[ CAS No. 135242-71-6 ] {[proInfo.proName]}

Name: 135242-71-6|3-Hydroxy-4-iodobenzaldehyde|98%
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Quality Control of [ 135242-71-6 ]

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Product Details of [ 135242-71-6 ]

CAS No. :	135242-71-6	MDL No. :	MFCD00114697
Formula :	C₇H₅IO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IHLOHISMHMTTAA-UHFFFAOYSA-N
M.W :	248.02	Pubchem ID :	2775270
Synonyms :

Safety of [ 135242-71-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 135242-71-6 ]

* 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 [ 135242-71-6 ]

[ 135242-71-6 ] Synthesis Path-Downstream 1~88

1
[ 704-13-2 ]
[ 135242-71-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

2
[ 135242-71-6 ]
2-iodo-5-methoxybenzoyl chloride [ No CAS ]
[ 121404-84-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

3
[ 224641-82-1 ]
[ 135242-71-6 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 8590 - 8593

4
[ 87905-78-0 ]
[ 135242-71-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2560 - 2563

5
[ 5292-43-3 ]
[ 135242-71-6 ]
[ 951659-66-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2560 - 2563

6
[ 135242-71-6 ]
C₆H₃((C(CH₃)3OCOCH₂O)(CONHCH₂COOCH₂C₆H₅))BF₃^(1-)*K⁽¹⁺⁾=C₆H₃((C(CH₃)3OCOCH₂O)(CONHCH₂COOCH₂C₆H₅))BF₃K [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2560 - 2563

7
[ 135242-71-6 ]
[ 951659-65-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2560 - 2563

8
[ 135242-71-6 ]
[ 951659-67-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2560 - 2563

9
[ 135242-71-6 ]
C₆H₃((C(CH₃)3OCOCH₂O)(CONHCH₂COOCH₂C₆H₅))BO₂C₂(CH₃)4 [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 2560 - 2563

10
[ 135242-71-6 ]
[ 121404-86-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

11
[ 135242-71-6 ]
2-Iodo-5-methoxy-benzoic acid 3-formyl-phenyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

12
[ 135242-71-6 ]
[ 84575-08-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320
[3]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

13
[ 135242-71-6 ]
[ 85318-25-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

14
[ 135242-71-6 ]
1-<3-hydroxy-4-(2-hydroxymethyl-4-methoxyphenyl)phenyl>-2-<4-hydroxy-3-(4-hydroxymethylphenoxy)phenyl>ethane [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

15
[ 135242-71-6 ]
[ 84575-09-7 ]

16
[ 135242-71-6 ]
2'-Hydroxymethyl-4-{2-[3-(4-hydroxymethyl-phenoxy)-4-methoxy-phenyl]-ethyl}-4'-methoxy-biphenyl-2-ol [ No CAS ]

17
[ 135242-71-6 ]
2-<4-hydroxy-3-(4-methoxycarbonylphenoxy)>-1-<8-methoxy-6-oxodibenzo<bd>pyran-3-yl>ethane [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

18
[ 135242-71-6 ]
[ 121404-90-8 ]

19
[ 135242-71-6 ]
[ 121404-89-5 ]

20
[ 135242-71-6 ]
[ 121404-88-4 ]

21
[ 135242-71-6 ]
1-<3-benzyloxy-4-(2-bromomethyl-4-methoxyphenyl)phenyl>-2-<4-benzyloxy-3-(4-bromomethylphenoxy)phenyl>ethane [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

22
[ 135242-71-6 ]
1-<3-benzyloxy-4-(2-hydroxymethyl-4-methoxyphenyl)phenyl>-2-<4-benzyloxy-3-(4-hydroxymethylphenoxy)phenyl>ethane [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320
[2]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

23
[ 135242-71-6 ]
[ 121404-87-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

24
[ 135242-71-6 ]
[ 121404-87-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

25
[ 135242-71-6 ]
(Z)-1-<4-benzyloxy-3-(4-methoxycarbonylphenoxy)>-2-<8-methoxy-6-oxodibenzo<bd>pyran-3-yl>ethene [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

26
[ 135242-71-6 ]
(E)-1-<4-benzyloxy-3-(4-methoxycarbonylphenoxy)>-2-<8-methoxy-6-oxodibenzo<bd>pyran-3-yl>ethene [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 315 - 320

27
[ 135242-71-6 ]
[ 100-39-0 ]
[ 877064-79-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; for 16h;Heating / reflux;	N-(2-Benzyloxy-5'-fluoro-2'-methoxy-biphenyl-4-ylmethyl)-2-trifluoromethoxy-benzenesulfonamide To a stirred solution of <strong>[135242-71-6]3-hydroxy-4-iodobenzaldehyde</strong> (4.0 g, 16.2 mmol) in acetone (50 ml) was added benzyl bromide (2.76 g, 16.2 mmol) and potassium carbonate (2.23 g, 16.2 mmol). The reaction mixture was heated under reflux for 16 h. The solvent was evaporated and the residue was dissolved in ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 3-benzyloxy-4-iodo-benzaldehyde (5.1 g) as orange oil. A mixture of 3-benzyloxy-4-iodobenzaldehyde (1.05 g, 3.24 mmol), 5-fluoro-2-methoxyphenyl boronic acid (1.12 g 6.6 mmol), potassium carbonate (1.22 g, 8.8 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.40 g, 0.35 mmol) in tetrahydrofuran (12.0 ml) and dimethylformamide (4 ml) was heated in a microwave oven at 120 C. for 30 min. The reaction mixture was diluted with diethyl ether, washed with 2M sodium hydroxide and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue flash chromatographed over silica gel eluting with 5:1 heptane/ethyl acetate to give 2-benzyloxy-5'-fluoro-2'-methoxy-biphenyl-4-carbaldehyde. To a stirred solution of 2-benzyloxy-5'-fluoro-2'-methoxy-biphenyl-4-carbaldehyde (0.50 g, 1.5 mmol) was added 2-methyl-2-propane sulfinamide (0.183 g, 1.51 mmol) and titanium(IV) isopropoxide (3 ml, 7.5 mmol) in tetrahydrofuran (10 ml). The reaction mixture was stirred at ambient temperature under nitrogen atmosphere for 16 h. Brine was added to reaction mixture which was then filtered through dicalite and extracted with dichloromethane The extract was dried over anhydrous sodium sulfate, the solvent evaporated and the residue flash chromatographed over silica gel eluting with 8:2 heptane/ethyl acetate to give 2-methyl-propane-2-sulfininic acid-2-benzyloxy-5'-fluoro-2'-methoxy-biphenyl-4-ylmethylene amide (0.3 g). To a stirred solution of 2-methyl-propane-2-sulfininic acid-2-benzyloxy-5'-fluoro-2'-methoxy-biphenyl-4-ylmethylene amide (0.3 g, 0.7 mmol) in dichloromethane (20 ml) was added diisobutylaluminium hydride (1M in tetrahydrofuran, 6 ml, 4.2 mmol) at -78 C. under nitrogen atmosphere. The reaction mixture warmed to ambient temperature over 16 h. Potassium sodium L-tartrate tetrahydrate was added and the mixture stirred for 30 min then extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and the solvent evaporated to give 2-methyl-propane-2-sulfininic acid-(2-benzyloxy-5'-fluoro-2'-methoxy-biphenyl-4-ylmethylene) amide (0.250 g). To a stirred solution of 2-methyl-propane-2-sulfininic acid-(2-benzyloxy-5'-fluoro-2'-methoxy-biphenyl-4-ylmethylene) amide (0.25 g, 0.57 mmol) in methanol (5 ml) was added Hydrogen chloride (1M in diethyl ether). The solution was left to stir at ambient temperature for 10 min and the solvent evaporated. The residue was dissolved in dichloromethane and purified on a SCX column (eluted with 2M ammonia in methanol) to give C-(2-Benzyloxy-5'-methoxy-biphenyl-4-yl)-methylamine (0.12 g). The title compound was then prepared in a similar manner to N-(5'-fluoro-2,2'-dimethoxy-biphenyl-4-ylmethyl)-4-methoxy-benzenesulfonamide (Example 6) using C-(2-benzyloxy-5'-methoxy-biphenyl-4-yl)-methylamine and 2-trifluromethoxybenzene sulfonyl chloride. MS (ESI) m/z: 562.2 [M+H]+.

Reference： [1]Patent: US2007/149577,2007,A1 .Location in patent: Page/Page column 9

28
[ 109-01-3 ]
[ 135242-71-6 ]
[ 1160924-02-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran; at 0 - 20℃;	3-Hydroxy-4-iodobenzaldehyde (2.0 g, 8.06 mmol) and 1-methyipiperazine (4.0 g, 40.34 mmol) were dissolved in THF (100 mL). Upon cooling to 0 0C, sodium triacetoxyborohydride (8.6 g, 40.34 mmol) was added to the reaction solution along with catalytic amount of HOAc. The mixture was slowly warmed to room temperature and stirred overnight. The suspension was filtered, and the filtrate was diluted with dichloromethane, washed with saturated aqueous <n="125"/>sodium bicarbonate, dried over MgSO4 and concentrated to give a light color syrup. The syrup was purified by column chromatography, eluting with 10-15% gradient methanol in dichloromethane, to give 2.36 g (88%) of 2-iodo-5-[(4-methylpiperazin-1-yl)methyl]phenol as a white solid; MS 333.2 (M+H).

Reference： [1]Patent: WO2009/76602,2009,A1 .Location in patent: Page/Page column 123-124

29
[ 135242-71-6 ]
[ 74-88-4 ]
[ 121404-83-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; In acetone; for 2h;Heating / reflux;	A mixture of <strong>[135242-71-6]3-hydroxy-4-iodobenzaldehyde</strong> (1.8 g, 7.26 mmol), iodomethane (3.2 g, 22.54 mmol) and potassium carbonate (1.51 g, 10.93 mmol) in 80 mL of acetone was heated at reflux for 2 h. The reaction was cooled and filtered. After the removal of the solvent from the filtrate, the residue was re-dissolved in EtOAc and washed with saturated aqueous sodium bicarbonate, dried over MgSO4 and concentrated to give off-white solid. The solid was eluted through silica gel with 50% EtOAc in hexanes to give 1.85 g (97%) of 4-iodo-3- methoxybenzaldehyde as a white solid; MS 263.0 (M+H).
93%	With potassium carbonate; In N,N-dimethyl-formamide; acetone; at 25℃;	Synthesis of 4-(4-Ethynyl-2-methoxy-phenyl)-2-methyl-pyridine; 4-Iodo-3-methoxy-benzaldehyde: 3~Hydroxy-4-iodo-benzaldehyde (2 g, 8.06 mmol) and Potassium Carbonate (1.672 g, 12.10 mmol) were suspended in acetone (19.15 ml) and dimethylformamide (1.008 ml) at 23 0C and stirred for 10 minutes before iodomethane (0.756 ml, 12.10 mmol) was added via syringe. The resulting suspension was stirred at 25 0C for 4 hours. The reaction was concentrated under reduced pressure and washed with 250 ml water. The tan precipitate was collected via filtration, rinsed with water and dissolved in 400 ml ethyl acetate. This solution was washed with twice with 100 ml of brine, dried over sodium sulfate and filtered. Evaporation of the solvent gave 4-Iodo-3-methoxy-benzaldehyde (1.956 g, 7.46 mmol, 93 % yield) as a tan solid.1H NMR (500 MHz, cdcB) 6 9.93 (s, IH), 7.96 (d, J= 7.8, IH), 7.27 (d, J= 1.6, IH), 7.16 (dd, J= 7.8, 1.7, IH), 3.94 (s, 3H).MS (EI) [M+H]+ calc'd 263.0 found 262.9.

Reference： [1]Patent: WO2009/76602,2009,A1 .Location in patent: Page/Page column 125
[2]Patent: WO2010/77582,2010,A1 .Location in patent: Page/Page column 20-21
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3828 - 3831

30
N-((1s,4s)-4-(5-fluoro-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)nicotinamido)cyclohexyl)-2-methylthiazole-4-carboxamide [ No CAS ]
[ 135242-71-6 ]
N-((1s,4s)-4-(5-fluoro-2-(4'-formyl-2'-hydroxybiphenyl-3-yloxy)nicotinamido)cyclohexyl)-2-methylthiazole-4-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In water; acetonitrile; at 70℃; for 1h;	Example 56N-((ls,4s)-4-(5-fluoro-2-(2'-hydroxy-4'-(morpholinomethyl)biphenyl-3- yloxy)nicotinamido)cyclohexyl)-2-methylthiazole-4-carboxamide <n="108"/>Step (a) N-((l s,4s)-4-(5-fluor o-2-(4 '-formyl-2 '-hydroxybiphenyl-3- yloxy)nicotinamido)cyclohexyl)-2-methylthiazole-4-carboxamideA solution of potassium carbonate (0.643 g, 4.65 mmol) in water (4.5 niL), 3-hydroxy-4- iodobenzaldehyde (0.385 g, 1.55 mmol) and N-((ls,4s)-4-(5-fluoro-2-(3-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)phenoxy)nicotinamido)cyclohexyl)-2-methylthiazole-4-carboxamide (0.9 g, 1.55 mmol) were added sequentially to a stirred solution of palladium(II) acetate (0.035 g, 0.16 mmol) and dicyclohexyl(2',6'-dimethoxybiphenyl-2-yl)phosphine (0.127 g, 0.31 mmol) in acetonitrile (6.0 mL) and heated at 70 0C for 1 h. The mixture was cooled to RT, extracted with EtOAc, washed with water and brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by chromatography on silica with 50 % EtOAc/isohexane as eluent to afford the sub-title compound as a light brown solid. Yield: 139 nig1H NMR (400 MHz, DMSO) delta 10.22 (s, IH), 9.91 (s, IH), 8.34 (d, J= 7.7 Hz, IH), 8.26 (d, J = 3.2 Hz, IH), 8.07 (s, IH), 8.03 (m, IH), 7.58 (d, J= 8.3 Hz, IH), 7.51 - 7.44 (m, 4H), 7.41 - 7.37 (m, 2H), 7.19 (m, IH), 4.01 (m, IH), 3.86 (m, IH), 2.62 (s, 3H), 1.81 - 1.62 (m, 8H). MS: APCI (+ve) 575 (M+l)

Reference： [1]Patent: WO2009/144494,2009,A1 .Location in patent: Page/Page column 106-107

31
[ 21211-65-4 ]
[ 135242-71-6 ]
5,15-bis(4-iodo-3-hydroxyphenyl)porphyrin [ No CAS ]

Reference： [1]Photochemistry and Photobiology,2010,vol. 86,p. 206 - 212

32
[ 135242-71-6 ]
[ 71670-77-4 ]
[ 1231191-97-1 ]

Yield	Reaction Conditions	Operation in experiment
36.8%		3-(1H-midazoI-2-ylmethoxy)-4-iodobenzaldehyde. To a flask, were added 3-hydroxy-4- iodobenzaldehyde (200 mg, 0.806 mmol), KOH (43.0 mg, 0.766 mmol) and DMSO (2 ml). The mixture was stirred at rt for 2h. 2-(chloromethyl)-lH-imidazole hydrochloride (105.4 mg, 0.689 mmol) in 1 ml of DMSO was added to this mixture and stirred overnight. The mixture was diluted with DCM and water. The organic phase was washed with brine, dried over sodium sulfate and concentrated to afford crude product, which was purified on silica gel (MeOH/DCM-8/92) to afford desire product (97.4 mg, 0.297 mmol, 36.8 % yield).

Reference： [1]Patent: WO2010/71741,2010,A1 .Location in patent: Page/Page column 29; 30

33
[ 100-83-4 ]
[ 135242-71-6 ]

Yield	Reaction Conditions	Operation in experiment
28%	With ammonium hydroxide; iodine; potassium iodide; In water; at 20℃; for 2h;	3-Hydroxybenzaldehyde (1.60 g, 13.18 mmol) was dissolved in 15 mL of 33% aqueousNH4OH in a 100 mL round-bottomed flask. Separately, iodine (3.72 g,14.65 mmol) was added to 25 mL of 30% (w/v) solution of KI in water. The lattersolution was added dropwise to the 3-hydroxybenzaldehyde solution, after which thereaction was stirred at rt for 2h. The reaction mixture was cooled then with an icebath and made acid with conc. HCl, which caused the appearance of a yellow gum.The gum was taken up in Et2O, and the remaining aqueous solution was extractedwith more Et2O (3 £ 10 mL). The organic layers were pooled together, washed with10 mL of an aqueous saturated solution of Na2S2O3, and dried over anh. Na2SO4.After filtration and solvent removal under reduced pressure, an orange-colored solidis obtained, which was crystallized from Et2O to afford 927 mg of 3-hydroxy-4-iodobenzaldehyde5 as a yellowish solid. Yield: 28%. M.p.: 128-130C, lit. mp. 128-129 C.25 1H RMN (300 MHz, CD3COCD3): d 9.94 (s, 1H), 9.67 (s, 1H), 8.00 (d, JD 8.0 Hz, 1H), 7.41 (d, J D 1.8 Hz, 1H), 7.20 (dd, J1 D 8.0 Hz, J2 D 1.8 Hz, 1H);1H RMN (300 MHz, CDCl3) d ppm: 9.92 (s, 1H), 7.88 (d, J D 8.1 Hz, 1H), 7.44 (d,J D 1.8 Hz, 1H), 7.18 (dd, J1 D 8.1 Hz, J2 D 1.8 Hz, 1H), 5.93 (br s, 1H); 13CRMN (75 MHz, CD3COCD3): d 193.2 (CHO), 159.2 (C-3), 142.1 (C-5), 140.2 (C-1),124.5 (C-6), 115.3 (C-2), 94.0 (C-4); 13C RMN (75 MHz, CDCl3): d 191.3 (CHO),155.8 (C-3), 139.3 (C-5), 138.3 (C-1), 123.0 (C-6), 114.8 (C-2), 93.9 (C-4); HRMS(EI) m/z: Calcd for C7H5IO2: 247.9334. Found: 247.9358.

Reference： [1]Chinese Chemical Letters,2010,vol. 21,p. 914 - 918
[2]Synthetic Communications,2010,vol. 40,p. 3506 - 3513
[3]Organic Preparations and Procedures International,2017,vol. 49,p. 265 - 272

34
[ 135242-71-6 ]
[ 910920-82-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3828 - 3831

35
[ 135242-71-6 ]
[ 910920-83-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3828 - 3831

36
[ 135242-71-6 ]
C₂₁H₂₁Cl₂NO₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3828 - 3831

37
[ 135242-71-6 ]
[ 910920-84-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3828 - 3831

38
[ 135242-71-6 ]
[ 910920-85-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3828 - 3831

39
[ 135242-71-6 ]
C₂₇H₃₃ClN₄O₃ [ No CAS ]
C₂₇H₃₃ClN₄O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3828 - 3831

40
[ 135242-71-6 ]
C₂₈H₃₆ClN₅O₃ [ No CAS ]
C₂₈H₃₆ClN₅O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3828 - 3831

41
[ 135242-71-6 ]
C₄₉H₂₇BF₂N₂O₃ [ No CAS ]

Reference： [1]Journal of Fluorescence,2013,vol. 23,p. 1007 - 1018

42
[ 135242-71-6 ]
C₅₆H₃₇BF₂N₂O₆ [ No CAS ]

Reference： [1]Journal of Fluorescence,2013,vol. 23,p. 1007 - 1018

43
[ 135242-71-6 ]
C₆₀H₄₀BF₂N₃O₈ [ No CAS ]

Reference： [1]Journal of Fluorescence,2013,vol. 23,p. 1007 - 1018

44
[ 135242-71-6 ]
C₃₁H₁₈BF₂IN₂O₃ [ No CAS ]

Reference： [1]Journal of Fluorescence,2013,vol. 23,p. 1007 - 1018

45
[ 1138343-25-5 ]
[ 135242-71-6 ]
C₃₁H₁₉IN₂O₃ [ No CAS ]

Reference： [1]Journal of Fluorescence,2013,vol. 23,p. 1007 - 1018

46
[ 135242-71-6 ]
C₂₈H₃₅BF₂IN₃O₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 6859 - 6869

47
[ 135242-71-6 ]
C₂₈H₃₈IN₃O₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 6859 - 6869

48
[ 135242-71-6 ]
C₂₈H₃₈IN₃O₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 6859 - 6869

49
[ 135242-71-6 ]
C₄₁H₅₄BF₂N₅O₄ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 6859 - 6869

50
[ 135242-71-6 ]
C₃₁H₃₆BF₂N₃O₂ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 6859 - 6869

51
[ 135242-71-6 ]
[ 88-10-8 ]
C₁₂H₁₄INO₃ [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 6859 - 6869

52
[ 773869-57-1 ]
[ 135242-71-6 ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 9216 - 9219

53
[ 41876-68-0 ]
[ 135242-71-6 ]
C₂₃H₂₇NO₂ [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 9216 - 9219

54
[ 135242-71-6 ]
C₃₇H₃₆N₂O₃ [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 9216 - 9219

55
[ 135242-71-6 ]
C₃₈H₃₅F₃N₂O₃ [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 9216 - 9219

56
[ 135242-71-6 ]
C₃₇H₃₆N₂O₂S [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 9216 - 9219

57
[ 135242-71-6 ]
C₂₄H₂₉NO [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 9216 - 9219

58
[ 625-82-1 ]
[ 109-63-7 ]
[ 135242-71-6 ]
C₁₉H₁₈BF₂IN₂O [ No CAS ]

Reference： [1]Journal of Photochemistry and Photobiology B: Biology,2017,vol. 167,p. 269 - 281

59
[ 625-82-1 ]
[ 135242-71-6 ]
[ 1434003-47-0 ]

Reference： [1]Journal of Photochemistry and Photobiology B: Biology,2017,vol. 167,p. 269 - 281

60
[ 135242-71-6 ]
[ 205877-26-5 ]
2-(4-(diphenylamino)phenyl)benzofuran-6-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.08 g	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 50℃; for 3h;Inert atmosphere;	[0134] To a 50 mL flask was added 4-ethynyltriphenylamine (1.01 g), 3-hydroxy-4- iodobenzaldehyde (0.77 g), bis(triphenylphosphine)palladium dichloride (0.066 g), and copper(l) iodide (0.054 g). The flask was purged with nitrogen for 20 minutes. A solution of triethylamine (2.18 mL) in anhydrous acetonitrile (15.6 mL) was degassed by bubbling nitrogen through for 20 minutes. The triethylamine solution was added to the reaction and the reaction then heated to 50 C for 3 hours. The reaction was cooled to room temperature and water (25 mL) added. The aqueous layer was extracted with ethyl acetate (3x30 mL) and the combined organic fractions washed with brine and dried over sodium sulfate. The organic layer was filtered and concentrated. The residue was purified via chromatography on silica gel (elution with 0 to 13% ethyl acetate in hexanes) to afford 2-(4-(diphenylamino)phenyl)benzofuran-6-carbaldehyde (1.08 g). 1 H-NMR (400 MHz, DMSO-d6): delta 10.04 (s, 1 H), 8.1 1 (d, 1 H), 7.86 (d, 2H), 7.80 (s, 2H), 7.42-7.34 (m, 5H), 7.17-7.10 (m, 6H), 7.03 (d, 2H).
1.08 g	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 50℃; for 3h;Inert atmosphere;	To a 50 mL flask was added 4-ethynyltriphenylamine (1.01 g), 3-hydroxy- 4-iodobenzaldehyde (0.77 g), bis(triphenylphosphine)palladium dichloride (0.066 g), and copper(l) iodide (0.054 g). The flask was purged with nitrogen for 20 minutes. A solution of triethylamine (2.18 mL) in anhydrous acetonitrile (15.6 mL) was degassed by bubbling nitrogen through for 20 minutes. The triethylamine solution was added to the reaction and the reaction then heated to 50 C for 3 hours. The reaction was cooled to room temperature and water (25 mL) added. The aqueous layer was extracted with ethyl acetate (3x30 mL) and the combined organic fractions washed with brine and dried over sodium sulfate. The organic layer was filtered and concentrated. The residue was purified via chromatography on silica gel (elution with 0 to 13% ethyl acetate in hexanes) to afford 2-(4-(diphenylamino)phenyl)benzofuran-6-carbaldehyde (1.08 g). 1H-NMR (400 MHz, DMSO-d6): delta 10.04 (s, 1H), 8.1 1 (d, 1H), 7.86 (d, 2H), 7.80 (s, 2H), 7.42-7.34 (m, 5H), 7.17-7.10 (m, 6H), 7.03 (d, 2H).

Reference： [1]Patent: WO2017/83488,2017,A1 .Location in patent: Paragraph 0134
[2]Patent: WO2018/208712,2018,A1 .Location in patent: Paragraph 0094

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2-((2-(4-(diphenylamino)phenyl)benzofuran-6-yI)methylene)malonamide [ No CAS ]