  • [ 71637-34-8 ]
  • [ 1641-09-4 ]
YieldReaction ConditionsOperation in experiment
90% With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-Phenylglycine; sodium hydroxide In methanol at 50℃; for 24 h; Cooling with ice General procedure: Benzyl alcohol was added in a 2L round-bottomed flask (108.02g, 1000mmol, i.e., of formula (I) wherein R is H, X = C, n = 1, m = 0),cuprous iodide (9.50g, 50mmol) , of N- phenylglycine (7.51g, 50mmol), TEMPO ( 7.80g, 50mmol),sodium carbonate (10.60g, 100mmol), aqueous ammonia (300mL, 25 ~ 28percent) ,800mL methanol, under ice-cooling, with the oxygen round bottom flask was evacuated of air ventilation 3 times, and then the system was stirred at 50 at 12h, after completion of the reaction, the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure and dried to give the product benzonitrile 95.79g, yield 93percent. The reactants used is 2-thiophene methanol (57.12g, 500mmol, i.e., of formula (I) wherein R is H, X = S, n = 0, m = 0), experimental methods and procedures were the same as in Example 1, except that: cuprous iodide (4.76g, 25mmol), N- phenylglycine (3.79g, 25mmol), TEMPO ( 3.91g, 25mmol), sodium hydroxide (2.03g, 50mmol), aqueous ammonia (60mL, 25 ~ 28percent), methanol 160mL, stirred at at 50 24h, to give the final product 49.05g, yield 90percent.
Reference: [1] Applied Organometallic Chemistry, 2018, vol. 32, # 4,
[2] Patent: CN105294646, 2016, A, . Location in patent: Paragraph 0041; 0064; 0065
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 20, p. 3349 - 3354
  • 23
  • [ 71637-34-8 ]
  • [ 498-62-4 ]
  • [ 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
  • 24
  • [ 71637-34-8 ]
  • [ 67-56-1 ]
  • [ 22913-26-4 ]
Reference: [1] Chinese Journal of Catalysis, 2018, vol. 39, # 7, p. 1249 - 1257
  • 25
  • [ 71637-34-8 ]
  • [ 201230-82-2 ]
  • [ 6964-21-2 ]
  • [ 616-44-4 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 3, p. 723 - 734
[2] Tetrahedron Letters, 1997, vol. 38, # 21, p. 3747 - 3750
  • 26
  • [ 71637-34-8 ]
  • [ 70260-16-1 ]
YieldReaction ConditionsOperation in experiment
91% at 20℃; for 0.75 h; To a solution of 3-hydroxymethylthiophene 12 (4.06 g, 35.6 mmol) in 18 mL of acetic acid was added N-bromosuccinimide (6.34 g, 35.6 mol) at room temperature and stirred for 45 minutes. The resulting mixture was quenched with 1 mL of water, poured into 250 mL ether and washed with 100 mL of water, 100 mL of 10percent NAHC03 aq. respectively. The organic layer was dried over NA2S04 and concentrated. 6.25 G of crude product 13 (91 percent) was obtained and used for the subsequent reaction without further purification.
77% With N-Bromosuccinimide In fluorobenzene at 20℃; for 24 h; Schlenk technique; Inert atmosphere According to the reported procedure, 15 (2-bromothien-3-yl)methanol was prepared by the bromination of 3-thienylmethanol (1.37 g, 12.0 mmol) with N-bromosuccinimide (2.56 g, 14.4 mmol) in PhF (120 mL), and isolated in 77percent yield (1.80 g) as a light orange oil by column chromatography on silica gel (hexane/EtOAc = 3/1). Its spectral and analytical data are shown below because they were not provided in reference 15.
Reference: [1] Organic Letters, 2008, vol. 10, # 17, p. 3665 - 3668
[2] Patent: WO2004/65384, 2004, A1, . Location in patent: Page 36; 16/19
[3] Chemistry Letters, 2013, vol. 42, # 10, p. 1170 - 1172
[4] Patent: WO2008/17164, 2008, A1, . Location in patent: Page/Page column 34
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 2227 - 2238
  • 27
  • [ 17303-83-2 ]
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  • [ 222840-73-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 2227 - 2238
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