*Storage:
*Shipping:
4.5
*For Research Use Only !
Change View
Size | Price | US Stock | Global Stock | In Stock |
5g | łÇͶÊÊ | Inquiry | Inquiry | |
10g | łÇď¶ÊÊ | Inquiry | Inquiry | |
25g | łËó¶ÊÊ | Inquiry | Inquiry | |
100g | łóó¶ÊÊ | Inquiry | Inquiry | |
500g | łËóÿ¶ÊÊ | Inquiry | Inquiry | |
1kg | łÿòî¶ÊÊ | Inquiry | Inquiry |
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
łÇͶÊÊ
łÇď¶ÊÊ
łËó¶ÊÊ
łóó¶ÊÊ
łËóÿ¶ÊÊ
łÿòî¶ÊÊ
In Stock
- +
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Additive Mixing of Emissive Ligands in Covalent Organic Frameworks for White Light Emission
Nyakuchena, James ; Chiromo, Humphrey ; Radpour, Shahrzad , et al. ACS Appl. Mater. Interfaces,2024,16(34):44921-44926.
Abstract: Emissive covalent organic frameworks (COFs) are a promising class of crystalline materials that have demonstrated applications for sensing and light-emitting diodes. However, white light emission from a single COF has not been achieved yet as it requires multicomponent organic chromophores that simultaneously emit blue, green, and red light. In this work, we report the successful synthesis of a single COF with efficient white light emission by utilizing tunable emission properties of 2,1,3- benzothiadazole after incorporating different functional groups on its core structure, which results in the formation of three ligands, i.e., 4′,4-(benzothiadiazole-4,7-diyl)-dibenzaldehyde (BTD), 4,4′-(benzoselenadiazole-4,7-diyl)-dibenzaldehyde (BSD), and 4,4′-(naphtho[2,3-c][1,2,3] selenadiazole-4,9-diyl)-dibenzaldehyde (NSD), that emit in the blue, green, and red regions of the visible light spectrum. We show that white light emission can only occur when BTD, BSD, and NSD are assembled in a single COF structure due to the facilitated energy transfer process from BTD to BSD/NSD. This work demonstrates a unique approach to developing new white light-emitting materials based on the COF structure.
Show More >
Keywords: covalent ; organic ; framework ; emissive ; white ; light
Show More >
Purchased from AmBeed: 13214-70-5 ; 15155-41-6 ; 87199-17-5 ; 78525-34-5
Show More >
Photophysical and Cellular Studies of pH-Sensitive Boron-Functionalised Far-Red Fluorophores
Anita Marfavi ; Liam D. Adair ; Elizabeth J. New , et al. J. Organomet. Chem.,2024,123132.
Abstract: Two novel chromenylium-based probes were developed by functionalisation of the 5-position of the xanthene core with either a para-N-methyldiaminoacetic acid (MIDA) boronate ester (CRpMD) or closo‑1,7-carborane (CRmCB). CRpMD revealed near-infrared emission at 655 nm, demonstrating a bathochromic shift compared to the analogous phenyl derivative (CRPh). Both boron-containing probes were found to be sensitive to changes in acidic pH, with CRpMD also displaying a dual fluorescence response at alkaline pH (pKa1 = 2.40 and pKa2 = 9.16). CRmCB showed a ca. 3-fold increase in fluorescence intensity at 638 nm from pH 7.01 to 2.00, with a pKa = 2.08. Moreover, CRpMD and CRmCB were successfully taken up by A549 lung cancer cells to assess their intracellular biodistributions, thereby showcasing the future potential of these probes for time-resolved pH measurements using confocal microscopy.
Show More >
Keywords: Near-infrared ; Fluorescence microscopy ; Fluorescent probes ; BoronpH sensor
Show More >
Purchased from AmBeed: 4408-64-4 ; 5809-23-4 ; 87199-17-5
Show More >
CAS No. : | 87199-17-5 |
Formula : | C7H7BO3 |
M.W : | 149.94 |
SMILES Code : | OB(C1=CC=C(C=O)C=C1)O |
MDL No. : | MFCD00151823 |
InChI Key : | VXWBQOJISHAKKM-UHFFFAOYSA-N |
Pubchem ID : | 591073 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H317-H401 |
Precautionary Statements: | P261-P272-P273-P280-P302+P352-P333+P313-P362+P364-P501 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 2 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 41.66 |
TPSA ? Topological Polar Surface Area: Calculated from | 57.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 0.29 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | -0.82 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | -0.36 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | -0.6 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | -0.3 |
Log S (ESOL):? ESOL: Topological method implemented from | -1.22 |
Solubility | 8.95 mg/ml ; 0.0597 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.06 |
Solubility | 13.1 mg/ml ; 0.087 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -1.22 |
Solubility | 9.08 mg/ml ; 0.0605 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -7.01 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 1.35 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With sodium carbonate In 1,4-dioxane; water at 80 - 100℃; | To a stirred solution of 2-trifluromethyl-bromobenzene (0.7 g, 2.75 mmol) and 4-carbaldehyde boronic acid (0.5 g, 3.3 mmol) in dioxane (20 ml_) under nitrogen at 80 5C was added Pd(PPh3)4 (0.05 g) followed by the addition of a solution of Na2CO3 (0.7 g) in H2O (5 m). The mixture was stirred at 100 5C for 6 h. The solvent was evaporated and the residue was diluted to 50 ml with EtOAc and washed with H2O. The solvent was devaporated to dryness and the residue was purified by FCC (SiO2) to give the title compound (0.61 g; 88percent), as creamy solid. 1H-NMR (CDCI3) 7.49 (d, 1 H, J = 7.41 Hz); 7.48 (d, 2H, J = 8.13 Hz); 7.61 - 7.53 (m, 2H); 7.76 (d, 1 H, J = 7.8 Hz); 7.91 (d, 2H, J = 8.34 Hz); 10.07 (s, 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In tetrahydrofuran; at 20℃; for 2h;Product distribution / selectivity; | To a solution of 4-formylphenylboronic acid (4.11 g) in anhydrous tetrahydrofuran (THF) (40 ml_) was added 2,2-dimethyl-1 ,3-propanediol (3.14 g) and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated to dryness. The residue was dissolved in dichloromethane (120 ml_), washed with water (80 ml_ x 3), dried and evaporated under vacuum to obtain 4-(5,5-dimethyl-[1 ,3,2]dioxaborinan-2-yl)-benzaldehyde (5.66 g, 95% yield). |
In toluene; for 2h;Heating / reflux;Product distribution / selectivity; | To a mixture of 4-formylphenylboronic acid (50 g) in toluene (250 ml_) was added 2,2-dimethyl-1 ,3-propanediol (34.39 g) and the dispersion was heated at reflux for 2 h. The water while formed was azeotropically separated and the residue (330 ml_) was used directly in the next step. 1H-NMR (400 MHz,CDCI3): delta 1.04 (s, 6 H, 2 CH3), 3.79 (s, 4 H, 2 CH2), 7.84 (d, J = 6.4 Hz, 2 H, H-Ar), 7.96 (d, J = 8 Hz, 2 H, H-Ar), 10.04 (s, 1 H, CHO) ppm. | |
In toluene; for 2h;Heating / reflux; | Example 1 : Preparation of 4-(5,5-dimethyl-H ,3,21dioxaborinan-2-yl)- benzaldehvde;To a mixture of 4-formylphenylboronic acid (50 g) in toluene (250 mL) was added 2,2-dimethyl-1 ,3-propanediol (34.39 g) and the dispersion was heated at reflux for 2 h. The water while formed was azeotropically separated and the residue (330 mL) was used directly in the next step.1H-NMR (400 MHz, CDCI3): delta 1.04 (s, 6 H, 2 CH3), 3.79 (s, 4 H, 2 CH2), 7.84 (d, J = 6.4 Hz, 2 H,H-Ar), 7.96 (d, J = 8 Hz, 2 H, H-Ar), 10.04 (s, 1 H, CHO) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; for 18h;Heating / reflux; | Step A Ethanol (13 ml) and 1.0M Na2CO3 (27.5 ml) were added to a suspension of 2-chloropyrazine (4.0 g, 34.6 mmole), 4-formylphenylboronic acid (6.8 g, 45.0 mmole), and tetrakis(triphenylphosphine)palladium(0) (2.0 g, 1.7 mmole) in toluene (55 ml). The mixture was refluxed for 18 hours then cooled, diluted with EtOAc, washed with NaHCO3, washed with brine, dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) yielded 6.2 g (97%) of 4-(2-pyrazinyl)benzaldehyde. |
42% | [0410] Step A: [0411] 1M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of 2-chloropyrazine (2.30 g, 20.06 mmol), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.56 g (42%) of 4-pyrazinylbenzaldehyde. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; for 20h;Heating / reflux; | Step B Ethanol (10 ml) and 1.0M Na2CO3 (18 ml) were added to a suspension of the compound from step A (2.8 g, 24.0 mmole), 4-formylphenylboronic acid (4.7 g, 31.2 mmole), and tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmole0 in toluene (35 ml). The mixture was refluxed for 20 hours then cooled, diluted with EtOAc, washed with NaHCO3, washed with brine, dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 4:1 hexanes/EtOAc) yielded 4.1 g (93percent) of 4-(3-pyridazinyl)benzaldehyde. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With KF;palladium diacetate; In tetrahydrofuran; | (4'-Formylbiphenyl-2-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S29). 4-Formylphenylboronic acid (4.97 g, 33.2 mmol), aryl bromide S28 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.884 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated moderately (30° C.) with stirring. After 24 h, the reaction was diluted with CH2Cl2 and was washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2 and the combined organics were then washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain a white solid (6.0 g, 63percent). 1H NMR (400 MHz, d6-DMSO): delta10.04 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.88 (d, 2H, J=7.5 Hz), 7.82 (t, 1H, J=5.9 Hz, NH), 7.67 (d, 2H, J=7.5 Hz), 7.59 (d, 2H, J=8.2 Hz), 7.43-7.30 (m, 7H), 7.24 (d, 1H, J=7.7 Hz), 4.29 (d, 2H, J=7.0 Hz), 4.19 (t, 1H, J=7.0 Hz), 4.12 (d, 2H, J=5.9 Hz). APCI/MS: 434 (M+H+). |
63% | With KF;palladium diacetate; In tetrahydrofuran; | (4'-Formylbiphenyl-2-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S29). 4-Formylphenylboronic acid (4.97 g, 33.2 mmol), aryl bromide S28 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.884 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated moderately (30° C.) with stirring. After 24 h, the reaction was diluted with CH2Cl2 and was washed with 1 M NaOH. The aqueous layer was extracted with CH2Cl2 and the combined organics were then washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude solid was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain a white solid (6.0 g, 63percent). 1H NMR (400 MHz, d6-DMSO): delta10.04 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.88 (d, 2H, J=7.5 Hz), 7.82 (t, 1H, J=5.9 Hz, NH), 7.67 (d, 2H, J=7.5 Hz), 7.59 (d, 2H, J=8.2 Hz), 7.43-7.30 (m, 7H), 7.24 (d, 1H, J=7.7 Hz), 4.29 (d, 2H, J=7.0 Hz), 4.19 (t, 1H, J=7.0 Hz), 4.12 (d, 2H, J=5.9 Hz). APCI/MS: 434 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With KF;palladium diacetate; In tetrahydrofuran; | (4'-Formylbiphenyl-3-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S30). 4-Formylphenylboronic acid (5.0 g, 33 mmol), aryl bromide S27 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.88 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated to reflux with stirring. After 5 h, the reaction was diluted with ethyl acetate, filtered through a celite pad and washed with 1 M NaOH. The aqueous layer was extracted with ethyl acetate and the combined organics were then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil (13 g). The crude oil was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain aldehyde S29 as a yellow oil (5.7 g, 60percent). 1H NMR (400 MHz, CDCl3): delta10.06 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.76 (d, 2H, J=7.5 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=7.5 Hz), 7.56 (m, 1H), 7.55 (s, 1H), 7.46 (dd, 1H, J=7.9 Hz, 7.9 Hz), 7.39 (dd, 2H, J=7.5 Hz, 7.5 Hz), 7.33 (m, 1H), 7.29 (dd, 2H, J=7.5 Hz, 7.5 Hz), 5.16 (broad s, 1H), 4.48 (d, 2H, J=7.0 Hz), 4.47 (s, 2H), 4.24 (t, 1H, J=7.0 Hz). ESI/MS: 456 (M+Na+). |
60% | With KF;palladium diacetate; In tetrahydrofuran; | (4'-Formylbiphenyl-3-ylmethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester (S30). 4-Formylphenylboronic acid (5.0 g, 33 mmol), aryl bromide S27 (9.0 g, 22 mmol), KF (3.8 g, 66 mmol), <strong>[224311-51-7]biphenyl-2-yl-di-tert-butyl-phosphane</strong> (0.26 g, 0.88 mmol), and palladium(II) acetate (0.099 g, 0.44 mmol) were charged into an oven-dried flask. After one evacuation/backfill cycle with Ar, the solids were dissolved in THF (45 mL) and heated to reflux with stirring. After 5 h, the reaction was diluted with ethyl acetate, filtered through a celite pad and washed with 1 M NaOH. The aqueous layer was extracted with ethyl acetate and the combined organics were then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford an orange oil (13 g). The crude oil was purified by flash column chromatography (silica gel, 30percent ethyl acetate/hexanes) to obtain aldehyde S29 as a yellow oil (5.7 g, 60percent). 1H NMR (400 MHz, CDCl3): delta10.06 (s, 1H), 7.95 (d, 2H, J=8.2 Hz), 7.76 (d, 2H, J=7.5 Hz), 7.74 (d, 2H, J=8.2 Hz), 7.59 (d, 2H, J=7.5 Hz), 7.56 (m, 1H), 7.55 (s, 1H), 7.46 (dd, 1H, J=7.9 Hz, 7.9 Hz), 7.39 (dd, 2H, J=7.5 Hz, 7.5 Hz), 7.33 (m, 1H), 7.29 (dd, 2H, J=7.5 Hz, 7.5 Hz), 5.16 (broad s, 1H), 4.48 (d, 2H, J=7.0 Hz), 4.47 (s, 2H), 4.24 (t, 1H, J=7.0 Hz). ESI/MS: 456 (M+Na+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cesium fluoride;tetrakis(triphenylphosphine)palladium (0); In 2-Methyl-1,2-propanediol; | Preparation 72 2-(4-formylphenyl)-4-pyridyl cyanide Benzaldehyde-4-boronic acid (1.36 g), 2-bromo-4-cyano pyridine (1.5 g), cesium fluoride (2.72 g) and tetrakis(triphenylphosphine)palladium(0) (285 mg) were mixed together in dimethyl ethylene glycol (30 ml). The reaction mixture was refluxed for 16 hrs under a atmosphere of nitrogen after which time the cooled mixture was diluted with diethyl ether (40 ml) and washed with water (40 ml), the organic layer was separated and washed with saturated brine, dried over MgSO4 and evaporated under reduced pressure. The crude product was purified by column chromatography eluding with Dichloromethane/Diethyl ether (97.5/2.5, v/v) to afford the title compound (0.81 g). Rf 0.3 (Dichloromethane/Diethyl ether, 97.5/2.5, v/v). deltaH (400 MHz, CDCl3): 10.15 (1H, s), 8.95 (1H, d), 8.20 (2H, d), 8.05 (3H, m), 7.55 (1H, d). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen;di-mu-hydroxo-bis[(N,N,N?,N?-tetramethylethylene-diamine)copper(II)] chloride; In 1,2-dichloro-ethane; at 60℃; for 20h; | Description 45; Ethyl 1-(4-formylphenyl)-1H-imidazole-2-carboxylate (D45); <strong>[33543-78-1]Ethyl imidazole-2-carboxylate</strong> (140 mg, 1.0 mmol), 4-formylbenzeneboronic acid (300 mg, 2.0 mmol) and catalyst [Copper(OH).TMEDA]2Cl2 (46 mg, 0.10 mmol) were dissolved in 1,2-dichloroethane (5 ml) and heated to 60° C. under an O2 atmosphere for 20 h. The mixture was diluted with DCM, filtered through Celite and evaporated to dryness. The crude residue was purified by column chromatography on silica, eluting with a 0-5percent [2M NH3 in MeOH]/DCM gradient to give the title compound (152 mg). deltaH (CDCl3, 250 MHz) 1.32 (3H, t), 4.32 (2H, q), 7.22 (1H, s), 7.34 (1H, s), 7.52 (2H, d), 8.01 (2H, d), 10.11 (1H, s). MS (ES): MH+ 245. | |
With oxygen;di-mu-hydroxo-bis[(N,N,N?,N?-tetramethylethylene-diamine)copper(II)] chloride; In 1,2-dichloro-ethane; at 60℃; for 20h; | Description 45; Ethyl 1-(4-formylphenyl)-1H-imidazole-2-carboxylate (D45); <strong>[33543-78-1]Ethyl imidazole-2-carboxylate</strong> (140mg, 1. Ommol), 4-formylbenzeneboronic acid (300mg, 2.0mmo.) and catalyst [Copper(OH).TMEDA] 2CI2 (46mg, 0.1 Ommol) were dissolved in 1 ,2-dichloroethane (5ml) and heated to 60°C under an O2 atmosphere for 2Oh. The mixture was diluted with DCM, filtered through Celite and evaporated to dryness. The crude residue was purified by column chromatography on silica, eluting with a 0-5percent [2M NH3 in MeOH]/DCM gradient to give the title compound (152mg). deltaH (CDCI3, 250MHz) 1.32 (3H, t), 4.32 (2H, q), 7.22 (1 H, s), 7.34 (1H, s), 7.52 (2H, d), 8.01 (2H, d), 10.11 (1H, s). MS (ES): MH+ 245. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 16h;Reflux; Inert atmosphere; | To a solution of <strong>[34259-99-9]<strong>[34259-99-9]4-bromothiazol</strong>e</strong> (see The Journal of Organic Chemistry, 71, 3754 (2006)) (1.31 g, 7.98 mmol) in 1,2-dimethoxyethane (38.0 ml) were added 4-formylphenylboronic acid (1.45 g, 9.67 mmol), sodium hydrogencarbonate (2.00 g, 23.8 mmol) and water (19 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (270 mg, 0.234 mmol) was then added, followed by heating to reflux for 16 hours under argon atmosphere. After completion of the reaction, a saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.29 g) as a slightly yellow solid. (Yield: 85percent) Mass spectrum (CI, m/z): 190 (M++1). 1H-NMR spectrum (CDCl3, ppm): 10.05 (s, 1H), 8.93 (d, J=2.0Hz, 1H), 8.14-8.10 (m, 2H), 799-7.94 (m, 2H), 7.73 (d, J=2.0Hz, 1H). |
85% | With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 16h;Inert atmosphere; Reflux; | 15-(a) 4-(Thiazol-4-yl)benzaldehyde To a solution of <strong>[34259-99-9]<strong>[34259-99-9]4-bromothiazol</strong>e</strong> (see The Journal of Organic Chemistry, 71, 3754 (2006)) (1.31 g, 7.98 mmol) in 1,2-dimethoxyethane (38.0 ml) were added 4-formylphenylboronic acid (1.45 g, 9.67 mmol), sodium hydrogencarbonate (2.00 g, 23.8 mmol) and water (19 ml), which was deaerated under reduced pressure, followed by argon substitution. Tetrakis(triphenylphosphine)palladium (270 mg, 0.234 mmol) was then added, followed by heating to reflux for 16 hours under argon atmosphere. After completion of the reaction, a saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with chloroform. The separated organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=4:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (1.29 g) as a slightly yellow solid. (Yield: 85percent) Mass spectrum (CI, m/z): 190 (M++1). 1H-NMR spectrum (CDCl3, deltappm): 10.05 (s, 1H), 8.93 (d, J=2.0Hz, 1H), 8.14-8.10 (m, 2H), 7.99-7.94 (m, 2H), 7.73 (d, J=2.0Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
A mixture of 1.0 g (7.04 mmol) of lH-<strong>[36193-65-4]indole-2-carbonitrile</strong> (I. Borza at al.Bioorg. Med. Chem. Lett. 2005, 15, 5439-5441), 1.5 g (7.28 mmol) of trimethyltin azide, and 50 mL of toluene was refluxed for 3 h. The reaction mixture was cooled to 20 C and the precipitated product was filtered off to yield 2.22 g of tin complex of the title compound. Mp.: 236-240 C. A mixture of 0.4 g (1.4 mmol) of 2-(2H-tetrazol-5-yl)-lH-indole, 0.31 g (2.06 mmol) of 4-formyl-phenylboronic acid, 0.42 g (2.77 mmol) of copper(II) acetate, 0.98 mL (5.6 mmol) of N^V-diisopropylethylamine, 0.7 g 3 A molecular sieves in 15 mL of N,N-dimethylformamide was vigorously stirred at room temperature with air bubbling for 14 h. The mixture was filtered through Celite. The filtrate was concentrated in vacuo. The residue was submitted to flash column chromatography using Kieselgel 60 (0.015-0.040 mm) as adsorbent (Merck) and chloroform:methanol:acetic acid = 10: 1 :0.1 as eluent to yield after crystallization from 2-propanol 0.12 g (19 %) of the title compound. Mp.: 210-212 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 2h;Inert atmosphere; | Step 3: Synthesis of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-5-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4'-formyl-4-methyl-[1,1'-biphenyl]-3-carboxamide To a stirred solution of <strong>[1403257-80-6]5-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-2-methylbenzamide</strong> (5.0 g, 10 mmol) and (4-formylphenyl)boronic acid (2.35 g, 15.8 mmol) in dioxane/water (30 mL/10 mL) was added Na2CO3 (4.01 g, 37.9 mmol). The solution was purged with argon for 15 min., Pd(PPh3)4 (1.21 g, 1.05 mmol) and the mixture was heated at 100 C. for 2 h. The mixture was allowed to cool to room temperature, diluted with water and extracted with 10% MeOH/CH2Cl2. The combined organic layers were dried over sodium sulphate and the solvent removed under reduced pressure. The resulting crude material was purified by column chromatography over silica gel to afford N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-5-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-4'-formyl-4-methyl-[1,1'-biphenyl]-3-carboxamide (3.5 g, 66%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water;Inert atmosphere; Reflux; | Under N2 atmosphere, the mixture of compound DPP-Br2 (100mg, 0.146mmoles), 4-formylphenylboronicacid (89.6mg, 0.6mmoles), Pd(PPh3)4 (20mg, 0.017mmole), 2M aqueous solution of Na2CO3 (3mL) in dry THF (15mL) was refluxed overnight. The reaction mixture was extracted with DCM, and washed with water and brine solutions. The organic layer was dried with anhydrous Na2SO4 and then the solvent was removed by rotary evaporation. The residue was purified by column chromatography on silica gel using Hexane and ethylacetate in the ratio of 10: 2 (v/v) as eluent to afford DPP-B-CHO Yield: 80.0%. 1H NMR (500MHz, CHCl3) delta 10.04 (s, 2H), 8.98-8.97 (d, J=4.1Hz, 2H), 7.95-7.94 (d, J=8.3Hz, 4H), 7.84-7.83 (d, J=8.2Hz, 4H), 7.61-7.58 (d, J=6.2Hz, 2H), 4.09 (t, J=7.2Hz, 4H), 1.40 (m, 9H), 1.30-1.16 (m, 7H), 1.01-0.89 (m, 7H), 0.89 (m, 7H). MALDI-TOF MS Calcd. for733.0; Found 733.71. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.9% | With potassium phosphate; In 1,4-dioxane; for 2h;Reflux; Inert atmosphere; | 4-Formylphenylboronic acid (s47) (75.9 g),4-bromo-2,3-difluoroethoxybenzene (s48) (100.0 g), potassium phosphate (269.0g), dichlorobistriphenylphosphinepalladium (II) (Pd(Ph3P)2Cl2;8.9 g) and 1,4-dioxane (500 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and the mixture was heated to reflux for 2 hours. After the reaction mixture had been cooled to 25 C, it was treated with water,and the aqueous layer was extracted with toluene. The combined organic layers were washed with water,and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by column chromatography with toluene as an eluent and silica gel as a stationary phase powder. The product was purified by recrystallization from a mixed solvent of heptane and toluene (heptane:toluene=l: 1 by volume) to give 4-ethoxy-4'-formyl-2,3-difluoro-l,l'-biphenyl (s49) (102.8g). The yield based on the compound (s48) was 92.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; | 3,6-dichloropyridazine (400 mg, 2.69 mmol) was dissolved in dioxane (6 mL) and distilled water (2 mL)After dissolving, 4-formyl phenylboronic acid (321 mg, 2.15 mmol),Potassium carbonate (920 mg, 6.71 mmol),PdCl2 (dppf) 2 (110 mg, 0.13 mmol) was added to a solution ofAnd stirred at 90 C.The reaction mixture was diluted with dichloromethane, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Purification by column chromatography (40% EtOAc / Hexane) provided 4- (6-chloropyridazin-3-yl) benzaldehyde (148 mg, 25%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.24% | With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; toluene; at 90℃;Inert atmosphere; | B.Compound <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong> (157.7 mg, 0.40 mmol)4-formylphenylboronic acid (129.7 mg, 0.87 mmol),Bis (triphenylphosphine) palladium dichloride Pd (PPh3) 2Cl2 (28.1 mg, 0.04 mmol)Was dissolved in 40 mL of a mixed solution of toluene and tetrahydrofuran (Vtoluene: VTHF = 1: 1)The reaction was refluxed at 90 ° C under nitrogen,Thin layer chromatography to the reaction is complete.After the resulting solution was spin off the organic solvent,Extracted with ethyl acetate,Organic layer washed three times,Saturated NaCl solution once,Dried over anhydrous sodium sulfate,The solvent is evaporated under reduced pressure;The crude product was passed through a column of petroleum ether and ethyl acetate mixed solvent (20: 1)4,4 '- (9-phenyl-9H-carbazole-3,6-diyl) benzaldehyde(Yellow powder, 123.1 mg, yield 68.24percent). |
Tags: 87199-17-5 synthesis path| 87199-17-5 SDS| 87199-17-5 COA| 87199-17-5 purity| 87199-17-5 application| 87199-17-5 NMR| 87199-17-5 COA| 87199-17-5 structure
A254605 [870777-33-6]
(3-Formyl-5-methylphenyl)boronic acid
Similarity: 0.98
A254605 [870777-33-6]
(3-Formyl-5-methylphenyl)boronic acid
Similarity: 0.98
A254605 [870777-33-6]
(3-Formyl-5-methylphenyl)boronic acid
Similarity: 0.98
A359358 [1256355-30-2]
(5-Fluoro-2-formylphenyl)boronic acid
Similarity: 0.78
A403216 [913835-76-4]
4-Chloro-2-formylphenylboronic acid
Similarity: 0.77
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :
Total Compounds: mg
The concentration of the dissolution solution you need to prepare is mg/mL