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Chemical Structure| 6214-35-3 Chemical Structure| 6214-35-3

Structure of 6214-35-3

Chemical Structure| 6214-35-3

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Product Details of [ 6214-35-3 ]

CAS No. :6214-35-3
Formula : C3H3IO2
M.W : 197.96
SMILES Code : O=C(O)/C=C\I
MDL No. :MFCD00274189
InChI Key :IBFDLVHJHUMSAC-UPHRSURJSA-N
Pubchem ID :643796

Safety of [ 6214-35-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 6214-35-3 ]

* 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.

  • Downstream synthetic route of [ 6214-35-3 ]

[ 6214-35-3 ] Synthesis Path-Downstream   1~35

  • 4
  • [ 6214-35-3 ]
  • [ 542-92-7 ]
  • [ 71702-11-9 ]
  • [ 71702-11-9 ]
  • 5
  • [ 2956-91-4 ]
  • [ 6214-35-3 ]
  • 7
  • [ 67-56-1 ]
  • [ 6214-35-3 ]
  • [ 6214-23-9 ]
  • [ 6213-88-3 ]
  • 8
  • [ 6214-35-3 ]
  • [ 623-43-8 ]
  • (E)-5-methoxycarbonyl-4-methyl-2-pentenoic acid [ No CAS ]
  • 9
  • [ 6214-35-3 ]
  • [ 75-35-4 ]
  • (E)-5,5-dichloro-2-pentenoic acid [ No CAS ]
  • 10
  • [ 6214-35-3 ]
  • [ 2680-03-7 ]
  • (E)-6-dimethylamino-6-oxo-2-hexenoic acid [ No CAS ]
  • 11
  • [ 6214-35-3 ]
  • [ 96-05-9 ]
  • (E)-5-allyloxycarbonyl-2-hexenoic acid [ No CAS ]
  • 12
  • [ 6214-35-3 ]
  • [ 109669-45-6 ]
  • [ 71443-20-4 ]
  • 13
  • [ 6214-35-3 ]
  • [ 6372-02-7 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogen iodide; In water; benzene; at 80℃; for 5h; To a solution of 55% aqueous HI (0.3 mL) and benzene(4.3 mL) was added (Z)- propenoic acid (3.6 g, 18 mmol). The mixture was heated at80 C for 5 h. After the mixture cooled to room temperature, ether was added, and thelayers were separated. The aqueous layer was extracted with ether, and the combinedorganic layers were washed with aqueous Na2S2O3 and dried (MgSO4). The solventwas evaporated in vacuo. The residue was washed with n-hexane, giving 3.4 g of(E)-propenoic acid in 95% yield as a white crystal. The spectral data was inaccordance with the literature [1].
89% With hydrogen iodide; In water; benzene; at 80℃; for 5h; The procedure of Step 2 was carried out according to the protocol put forth by Takeuchi et al, Journal of Organic Chemistry, 2000 (65), 1558-61. (Z)-3- Iodo-acrylic acid (5.94 g, 30 mmol)was added to a solution of 55% aqueous hydroiodic acid (0.6 mL) and benzene (8 mL). The mixture was heated at 800C for 5 hours, cooled to ambient temperature, diluted with ether and extracted. The aqueous layer was extracted with ether, and the combined organic layers were washed with aqueous sodium thiosulphate and dried magnesium sulfate. The solvent was evaporated in vacuo. The solvent was evaporated in vacuo, <n="63"/>and the residue was washed with n-hexane to give the title compound as a pale yellow solid, yield 5.29 g (89%); mp 144-147 0C. 1H NMR (270 MHz, CDCl3) δ 6.90 (d, J = 14.8 Hz, IH), 8.09 (d, J = 14.8 Hz, IH), 10.0 (br, IH). 13C NMR (67.8 MHz, CDCl3) δ 103.2, 135.7, 169.4.
  • 15
  • [ 6214-35-3 ]
  • [ 107-13-1 ]
  • (E)-5-cyano-2-pentenoic acid [ No CAS ]
  • 16
  • [ 6214-35-3 ]
  • [ 292638-85-8 ]
  • [ 89898-52-2 ]
  • 17
  • [ 6214-35-3 ]
  • [ 80-62-6 ]
  • (E)-5-methoxycarbonyl-2-hexenoic acid [ No CAS ]
  • 18
  • [ 6214-35-3 ]
  • [ 126-98-7 ]
  • (E)-5-cyano-2-hexenoic acid [ No CAS ]
  • 19
  • [ 471-25-0 ]
  • [ 74-88-4 ]
  • [ 6214-35-3 ]
  • 20
  • [ 471-25-0 ]
  • [ 6214-35-3 ]
YieldReaction ConditionsOperation in experiment
96% With hydrogen iodide; In water; at 50℃; for 17h; To a solution of 55% aqueous HI (5.0 mL) and H2O (5.0mL) was added propynoic acid (1.2 mL, 20 mmol). The mixture was heated at 50 Cfor 17 h. After the mixture cooled to room temperature, ether was added, and thelayers were separated. The aqueous layer was extracted with ether, and the combinedorganic layers were washed with aqueous Na2S2O3 and dried (MgSO4). The solventwas evaporated in vacuo. The residue was washed with n-hexane, giving 3.8 g of(Z)-propenoic acid in 96% yield as a white soild. The spectral data was in accordancewith the literature [1].
90% With hydrogen iodide; In water; at 50℃; for 17h; The procedure of Step 1 was carried out according to the protocol put forth by Takeuchi et al, Journal of Organic Chemistry, 2000 (65), 1558-61. To a solution of 55% aqueous hydroiodic acid (20 mL) and water (30 mL) was added propynoic acid (7.0 g, 100 mmol). The mixture was heated at 500C for 17 hours. After the mixture cooled to ambient temperature, ether was added, and the layers were separated. The aqueous layer was extracted with ether, and the combined organic layers were washed with aqueous sodium thiosulphate and dried magnesium sulfate. The solvent was evaporated in vacuo, and the residue was washed with n-hexane to give the title compound as a pale yellow solid which is used directly in the next step; yield 17.8 g (90%). mp 68-70 0C (lit.10b mp 63-64 0C). 1H NMR (270 MHz, CDCl3) δ 6.99 (d, J = 9.2 Hz, IH), 7.69 (d, J = 9.2 Hz, IH), 9.94 (br, IH). 13C NMR (67.8 MHz, CDCl3) δ 98.2, 129.4, 169.7.
87% With hydrogen iodide; In water; at 50℃; for 24h; To a solution of 57 % hydrogen iodide (60 mL) in water (90 mL) was added propynoic acid (propiolic acid) 20 (20 g). The resulting mixture was heated at 50 C for 24 h. The mixture was cooled to room temperature and MTBE (100 mL) was added. The two layers were separated. The aqueous layer was extracted with MTBE (100 mL). The combined organic phase was washed with 2 M NaS203 (2 x 50 mL), 5 % NaCl and dried over MgS04. The solution was filtered and concentrated to dryness to afford a beige solid product 21 (49 g, 87%). To a solution of (Z)-3-iodo- acrylic acid 21 (48 g) and t-BuOAc (140 g) in CH2CI2 (144 mL, 3 vol.) was added TfOH (1.8 g). The solution was stirred at room temperature for 1 h. The reaction was deemed complete (acid: HPLC area% 20.27%). The solution was neutralized with 2 M K2CO3 (242 mL). Heptane (144 mL) was added. The two layers were separated. The aqueous layer was extracted with heptane (144 mL). The combined organic phase was washed with water (144 mL) and dried over MgS04. The solution was filtered and concentrated to dryness to afford an oil product 5 (49 g, 80%, HPLC area%: 98.22%).
87% With hydrogen iodide; In tert-butyl methyl ether; water; at 50℃; for 24h; To a solution of 57 % HI (60 mL) in water (90 mL) was added propynoic acid 20 (20 g). The resulting mixture was heated at 50 c for 24 h. The mixture was cooledto room temperature and MTBE (100 mL) was added. The two layers were separated. The aqueous layer was extracted with MTBE (100 mL). The combined organic phase was washed with 2 M Na5203 (2 x 50 mL), 5 % Nacl and dried over Mg504. The solution was filtered and concentrated to dryness to afford a beige solids product 21 (49 g, 87%). To a solution of (Z)-3-iodo-acrylic acid 21 (48 g) and t-BuOAc (140 g) inCH2C12 (144 mL, 3 vol.) was added TfOH (1.8 g). The solution was stirred at room temperature for 1 h. The reaction was deemed complete (acid: HPLC area% 20.27%). The solution was neutralized with 2 M K2c03 (242 mL). Heptane (144 mL) was added. The two layers were separated. The aqueous layer was extracted with heptane (144 mL). The combined organic phase was washed with water (144 mL) and dried overMg504. The solution was filtered and concentrated to dryness to afford an oil product5 (49 g, 80%, HPLC area%: 98.22%).
87% With hydrogen iodide; In water; at 50℃; for 24h; To a solution of 57 % HI (60 mL) in water (90 mL) is added propionic acid 20 (20 g). The resulting mixture is heated at 50C for 24 h. The mixture is cooled to room temperature and MTBE (100 mL) was added. The two layers were separated. The aqueous layer was extracted with MTBE (100 mL). The combined organic phase is washed with 2 M NaS203(2 x 50 mL), 5 % NaCl and dried over MgS04. The solution was filtered and concentrated to dryness to afford a beige solids product 21 (49 g, 87%). To a solution of (Z)-3-iodo-acrylic acid 21 (48 g) and t-BuOAc (140 g) in CH2CI2(144 mL, 3 vol.) was added TfOH (1.8 g). The solution is stirred at room temperature for 1 h. The reaction is deemed complete (acid: HPLC area% 20.27%). The solution is neutralized with 2 M K2CO3(242 mL). Heptane (144 mL) was added. The two layers are separated. The aqueous layer is extracted with heptane (144 mL). The combined organic phase is washed with water (144 mL) and dried over MgS04. The solution is filtered and concentrated to dryness to afford an oil product 5 (49 g, 80%, HPLC area%: 98.22%).
87% With hydrogen iodide; In water; at 50℃; for 24h; To a solution of 57 % HI (60 mL) in water (90 mL) was added propynoic acid 20’ (20 g). The resulting mixture was heated at 50 C for 24 h. The mixture was cooled to room temperature and MTBE (100 mL) was added. The two layers were separated. The aqueous layer was extracted with MTBE (100 mL). The combined organic phase was washed with 2 M NaS CT, (2 x 50 mL), 5 % NaCl and dried over MgSCL. The solution was filtered and concentrated to dryness to afford a beige solids product 21’ (49 g, 87%). To a solution of (Z)-3-iodo-acrylic acid 21’ (48 g) and t-BuOAc (140 g) in CH2CI2 (144 mL, 3 vol.) was added TfOH (1.8 g). The solution was stirred at room temperature for 1 h. The reaction was deemed complete (acid: HPLC area% 20.27%). The solution was neutralized with 2 M K2CO3 (242 mL). Heptane (144 mL) was added. The two layers were separated. The aqueous layer was extracted with heptane (144 mL). The combined organic phase was washed with water (144 mL) and dried over MgSCL. The solution was filtered and concentrated to dryness to afford an oil product 5’ (49 g, 80%, HPLC area%: 98.22%).
79% With hydrogen iodide; In water; at 55℃; for 18h;Inert atmosphere; Large scale; A 5-L three-neck round-bottom flask was equipped with overhead stirrer, temperature probe, argon inlet and outlet, and water-cooling condenser. The flask was charged with propiolic acid 25 (500 g, 7.14 mol), DI-water (2 L, 4 vol) and hydriodic acid (1.3 kg, 10.3 mol, 1.6 equiv.). The reaction mixture was heated to 55 C under argon for 18 h. HPLC analysis of the sample showed the presence of (Z)-3-iodo-acrylic acid 26 (>99% AUC). After cooling to ambient temperature, the solution was transferred to a 6-L separatory funnel. The product was extracted with MTBE (2 x 1 L) and the combined organic phase was washed with saturated sodium sulfite (200 mL) and brine (200 mL); dried over sodium sulfate for 3 h. Ethyl acetate (1 L) was added to dissolve the solid product (some crystallized during dryness). After filtration, the filtrates were concentrated on a rotary evaporator to remove most solvents. MTBE (500 mL) and heptane (500 mL) were added and the product was crystallized at ambient temperature for 18 h. The white solid was collected by filtration and dried in a vacuum oven at 45 C overnight to obtain 1.1 kg, of 26 (yield, 79%, purity 99% (AUC)).
40.44% With acetic acid; sodium iodide; at 1000℃; Synthesis of (Z)-3-iodoacrylic acid:0Nal ^ ^OHOH " γ YI oA 250-mL, three-necked, roubd-bottomed flask equipped with nitrogen inlet was added propiolic acid (7.0 g,1.0 eq) dissolved in acetic acid (70 mL,10V) and sodium iodide (29.96 g, 2.0eq). The reaction mixture was refluxed at 1000 C for 2-3 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% MeOH:DCM as mobile phase. SM Rf =0.3 and Product Rf = 0.5. Reaction mixture was poured into ice water (700 mL) and neutralized with saturated solidum bicarbonate solution. The reaction mixture was extracted with EtOAc (3 x 100 mL). The combined organic layers were washed with brine solution (3 x 100 mL), dried over MgS04, filtered, and concentrated by rotary evaporation (25 C, 20 mmHg) to afford 12.0 g of crude compound which was purified by column chromatography using silica 60/120 using MeOH:DCM as mobile phase. The column (5 x 10 cm) was packed in DCM and started eluting in MeOH in gradient manner starting with fraction collection (50- mL fractions) from 2% to 5% MeOH in DCM. Compound started eluting with 2% MeOH in DCM. Fractions containing such TLC profile were combined to obtain 8.0 gm of desired compound (yield 40.44%).

References: [1]Chinese Chemical Letters,2022.
[2]Synthesis,1996,p. 82 - 86.
[3]Journal of Organic Chemistry,2002,vol. 67,p. 4127 - 4137.
[4]Tetrahedron Letters,2001,vol. 42,p. 1691 - 1694.
[5]Journal of Organic Chemistry,2000,vol. 65,p. 1558 - 1561.
[6]Patent: WO2008/73863,2008,A2 .Location in patent: Page/Page column 60-61.
[7]Journal of the Chemical Society. Chemical communications,1990,p. 1643 - 1644.
[8]Journal of Organic Chemistry,1992,vol. 57,p. 709 - 713.
[9]Organic letters,2000,vol. 2,p. 65 - 67.
[10]Patent: WO2017/193016,2017,A1 .Location in patent: Page/Page column 202.
[11]Patent: WO2017/193017,2017,A1 .Location in patent: Page/Page column 108.
[12]Patent: WO2019/234509,2019,A2 .Location in patent: Page/Page column 173.
[13]Patent: WO2020/115547,2020,A2 .Location in patent: Page/Page column 79.
[14]Journal of Organic Chemistry,2007,vol. 72,p. 2525 - 2532.
[15]Organic Letters,2018,vol. 20,p. 7679 - 7683.
[16]Tetrahedron Letters,2019,vol. 60,p. 371 - 374.
[17]Canadian Journal of Chemistry,1994,vol. 72,p. 1816 - 1819.
[18]Journal of the American Chemical Society,1989,vol. 111,p. 6729 - 6734.
[19]Tetrahedron Letters,2013,vol. 54,p. 2151 - 2155.
[20]Synthesis,1997,p. 121 - 128.
[21]Patent: WO2013/19548,2013,A1 .Location in patent: Page/Page column 88.
[22]Bulletin of the Polish Academy of Sciences: Chemistry,1984,vol. 32,p. 85 - 95.
[23]Synthetic Communications,1998,vol. 28,p. 239 - 249.
[24]Journal of Organic Chemistry,1998,vol. 63,p. 2968 - 2974.
[25]Synthetic Communications,2006,vol. 36,p. 3461 - 3471.
[26]Organic Letters,2000,vol. 2,p. 2479 - 2481.
[27]Synthesis,2006,p. 2951 - 2970.
[28]Synthesis,2008,p. 3465 - 3472.
  • 21
  • [ 6214-35-3 ]
  • [ 498-66-8 ]
  • bicyclo<2.2.1>heptane-exo,exo-2,3-diylbis<(E/Z)-acrylic acid> [ No CAS ]
  • 22
  • [ 6214-35-3 ]
  • [ 7486-35-3 ]
  • [ 29739-67-1 ]
  • 23
  • [ 6214-35-3 ]
  • [ 166986-35-2 ]
  • (2Z,4E)-7,7-diethoxyhepta-2,4-dienoic acid [ No CAS ]
  • 24
  • [ 6214-35-3 ]
  • C7H11BrZn [ No CAS ]
  • [ 175288-15-0 ]
  • 25
  • [ 6214-35-3 ]
  • C4H5BrOZn [ No CAS ]
  • (Z)-6-methoxyhex-2-en-4-ynoic acid [ No CAS ]
  • 26
  • [ 6214-35-3 ]
  • zinc bromide trimethylsilylacetylide [ No CAS ]
  • [ 175288-16-1 ]
  • 27
  • [ 6214-35-3 ]
  • [ 92081-13-5 ]
  • [ 68676-77-7 ]
  • 28
  • [ 6214-35-3 ]
  • [ 23895-60-5 ]
  • [ 177905-30-5 ]
  • [ 177905-25-8 ]
  • 29
  • [ 6214-35-3 ]
  • [ 536-74-3 ]
  • [ 35304-86-0 ]
  • (E)-4-[5-Oxo-5H-furan-(2Z)-ylidene]-4-phenyl-but-2-enoic acid [ No CAS ]
  • 30
  • [ 6214-35-3 ]
  • [ 185198-21-4 ]
  • [ 208336-74-7 ]
  • 31
  • [ 6214-35-3 ]
  • [ 208336-86-1 ]
  • [ 208336-87-2 ]
  • 32
  • [ 5664-20-0 ]
  • [ 6214-35-3 ]
  • 5-Cyclohexylidene-5,6-dihydro-pyran-2-one [ No CAS ]
  • 5-Methylene-1-oxa-spiro[5.5]undec-3-en-2-one [ No CAS ]
  • 33
  • [ 6214-35-3 ]
  • [ 13169-00-1 ]
  • 6-Methoxy-5-methylene-5,6-dihydro-pyran-2-one [ No CAS ]
  • 34
  • [ 6214-35-3 ]
  • [ 56956-46-8 ]
  • 5-Methylene-6-octyl-5,6-dihydro-pyran-2-one [ No CAS ]
  • 5-Non-(E)-ylidene-5,6-dihydro-pyran-2-one [ No CAS ]
  • 35
  • [ 471-25-0 ]
  • [ 6214-35-3 ]
  • [ 6372-02-7 ]
 

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Technical Information

Categories

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[ 6214-35-3 ]

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