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[ CAS No. 100980-82-3 ] {[proInfo.proName]}

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Chemical Structure| 100980-82-3
Chemical Structure| 100980-82-3
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Product Details of [ 100980-82-3 ]

CAS No. :100980-82-3 MDL No. :MFCD00804656
Formula : C13H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LUWJPGMZEAYDBA-UHFFFAOYSA-N
M.W : 198.22 Pubchem ID :2759299
Synonyms :

Safety of [ 100980-82-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 100980-82-3 ]

* 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 [ 100980-82-3 ]

[ 100980-82-3 ] Synthesis Path-Downstream   1~62

  • 1
  • [ 2403-54-5 ]
  • [ 106-41-2 ]
  • [ 92-88-6 ]
  • [ 66-98-8 ]
  • [ 100980-82-3 ]
  • 2
  • [ 111-85-3 ]
  • [ 100980-82-3 ]
  • [ 103481-60-3 ]
  • 3
  • [ 100980-82-3 ]
  • LY264826 triacetate [ No CAS ]
  • C86H96Cl2N10O27 [ No CAS ]
  • 4
  • [ 87199-17-5 ]
  • polystyrene-Wang resin-CH2O-(4-iodophenyl) [ No CAS ]
  • [ 100980-82-3 ]
  • 5
  • [ 100980-82-3 ]
  • (E)-4'-hydroxybiphenyl-4-carbaldehyde oxime [ No CAS ]
  • 6
  • [ 716344-19-3 ]
  • [ 100980-82-3 ]
YieldReaction ConditionsOperation in experiment
100% With potassium fluoride; hydrogen bromide; In DMF (N,N-dimethyl-formamide); water; at 20.0℃; for 2.5h; A mixture of 4'-[tert-butyl (dimethyl) silyl] OXY}-1, 1 -BIPHENYL-4-CARBALDEHYDE (320 mg, 1.03 MMOL), anhydrous KF (120mg, 2.06 mmol) and 48 % aqueous HBr (35UL, 0. 3 lmmol) in 6 mL dry DMF was stirred at room temperature under N2 for IH. TLC indicated starting material present and therefore more 48 % aqueous HBr (35 uL, 0. 3 1 MMOL) was added into the reaction and the mixture was continued to stir for 1. 5 H. The mixture was then poured, with cooling, into 1 N aqueous HCl (30mL). The aqueous mixture was extracted with EtOAc (3x). The combined extracts were washed with saturated NaCl solution, and dried over NA2S04. The solvent was evaporated under reduced pressure and the product (100%) which was used directly in the next steps NMR (DMSO-d6) : 8 6.89 (2H, d, J= 8.43 Hz), 7.63 (2H, d, J= 8.46 Hz), 7.83 (2H, d, J = 8.16 Hz), 7.94 (2H, d, J= 8.02 Hz), 9.79 (1H, s), 10.01 (1H, s).
  • 7
  • [ 67963-68-2 ]
  • [ 100980-82-3 ]
  • 8
  • [ 159191-56-7 ]
  • [ 100980-82-3 ]
  • 9
  • [ 100980-82-3 ]
  • (4-Octyloxy-benzyl)-((S)-1-phenyl-ethyl)-amine [ No CAS ]
  • 11
  • [ 256381-32-5 ]
  • [ 100980-82-3 ]
  • C30H30O7 [ No CAS ]
  • 13
  • [ 850200-31-6 ]
  • [ 100980-82-3 ]
  • C75H74O14S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; Coupling of commercially available 4'-hydroxy-biphenyl-4- carbaldehyde with sulfonyl chloride 4B (prepared according to the method of Kvεernø et al., Org. Lett. 2005, 4, 1145-1148) in the presence of triethylamine gives the desired product 31B. Condensation of 31B with 4-fluoroaniline gives the imine 32B. In the next step, 3aB was treated with titanium tetrachloride and N-ethyldiisopropylamine followed by treatment with 32B to effect enantiospecific condensation to provide 33B. Treatment of 33B with excess N,O-bistrimethylsilyl-acetamide followed by a catalytic amount of tetrabutylammonium fluoride hydrate results in ring closure to the desired beta-lactam (34aB). Finally, catalytic hydrogenation of 34aB over Pearlman's catalyst gives the deprotected derivative 34bB.
  • 14
  • [ 100980-82-3 ]
  • [ 67-68-5 ]
  • [ 133123-02-1 ]
  • [ 217651-49-5 ]
YieldReaction ConditionsOperation in experiment
With potassium iodide; potassium carbonate; In acetone; b) A mixture of 1.0 g of 4'-hydroxybiphenyl-4-carboxaldehyde, 1.1 g of 6-chlorohexyl acrylate, 0.083 g of potassium iodide, 1.05 g of pulverised potassium carbonate and 15 ml of dimethyl sulphoxide was heated for 21 hours to 75 C. After cooling, it was poured into water and extracted with diethyl ether. The organic phase was washed with water until it was neutral, dried over sodium sulphate, filtered and concentrated. Chromatography of the residue on 45 g of silica gel with toluene/acetone 49:1 resulted in 1.46 g of 4'-(6-acryloxyhexyloxy)biphenyl-4-carboxaldehyde; boiling point 53.2-54.5 C.
  • 15
  • C36H38NO3Pol [ No CAS ]
  • [ 100980-82-3 ]
  • 16
  • [ 1072896-39-9 ]
  • [ 100980-82-3 ]
  • [ 1072896-70-8 ]
  • 17
  • [ 1263192-84-2 ]
  • [ 100980-82-3 ]
  • [ 1296131-50-4 ]
YieldReaction ConditionsOperation in experiment
Ca. 68% With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol; at 20.0℃; for 24h; General procedure: To a mixture of the amine (3 or 4, 0.084 mmol) and <strong>[100980-82-3]4'-hydroxybiphenyl-4-carbaldehyde</strong>6 (8.5 mg, 0.043 mmol) in dry MeOH (3 mL) was added acetic acid (0.1 mL), followed by NaBH3CN (1.0 M in THF, 60 μL, 0.060 mmol). After stirring at rt for 24 h, the reaction mixture was concentrated, reconstituted into water and loaded on a silica reversed phase column pre-equilibrated in water. The compounds were eluted with a gradient of methanol-water (0:1-60:100) to afford the title compounds 7 or 8 in about 68% yield as a white fluffy solid after a final lyophilization from water. The solvent system (ethyl acetate/methanol/water/acetic acid 10:3:3:1) was used for following up the reaction.
  • 18
  • [ 1195053-34-9 ]
  • [ 100980-82-3 ]
  • [ 1296131-52-6 ]
YieldReaction ConditionsOperation in experiment
Ca. 68% With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; methanol; at 20.0℃; for 24h; General procedure: To a mixture of the amine (3 or 4, 0.084 mmol) and <strong>[100980-82-3]4'-hydroxybiphenyl-4-carbaldehyde</strong>6 (8.5 mg, 0.043 mmol) in dry MeOH (3 mL) was added acetic acid (0.1 mL), followed by NaBH3CN (1.0 M in THF, 60 μL, 0.060 mmol). After stirring at rt for 24 h, the reaction mixture was concentrated, reconstituted into water and loaded on a silica reversed phase column pre-equilibrated in water. The compounds were eluted with a gradient of methanol-water (0:1-60:100) to afford the title compounds 7 or 8 in about 68% yield as a white fluffy solid after a final lyophilization from water. The solvent system (ethyl acetate/methanol/water/acetic acid 10:3:3:1) was used for following up the reaction.
  • 20
  • [ 100980-82-3 ]
  • [ 1611445-30-7 ]
  • 21
  • [ 100980-82-3 ]
  • [ 1611443-82-3 ]
  • 22
  • [ 1266120-65-3 ]
  • [ 100980-82-3 ]
  • [ 1611443-81-2 ]
YieldReaction ConditionsOperation in experiment
41% With caesium carbonate; In tert-butyl alcohol; for 48h;Reflux; Example 96: (S)- 1-(4’ -(4-(Trifluoromethyl)cyclohexyloxy)biphenylcarbonyl) pyrrolidine-3-carboxylic acidStep 1: 4’-(4-(Trifluoromethyl)cyclohexyloxy)biphenyl-4-carbaldehyde [00249] Into a solution of <strong>[100980-82-3]4’-hydroxybiphenyl-4-carbaldehyde</strong> (6.0 g, 30 mmol) in tBuOH (50 mL) was added Cs2CO3 (19.8 g, 61 mmol, 2.0 eq) and 4- (trifluoromethyl)cyclohexyl methanesulfonate (15.0 g, 61 mmol, 2.0 eq). The reaction mixture was heated at reflux for 48 h and cooled down. The mixture was filtered and cake was washed with THF. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (petroleum ether/EtOAc = 10/1) to give the title compound as a gray solid (4.3 g, 41% yield). ‘H NMR (300 MHz, CDC13) ö: 10.04 (s, 1H), 7.92 (d, J= 7.8 Hz, 2H), 7.70 (d, J= 8.7 Hz, 2H), 7.58 (d, J= 9.0 Hz, 2H), 6.98 (d, J= 9.0 Hz, 2H), 4.25 (s, 1H), 2.3 1-2.28 (m, 2H), 2.09-2.04 (m, 2H), 1.52-1.46 (m, 5H).
  • 23
  • [ 319014-74-9 ]
  • [ 100980-82-3 ]
  • (Z)-2,3-bis(4’-hydroxybiphenyl-4-yl)acrylonitrile [ No CAS ]
  • 24
  • [ 100980-82-3 ]
  • (E)-2,3-bis(4'-((12-bromododecyl)oxy)biphenyl-4-yl)acrylonitrile [ No CAS ]
  • 25
  • [ 100980-82-3 ]
  • C61H75N3O2(2+)*2Br(1-) [ No CAS ]
  • 26
  • [ 100980-82-3 ]
  • C61H75N3O2(2+)*2Br(1-) [ No CAS ]
  • 27
  • [ 312-68-5 ]
  • [ 100980-82-3 ]
  • 4'-(3-fluoropropoxy)-[1,1'-biphenyl]-4-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
61.3% With caesium carbonate; In N,N-dimethyl-formamide; at 20.0℃; General procedure: A suspension of the phenol, 3-fluoropropyl p-toluenesulfonate, and cesium carbonate in dimethylformamide was heated to 60-65 C. and maintained overnight. After cooling to ambient temperature, the resulting mixture was treated with water, and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with water, saturated aqueous sodium chloride, dried over sodium sulfate, filtered and concentrated in vacuo.
61.3% With caesium carbonate; In N,N-dimethyl-formamide; at 20.0℃; General procedure: Phenol , 3-fluoropropyl p-toluene sulfonate , and the suspension in dimethyl formamide of cesium carbonate and heated to 60 ~ 65C , and kept overnight . After cooling to ambient temperature , the resulting mixture was treated with water and the aqueous layer was extracted with ethyl acetate . The combined organic layers were washed with water, saturated aqueous sodium chloride , dried over sodium sulfate , filtered , and concentrated in vacuo .In accordance with the general method F, 4'- hydroxy - [1,1 'biphenyl] -4-carbaldehyde (0.500g, 2.52mmol), 3- fluoro-propyl p- toluene sulfonate (0.557g, 2.40mmol ) and cesium carbonate (1.25 g, 3.84 mmol of), were prepared by using in ambient temperature dimethylformamide (25.2 mL).A coarse material, silica gel chromatography (ethyl acetate in hydroxyhexanamide 0-60%)is further purified by, as solid white to obtain a desired product (0. 380g, 61. 3% yield).1H NMR (CDCl3, 300MHz): δ10. 03 (s, 1H), 7. 97-7. 87 (m, 2H), 7. 75-7. 68 (m, 2H), 7. 63-7. 53 (m, 2H), 7. 06-6. 96 (m, 2H), 4. 75 (t, J = 5. 7Hz, 1H), 4. 59 (t, J = 5. 7Hz, 1H), 4. 16 (t, J = 6. 1Hz, 2H), 2. 21 (m, 2H);13C NMR (CDCl3, 75MHz, CDCl3) δ191. 8,159. 3,146. 7,134. 7,132. 2,130. 2,128. 5,127. 0,115. 0, 80. 6 (d, JCF= 165Hz), 63. 7 (d, JCF= 7. 5Hz), 30. 4 (d, JCF= 22. 5Hz); HRMS-TOF(m/z) : [M+H]+HRMS: C16H15FO2calculated value to: 259. 1129, actual value 259. 1131.
  • 28
  • [ 100980-82-3 ]
  • (4'-(3-fluoropropoxy)-[1,1'-biphenyl]-4-yl)methanol [ No CAS ]
  • 29
  • [ 100980-82-3 ]
  • 2-(tert-butyl)-4-chloro-5-((4'-(3-fluoropropoxy)-[1,1'-biphenyl]-4-yl)methoxy)pyridazin-3(2H)-one [ No CAS ]
  • 30
  • [ 106-41-2 ]
  • [ 87199-17-5 ]
  • [ 100980-82-3 ]
YieldReaction ConditionsOperation in experiment
94% With sodium carbonate; In 1,4-dioxane; water; at 40.0℃; for 0.166667h;Catalytic behavior; General procedure: Aryl halide (1 equiv.), arylboronic acid (1.2 equiv.), Na2CO3 (1.5 equiv.), and TMRTH-PdNps (0.006 mmol) were charged in a round-bottomed flask equipped with a stirrer in 10 mL mixture of 1,4-dioxane-water (1:1). The flask was placed in an oil-bath and the mixture was stirred at 40 C for 10 min. Products were extracted with 3 ×10 mL of ethyl acetate and washed with 3 ×10 mL of water before drying over Na2SO4. The organic layer was evaporated under vacuum using a rotary evaporator to obtain the solid product. Thereafter, the solid was dried and weighed to record the yield. The products have been characterized by 1H NMR and electrospray ionization mass spectrometry.
  • 31
  • [ 5720-07-0 ]
  • [ 100980-82-3 ]
  • 32
  • [ 52988-34-8 ]
  • [ 100980-82-3 ]
YieldReaction ConditionsOperation in experiment
72% With boron tribromide; In dichloromethane; at -78℃; for 16h; [00134] In a similar fashion as general procedure 5, a mixture of 4?-methoxy-[l,l?- biphenylj-4-carbaldehyde 3 (530 mg, 2.12 mmol) and boron tribromide (1M in DCM, 2.1 mL, 2.10 mmol) in DCM (4 mL) was stirred at -78 C for 16 h. After workup, the crude product was purified by silica gel column chromatography eluting with 8-10% ethyl acetate in n-hexane to provide the title compound 4 as an off-white solid (100 mg, 72%). ?H NMR (400 MHz, CDC13) = 10.04 (s, 1H), 7.93 (d, J=8.43 Hz, 2H), 7.71 (d, J=8.43 Hz, 2H), 7.51- 7.57 (m, 2H), 6.92-6.97 (m, 2H).
  • 33
  • [ 1122-91-4 ]
  • [ 100980-82-3 ]
  • 34
  • [ 141-84-4 ]
  • [ 100980-82-3 ]
  • (Z)-5-((4’-hydroxy-[1,1‘-biphenyl]-4-yl)methylene)-2-thioxothiazolidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% With sodium acetate; acetic acid; at 120.0℃; for 16h; [00135] In a similar fashion as general procedure 3, a mixture of 4’-hydroxy-[l,l’- biphenylj-4-carbaldehyde 4 (60 mg, 0.30 mmol), 2-thioxothiazolidin-4-one 5 (40 mg, 0.30 mmol) and sodium acetate (36 mg, 0.45 mmol) in glacial acetic acid (2 mL) was heated at 120 C for 16 h. After workup, the crude product was purified by triturating with ethanol. The title compound NADi-170, 6 mg (19% yield) was isolated as a yellow solid. ‘H NMR (400 MHz, DMSO-d6) = 13.83 (br. s, 1H), 9.73 (s, 1H), 7.79 (d, J=8.38 Hz, 2H), 7.57-7.70 (m, 5H), 6.83-6.91 (m, 2H); MS (ES+): mlz = 312 [M-Hj; HPLC = 96.82%.
  • 35
  • [ 540-38-5 ]
  • [ 87199-17-5 ]
  • [ 100980-82-3 ]
  • 36
  • [ 100980-82-3 ]
  • [ 64-04-0 ]
  • (4'-phenethylamino)methyl-1,1'-biphenyl-4-ol [ No CAS ]
  • 37
  • [ 110-52-1 ]
  • [ 100980-82-3 ]
  • C17H17BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.1% With potassium carbonate; In acetone; for 18h;Reflux; 5.94 g (30 mmol) of the starting material molecule b and 12.96 g (60 mmol) of the starting material C-4 were refluxed with 8.29 g (60 mmol) of potassium carbonate in 50 mL of acetone for 18 h, and the reaction was monitored by TLC thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was evaporated to dryness. Column chromatography gave the intermediate b-4 in a yield of 70.1%.
  • 38
  • [ 629-03-8 ]
  • [ 100980-82-3 ]
  • C19H21BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.4% With potassium carbonate; In acetone; for 20h;Reflux; 5.94 g (30 mmol) of the starting material molecule b and 14.64 g (60 mmol) of the starting material C-6 were refluxed with 8.29 g (60 mmol) of potassium carbonate in 50 mL of acetone for 20 h, and the reaction was monitored by TLC thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was evaporated to dryness. Column chromatography gave the intermediate b-6 in a yield of 68.4%.
  • 39
  • [ 4549-32-0 ]
  • [ 100980-82-3 ]
  • C21H25BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
59.5% With potassium carbonate; In acetone; for 20h;Reflux; 5.94 g (30 mmol) of the starting material molecule b and 16.32 g (60 mmol) of the starting material C-8 were refluxed with 8.29 g (60 mmol) of potassium carbonate in 50 mL of acetone for 20 h, and the reaction was monitored by TLC thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was evaporated to dryness. Column chromatography gave intermediate b-8 in a yield of 59.5%.
  • 40
  • [ 100980-82-3 ]
  • [ 4101-68-2 ]
  • C23H29BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.8% With potassium carbonate; In acetone; for 24h;Reflux; 5.94 g (30 mmol) of the starting material molecule b and 18.00 g (60 mmol) of the starting material C-10 were refluxed with 8.29 g (60 mmol) of potassium carbonate in 50 mL of acetone for 24 hours, and the reaction was monitored by TLC thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was evaporated to dryness. Column chromatography gave the intermediate b-10, yield 47.8%.
  • 41
  • [ 3344-70-5 ]
  • [ 100980-82-3 ]
  • C25H33BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40.2% With potassium carbonate; In acetone; for 24h;Reflux; 5.94 g (30 mmol) of the starting material molecule b and 19.68 g (60 mmol) of the starting material C-12 were refluxed with 8.29 g (60 mmol) of potassium carbonate in 50 mL of acetone for 24 h, and the reaction was monitored by TLC thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was evaporated to dryness. Column chromatography gave the intermediate b-12 in a yield of 40.2%.
  • 42
  • [ 100980-82-3 ]
  • C28H40N2O2 [ No CAS ]
  • 43
  • [ 100980-82-3 ]
  • C63H84N4O4 [ No CAS ]
  • 44
  • [ 100980-82-3 ]
  • C30H44N2O2 [ No CAS ]
  • 45
  • [ 100980-82-3 ]
  • C67H92N4O4 [ No CAS ]
  • 46
  • [ 100980-82-3 ]
  • C32H48N2O2 [ No CAS ]
  • 47
  • [ 100980-82-3 ]
  • C71H100N4O4 [ No CAS ]
  • 48
  • [ 100980-82-3 ]
  • C34H52N2O2 [ No CAS ]
  • 49
  • [ 100980-82-3 ]
  • C75H108N4O4 [ No CAS ]
  • 50
  • [ 100980-82-3 ]
  • C36H56N2O2 [ No CAS ]
  • 51
  • [ 100980-82-3 ]
  • C79H116N4O4 [ No CAS ]
  • 52
  • [ 100980-82-3 ]
  • C38H60N2O2 [ No CAS ]
  • 53
  • [ 100980-82-3 ]
  • C83H124N4O4 [ No CAS ]
  • 54
  • [ 100980-82-3 ]
  • [ 106-93-4 ]
  • C15H13BrO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.4% With potassium carbonate; In acetone; for 18h;Reflux; 5.94 g (30 mmol) of the starting material molecule b and 11.27 g (60 mmol) of the starting material C-2 were refluxed with 8.29 g (60 mmol) of potassium carbonate in 50 mL of acetone for 18 h, and the reaction was monitored by TLC thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature, filtered, and the filtrate was evaporated to dryness. Column chromatography gave the intermediate b-2 in a yield of 80.4%.
  • 55
  • [ 100980-82-3 ]
  • 4'-formylbiphenyl-4-yl fluorosulfate [ No CAS ]
  • 56
  • 1-(4-nitrophenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione [ No CAS ]
  • [ 100980-82-3 ]
  • 4'-(4-(4-nitrophenyl)-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)-[1,1'-biphenyl]-4-ol [ No CAS ]
  • 57
  • C56H88N2O6 [ No CAS ]
  • [ 100980-82-3 ]
  • C69H96N2O7 [ No CAS ]
  • 58
  • C56H88N2O6 [ No CAS ]
  • [ 100980-82-3 ]
  • C73H98N4O9 [ No CAS ]
  • 59
  • C56H89ClN2O4 [ No CAS ]
  • [ 100980-82-3 ]
  • C69H98N2O6 [ No CAS ]
  • 60
  • [ 100980-82-3 ]
  • C39H39NO4 [ No CAS ]
  • 61
  • [ 100980-82-3 ]
  • C78H78N2O8 [ No CAS ]
  • 62
  • [ 100980-82-3 ]
  • C39H37Br2NO4 [ No CAS ]
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