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Chemical Structure| 140-10-3
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Product Details of [ 140-10-3 ]

CAS No. :140-10-3 MDL No. :MFCD00004369
Formula : C9H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WBYWAXJHAXSJNI-VOTSOKGWSA-N
M.W : 148.16 Pubchem ID :444539
Synonyms :
trans-3-Phenylacrylic acid;Cinnamylic acid;Isocinnamic acid;Benzenepropenoic acid;3-Phenylacrylic acid|(E)-Cinnamic acid;Phenylacrylic acid;Cinnamic acid
Chemical Name :(2E)-2-Phenyl-2-propenoic acid

Safety of [ 140-10-3 ]

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

Application In Synthesis of [ 140-10-3 ]

* 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 [ 140-10-3 ]
  • Downstream synthetic route of [ 140-10-3 ]

[ 140-10-3 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 106-44-5 ]
  • [ 140-10-3 ]
  • [ 40546-94-9 ]
YieldReaction ConditionsOperation in experiment
77% With Preyssler catalyst In neat (no solvent) at 130℃; for 2 h; Green chemistry General procedure: The catalyst was dried overnight prior to use. A mixture of the correspondingphenol (1 mmol), cinnamic acid (1 mmol) and PA catalyst (0.5 mmol percent) wasplaced in an open glass tube (20 ml) and stirred at 130 C for the indicated time.When the reaction time was over, the reaction mixture was extracted with hottoluene (2 9 3 ml). The extract was washed with H2O (2 ml) and then dried withanhydrous sodium sulfate and filtered. Evaporation of the solvent under reducedpressure and recrystallization from methanol or ethanol gave the pure products.
70% With iodine In neat (no solvent) at 130℃; for 3 h; To a solution of trans-cinnamic acid (10.22 g, 69 mmol) in p-cresol (7.2 mL, 69 mmol, 1 equiv) was added I2 (3.5 g, 13.8 mmol, 20 mol percent).
The solution was stirred at 130 °C for 3 h.
It was then allowed to cool to room temperature, dissolved in ethyl acetate (300 mL) and washed with saturated aqueous sodium thiosulfate solution (2 * 100 mL), H2O (100 mL) and brine (200 mL).
The organic layer was then passed through a silica plug and the solvent was removed under reduced pressure.
The residue was purified by column chromatography on silica gel with hexane/diethyl ether (5:1) to afford the pure product (+-)-5 (11.06 g, 70percent) as a white solid (mp 76-78 °C).
νmax/cm-1 (ATR): 3028 (C-H), 1763 (C=O), 1493, 1126 (C-O).
1H NMR (300 MHz, CDCl3): δ 7.38-7.27 (m, 3H, ArH), 7.18-7.13 (m 3H, ArH), 7.09 (dd, J = 8.3 Hz, J = 1.8 Hz, 1H, ArH), 6.78 (s, 1H, ArH), 4.29 (app t, J = 6.9 Hz, CH), 3.10-2.93 (m, 2H, CH2), 2.25 (s, 3H, CH3); 13C NMR (75.5 MHz, CDCl3): δ 168.0 (C=O), 149.8, 140.7, 134.5, 129.5, 129.3, 128.8, 127.8, 127.7, 125.5, 117.0 (10 * ArC), 40.9 (CH), 37.3 (CH2), 20.9 (CH3).
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[11] Patent: WO2012/137047, 2012, A1, . Location in patent: Page/Page column 9-10
[12] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 653 - 659
  • 2
  • [ 140-10-3 ]
  • [ 4774-24-7 ]
Reference: [1] Acta Poloniae Pharmaceutica - Drug Research, 2018, vol. 75, # 4, p. 891 - 901
  • 3
  • [ 140-10-3 ]
  • [ 102-92-1 ]
YieldReaction ConditionsOperation in experiment
100% for 2 h; Reflux General procedure: A mixture of various carboxylic acids (1.0mmol), an excess of thionyl chrolide (5mL) was refluxed for 2h and concentrated in vacuo to give corresponding acyl chloride (quant).
100% With thionyl chloride In N,N-dimethyl-formamide for 4 h; Reflux General procedure: To a solution of 1.2 equiv of substituted cinnamic acid 1a–l (5 mmol) in 5 equiv of thionyl chloride(3.6 mL), a catalytic amount of DMF was added. The reaction mixture was refluxed for 4 h, andthen, solvent was evaporated under vacuum to get the product 2a–l in the form of a solid residue inquantitative yield. The solid residue was directly added partially to an ice-cold stirred solution of1.0 equiv of tert-butyl (2-aminoethyl)carbamate or tert-butyl (3-aminopropyl)carbamate and 2.0 equivtriethylamine in DCM (20 mL). After the addition, the mixture was warmed to room temperature andstirred for 2 h. Then, DCM (20 mL) was added and washed with 0.2 M HCl (40 mL), H2O (40 mL),5percent saturated. NaHCO3 (40 mL) and brine (40 mL), then dried over anhydrous magnesium sulfate.The solvent was removed in vacuo to give the corresponding cinnamamide derivatives 3a–l (65percent–75percent,from 1a–l) and 4a–g (59percent–70percent, from 1a–g) as a white solid. 3a–l, 4a–g (4 mmol) in DCM/TFA(9:1, 40 mL) were stirred at room temperature for 1 h. Solvents were removed in vacuo to yield 5a–l(100percent) and 6a–g (100percent) as a colorless oil.
99% at 40℃; for 24 h; Cinnamic acid 28 (18.06 mmol) and thionyl chloride (180.6 mmol) were mixed under inert argon atmosphere at 40 °C for 24 hours. Solvent was evaporated under vacuum, followed by dissolving the evaporation residue twice in dichlorom ethane and evaporation, thus giving cinnamic acid chloride 29 (yield: 99 percent).
96.4% With thionyl chloride In N,N-dimethyl-formamide; toluene at 20℃; for 2 h; Reflux (0.1 mol) of cinnamic acid, 150 mL of toluene and 14.3 g (0.12 mol) of thionyl chloride were sequentially added to a 250 mL three-necked flask, and 0.2 mL of N, N-dimethylformamide was added dropwise at room temperature with stirring, Reflux 2h. TLC to monitor the completion of the reaction, rotary evaporation of the solvent and excessive thionyl chloride, 16. Lg light yellow oily liquid, yield 96.4percent

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  • 4
  • [ 79-37-8 ]
  • [ 140-10-3 ]
  • [ 102-92-1 ]
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  • 5
  • [ 50966-31-9 ]
  • [ 140-10-3 ]
  • [ 102-92-1 ]
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  • 6
  • [ 7719-09-7 ]
  • [ 140-10-3 ]
  • [ 102-92-1 ]
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  • 7
  • [ 140-10-3 ]
  • [ 645-45-4 ]
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[2] Organic and Biomolecular Chemistry, 2017, vol. 16, # 1, p. 77 - 88
  • 8
  • [ 50-01-1 ]
  • [ 54081-33-3 ]
  • [ 140-10-3 ]
  • [ 769-39-1 ]
  • [ 6340-72-3 ]
YieldReaction ConditionsOperation in experiment
16% With sodium hydride In N,N-dimethyl-formamide at 50℃; for 1.5 h; Chalcone 1d, 1.0 g (3.4 mmol), was added to a solution of 0.64 g (6.7 mmol) of guanidine hydrochloride and 0.32 g (13.4 mmol) of sodium hydride in 10 mL of DMF. The mixture was stirred for 1.5 h at 50°C, cooled, poured onto ice, and treated with ethyl acetate. The undissolved material at the phase boundary was filtered off. We thus isolated 0.1 g (16percent) of 2-amino-6-phenyl-5,6-dihydropyrimidin-4(1H)-one (7a) which was identical to a sample described in [19] in 1H NMR data and melting point (mp 255–257°C; 257.3°C [19]). The extract was washed with water and dried over CaCl2, the solvent was removed under reduced pressure ona rotary evaporator, and the residue, 0.29 g, was analyzed by NMR and GC/MS.
Reference: [1] Russian Journal of Organic Chemistry, 2015, vol. 51, # 12, p. 1745 - 1752[2] Zh. Org. Khim., 2015, vol. 51, # 12, p. 1778 - 1785,8
  • 9
  • [ 75-11-6 ]
  • [ 140-10-3 ]
  • [ 5685-38-1 ]
YieldReaction ConditionsOperation in experiment
62%
Stage #1: With diethylzinc; trifluoroacetic acid In hexane; dichloromethane at 0℃; for 0.666667 h; Inert atmosphere
Stage #2: at 20℃; for 5 h; Inert atmosphere
To a solution of Et2Zn (1.0 M in hexane, 4.08 mL, 4.08 mmol) in CH2Cl2 (3.0 mL) was added a solution of TFA (0.314 mL, 4.08 mmol) in CH2Cl2 (1.5 mL) at 0 °C under an argon atmosphere. After 20 min, a solution of CH2I2 (0.329 mL, 4.08 mmol) in CH2Cl2 (1.5 mL) was added to the mixture. After 20 min of stirring, a solution of cis-2 (0.200 g, 1.36 mmol) in CH2Cl2 (4.0 mL) was added to the mixture. The reaction was stirred at room temperature for 5 h, quenched with saturated aqueous NH4Cl, extracted with Et2O, and the organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel CC (EtOAc/hexane, 30:70) and, following recrystallization (toluene), yielded cis-14 (0.137 g, 0.845 mmol, 62percent) as colorless needles; mp 103-105 °C; 1H NMR (CDCl3, 400 MHz) δ: 1.39 (m, 1H, c-Pr), 1.69 (m, 1H, c-Pr), 2.07 (m, 1H, -CH-CO2-), 2.66 (dd, J = 8.8, 16.8 Hz, 1H, Ar-CH-), 7.13-7.38 (m, 5H, Ar-H); 13C NMR (CDCl3, 100 MHz) 12.0 (t, c-Pr), 21.3 (d, c-Pr), 26.5 (d, c-Pr), 126.8 (d, Ar), 128.0 (d, Ar), 129.3 (d, Ar), 135.9 (s, Ar), δ 176.3 (s, C=O);; IR (KBr) 1703 cm-1; ESI-MS m/z 161 (M+-H); Anal. calcd for C9H8O2: C, 74.06; H, 6.21. Found: C, 73.82; H, 6.29; The spectroscopic data were in agreement with those in the literature ( Concellón et al., 2007 ).
Reference: [1] Phytochemistry (Elsevier), 2012, vol. 84, p. 56 - 67,12
  • 10
  • [ 701-97-3 ]
  • [ 140-10-3 ]
  • [ 56453-86-2 ]
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  • 11
  • [ 140-10-3 ]
  • [ 108-95-2 ]
  • [ 2657-25-2 ]
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  • 12
  • [ 140-10-3 ]
  • [ 127033-74-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5561 - 5578
  • 13
  • [ 75-47-8 ]
  • [ 140-10-3 ]
  • [ 939-89-9 ]
Reference: [1] Organic Letters, 2007, vol. 9, # 14, p. 2685 - 2688
  • 14
  • [ 140-10-3 ]
  • [ 851789-43-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 653 - 659
[2] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 9, p. 2157 - 2167
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