Home Cart 0 Sign in  

[ CAS No. 29558-77-8 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 29558-77-8
Chemical Structure| 29558-77-8
Structure of 29558-77-8 *Storage: {[proInfo.prStorage]}

Quality Control of [ 29558-77-8 ]

Related Doc. of [ 29558-77-8 ]

SDS
Alternatived Products of [ 29558-77-8 ]
Alternatived Products of [ 29558-77-8 ]

Product Details of [ 29558-77-8 ]

CAS No. :29558-77-8MDL No. :MFCD00059076
Formula : C12H9BrO Boiling Point : 355.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :249.10Pubchem ID :95093
Synonyms :

Computed Properties of [ 29558-77-8 ]

TPSA : 20.2 H-Bond Acceptor Count : 1
XLogP3 : - H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 1

Safety of [ 29558-77-8 ]

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

Application In Synthesis of [ 29558-77-8 ]

  • Upstream synthesis route of [ 29558-77-8 ]
  • Downstream synthetic route of [ 29558-77-8 ]

[ 29558-77-8 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 58743-83-2 ]
  • [ 29558-77-8 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 17, p. 4289 - 4300
[2] RSC Advances, 2016, vol. 6, # 97, p. 95137 - 95148
  • 2
  • [ 92-66-0 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Nature, 2013, vol. 499, # 7457, p. 192 - 196
  • 3
  • [ 589-87-7 ]
  • [ 108-95-2 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 12, p. 3571 - 3574
  • 4
  • [ 106-37-6 ]
  • [ 71597-85-8 ]
  • [ 29558-77-8 ]
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 68, p. 192 - 202
  • 5
  • [ 84244-98-4 ]
  • [ 29558-77-8 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 131, p. 1 - 8
  • 6
  • [ 148-86-7 ]
  • [ 29558-77-8 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 131, p. 1 - 8
  • 7
  • [ 92-69-3 ]
  • [ 29558-77-8 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
[2] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23
  • 8
  • [ 696-62-8 ]
  • [ 29558-77-8 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 97, p. 95137 - 95148
  • 9
  • [ 5467-74-3 ]
  • [ 29558-77-8 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 97, p. 95137 - 95148
  • 10
  • [ 94375-26-5 ]
  • [ 29558-77-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23
  • 11
  • [ 2170-13-0 ]
  • [ 29558-77-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23
  • 12
  • [ 95-56-7 ]
  • [ 29558-77-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 270
  • 13
  • [ 540-38-5 ]
  • [ 5467-74-3 ]
  • [ 29558-77-8 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 5, p. 2450 - 2461
  • 14
  • [ 17333-82-3 ]
  • [ 108-95-2 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 270
  • 15
  • [ 145014-14-8 ]
  • [ 29558-77-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1943, vol. 62, p. 12,14
  • 16
  • [ 3185-74-8 ]
  • [ 29558-77-8 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1943, vol. 62, p. 12,14
  • 17
  • [ 3365-82-0 ]
  • [ 29558-77-8 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 1131
[2] Gazzetta Chimica Italiana, 1928, vol. 58, p. 634
  • 18
  • [ 29558-77-8 ]
  • [ 725-14-4 ]
Reference: [1] Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 131, p. 1 - 8
  • 19
  • [ 92-66-0 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Nature, 2013, vol. 499, # 7457, p. 192 - 196
  • 20
  • [ 589-87-7 ]
  • [ 108-95-2 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 12, p. 3571 - 3574
  • 21
  • [ 17333-82-3 ]
  • [ 108-95-2 ]
  • [ 29558-77-8 ]
  • [ 21849-89-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 270
  • 22
  • [ 110-53-2 ]
  • [ 29558-77-8 ]
  • [ 63619-51-2 ]
YieldReaction ConditionsOperation in experiment
95.9% With potassium carbonate In butanone for 8 h; Reflux General procedure: A suspension of 4-bromo-4'-hydroxybiphenyl (13) (3.5 g, 14.11 mmol), 1-bromoheptane (3.75 g, 21.05 mmol) and K2CO3 (4.9 g, 35.28 mmol) in 2-butanone (25 mL) was refluxed for 8 h. After cooling, the reaction mixture was diluted by CH2Cl2 (50 mL). After filtration, the organic layer was washed by H2O (50 mL) and saturated brine (50 mL), dried over anhydrous Na2SO4, and filtrated. The solvent was condensed to 15 mL under reduced pressure, and the residue was collected and washed by cool hexane (0 °C) to afford 14c (4.6 g, yield 94.3percent) as white solid.
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 196 - 208
[2] Chemistry Letters, 2010, vol. 39, # 5, p. 513 - 515
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1474 - 1477
[4] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
[5] Patent: US5948753, 1999, A,
[6] Patent: US5514651, 1996, A,
[7] Patent: US5516756, 1996, A,
[8] Patent: US5646245, 1997, A,
[9] Patent: US5741775, 1998, A,
[10] Patent: US5854213, 1998, A,
[11] Patent: US6268338, 2001, B1,
  • 23
  • [ 628-17-1 ]
  • [ 29558-77-8 ]
  • [ 63619-51-2 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydroxide; tetrabutylammomium bromide In water Alternative Preparation of 4-bromo-4'-pentyloxybiphenyl 1(a):
4-Bromo-4'-hydroxybiphenyl (12.5 g, 50.2 mmol) was added to a solution of NaOH (2.28 g, 97percent pure, 55.2 mmol) in deionized H2O (150 ml), followed by the addition of 1-iodopentane (11.9 g, 60.2 mmol) and tetrabutylammonium bromide (0.82 g, 2.5 mmol).
The mixture was stirred at 90° C. for 3.75 h until the solids went into solution.
Then, as the reaction proceeded, the desired product began to precipitate.
The mixture was slowly cooled and then filtered to provide a solid which was washed with deionized water until the pH of the filtrate was neutral and then dried for 16 h in a vacuum oven at 30° C. Yield: 15.41 g (96percent) of 5a. Rf 0.5 (97:3 hexanes/EtOAc).
1H NMR: δ 0.93 (t, 3H, J=6.9 Hz); 1.41 (m, 4H); 1.79 (m, 2H); 3.97 (t, 2H, J=6.6 Hz); 6.98 (m, 2H); 7.23 (m,6H).
13C NMR: δ 14.03; 22.43; 28.22; 28.98; 68.12; 114.91; 120.71; 127.93; 128.27; 131.77; 132.24; 139.82; 159.03. MS(FAB+): m/z 320. IR(CHCl3): 2960, 2936, 2874, 1608, 1518, 1485, 1475 cm-1 Analysis for C17H19BrO: Calcd: C, 63.96; H. 6.00; Br, 25.0; Found: C, 64.10; H. 5.97; Br, 25.28.
96% With sodium hydroxide; tetrabutylammomium bromide In water Alternative Preparation of 4-bromo-4'-pentyloxybiphenyl 1(a):
4-Bromo-4'-hydroxybiphenyl (12.5 g, 50.2 mmol) was added to a solution of NaOH (2.28 g, 97percent pure, 55.2 mmol) in deionized H2O (150 ml), followed by the addition of 1-iodopentane (11.9 g, 60.2 mmol) and tetrabutylammonium bromide (0.82 g, 2.51 mmol).
The mixture was stirred at 90° C. for 3.75 h until the solids went into solution.
Then, as the reaction proceeded, the desired product began to precipitate.
The mixture was slowly cooled and then filtered to provide a solid which was washed with deionized water until the pH of the filtrate was neutral and then dried for 16 h in a vacuum oven at 30° C. Yield: 15.41 g (96percent) of 5a. Rf 0.5 (97:3 hexanes/EtOAc).
1H NMR: δ0.93 (t, 3H, J=6.9 Hz); 1.41 (m, 4H); 1.79 (m, 2H); 3.97 (t, 2H, J=6.6 Hz); 6.98 (m, 2H); 7.23 (m, 6H).
13C NMR: δ14.03; 22.43; 28.22; 28.98; 68.12; 114.91; 120.71; 127.93; 128.27; 131.77; 132.24; 139.82; 159.03. MS(FAB+): m/z 320. IR(CHC13): 2960, 2936, 2874, 1608, 1518, 1485, 1475 cm-1.
Analysis for C17H19BrO: Calcd: C, 63.96; H. 6.00; Br, 25.0; Found: C, 64.10; H. 5.97; Br, 25.28.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 489 - 493
[2] Patent: US2003/54981, 2003, A1,
[3] Patent: US2002/151474, 2002, A1,
[4] Patent: US2002/160942, 2002, A1,
[5] Patent: EP906915, 1999, A1,
  • 24
  • [ 628-17-1 ]
  • [ 29558-77-8 ]
  • [ 78-93-3 ]
  • [ 63619-51-2 ]
Reference: [1] Patent: US2002/151474, 2002, A1,
[2] Patent: US2002/160942, 2002, A1,
[3] Patent: EP906915, 1999, A1,
  • 25
  • [ 29558-77-8 ]
  • [ 158938-08-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 489 - 493
[2] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 196 - 208
  • 26
  • [ 29558-77-8 ]
  • [ 496868-77-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4931 - 4946
[2] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 909 - 912
[3] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259
  • 27
  • [ 29558-77-8 ]
  • [ 158937-25-8 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158
[2] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 196 - 208
Historical Records