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[ CAS No. 7686-77-3 ]

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type HazMat fee
Excepted Quantity Free
Inaccessible (Haz class 6.1), Domestic USD 41.00
Inaccessible (Haz class 6.1), International USD 64.00
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 83.00
Accessible (Haz class 3, 4, 5 or 8), International USD 133.00
Chemical Structure| 7686-77-3
Chemical Structure| 7686-77-3
Structure of 7686-77-3 * Storage: {[proInfo.prStorage]}

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Product Details of [ 7686-77-3 ]

CAS No. :7686-77-3 MDL No. :MFCD00101764
Formula : C6H8O2 Boiling Point : 227.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :112.13 g/mol Pubchem ID :853756
Synonyms :

Safety of [ 7686-77-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405 UN#:3265
Hazard Statements:H314-H290 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7686-77-3 ]

  • Upstream synthesis route of [ 7686-77-3 ]
  • Downstream synthetic route of [ 7686-77-3 ]

[ 7686-77-3 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 84646-68-4 ]
  • [ 7686-77-3 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 4, p. 940 - 943
[2] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 2, p. 451 - 452
[3] ChemMedChem, 2011, vol. 6, # 9, p. 1559 - 1565
  • 2
  • [ 99-67-2 ]
  • [ 7686-77-3 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2542 - 2553
  • 3
  • [ 88326-51-6 ]
  • [ 7686-77-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 2, p. 451 - 452
[2] ChemMedChem, 2011, vol. 6, # 9, p. 1559 - 1565
[3] Organic Syntheses, 1998, vol. 75, p. 195 - 195
[4] Journal of Organic Chemistry, 1962, vol. 27, p. 2395 - 2398
[5] Journal of Organic Chemistry, 1984, vol. 49, # 5, p. 928 - 931
[6] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2784 - 2794
[7] Organic Letters, 2006, vol. 8, # 26, p. 5947 - 5950
  • 4
  • [ 7686-78-4 ]
  • [ 7686-77-3 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 3, p. 907 - 909
[2] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2784 - 2794
  • 5
  • [ 21622-00-4 ]
  • [ 7686-77-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2784 - 2794
  • 6
  • [ 124-38-9 ]
  • [ 1781-66-4 ]
  • [ 7686-77-3 ]
Reference: [1] Tetrahedron, 1965, vol. 21, p. 25 - 30
[2] Journal of Organic Chemistry, 1989, vol. 54, # 2, p. 383 - 389
  • 7
  • [ 3195-24-2 ]
  • [ 7686-77-3 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2542 - 2553
  • 8
  • [ 4372-31-0 ]
  • [ 7686-77-3 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2542 - 2553
  • 9
  • [ 4492-41-5 ]
  • [ 7686-77-3 ]
Reference: [1] Journal of Organic Chemistry, 1969, vol. 34, # 4, p. 860 - 864
  • 10
  • [ 14320-38-8 ]
  • [ 7686-77-3 ]
Reference: [1] Journal of Organic Chemistry, 1969, vol. 34, # 4, p. 860 - 864
  • 11
  • [ 67886-24-2 ]
  • [ 74-88-4 ]
  • [ 7686-77-3 ]
  • [ 6240-43-3 ]
  • [ 4541-43-9 ]
Reference: [1] Synthesis, 1991, # 5, p. 395 - 398
  • 12
  • [ 67-56-1 ]
  • [ 7686-77-3 ]
  • [ 58101-60-3 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃; for 4 h;
To a solution of 1.1 (10 g, 89 mmol) in DCM (100 mL) at 0° C. under N2 atmosphere was added 1,1-carbonyldiimidazole (43 g, 267 mmol). The mixture was stirred at room temperature for 4 hours, then MeOH (100 mL) was added. The mixture was allowed to stir overnight. The solvent was evaporated at low temperature to afford 2 (11.2 g, 99percent).
Reference: [1] Patent: US2007/254952, 2007, A1, . Location in patent: Page/Page column 35
[2] Nucleosides, Nucleotides and Nucleic Acids, 2001, vol. 20, # 4-7, p. 661 - 664
[3] ChemMedChem, 2011, vol. 6, # 9, p. 1559 - 1565
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5336 - 5339
  • 13
  • [ 7686-77-3 ]
  • [ 74-88-4 ]
  • [ 58101-60-3 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16 h; To a solution of 3-cyclopentene-1-carboxylic acid (Org. Synth. 75, PL95-200, 1998) (31.5 g, 281 mmol) in anhydrous N, N-DIMETHYLFORMAMIDE (300 mL), under an atmosphere of nitrogen, was added potassium carbonate (97 g, 703 mmol), and iodomethane (35 mL, 563 mmol). The resulting mixture was stirred at room temperature for 16 hours, then poured into water (1 litre), and extracted with diethyl ether (3 x 400 mL). The combined diethyl ether layers were washed with water (3 x 500 mL), saturated NACL (200 mL), dried over MGS04, filtered and concentrated I71 VACUO, to give 34 g (96 percent) of crude product. H NMR (CDC13, 500 MHz) : 8 5.64 (s, 2H), 3.68 (s, 3H), 3.11 (quintet, J = 8.5 Hz, 1H), 2.63 (d, J = 8.3 Hz, 4 H).
96% With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16 h; To a solution of 3-CYCLOPENTENE-1-CARBOXYLIC acid (Org. Synth. 75, PL95-200, 1998) (31.5 g, 281 mmol) in anhydrous N, N-DIMETHYLFORMAMIDE (300 mL), under an atmosphere of nitrogen, was added potassium carbonate (97 g, 710 MMOL), and iodomethane (35 mL, 560 mmol). The resulting mixture was stirred at room temperature for 16 h, then poured into water (1 L), and extracted with diethyl ether (3 x 400 mL). The combined diethyl ether layers were washed with water (3 x 500 mL), saturated NACI (200 ML), dried over MGS04, filtered and concentrated in vacuo, to give 34 g (96 percent). 'H NMR (CDCL3, 500 MHz) : 8 5.64 (s, 2H), 3.68 (s, 3H), 3.11 (quintet, J = 8.5 Hz, 1H), 2.63 (d, J = 8.3 Hz, 4 H).
96% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16 h; INTERMEDIATE 21; Step A; To a solution of 3-cyclopentene-1-carboxylic acid (Org. Synth. 75, p195-200, 1998) (31.5 g, 281 mmol) in anhydrous N,N-dimethylformamide (300 mL), under an atmosphere of nitrogen, was added potassium carbonate (97 g, 710 mmol), and iodomethane (35 mL, 560 mmol). The resulting mixture was stirred at room temperature for 16 h, then poured into water (1 L), and extracted with diethyl ether (3.x.400 mL). The combined diethyl ether layers were washed with water (3.x.500 mL), saturated NaCl (200 mL), dried over MgSO4, filtered and concentrated in vacuo, to give 34 g (96percent).1H NMR (CDCl3, 500 MHz): δ 5.64 (s, 2H), 3.68 (s, 3H), 3.11 (quintet, J=8.5 Hz, 1H), 2.63 (d, J=8.3 Hz, 4H).
Reference: [1] Patent: WO2004/41777, 2004, A2, . Location in patent: Page 41-42
[2] Patent: WO2004/94371, 2004, A2, . Location in patent: Page 81-82
[3] Patent: US2008/81803, 2008, A1, . Location in patent: Page/Page column 35
[4] Chemical Communications, 2013, vol. 49, # 100, p. 11758 - 11760
  • 14
  • [ 7686-77-3 ]
  • [ 58101-60-3 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 22, p. 3197 - 3204
  • 15
  • [ 7686-77-3 ]
  • [ 25125-21-7 ]
YieldReaction ConditionsOperation in experiment
85% With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 7 h; (a) cyclopent-3-enylmethanol (0164) (0165) To a suspension of lithium aluminum hydride (0.5083 g, 13.37 mmol, 3eq) in dry 100 ml THF at −78° C., cyclopent-3-enecarboxylic acid (0.5000 g, 4.45 mmol) was added drop wise over 1 h. The mixture was stirred for 6 h, and then quenched with 15 ml 1M NaOH. Mixture was stirred for an additional 2 h, then concentrated and up taken in diethyl ether and dried over MgSO4 to afford clear liquid (3.79 mmol, MW 98.14 g/mol, 85percent).1H NMR (300 MHz, CDCl3): δ 2.12-2.16; (ttt 1H), 2.49-2.53; (dd, 2H), 3.57-3.58 (d, 3H, 5.14 Hz), 5.69; (s, 2H).
Reference: [1] Tetrahedron, 2003, vol. 59, # 5, p. 671 - 676
[2] Journal of the American Chemical Society, 1982, vol. 104, p. 7105
[3] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 14, p. 2175 - 2178
[4] European Journal of Organic Chemistry, 2004, # 2, p. 289 - 303
[5] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 2, p. 451 - 452
[6] Journal of Organic Chemistry, 1989, vol. 54, # 2, p. 383 - 389
[7] Chemical Communications, 2013, vol. 49, # 100, p. 11758 - 11760
[8] Patent: US2016/206748, 2016, A1, . Location in patent: Paragraph 0164-0165
[9] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 9, p. 2784 - 2794
[10] Canadian Journal of Chemistry, 1968, vol. 46, p. 3758 - 3762
[11] Journal of Organic Chemistry, 1969, vol. 34, # 4, p. 860 - 864
[12] Journal of Organic Chemistry, 1970, vol. 35, # 8, p. 2803 - 2806
[13] Tetrahedron: Asymmetry, 1994, vol. 5, # 3, p. 337 - 338
[14] Journal of the American Chemical Society, 1982, vol. 104, # 3, p. 907 - 909
[15] Organic Letters, 2006, vol. 8, # 26, p. 5947 - 5950
[16] Synlett, 2006, # 10, p. 1583 - 1585
[17] Organic Letters, 2008, vol. 10, # 2, p. 169 - 171
[18] Patent: WO2003/99795, 2003, A1, . Location in patent: Page 58
[19] Patent: WO2003/99289, 2003, A2, . Location in patent: Page 63
[20] Patent: WO2010/62415, 2010, A1, . Location in patent: Page/Page column 22
[21] Patent: EP2433926, 2012, A1, . Location in patent: Paragraph 0078; 0080
[22] Patent: WO2012/31307, 2012, A1, . Location in patent: Page/Page column 21
[23] Patent: WO2016/106623, 2016, A1, . Location in patent: Page/Page column 115
[24] Patent: WO2016/106624, 2016, A1, . Location in patent: Page/Page column 78-79
  • 16
  • [ 7686-77-3 ]
  • [ 193751-54-1 ]
Reference: [1] Patent: US5998398, 1999, A,
  • 17
  • [ 7686-77-3 ]
  • [ 75-65-0 ]
  • [ 193751-54-1 ]
Reference: [1] Patent: US2004/87601, 2004, A1, . Location in patent: Page 14
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