[ CAS No. 42933-43-7 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 42933-43-7
Chemical Structure| 42933-43-7
Structure of 42933-43-7

Quality Control of [ 42933-43-7 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 42933-43-7 ]

SDS

Product Details of [ 42933-43-7 ]

CAS No. :42933-43-7MDL No. :MFCD03617969
Formula :C8H9NOBoiling Point :289.4°C at 760 mmHg
Linear Structure Formula :-InChI Key :YJMADHMYUJFMQE-UHFFFAOYSA-N
M.W :135.16Pubchem ID :3841102
Synonyms :

Computed Properties of [ 42933-43-7 ]

TPSA : 35.2 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.25 Rotatable Bond Count : 0

Safety of [ 42933-43-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 42933-43-7 ]

  • Upstream synthesis route of [ 42933-43-7 ]
  • Downstream synthetic route of [ 42933-43-7 ]

[ 42933-43-7 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 17403-47-3 ]
  • [ 42933-43-7 ]
YieldReaction ConditionsOperation in experiment
97.2% With hydrogen In methanol at 20℃; Step 2: Preparation of 5-amino-2,3-dihydrobenzofuran [Show Image] The product (1 g, 6.1 mmol) obtained in Step 1, Raney Ni (0.1 g) and MeOH(10 mL) were used for hydrogenation at room temperature and hydrogen pressure of 50 PSI, until the reaction was finished. The catalyst was removed by filtration, the fitrate was concentrated under vacuum to obtain a product (800 mg, 97.2percent).
90% With palladium 10% on activated carbon; hydrogen In ethanol; water for 13.00 h; A mixture of 21 (6.3 g, 38.1 mmol) and 10percent palladium on carbon (1.0 g) in EtOH (50 mL) and THF (50 mL) was stirred under an atmosphere of H2 (1 atm) at room temperature for 13 h. The catalyst was removed by filtration, and then the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 with a gradient eluent of 0-10percent MeOH/EtOAc to provide 22 (4.63 g, 90percent) as a pale brown powder; 1H NMR (CDCl3) δ: 3.12 (2H, t, J = 8.6 Hz), 3.37 (2H, s), 4.49 (2H, t, J = 8.6 Hz), 6.43-6.47 (1H, m) 6.57-6.61 (2H, m); Anal. Calcd for C8H9NO: C, 71.09; H, 6.71; N, 10.36. Found: C, 70.92; H, 6.60; N, 10.09.
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 18, p. 6681 - 6698
[2] Patent: EP2532665, 2012, A1. Location in patent: Page/Page column 21
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6430 - 6446
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4161 - 4172
[6] Patent: WO2003/82787, 2003, A1. Location in patent: Page/Page column 139
[7] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
  • 2
  • [ 18761-31-4 ]
  • [ 42933-43-7 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogen In ethanol for 5.00 h; Preparation 101 ; 2, 3-Dihvdro-benzofuran-5-vlamine; The product of preparation 100 (5. 0g, 31mmol) and 10percent Pd/C (1.25g) was added to ethanol (100mL) and the mixture was stirred under 55psi of hydrogen gas for 5 hours. The reaction mixture was then filtered through Celite and the filtrate was concentrated in vacuo to afford the title product as a pale brown powder in 92percent yield. MS ES+ m/z 135 [M+]. m. p. 73-77°C
Reference: [1] Patent: WO2005/82866, 2005, A2. Location in patent: Page/Page column 97
[2] Patent: US2003/195201, 2003, A1
  • 3
  • [ 496-16-2 ]
  • [ 42933-43-7 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 12, p. 8162 - 8165
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6430 - 6446
[3] Patent: EP2532665, 2012, A1
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601
  • 4
  • [ 58546-89-7 ]
  • [ 42933-43-7 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 27, p. 4631 - 4634
  • 5
  • [ 496-16-2 ]
  • [ 42933-43-7 ]
  • [ 13414-56-7 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567
  • 6
  • [ 17403-47-3 ]
  • [ 42933-43-7 ]
Reference: [1] Patent: US3963717, 1976, A
  • 7
  • [ 7169-34-8 ]
  • [ 42933-43-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
  • 8
  • [ 17403-47-3 ]
  • [ 42933-43-7 ]
YieldReaction ConditionsOperation in experiment
97.2% With hydrogen In methanol at 20℃; Step 2: Preparation of 5-amino-2,3-dihydrobenzofuran [Show Image] The product (1 g, 6.1 mmol) obtained in Step 1, Raney Ni (0.1 g) and MeOH(10 mL) were used for hydrogenation at room temperature and hydrogen pressure of 50 PSI, until the reaction was finished. The catalyst was removed by filtration, the fitrate was concentrated under vacuum to obtain a product (800 mg, 97.2percent).
90% With palladium 10% on activated carbon; hydrogen In ethanol; water for 13.00 h; A mixture of 21 (6.3 g, 38.1 mmol) and 10percent palladium on carbon (1.0 g) in EtOH (50 mL) and THF (50 mL) was stirred under an atmosphere of H2 (1 atm) at room temperature for 13 h. The catalyst was removed by filtration, and then the filtrate was concentrated. The residue was purified by flash chromatography on SiO2 with a gradient eluent of 0-10percent MeOH/EtOAc to provide 22 (4.63 g, 90percent) as a pale brown powder; 1H NMR (CDCl3) δ: 3.12 (2H, t, J = 8.6 Hz), 3.37 (2H, s), 4.49 (2H, t, J = 8.6 Hz), 6.43-6.47 (1H, m) 6.57-6.61 (2H, m); Anal. Calcd for C8H9NO: C, 71.09; H, 6.71; N, 10.36. Found: C, 70.92; H, 6.60; N, 10.09.
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 18, p. 6681 - 6698
[2] Patent: EP2532665, 2012, A1. Location in patent: Page/Page column 21
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6430 - 6446
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601
[5] Journal of Medicinal Chemistry, 2009, vol. 52, # 14, p. 4161 - 4172
[6] Patent: WO2003/82787, 2003, A1. Location in patent: Page/Page column 139
[7] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
  • 9
  • [ 18761-31-4 ]
  • [ 42933-43-7 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogen In ethanol for 5.00 h; Preparation 101 ; 2, 3-Dihvdro-benzofuran-5-vlamine; The product of preparation 100 (5. 0g, 31mmol) and 10percent Pd/C (1.25g) was added to ethanol (100mL) and the mixture was stirred under 55psi of hydrogen gas for 5 hours. The reaction mixture was then filtered through Celite and the filtrate was concentrated in vacuo to afford the title product as a pale brown powder in 92percent yield. MS ES+ m/z 135 [M+]. m. p. 73-77°C
Reference: [1] Patent: WO2005/82866, 2005, A2. Location in patent: Page/Page column 97
[2] Patent: US2003/195201, 2003, A1
  • 10
  • [ 496-16-2 ]
  • [ 42933-43-7 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 12, p. 8162 - 8165
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6430 - 6446
[3] Patent: EP2532665, 2012, A1
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5579 - 5601
  • 11
  • [ 58546-89-7 ]
  • [ 42933-43-7 ]
Reference: [1] Tetrahedron Letters, 1996, vol. 37, # 27, p. 4631 - 4634
  • 12
  • [ 496-16-2 ]
  • [ 42933-43-7 ]
  • [ 13414-56-7 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567
  • 13
  • [ 17403-47-3 ]
  • [ 42933-43-7 ]
Reference: [1] Patent: US3963717, 1976, A
  • 14
  • [ 7169-34-8 ]
  • [ 42933-43-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 13, p. 3821 - 3830
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