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[ CAS No. 13679-70-4 ] {[proInfo.proName]}

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Chemical Structure| 13679-70-4
Chemical Structure| 13679-70-4
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Jiang Zhang ; Zijian Wang ; Mugeng Chen , et al. DOI:

Abstract: Deoxygenative upgrading of 5-hydromethylfurfural (HMF) into valuable chemicals has attracted intensive research interest in recent years, with product selectivity control remaining an important topic. Herein, TiO2 supported gold catalysts coated with a thin N-doped porous carbon (NPC) layer were developed via a polydopamine-coating-carbonization strategy and utilized for pathway-specific conversion of HMF into 5-methylfurfural (5-MF) with the use of renewable formic acid (FA) as the deoxygenation reagent. The as-fabricated Au/TiO2@NPC exhibited excellent catalytic performance with a high yield of 5-MF (>95%). The catalytic behavior of Au@NPC-based catalysts was shown to be correlated with the suitable combination of highly dispersed Au nanoparticles and favorable interfacial interactions in the Au@NPC core-shell hetero-nanoarchitectures, thereby facilitating the preferential esterification of HMF with FA and suppressing unproductive FA dehydrogenation, which promoted the selective formylation/decarboxylation of hydroxy-methyl group in HMF in a pathway-specific manner. The present NPC/metal interfacial engineering strategy may provide a potential guide for the rational design of advanced catalysts for a wide variety of heterogeneous catalysis processes in terms of the conversion of biomass source.

Keywords: 5‐Hydroxymethylfurfural ; 5‐Methylfurfural ; Gold catalysis ; N‐doped porous carbon ; Biomass upgrading

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Product Details of [ 13679-70-4 ]

CAS No. :13679-70-4 MDL No. :MFCD00005434
Formula : C6H6OS Boiling Point : -
Linear Structure Formula :CHOC4H2SCH3 InChI Key :VAUMDUIUEPIGHM-UHFFFAOYSA-N
M.W : 126.18 Pubchem ID :61663
Synonyms :
Chemical Name :5-Methylthiophene-2-carbaldehyde

Calculated chemistry of [ 13679-70-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.67
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) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.5
Log Po/w (XLOGP3) : 1.8
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 0.75
Log Po/w (SILICOS-IT) : 3.11
Consensus Log Po/w : 1.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 0.888 mg/ml ; 0.00703 mol/l
Class : Soluble
Log S (Ali) : -2.37
Solubility : 0.538 mg/ml ; 0.00426 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.96
Solubility : 1.38 mg/ml ; 0.011 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.8

Safety of [ 13679-70-4 ]

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 [ 13679-70-4 ]

* 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 [ 13679-70-4 ]
  • Downstream synthetic route of [ 13679-70-4 ]

[ 13679-70-4 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 554-14-3 ]
  • [ 68-12-2 ]
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YieldReaction ConditionsOperation in experiment
99%
Stage #1: With ethylmagnesium chloride; N-cyclohexyl-cyclohexanamine In tetrahydrofuran at 60℃; for 24 h; Inert atmosphere
Stage #2: at 20℃; for 1 h;
General procedure: To a solution of 0.99 M EtMgCl (0.61 mL, 0.6 mmol) in THF were added dicyclohexylamine (0.01 mL, 0.05 mmol), and 2-methylthiophene (1a, 0.048 mL, 0.50 mmol) dropwise under an nitrogen atmosphere. After stirring at 60 °C for 24 h, 1.4 mL of THF and N,N-dimethylformamide (0.5 mL, 6.46 mmol) were successively added and stirring was continued for further 1 h. The mixture was quenched by saturated aqueous solution of ammonium chloride (1.0 mL) and the solution was poured into the mixture of diethyl ether/water to result in separation into two phases. Aqueous was extracted with diethyl ether twice and the combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to leave a crude oil, which was purified by column chromatography on silica gel (hexane/EtOAc = 20/1) to afford 62.3 mg of 2-formyl-5-methylthiophene (1a-CHO, colorless oil, 99percent).
80.2%
Stage #1: at 0 - 35℃; for 18 h;
Stage #2: With sodium hydroxide; water In diethyl ether
Reference Example 1:
Synthesis of 2-formyl-5-methylthiophene
Into a 50 ml, three-necked flask equipped with a magnetic stirrer, a reflux condenser and a thermometer were added 10.9 g (0.15 mol) of dimethylformamide and 15.3 g (0.15 mol) of phosphorus oxychloride.
The mixture was cooled to 0 °C with stirring.
Then, 9.8 g (0.1 mol) of 2-methylthiophene was added to the system, followed by stirring at 25 to 35°C for 18 hours.
To the reaction mixture were added 30 ml of water and 50 ml of ether.
Further, an aqueous solution containing 23percent of sodium hydroxide was added carefully until a pH of >11 was reached.
The mixture was subjected to phase separation.
Then, there were conducted washing with a saturated aqueous sodium chloride solution, drying over anhydrous sodium sulfate, and distillation under reduced pressure for ether removal.
The residue was subjected to Kugel-rohr distillation to obtain 10.1 g of a colorless oil.
The oil contained, as a component, >99.9percent (in terms of areal ratio of gas chromatography) (yield: 80.2percent) of 2-formyl-5-methylthiophene.
Gas mass chromatography was conducted to confirm a molecular ion peak [M+] of 126.
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 9, p. 1173 - 1176
[2] Dyes and Pigments, 2014, vol. 106, p. 154 - 160
[3] Patent: EP1555257, 2005, A1, . Location in patent: Page/Page column 25-26
[4] Pharmaceutical Chemistry Journal, 1989, vol. 23, # 7, p. 592 - 596[5] Khimiko-Farmatsevticheskii Zhurnal, 1989, vol. 23, # 7, p. 840 - 843
[6] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1047 - 1060
[7] Journal of Materials Chemistry, 2007, vol. 17, # 12, p. 1166 - 1177
[8] Journal of the American Chemical Society, 1953, vol. 75, p. 989
[9] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 5, p. 1221 - 1230
[10] Advanced Synthesis and Catalysis, 2010, vol. 352, # 13, p. 2116 - 2120
[11] Dyes and Pigments, 2011, vol. 91, # 3, p. 404 - 412
[12] Applied Organometallic Chemistry, 2013, vol. 27, # 5, p. 283 - 289
[13] Chemical Communications, 2015, vol. 51, # 18, p. 3842 - 3845
  • 2
  • [ 638-02-8 ]
  • [ 13679-70-4 ]
YieldReaction ConditionsOperation in experiment
84% With trichlorophosphate In N,N-dimethyl-formamide at 100℃; for 8 h; Cooling with ice General procedure: To a stirred solution of 9ha–9hd (200 mmol) in dried DMF (43.86 g, 600 mmol) cooled in anice-water bath was added dropwise POCl3 (46.00 g, 300 mmol). The resulting mixture was stirred atthis temperature for 30 min and then at 100 °C for another 5 h. After cooling to room temperature,the reaction mixture was poured carefully into ice-water (300 mL). The mixture thus obtained wasextracted with CH2Cl2 (300 mL × 3), and the combined extracts were washed successively with 5percentbrine (200 mL), 10percent aqueous K2CO3 (200 mL) and 5percent brine (200 mL), dried (Na2SO4) and evaporatedon a rotary evaporator to afford a residue, which was purified by column chromatography to yield10ha–10hd.
Reference: [1] Molecules, 2018, vol. 23, # 2,
  • 3
  • [ 554-14-3 ]
  • [ 75-27-4 ]
  • [ 13679-70-4 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; acetic anhydride; silver carbonate In acetonitrile at 60℃; for 24 h; Schlenk technique; Inert atmosphere
Stage #2: With hydrogenchloride In dichloromethane at 30℃;
General procedure: To a 50 mL of Schlenk tube were added 1 or 3 (0.2 mmol, 1.0 equiv), Pd(OAc)2 (10 molpercent), dppf (10 molpercent) under air, followed by K3PO4·3H2O (0.3 mmol, 1.5 equiv) and Ag2CO3 (0.3 mmol, 1.5 equiv) . The mixture was then evacuated and back filled with N2 (3 times). Bromodichoromethane (0.4 mmol, 2.0 equiv), Ac2O (2 mmol, 190 uL) and CH3CN (1 mL) were added subsequently. The Schlenk tube was screw capped and put into a preheated oil bath (60 °C). After stirring for 24 hours, the reaction mixture was cooled to room temperature, diluted with CH2Cl2 and Ethyl Acetate, then filtered with a pad of silica gel. The isolated yield was given by a hydrolysis pathway, in which the concentrated reaction mixture was diluted with 5 mL CH2Cl2 and 10 mL 3 N HCl and stirred over night. The reaction mixture was extracted with dichloromethane (3 times) and the solvent was removed under rotary evaporation. The residue was then purified by a preparative TLC to give product 2 or 4.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 32, p. 3147 - 3150
  • 4
  • [ 63826-59-5 ]
  • [ 13679-70-4 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 111, p. 91594 - 91600
  • 5
  • [ 554-14-3 ]
  • [ 75-44-5 ]
  • [ 107-06-2 ]
  • [ 13679-70-4 ]
Reference: [1] Patent: US5412106, 1995, A,
  • 6
  • [ 554-14-3 ]
  • [ 93-61-8 ]
  • [ 13679-70-4 ]
Reference: [1] Journal of the Chemical Society, 1950, p. 2130,2134
[2] Journal of Organic Chemistry, 1949, vol. 14, p. 790,795
[3] Journal of the American Chemical Society, 1950, vol. 72, p. 1422
[4] Journal of Organic Chemistry, 1948, vol. 13, p. 635,637
  • 7
  • [ 638-02-8 ]
  • [ 13679-70-4 ]
  • [ 31819-38-2 ]
  • [ 72306-62-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 11, p. 2817 - 2820
  • 8
  • [ 98-03-3 ]
  • [ 13679-70-4 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 18, p. 3803 - 3812
  • 9
  • [ 554-14-3 ]
  • [ 96-43-5 ]
  • [ 68-12-2 ]
  • [ 13679-70-4 ]
  • [ 7283-96-7 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1047 - 1060
  • 10
  • [ 52380-98-0 ]
  • [ 13679-70-4 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1911, vol. 43, p. 804 Anm.[2] Chem. Zentralbl., 1911, vol. 82, # II, p. 1239
[3] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 792[4] Chem. Zentralbl., 1915, vol. 86, # I, p. 837
  • 11
  • [ 638-02-8 ]
  • [ 108-24-7 ]
  • [ 13679-70-4 ]
  • [ 72306-62-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 11, p. 2817 - 2820
  • 12
  • [ 554-14-3 ]
  • [ 13679-70-4 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1911, vol. 43, p. 804 Anm.[2] Chem. Zentralbl., 1911, vol. 82, # II, p. 1239
[3] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 792[4] Chem. Zentralbl., 1915, vol. 86, # I, p. 837
  • 13
  • [ 16494-36-3 ]
  • [ 13679-70-4 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1911, vol. 43, p. 804 Anm.[2] Chem. Zentralbl., 1911, vol. 82, # II, p. 1239
[3] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 792[4] Chem. Zentralbl., 1915, vol. 86, # I, p. 837
  • 14
  • [ 123-76-2 ]
  • [ 13679-70-4 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1914, vol. 46, p. 792[2] Chem. Zentralbl., 1915, vol. 86, # I, p. 837
  • 15
  • [ 98-03-3 ]
  • [ 74-88-4 ]
  • [ 13679-70-4 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 1, p. 104 - 109
  • 16
  • [ 98-03-3 ]
  • [ 74-88-4 ]
  • [ 13679-70-4 ]
  • [ 5834-16-2 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 1, p. 104 - 109
  • 17
  • [ 638-02-8 ]
  • [ 67-56-1 ]
  • [ 13679-70-4 ]
  • [ 31819-38-2 ]
  • [ 72306-62-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 11, p. 2817 - 2820
  • 18
  • [ 638-02-8 ]
  • [ 124-41-4 ]
  • [ 13679-70-4 ]
  • [ 31819-38-2 ]
  • [ 138369-87-6 ]
  • [ 138369-87-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 11, p. 2817 - 2820
  • 19
  • [ 104208-13-1 ]
  • [ 74-88-4 ]
  • [ 13679-70-4 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 18, p. 3803 - 3812
  • 20
  • [ 638-02-8 ]
  • [ 124-41-4 ]
  • [ 13679-70-4 ]
  • [ 31819-38-2 ]
  • [ 138369-89-8 ]
  • [ 138369-87-6 ]
  • [ 138369-87-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1991, # 11, p. 2817 - 2820
  • 21
  • [ 554-14-3 ]
  • [ 96-43-5 ]
  • [ 68-12-2 ]
  • [ 13679-70-4 ]
  • [ 7283-96-7 ]
Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1047 - 1060
  • 22
  • [ 13679-70-4 ]
  • [ 26421-44-3 ]
Reference: [1] Journal of Organic Chemistry, 1949, vol. 14, p. 638,639
  • 23
  • [ 13679-70-4 ]
  • [ 72835-25-7 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With sodium bromate; ammonia In water at 80℃; for 4 h;
Stage #2: With sodium hydroxide In diethyl ether; water
Into a 50 ml, three-necked flask equipped with a magnetic stirrer, a reflux condenser and a thermometer were added 6.3 g (50 mmol) of 2-formyl-5-methylthiophene, 3.0 g (20 mmol) of sodium bromate, 10 ml (174 mmol) of acetic acid and 5 g (74 mmol) of 25percent aqueous ammonia, followed by stirring at 80°C for 4 hours. To the reaction mixture were added 30 ml of water and 50 ml of ether. Further, an aqueous solution containing 23percent of sodium hydroxide was added carefully until a pH of >11 was reached. The mixture was subjected to phase separation. Then, there were conducted washing with water and a saturated aqueous sodium chloride solution in this order, drying over anhydrous sodium sulfate, and distillation under reduced pressure for ether removal, to obtain 6.5 g of an oil as a residue. The oil was subjected to Kugel-rohr distillation to obtain 5.9 g of a colorless oil. The oil contained, as a component, 94.0percent (in terms of areal ratio of liquid chromatography) (yield: 96.0percent) of 2-cyano-5-methylthiophene. Liquid mass chromatography was conducted to confirm a molecular ion peak [(M-1)+] of 122.
Reference: [1] Patent: EP1555257, 2005, A1, . Location in patent: Page/Page column 23-24
[2] Patent: EP1270577, 2003, A1,
  • 24
  • [ 13679-70-4 ]
  • [ 2530-10-1 ]
Reference: [1] Dyes and Pigments, 2014, vol. 106, p. 154 - 160
  • 25
  • [ 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
  • 26
  • [ 13679-70-4 ]
  • [ 59207-23-7 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 3, p. 826 - 829
[2] Patent: WO2015/21432, 2015, A1,
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 1061 - 1073
[4] Patent: WO2006/106326, 2006, A1,
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