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Chemistry
Organic Building Blocks
Aryls
biphenyl
3-Bromo-[1,1'-biphenyl]-4-ol
Chemistry
Organic Building Blocks
Aryls
Bromides Phenols Benzene Compounds
biphenyl

[ CAS No. 92-03-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 92-03-5
Chemical Structure| 92-03-5
Chemical Structure| 92-03-5
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Product Details of [ 92-03-5 ]

CAS No. :92-03-5 MDL No. :MFCD00053297
Formula : C12H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :DZGMMVYPLBTLRQ-UHFFFAOYSA-N
M.W : 249.10 Pubchem ID :27297
Synonyms :

Safety of [ 92-03-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 92-03-5 ]

* 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 [ 92-03-5 ]

[ 92-03-5 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 111-24-0 ]
  • [ 92-03-5 ]
  • 1-[5-(3-bromo-biphenyl-4-yloxy)-pentyl]-piperidine [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5398
  • 2
  • [ 64-67-5 ]
  • [ 92-03-5 ]
  • [ 872810-55-4 ]
Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 1514
  • 3
  • [ 629-03-8 ]
  • [ 92-03-5 ]
  • 1-[6-(3-bromo-biphenyl-4-yloxy)-hexyl]-piperidine [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 5398
  • 4
  • [ 92-69-3 ]
  • [ 92-03-5 ]
YieldReaction ConditionsOperation in experiment
With bromine; acetic acid; at 0℃; for 0.5h; The synthesis of compound 1a was examplified. A solution of phenol (1.00 g, 10.63 mmol) and Br2 (0.49 mL, 9.56 mmol) in AcOH (7 mL) was stirred for 30 min at 0 C, the reaction mixture was poured into a separatory funnel with ice water (10 mL) and the aqueous phase was extracted with DCM (3 × 15 mL). The combined organic extracts were washed with saturated NaCl (aq) and dried over MgSO4 and concentrated under reduced pressure. The crude product was dissolved in THF (15 mL) and added to HMDS (2.44 mL, 11.69 mmol) for reflux at 70 C for 2 h. The solvent was evaporated under reduced pressure and the crude product was dissolved in THF (15 mL). Finally, the solution was cooled to -78 C and n-BuLi (5.53 mL, 2.5 M, 13.82 mmol) was added dropwise and stirred for 1 h. Tf2O (1.97 mL, 11.69 mmol) was added dropwise and was stirred for 1.5 h. Cold saturated aqueous NaHCO3 (20 mL) was added after separation, and the aqueous layer was extracted with Et2O. The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give 1a. The remaining compounds 1b-1m (structures showed in Figure 1) were obtained by the same synthetic route.
Reference： [1]Organic Letters,2019,vol. 21,p. 345 - 349
[2]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
[3]European Journal of Organic Chemistry,2001,p. 1563 - 1567
[4]Journal of the Chemical Society,1927,p. 1131
[5]Journal of the American Chemical Society,1939,vol. 61,p. 1447
[6]Russian Journal of Organic Chemistry,2008,vol. 44,p. 1384 - 1388
[7]Tetrahedron Letters,2011,vol. 52,p. 5149 - 5152
[8]Tetrahedron,2013,vol. 69,p. 1857 - 1871
[9]Tetrahedron Letters,2019,vol. 60,p. 1389 - 1392
  • 5
  • [ 92-03-5 ]
  • [ 92-05-7 ]
Reference： [1]Bulletin of the Chemical Society of Japan,1943,vol. 18,p. 93,96
  • 6
  • [ 92-03-5 ]
  • 3-bromo-5-iodobiphenyl-4-ol [ No CAS ]
Reference： [1]Tetrahedron,2013,vol. 69,p. 1857 - 1871
[2]Journal of the American Chemical Society,1945,vol. 67,p. 1416,1417
[3]Tetrahedron Letters,2011,vol. 52,p. 5149 - 5152
  • 7
  • [ 92-03-5 ]
  • [ 3282-30-2 ]
  • pivalic acid-(3-bromo-biphenyl-4-yl ester) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 140
  • 8
  • [ 92-03-5 ]
  • [ 108-24-7 ]
  • [ 7466-03-7 ]
Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 3037
  • 9
  • [ 92-03-5 ]
  • [ 98-88-4 ]
  • benzoic acid-(3-bromo-biphenyl-4-yl ester) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1447
  • 10
  • [ 50-00-0 ]
  • [ 92-03-5 ]
  • [ 109-89-7 ]
  • 3-bromo-5-diethylaminomethyl-biphenyl-4-ol [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 1894,1896
  • 11
  • [ 92-03-5 ]
  • [ 78-95-5 ]
  • (3-bromo-biphenyl-4-yloxy)-acetone [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 6304
  • 12
  • [ 92-03-5 ]
  • [ 79-04-9 ]
  • chloro-acetic acid-(3-bromo-biphenyl-4-yl ester) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1942,vol. 64,p. 2449
  • 13
  • [ 92-03-5 ]
  • [ 598-21-0 ]
  • bromo-acetic acid-(3-bromo-biphenyl-4-yl ester) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1943,vol. 65,p. 987
  • 14
  • [ 92-03-5 ]
  • [ 98-09-9 ]
  • benzenesulfonic acid-(3-bromo-biphenyl-4-yl ester) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1937,vol. 59,p. 1087
  • 15
  • [ 92-03-5 ]
  • [ 77-78-1 ]
  • [ 74447-73-7 ]
Reference： [1]European Journal of Organic Chemistry,2001,p. 1563 - 1567
[2]Patent: US1887757,1929,A
[3]Patent: US1832484,1928,A
  • 16
  • [ 109-65-9 ]
  • [ 92-03-5 ]
  • [ 6725-73-1 ]
Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 1139 - 1144
  • 17
  • [ 50-00-0 ]
  • [ 92-03-5 ]
  • [ 16396-76-2 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
[2]Russian Journal of Organic Chemistry,2008,vol. 44,p. 1384 - 1388
[3]Polish Journal of Chemistry,2009,vol. 83,p. 493 - 502
  • 18
  • [ 50-00-0 ]
  • [ 92-03-5 ]
  • [ 108816-98-4 ]
Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3200 - 3205
  • 19
  • [ 92-03-5 ]
  • [ 100-39-0 ]
  • [ 114250-18-9 ]
Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1437 - 1445
  • 20
  • [ 121767-83-7 ]
  • [ 92-69-3 ]
  • [ 92-03-5 ]
  • [ 121767-87-1 ]
Reference： [1]Synthesis,1988,p. 950 - 952
  • 21
  • [ 92-03-5 ]
  • [ 107-06-2 ]
  • [ 121767-83-7 ]
Reference： [1]Synthesis,1988,p. 950 - 952
  • 22
  • [ 3348-44-5 ]
  • [ 92-03-5 ]
  • C16H20N2OP(1-)*Li(1+) [ No CAS ]
Reference： [1]Journal of Organometallic Chemistry,2002,vol. 643-644,p. 237 - 246
  • 23
  • [ 98355-34-1 ]
  • [ 92-03-5 ]
Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 8090 - 8097
  • 24
  • [ 92-03-5 ]
  • [ 232618-88-1 ]
  • [ 887280-27-5 ]
Reference： [1]European Journal of Organic Chemistry,2006,p. 1499 - 1507
  • 25
  • 2-allyl benzyl ether [ No CAS ]
  • [ 557-40-4 ]
  • [ 92-03-5 ]
  • [ 106-95-6 ]
  • [ 1072073-80-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In 1,3,5-trimethyl-benzene; EXAMPLE 344 (+-)-[(5,7-diphenyl-2,3-dihydro-1-benzofuran-2-yl)methyl]amine Treatment of <strong>[92-03-5]3-bromo-4-hydroxybiphenyl</strong> (15.7 g, 63.0 mmol) with potassium carbonate (34.84 g, 252.0 mmol) and allyl bromide (9.15 g, 75.63 mmol), followed by refluxing the resultant allyl ether in mesitylene generally according to the procedure described for Intermediate 8 provided 3-allyl-5-bromobiphenyl-4-ol.
Reference： [1]Patent: US2005/261347,2005,A1
  • 26
  • [ 1450-14-2 ]
  • [ 92-03-5 ]
  • (2-bromo-4-phenyl)phenol trimethylsilyl ether [ No CAS ]
Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 409 - 412
  • 27
  • [ 92-03-5 ]
  • 2-bromo-4-hydroxy-4-phenylcyclohexa-2,5-dienone [ No CAS ]
Reference： [1]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 643 - 645
[2]Tetrahedron,2010,vol. 66,p. 5833 - 5840
[3]Tetrahedron Letters,2007,vol. 48,p. 409 - 412
  • 28
  • [ 92-03-5 ]
  • [ 141852-54-2 ]
Reference： [1]European Journal of Organic Chemistry,2001,p. 1563 - 1567
  • 29
  • [ 92-03-5 ]
  • [ 348625-60-5 ]
Reference： [1]European Journal of Organic Chemistry,2001,p. 1563 - 1567
  • 30
  • [ 92-03-5 ]
  • [ 348625-62-7 ]
Reference： [1]European Journal of Organic Chemistry,2001,p. 1563 - 1567
  • 31
  • [ 92-03-5 ]
  • [ 348625-61-6 ]
Reference： [1]European Journal of Organic Chemistry,2001,p. 1563 - 1567
  • 32
  • [ 92-03-5 ]
  • [ 56926-48-8 ]
Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1437 - 1445
  • 33
  • [ 92-03-5 ]
  • [ 114250-10-1 ]
Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1437 - 1445
  • 34
  • [ 92-03-5 ]
  • [ 114250-24-7 ]
Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1437 - 1445
  • 35
  • [ 92-03-5 ]
  • [ 114250-20-3 ]
Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1437 - 1445
  • 36
  • [ 92-03-5 ]
  • [ 114250-31-6 ]
Reference： [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1437 - 1445
  • 37
  • [ 92-03-5 ]
  • [ 108816-99-5 ]
Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3200 - 3205
  • 38
  • [ 92-03-5 ]
  • [ 108817-00-1 ]
Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3200 - 3205
  • 39
  • [ 92-03-5 ]
  • [ 108817-07-8 ]
Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3200 - 3205
  • 40
  • [ 92-03-5 ]
  • [ 108817-03-4 ]
Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3200 - 3205
  • 41
  • [ 92-03-5 ]
  • [ 108817-06-7 ]
Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3200 - 3205
  • 42
  • [ 92-03-5 ]
  • [ 108817-02-3 ]
Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3200 - 3205
  • 43
  • [ 92-03-5 ]
  • [ 108817-13-6 ]
Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3200 - 3205
  • 44
  • [ 92-03-5 ]
  • [ 108817-14-7 ]
Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 3200 - 3205
  • 45
  • [ 92-03-5 ]
  • [ 60705-63-7 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 46
  • [ 92-03-5 ]
  • [ 81535-85-5 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 47
  • [ 92-03-5 ]
  • [ 81535-86-6 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 48
  • [ 92-03-5 ]
  • [ 81535-87-7 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 49
  • [ 92-03-5 ]
  • [ 81535-88-8 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 50
  • [ 92-03-5 ]
  • [ 81535-93-5 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 51
  • [ 92-03-5 ]
  • [ 81535-89-9 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 52
  • [ 92-03-5 ]
  • [ 81535-92-4 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 53
  • [ 92-03-5 ]
  • [ 81535-90-2 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 54
  • [ 92-03-5 ]
  • [ 81535-91-3 ]
Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2708 - 2712
  • 55
  • [ 92-03-5 ]
  • [ 872810-56-5 ]
Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 1514
  • 56
  • [ 92-03-5 ]
  • ethyl-(3,5,4'-tribromo-biphenyl-4-yl)-ether [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 1514
  • 57
  • [ 92-03-5 ]
  • diethyl-[2-(3-bromo-5-iodo-biphenyl-4-yloxy)-ethyl]-amine [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 1416,1417
  • 58
  • [ 92-03-5 ]
  • [ 10393-15-4 ]
Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 1139 - 1144
  • 59
  • [ 92-03-5 ]
  • [ 10393-18-7 ]
Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 1139 - 1144
  • 60
  • [ 92-03-5 ]
  • [ 10393-21-2 ]
Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 1139 - 1144
  • 61
  • [ 92-03-5 ]
  • [ 20803-70-7 ]
Reference： [1]Journal of Medicinal Chemistry,1968,vol. 11,p. 1139 - 1144
  • 62
  • [ 92-03-5 ]
  • [ 57561-39-4 ]
  • [2-(3-bromobiphenyl-4-yloxy)ethyl]-methylcarbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stir a solution of 3-bromobiphenyl-4-ol (0.50 g, 2.00 mmol), 1,1'- (azodicarbonyl) dipiperidide (ADDP) (0.76 g, 3.00 mmol) and (2-hydroxyethyl)- methylcarbamic acid tert-butyl ester (0.53 g, 3.00 mmol) in toluene (20 mL) at room temperature. Next add tri-n-butylphosphine (747 µL, 3.00 mmol) portionwise via syringe. Stir at room temperature for 30 min amd heat at 80 C overnight. Dilute with diethyl ether and allow to cool to room temperature. Filter the white precipitate, concentrate the filtrate and purify (silica gel chromatography, eluting with 10: 90 to 50:50 ethyl acetate: hexanes) to give the title compound (0.54 g, 66%). ¹H NMR (300 MHz, CDC13) No. 1.51 (9H, s), 3.13 (3H, s), 3.71 (2H, t, J = 5.6 Hz), 4.22 (2H, t, J = 5 .6 Hz), 6.97 (1H, d, J = 8.6 Hz), 7.3 6-7.5 8 (6H, m), 7.83 (1H, d, J = 1.9 Hz) ; MS (ES): 306, 308
Reference： [1]Patent: WO2005/100301,2005,A1 .Location in patent: Page/Page column 72
  • 63
  • [ 92-03-5 ]
  • 3-bromo-5-methoxy-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
842 mg (80%) With methyl iodide; In N,N-dimethyl-formamide; mineral oil; EXAMPLE 14 STR106 To a stirred solution of 995 mg (4 mmole) of <strong>[92-03-5]3-bromo-4-hydroxybiphenyl</strong> in 10 mL sieve dried DMF at ambient temperature was added 173.3 mg (4.4 mmole) of 61.1% mineral oil dispersion of NaH. The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 10 minutes and 1.71 g (12 mmole) of neat MeI was added. The mixture was stirred further at ambient temperature for 0.5 hour. The mixture was poured onto ice-H2 O and extracted with Et2 O. The extract was washed with ice-H2 O (2x), and then saturated NaCl solution; dried over Na2 SO4, filtered, and evaporated. The residue was purified by silica gel chromatography with petroleum ether solvent to give 842 mg (80%) of 3-bromo-5-methoxybiphenyl; NMR (CDCl3) δ: 3.87 (s, OCH3), 7.07 (m, 2Ar--H), 7.48 (m, 6Ar--H).
842 mg (80%) With methyl iodide; In N,N-dimethyl-formamide; mineral oil; EXAMPLE 14 STR34 To a stirred solution of 995 mg (4 mmole) of <strong>[92-03-5]3-bromo-4-hydroxybiphenyl</strong> in 10 mL sieve dried DMF at ambient temperature was added 173.3 mg (4.4 mmole) of 61.1% mineral oil dipersion of NaH. The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 10 minutes and 1.71 g (12 mmole) of neat MeI was added. The mixture was stirred further at ambient temperature for 0.5 hour. The mixture was poured onto ice-H2 O and extracted with Et2 O. The extract was washed with ice-H2 O (2*), and then saturated NaCl solution; dried over Na2 SO4, filtered, and evaporated. The residue was purified by silica gel chromatography with petroleum ether solvent to give 842 mg (80%) of 3-bromo-5-methoxybiphenyl; NMR (CDCl3) δ: 3.87 (s, OCH3), 7.07 (m, 2Ar-H), 7.48 (m, 6Ar-H).
Reference： [1]Patent: US5011832,1991,A
[2]Patent: US5025006,1991,A
  • 64
  • [ 92-03-5 ]
  • [ 75-36-5 ]
  • [ 122927-29-1 ]
YieldReaction ConditionsOperation in experiment
aluminium trichloride; In carbon disulfide; ethanol; water; Step 1 3'-Bromo-4'-hydroxy-4-hydroxy-4-acetylbiphenyl ((V), n=1) A solution of <strong>[92-03-5]3-bromo-4-hydroxybiphenyl</strong> (124.5 g, m.p. 96 C.) in carbon disulfide (650 ml) was added over 15 minutes to aluminum chloride (135 g) on an iced water bath. The mixture was then gently boiled under reflux, followed by adding acetyl chloride (79 g) over 40 minutes, refluxing the mixture for further 5 hours, cooling in an ice bath, treating the reaction mixture with water (400 ml), distilling off carbon disulfide on a boiling water bath, collecting solid residue by suction and recrystallizing from ethanol to obtain 3'-bromo-4'-acetoxy-4-acetylbiphenyl (77 g, m.p. 100~100.5 C.).
Reference： [1]Patent: US4886622,1989,A
  • 65
  • [ 92-03-5 ]
  • [ 70-11-1 ]
  • [ 71024-69-6 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In acetone; Step A. A mixture of 137 g. (0.55 mole) of <strong>[92-03-5]2-bromo-4-phenylphenol</strong>, 109 g. (0.55 mole) of α-bromoacetophenone and 75 g. of sodium carbonate in 1.5 liters of acetone is heated at its reflux temperature for six days, filtered, then evaporated. The white residue is recrystallized from a benzene-hexane mixture to provide white needles of α-(2-bromo-4-phenylphenoxy)acetophenone, m.p. 93-95 C.
Reference： [1]Patent: US4153721,1979,A
  • 66
  • [ 92-03-5 ]
  • 3-bromobiphenyl-4-yl sulfamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In diethyl ether; hexane; Example 85 The procedure of Example 1 was repeated, except that 25 mg of 3-bromobiphenyl-4-ol was used in place of 2'-nitrobiphenyl-4-ol. The resulting crude product was purified by TLC (using a 1:1 mixture of diethyl ether and hexane as the developing solvent) to obtain 17 mg of 3-bromobiphenyl-4-yl sulfamate. 1H-NMR(CDCl3, δ): 7.30-7.80(8H, m). MS(m/z): 329(M++2), 327(M+), 249.
Reference： [1]Patent: EP1193250,2002,A1
  • 67
  • [ 201230-82-2 ]
  • [ 442158-18-1 ]
  • [ 92-03-5 ]
  • [ 1202754-29-7 ]
Reference： [1]Organic Letters,2010,vol. 12,p. 192 - 195
  • 68
  • [ 68820-12-2 ]
  • [ 201230-82-2 ]
  • [ 92-03-5 ]
  • 2-phenyl-10-tosyl-6,7,8,9,9a,10-hexahydrodibenzo[b,f][1,4]oxazepin-11(5aH)-one [ No CAS ]
Reference： [1]Organic Letters,2010,vol. 12,p. 192 - 195
  • 69
  • [ 92-03-5 ]
  • [ 132559-91-2 ]
  • [ 1259312-88-3 ]
Reference： [1]Dalton Transactions,2010,vol. 39,p. 10391 - 10400
  • 70
  • [ 92-03-5 ]
  • [ 132559-91-2 ]
  • [ 1259312-75-8 ]
Reference： [1]Dalton Transactions,2010,vol. 39,p. 10391 - 10400
  • 71
  • [ 1252036-60-4 ]
  • potassium phenyltrifluoborate [ No CAS ]
  • [ 92-03-5 ]
Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 4914 - 4920
  • 72
  • [ 92-03-5 ]
  • [ 1335094-12-6 ]
Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5149 - 5152
[2]Tetrahedron,2013,vol. 69,p. 1857 - 1871
  • 73
  • [ 92-03-5 ]
  • [ 1335094-31-9 ]
Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5149 - 5152
[2]Tetrahedron,2013,vol. 69,p. 1857 - 1871
  • 74
  • [ 5292-43-3 ]
  • [ 92-03-5 ]
  • [ 1240288-34-9 ]
Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7299 - 7317
  • 75
  • [ 92-03-5 ]
  • [ 1386320-13-3 ]
Reference： [1]Tetrahedron,2012,vol. 68,p. 6193 - 6197
  • 76
  • [ 92-03-5 ]
  • [ 1386320-08-6 ]
Reference： [1]Tetrahedron,2012,vol. 68,p. 6193 - 6197
  • 77
  • [ 92-03-5 ]
  • [ 1386320-09-7 ]
Reference： [1]Tetrahedron,2012,vol. 68,p. 6193 - 6197
  • 78
  • [ 92-03-5 ]
  • [ 1386320-11-1 ]
Reference： [1]Tetrahedron,2012,vol. 68,p. 6193 - 6197
  • 79
  • [ 92-03-5 ]
  • [ 7460-82-4 ]
  • [ 1386320-03-1 ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 18h; Precursory dibromides Ph2bBr and Ph3bBr (3-oxapentane-1,5-diyldioxy- and 3,6-dioxaoctane-1,8-diyldioxybis(2-bromo-4-phenylbenzene)s, respectively) were prepared from <strong>[92-03-5]2-bromo-4-phenylphenol</strong>22 with diethylene and triethylene glycol tosylates, respectively, according to the Williamson procedure (by using potassium carbonate as a base in N,N-dimethylformamide; 120 C, 18 h). Ph2bBr: yield, 76%. Mp 78-80 C. 1H NMR (500 MHz, CDCl3) δ 7.77 (d, J=2 Hz, 2H), 7.50 (d, J=9 Hz, 4H), 7.45 (dd, J=9 Hz, 2 Hz, 2H), 7.40 (t, J=9 Hz, 4H), 7.32 (t, J=9 Hz, 2H), 7.00 (d, J=9 Hz, 2H), 4.27 (t, J=5 Hz, 4H), 4.09 (t, J=5 Hz, 4H). 13C NMR (125.8 MHz, CDCl3) δ 154.8, 139.5, 135.6, 132.0, 128.9, 127.3, 127.0, 126.8, 114.0, 112.9, 70.2, 69.5.
Reference： [1]Tetrahedron,2012,vol. 68,p. 6193 - 6197
  • 80
  • [ 92-03-5 ]
  • [ 19249-03-7 ]
  • [ 1386320-05-3 ]
YieldReaction ConditionsOperation in experiment
86% With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 18h; Precursory dibromides Ph2bBr and Ph3bBr (3-oxapentane-1,5-diyldioxy- and 3,6-dioxaoctane-1,8-diyldioxybis(2-bromo-4-phenylbenzene)s, respectively) were prepared from <strong>[92-03-5]2-bromo-4-phenylphenol</strong>22 with diethylene and triethylene glycol tosylates, respectively, according to the Williamson procedure (by using potassium carbonate as a base in N,N-dimethylformamide; 120 C, 18 h). Ph3bBr: yield, 86%. Mp 82-83 C. 1H NMR (500 MHz, CDCl3) δ 7.77 (d, J=2 Hz, 2H), 7.50 (d, J=9 Hz, 4H), 7.44 (dd, J=9, 2 Hz, 2H), 7.40 (t, J=9 Hz, 4H), 7.32 (t, J=9 Hz, 2H), 6.97 (d, J=9 Hz, 2H), 4.23 (t, J=5 Hz, 4H), 3.96 (t, J=5 Hz, 4H), 3.85 (s, 4H). 13C NMR (125.8 MHz, CDCl3) δ 154.8, 139.4, 135.5, 132.0, 128.9, 127.3, 127.1, 126.8, 113.8, 112.8, 71.4, 69.7, 69.3.
Reference： [1]Tetrahedron,2012,vol. 68,p. 6193 - 6197
  • 81
  • [ 68820-12-2 ]
  • [ 92-03-5 ]
  • trans-4a,10a-8-phenyl-10-tosyl-2,3,4,4a,10,10a-hexahydro-1H-phenoxazine [ No CAS ]
Reference： [1]Tetrahedron,2012,vol. 68,p. 9090 - 9094
  • 82
  • [ 6329-78-8 ]
  • potassium phenyltrifluoborate [ No CAS ]
  • [ 92-52-4 ]
  • [ 92-03-5 ]
Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 463 - 476
  • 83
  • [ 92-03-5 ]
  • [ 98-80-6 ]
  • [ 6093-03-4 ]
Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 10598 - 10601
    Angew. Chem.,2013,vol. 125,p. 10792 - 10795,4
  • 84
  • [ 92-03-5 ]
  • [ 1620620-04-3 ]
  • (S)-3-((3-bromo-[1,1′-biphenyl]-4-yl)oxy)-2-((tert-butoxycarbonyl)amino)propanoic acid [ No CAS ]
Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 3211 - 3219
  • 85
  • [ 92-69-3 ]
  • [ 92-03-5 ]
  • [ 4400-05-9 ]
YieldReaction ConditionsOperation in experiment
89% General procedure: A solution of the starting material (~10 mmol) and pTsOH (10 mol %) in MeOH (1.0 mL per mmol starting material) was stirred for 10 min, then a solution of NBS (100 mol %; recrystallized from H2O) in MeOH (0.1 M) was added dropwise over 20 min from a foiled reaction flask. The reaction mixture was stirred for a further 5 min and then concentrated in vacuo. The resultant residue was purified using column chromatography (CH2Cl2, or 1% MeOH in CH2Cl2). 3.3. Characterization of Products2-Bromo-4-methylphenol (10) [23]: 10.1 mmol; 1.73 g (92%);
Reference： [1]Molecules,2016,vol. 21
  • 86
  • [ 50-00-0 ]
  • [ 92-03-5 ]
  • [ 70-11-1 ]
  • [ 102183-99-3 ]
Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2819 - 2823
  • 87
  • [ 50-00-0 ]
  • [ 92-03-5 ]
  • [ 135-73-9 ]
  • [ 1370015-91-0 ]
Reference： [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 2819 - 2823
  • 88
  • [ 1413732-47-4 ]
  • [ 92-03-5 ]
  • 2,2-difluoro-5-phenylbenzo[d][1,3]oxathiole [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With potassium fluoride; In acetonitrile; at 100.0℃; for 16.0h;Industrial scale; Place a teflon magnet in a 25 mL reaction tube and add 0.30 mmol of 2-bromo-4-phenylphenol, 0.36 mmol of copper (bpy) CuSCF3, 0.339 mmol of potassium fluoride and 2.5 mL of acetonitrile , The reaction was stirred at 100 in a closed system for 16 h, extracted three times with n-pentane,The organic phases were combined, washed with water and evaporated to remove the organic solvent. The obtained crude product was purified by silica gel column chromatography using n-pentane and diethyl ether (10: 1, v / v) as eluant to obtain 2,2- -5-phenyl-1,3-benzoxaspirone (yield 77%).
Reference： [1]Patent: CN107382956,2017,A .Location in patent: Paragraph 0015
[2]Organic Letters,2018,vol. 20,p. 481 - 484
  • 89
  • [ 92-03-5 ]
  • [ 96-32-2 ]
  • methyl 2-((3-bromo-[1,1'-biphenyl]-4-yl)oxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 0.5h; To a solution of 3-bromo[l,l'-biphenyl]-4-ol (100 mg, 0.401 mmol) in DMF (2.01mL) was added potassium carbonate (166 mg, 1.20 mmol) followed by methyl bromoacetate (41.8 μ, 0.442 mmol). The reaction was stirred vigorously at RT. After 30 min, the reaction mixture was diluted with EtOAc, filtered over celite and washed with 10% LiCl (aq). The organic phase was dried over MgS04, filtered and concentrated in vacuo to give Intermediate 069a (117 mg, 0.364 mmol, 91 % yield) as a white amorphous solid. 1H NMR (400MHz, CDCl3) δ 7.81 (d, J=2.2 Hz, 1H), 7.54 - 7.49 (m, 2H), 7.46 (dd, J=8.5, 2.3 Hz, 1H), 7.44 - 7.39 (m, 2H), 7.36 - 7.30 (m, 1H), 6.88 (d, J=8.6 Hz, 1H), 4.75 (s, 2H), 3.82 (s, 3H).
Reference： [1]Patent: WO2018/5591,2018,A1 .Location in patent: Page/Page column 156
  • 90
  • [ 133430-98-5 ]
  • [ 98-80-6 ]
  • [ 92-03-5 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 100℃;Inert atmosphere; 2-Bromo-4-iodophenol (6 g, 0.02 mol), phenylboronic acid (3.6 g, 0.03 mol), potassium carbonate (3 eq.) and tetrakis(triphenylphosphine)palladium(0) (3 mol %) are suspended in the mixture of DME/water 5/1 (v/v). The reaction mixture is degassed and heated to reflux under nitrogen overnight. The reaction mixture is cooled down, organic phase is separated and evaporated. The residue is subjected to column chromatography on silica gel column, eluted with gradient mixture heptane/ethylacetate, providing pure 3-bromo-[1,1'-biphenyl]-4-ol.
Reference： [1]Patent: US2018/83203,2018,A1 .Location in patent: Paragraph 0014
  • 91
  • [ 92-03-5 ]
  • 3-(trimethylsilyl)-[1,1’-biphenyl]-4-yl trifluoromethanesulfonate [ No CAS ]
Reference： [1]Patent: US2018/83203,2018,A1
[2]Tetrahedron Letters,2019,vol. 60,p. 1389 - 1392
  • 92
  • [ 2857-97-8 ]
  • [ 92-03-5 ]
  • 3-(trimethylsilyl)-[1,1‘-biphenyl]-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
3-Bromo-[1,1’-biphenyl]-4-ol is dissolved in dry THF under nitrogen, and solution is cooled in the C02/IPA bath to -78 C. n-l3uLi (2.5 M solution in heptanes, 1.1 eq.) is added dropwise, the reaction mixture is stirred for 2 h, then trimethylsilyl bromide (2 eq) is added dropwise. The reaction mixture is allowed to warm up to room temperature, quenched with ammonium chloride 10% solution, and extracted with ethyl acetate. 3-(Trimethylsilyl)-[ 1,1 ‘-biphenyl]-4-ol is purified by column chromatography on silica gel column.
Reference： [1]Patent: US2018/83203,2018,A1 .Location in patent: Paragraph 0015
  • 93
  • [ 92-03-5 ]
  • cesium trifluoromethanethiolate [ No CAS ]
  • 2,2-difluoro-5-phenylbenzo[d][1,3]oxathiole [ No CAS ]
Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4558 - 4562
  • 94
  • [ 13057-17-5 ]
  • [ 92-03-5 ]
  • C14H13BrO2 [ No CAS ]
Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4005 - 4011
  • 95
  • [ 92-03-5 ]
  • [ 4039-32-1 ]
  • 3-(trimethylsilyl)-[1,1‘-biphenyl]-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 70℃; for 2h; The synthesis of compound 1a was examplified. A solution of phenol (1.00 g, 10.63 mmol) and Br2 (0.49 mL, 9.56 mmol) in AcOH (7 mL) was stirred for 30 min at 0 C, the reaction mixture was poured into a separatory funnel with ice water (10 mL) and the aqueous phase was extracted with DCM (3 × 15 mL). The combined organic extracts were washed with saturated NaCl (aq) and dried over MgSO4 and concentrated under reduced pressure. The crude product was dissolved in THF (15 mL) and added to HMDS (2.44 mL, 11.69 mmol) for reflux at 70 C for 2 h. The solvent was evaporated under reduced pressure and the crude product was dissolved in THF (15 mL). Finally, the solution was cooled to -78 C and n-BuLi (5.53 mL, 2.5 M, 13.82 mmol) was added dropwise and stirred for 1 h. Tf2O (1.97 mL, 11.69 mmol) was added dropwise and was stirred for 1.5 h. Cold saturated aqueous NaHCO3 (20 mL) was added after separation, and the aqueous layer was extracted with Et2O. The combined organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to give 1a. The remaining compounds 1b-1m (structures showed in Figure 1) were obtained by the same synthetic route.
Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 1389 - 1392
  • 96
  • [ 110-87-2 ]
  • [ 92-03-5 ]
  • C17H17BrO2 [ No CAS ]
Reference： [1]Chemical Communications,2020,vol. 56,p. 1553 - 1556
  • 97
  • [ 92-03-5 ]
  • C24H18BrN [ No CAS ]
  • C36H26BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.5% With potassium phosphate; copper(l) iodide; In N,N-dimethyl-formamide; at 90℃; for 24h;Inert atmosphere; Under the protection of nitrogen, Intermediate 1 (30mmol) and Intermediate 2 (30mmol) were dissolved in anhydrous DMF (12mmol) solution, and dried potassium phosphate (60mmol) was added, followed by the addition of N,N'-bis(2 -Phenylphenyl) oxalic acid (BPPO) (0.6mmol) and cuprous iodide (CuI) (0.6mmol), stir the mixture, heat up to 90C, reflux and react for 24 hours, after the solution is cooled to room temperature, the solution is slowly Add dropwise to water, and stir for 1 hour, let the solution stand still, and there will be precipitation, and the solid is obtained by suction filtration, which is rinsed with 300 mL of absolute ethanol and 200 mL of petroleum ether in turn, and dried. Use a small amount of dichloromethane to completely dissolve the solid organic matter, then slowly add it dropwise to the petroleum ether solution, stir evenly, precipitate precipitation, suction filtration to obtain the solid, followed by rinsing with 300mL absolute ethanol, 200mL petroleum ether, drying, Intermediate 3 (13.90 g, yield of 81.5%, MW: 568.53) was obtained.
Reference： [1]Patent: CN112812123,2021,A .Location in patent: Paragraph 0058; 0060; 0065-0066
  • 98
  • [ 98437-23-1 ]
  • [ 92-03-5 ]
  • 3-(benzo[b]thiophen-2-yl)-[1,1'-biphenyl]-4-ol [ No CAS ]
Reference： [1]Organic Letters,2021,vol. 23,p. 4322 - 4326
  • 99
  • [ 95-56-7 ]
  • [ 98-80-6 ]
  • [ 92-03-5 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 4h;Reflux; (1) Add 0.01mol of raw material I-1, 0.012mol of raw material I-2, 0.02mol of potassium carbonate, 5×10-5mol of Pd(PPh3)4 to a three-necked flask, then add 250ml of toluene and 50ml of ethanol to dissolve it, and stir. Reflux for 4 hours and observe the reaction by TLC until the reaction is complete. Naturally cool to room temperature, filter, and spin-evaporate the filtrate until there is no distillate. The resulting material was purified by a silica gel column (petroleum ether as the eluent) to obtain Intermediate II-1.
Reference： [1]Patent: CN113563316,2021,A .Location in patent: Paragraph 0049-0051
  • 100
  • [ 92-03-5 ]
  • [ 1993-03-9 ]
  • C18H13FO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 4h;Reflux; (2) Add 0.01mol intermediate II-1, 0.012mol raw material I-3, 0.02mol potassium carbonate, 5×10-5 molPd(PPh3)4 to a three-necked flask, and then add 250ml toluene and 50ml ethanol to dissolve it. Stir and reflux for 4 hours, and observe the reaction by TLC until the reaction is complete. Naturally cool to room temperature, filter, and spin-evaporate the filtrate until there is no distillate. The resulting material was purified by a silica gel column (petroleum ether as the eluent) to obtain Intermediate II-2.
Reference： [1]Patent: CN113563316,2021,A .Location in patent: Paragraph 0049-0050; 0052
  • 101
  • [ 306935-88-6 ]
  • [ 92-03-5 ]
Reference： [1]Green Chemistry,2022,vol. 24,p. 1469 - 1473

Tags: 92-03-5 synthesis path| 92-03-5 SDS| 92-03-5 COA| 92-03-5 purity| 92-03-5 application| 92-03-5 NMR| 92-03-5 COA| 92-03-5 structure

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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Acidity of Phenols • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Chan-Lam Coupling Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conjugate Additions of p-Benzoquinones • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Decomposition of Arenediazonium Salts to Give Phenols • Deprotonation of Methylbenzene • Diazo Coupling • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Halogenation of Phenols • Hiyama Cross-Coupling Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kolbe-Schmitt Reaction • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Phenols • Pechmann Coumarin Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reductive Removal of a Diazonium Group • Reimer-Tiemann Reaction • Reverse Sulfonation——Hydrolysis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Vilsmeier-Haack Reaction • Williamson Ether Syntheses
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; ;