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[ CAS No. 1527-89-5 ]

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Chemical Structure| 1527-89-5
Chemical Structure| 1527-89-5
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CAS No. :1527-89-5 MDL No. :MFCD00001801
Formula : C8H7NO Boiling Point : 233.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :133.15 g/mol Pubchem ID :73712
Synonyms :

Safety of [ 1527-89-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1527-89-5 ]

  • Upstream synthesis route of [ 1527-89-5 ]
  • Downstream synthetic route of [ 1527-89-5 ]

[ 1527-89-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 1527-89-5 ]
  • [ 925-90-6 ]
  • [ 37951-49-8 ]
YieldReaction ConditionsOperation in experiment
99% With ammonium chloride In tetrahydrofuran; diethyl ether; water EXAMPLE 27
(R)-N-(2-(3-(3-Methoxyphenyl)-3-(2-methylphenyl)-2-propen-1-yloxy)ethyl)-3-piperidinecarboxylic acid hydrochloride
A solution of ethyl magnesium bromide in diethyl ether (58 ml, 3 M) was added dropwise at room temperature to a mixture of 3-methoxy benzonitrile (21.2 g, 0.159 mol) and dry THF (250 ml).
When addition was complete the mixture was stirred for 1 h at room temperature, 3 h at 40° C. and finally stirred overnight at room temperature.
Water (250 ml) was added followed by a saturated ammonium chloride solution (250 ml) and the mixture was stirred for 1 h at room temperature.
The phases were separated and the aqueous phase was extracted with ethyl acetate (100 ml).
The combined organic phases was dried over magnesium sulphate and the solvent evaporated in vacuo to give 25.9 g (99percent) of 3'-methoxypropiophenone.
99% With ammonium chloride In tetrahydrofuran; diethyl ether; water Example 30
(R)-N-(2-(3-(3-Methoxyphenyl)-3-(2-methylphenyl)-2-propen-1-yloxy)-ethyl)-3-piperidinecarboxylic acid hydrochloride
A solution of ethyl magnesium bromide in diethyl ether (58 ml, 3 M) was added dropwise at room temperature to a mixture of 3-methoxybenzonitrile (21.2 g, 0.159 mol) and dry THF (250 ml).
When addition was complete the mixture was stirred for 1 h at room temperature, 3 h at 40° C. and finally stirred overnight at room temperature.
Water (250 ml) was added followed by a saturated ammonium chloride solution (250 ml) and the mixture was stirred for 1 h at room temperature.
The phases were separated and the aqueous phase was extracted with ethyl acetate (100 ml).
The combined organic phases was dried (MgSO4) and the solvent evaporated in vacuo to give 25.9 g (99percent) of 3-methoxypropiophenone.
Reference: [1] Bulletin de la Societe Chimique de France, 1940, vol. <5> 7, p. 527,669
[2] Patent: US5198451, 1993, A,
[3] Patent: US6174898, 2001, B1,
  • 2
  • [ 1527-89-5 ]
  • [ 37951-49-8 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 18, p. 2226 - 2230
  • 3
  • [ 1527-89-5 ]
  • [ 5071-96-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 47, p. 14653 - 14657[2] Angew. Chem., 2016, vol. 128, # 47, p. 14873 - 14877,5
[3] Small, 2018, vol. 14, # 37,
[4] Tetrahedron, 2002, vol. 58, # 11, p. 2211 - 2213
[5] Tetrahedron, 1991, vol. 47, # 40, p. 8587 - 8600
[6] Journal of the American Chemical Society, 1927, vol. 49, p. 2908
[7] Journal of the American Chemical Society, 2017, vol. 139, # 38, p. 13554 - 13561
[8] Chemical Science, 2018, vol. 9, # 45, p. 8553 - 8560
  • 4
  • [ 1527-89-5 ]
  • [ 873-62-1 ]
YieldReaction ConditionsOperation in experiment
90% at 105℃; for 6.5 h; General procedure: To a stirred solution of aryl methyl ether (20 mmol) and 47percent aqueous HBr (4.5 mmol equiv. of substrate) added Aliquat-336 (10 wt. percent of substrate) in a single lot. The resulting reaction mixture was heated at 105±5 °C, and the progress of reaction was monitored by TLC. After completion of reaction, the reaction mixture was cooled to room temperature and quenched by adding water (25 ml). The resulting reaction mass was extracted with 3x30 ml ethyl acetate. Ethyl acetate layer washed twice with 20 ml of water, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using ethyl acetate/hexane system.
Reference: [1] Synthetic Communications, 2013, vol. 43, # 24, p. 3272 - 3280
[2] Tetrahedron Letters, 2004, vol. 45, # 19, p. 3729 - 3732
[3] Synthetic Communications, 2011, vol. 41, # 12, p. 1852 - 1857
[4] Journal of Organic Chemistry, 1999, vol. 64, # 26, p. 9719 - 9721
  • 5
  • [ 1527-89-5 ]
  • [ 873-62-1 ]
  • [ 100-66-3 ]
Reference: [1] Journal of the American Chemical Society, 1984, vol. 106, # 10, p. 2799 - 2805
  • 6
  • [ 1527-89-5 ]
  • [ 26113-44-0 ]
Reference: [1] Journal of the Chemical Society, 1946, p. 362,365
  • 7
  • [ 1527-89-5 ]
  • [ 145091-60-7 ]
  • [ 35461-93-9 ]
Reference: [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 9, p. 1641 - 1645
  • 8
  • [ 1527-89-5 ]
  • [ 177476-76-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 6, p. 1187 - 1202
  • 9
  • [ 5419-55-6 ]
  • [ 1527-89-5 ]
  • [ 126-30-7 ]
  • [ 883898-97-3 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 6, p. 2518 - 2520
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