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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
2-Methoxybenzaldehyde (o-Anisaldehyde) is isolated from cinnamon oil and exhibits antimicrobial and antifungal activities.
Synonyms: o-Anisaldehyde
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Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 135-02-4 |
Formula : | C8H8O2 |
M.W : | 136.15 |
SMILES Code : | O=CC1=CC=CC=C1OC |
Synonyms : |
o-Anisaldehyde
|
MDL No. : | MFCD00003308 |
InChI Key : | PKZJLOCLABXVMC-UHFFFAOYSA-N |
Pubchem ID : | 8658 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 |
---|---|---|
97%Chromat. | With lithium diisobutylmorpholinoaluminum hydride; In tetrahydrofuran; hexane; at 0℃; for 0.5h; | General procedure: The following procedure for reduction of N,N-dimethylbenzamide with LDBMOA is representative. To a solution of N,N-dimethylbenzamide (0.149 g, 1.0 mmol) in THF (10.0 mL) containing naphthalene as an internal standard was added LDBMOA (2.4 mL, 0.5 M in THF-hexanes, 1.2 mmol) at 0 C. After 30 min, the reaction mixture was hydrolyzed with 1 N aq HCl (10 mL) and extracted with diethyl ether. The combined organic layers were dried over anhydrous magnesium sulfate, and filtered. After the removal of solvents in vacuum and purification of residue by column chromatography on silica gel gave benzaldehyde (0.103 g, 97%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With trifluorormethanesulfonic acid; trimethylsilylazide; In acetonitrile; at 25℃; for 0.00138889h;Flow reactor; | General procedure: General procedure for synthesis of nitriles from aldehydes incontinuous ow is as follows. Take benzaldehyde as an example,benzaldehyde (0.6 mmol) and TfOH (0.9 mmol) were dissolved in3 mL MeCN and pumped into inlet A. TMSN 3 (0.6 mmol) wasdissolved in 3 mL MeCN and pumped into inlet B (ow rate A:B = 54 m L/min:65 m L/min for 5 s residence time). The whole systemwas maintained at 25C. The ow system was equilibrated (about5 min), then the product stream was quenched and collected in aglass vessel with saturated aqueous NaClO in it. The ow systemwas stopped after the inlet A reduced 0.5 mL. The crude mixturewas dissolved in ethyl acetate and washed with saline solution. Thecombined organic layers were dried over magnesium sulfate,ltered, and concentrated under reduced pressure. The resultingcrude product was puried by ash chromatography on silica gelwith hexane and EtOAc as eluent to afford the product |
95% | With hexamethylene bis(N-methylimidazolium)bis(dichloroiodate); ammonia; In water; acetonitrile; at 20℃; for 1.5h; | General procedure: The mixture of HMBMIBDCI (0.5 mmol, 322 mg) in CH3CN (5 ml) was added into a solution of p-chlorobenzaldehyde (0.5 mmol, 70 mg) in NH3(aq) (1.5 ml) and the resulting dark mixture was stirred for the specified time designated in Table 2 at room temperature. The progress of the reaction was followed by TLC and the dark heterogeneous solution gradually changed to a red solution. To the mixture was added CHCl3 (30 ml) and then the organic phase was washed with an aqueous solution of NaHSO3 (5%, 20 ml). The organic layer was dried over MgSO4 and evaporated under reduced pressure. The crude material obtained was practically pure in most cases with no need for further purification. Otherwise, the crude products were purified by recrystallization or preparative TLC. All the nitrile products were identified by comparing melting point, 1H, and 13C NMR with those of authentic samples reported in the literature. 2-Methoxybenzonitrile (Table 2, entry 9). Oil [26]; 1H NMR (400 MHz, CDCl3): δ (ppm) = 7.59-7.54 (m, 2 H), 7.03 (dd, J = 8.0, 0.8 Hz, 1 H), 7.00 (d, J = 8.0 Hz, 1 H). 13C NMR (100 MHz, CDCl3): δ (ppm) = 161.25, 134.39, 133.77, 120.76, 116.51, 111.29, 101.82, 56.00. |
92% | With (2-hydroxyethyl)trimethylazanium urea chloride; hydroxylamine hydrochloride; In neat (no solvent); at 140℃; for 0.166667h;Microwave irradiation; Green chemistry; | General procedure: Microwave irradiation: A mixture of benzaldehyde (0.106 g, 1 mmol), hydroxylamine hydrochloride (0.083 g, 1.2 mmol) and catalyst (15 mol%) was irradiated in microwave oven at 140 C for 10 min. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mass was cooled to r.t. The product was extracted into EtOAc. The solid product was obtained after evaporation of EtOAc. The obtained solid was purified by column chromatography (silica gel). The pure product was characterized by GC-MS and 1H NMR. |
90% | With hydroxylamine hydrochloride; In methanol; water; at 20℃; for 19h;Irradiation; | General procedure: A round bottom flask was charged with a mixture of benzaldehyde 1(1.0 mmol), NH2OH.HCl 2 (1.5 mmol), Cog-C3N4 (20 mg) in H2O/MeOH (1:1, 5 mL) and stirred under the visible light condition at roomtemperature for 14-20 h. After completion of the reaction (monitored by TLC), the catalyst was filtered and added EtOAc (10 mL). Remaining organic layer was washed with brine (2×5 mL) and distilled water(1×10 mL) and dried over anhydrous sodium sulfate. Solvent was evaporated under reduced pressure to afford the crude residue, which was further purified by flash chromatography, EtOAc/n-hexane: 10:90 to obtain the analytically pure product 3 |
85% | With ammonium sulfate; sodium carbonate; sulfur; In dimethyl sulfoxide; at 120℃; for 10h;Sealed tube; | Combine 2-methoxybenzaldehyde (68.0mg, 0.5mmol), ammonium sulfate (66.1mg, 0.5mmol), sodium carbonate (53.0mg, 0.5mmol), sulfur powder (32.0mg, 1mmol), and 0.5 ml of solvent DMSO Put it into the reaction tube and seal the reaction tube. The reaction tube was placed in a 120C oil bath reaction pot with magnetic stirring for 10 hours. After cooling to room temperature. Then it was extracted with ethyl acetate and the organic phases were combined. The organic phase was washed with saturated brine, after separation, the organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure.Ethyl acetate: petroleum ether = 1:200 (volume ratio) as the developing solvent thin layer chromatography to separate pure products. Yellow oil, yield 85% |
85.5% | With oxygen; ammonium carbonate; In dimethyl sulfoxide; at 120℃; for 8h;Sealed tube; Green chemistry; | General procedure: The typical experimental procedure for the ammoxidation of aldehydeswith ammonium carbonate was as follows: powdered catalyst (10mg), aldehydes (0.2 mmol), ammonium salt (0.4 mmol), and 2 mL solventwere added into a glass tube (10 mL) under an O2 atmosphere. Themixture in this sealed glass tube was reacted at a suitable temperaturefor determined reaction times. Then, the reaction mixture in the sealedtube was centrifuged to obtain the liquid phase, which was analyzed onan Agilent 7890B gas chromatograph (GC) that was equipped with aflame ionization detector and an HP-5 capillary column (30 m, 0.32 mminner diameter, and 0.25 μm film), and using methylbenzene as an internalstandard. The temperature program of the column oven was asfollows: from an initial temperature of 50 C, the oven was heated to180 C at a rate of 15 Cmin 1 and subsequently heated to 280 C at arate of 20 Cmin 1. The conversion and product selectivity werecalculated as follows. The pure product was isolated by silica-gel column chromatographyusing petroleum ether and ethyl acetate as eluents. The obtained purecompounds were characterized by proton nuclear magnetic resonance(1H NMR) spectroscopy on a BURCKER AVANCE II 500 M spectrometerat 20 C using CDCl3 as the solvent. |
76% | With trimethylsilylazide; copper(ll) bromide; In acetonitrile; at 80℃; for 3h;Sealed tube; | In a round bottom flask was added 2- methoxybenzaldehyde (1.0 mmol), acetonitrile (2ml), trimethylsilyl azide (3.0mmol), stirred at 80 deg.] C heating block for 1-2 minutes, then added CuBr2(2.0mmol), and then the system was sealed and heated at 80 , 3 hours, and extracted with ethyl acetate, after completion of the reaction, was concentrated by a simple column chromatography (eluent petroleum ether (60 ~ 90 ) and a mixed solvent of ethyl acetate) to give the product 2-methoxy-benzonitrile, a yield of 76%. |
70% | With trifluorormethanesulfonic acid; trimethylsilylazide; In acetonitrile; at 20℃; for 1h;Sealed tube; Inert atmosphere; | General procedure: To a solution of an aromatic aldehyde 1 (0.500 mmol, 1.0 equiv) and TMSN3 (115 mg, 1.00 mmol,2.0 equiv) in a premixed HFIP/ACN mixture (2.0 mL, 1:1) in a nitrogen-flushed two dram vial wasadded triflic acid (TfOH; 17.7 L, 0.200 mmol, 0.40 equiv) (exotherm and brisk effervescence due tonitrogen gas evolution was immediately observed). The vial was capped and the reaction mixture wasallowed to stir at rt for 20-75 min. The reaction mixture was concentrated under nitrogen. The residueobtained was suspended in CH2Cl2/hexanes mixture and loaded on a silica gel in a 5 g samplecartridge. Purification using a normal phase silica flash column on a CombiFlash purification systemafforded a corresponding aromatic nitrile 2 upon concentration of appropriate fractions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In glycerol; | (5g) 5-hydroxy-2-(2-methoxyphenyl)-1,3-dioxane: Using the method of Example 5e, 40.8 g 2-methoxybenzaldehyde and 27.6 g glycerol were reacted to form 5-hydroxy-2-(2-methoxyphenyl)-1,3-dioxane, crude b.p. 150-155 C/10-5 mm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 238 4-Methoxy-3-(2-methoxy-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 2-methoxybenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 177-179 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | General procedure: N-Pivaloyl-4-chloroaniline (33, 595 mg, 2.81 mmol) was dissolved in THF (50 ml), and the solution was added sec-butyl lithium c-hexane, n-hexane solution (0.99 M, 5.96 ml, 6.18 mmol) at -78 C, and then stirred at 0 C for 2 h. The mixture was added 2-chloro-3-fluoro-benzaldehyde (490 mg, 3.09 mmol) at the same temperature for 30 min. The reaction mixture was poured saturated with NH4Claq and AcOEt. The organic layer was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (n-hexane/AcOEt = 9:1) to give the title compound (676 mg, 65%) as light yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; | 4-(2-methoxyphenyl)-7,7-dimethyl-3-(trifluoromethyl)-6,7,8,9-tetrahydro-2H-pyrazolo[3,4-b]quinolin-5(4H)-one 5,5-Dimethylcyclohexane-1,3-dione (824 mg, 5.88 mmol), 2-methoxybenzaldehyde (800 mg, 5.88 mmol) and <strong>[852443-61-9]3-(trifluoromethyl)-1H-pyrazol-5-amine</strong> (1199 mg, 7.93 mmol) were mixed together in a microwave vial and ethanol (14.7 mL, 0.4 M) was added to it. The reaction mixture was heated in microwave for 15 min at 150 C. The mixture was cooled and the solvent was evaporated. The resultant mixture was then purified by column chromatography over silica gel (hexane/ethyl acetate: 100/0 to 20/80) to afford the desired product as a white solid (372.0 mg). 1H NMR (300 MHz, MeOD) delta 7.19 (d, J=7.4 Hz, 1H), 7.12-7.03 (m, 1H), 6.78 (dd, J=13.8, 7.4 Hz, 2H), 5.39 (s, 1H), 3.67 (s, 3H), 2.56 (d, J=16.8 Hz, 1H), 2.42 (d, J=16.7 Hz, 1H), 2.24 (d, J=16.5 Hz, 1H), 2.04 (d, J=16.5 Hz, 1H), 1.08 (s, 3H), 0.97 (s, 3H). LRMS (ESI+) (M+): 391.82. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Ammonium salt 6 (1 equiv.) was suspended in dry THF (0.05 M) andstirred at 40 °C. t-BuOK (4 equiv.) was added and the mixture was stirred vigorously. After 10 minutes 2 equiv. of aldehyde 2 were added and the mixture was stirred for 3 hours at 40 °C. The reaction was then quenched by addition of a half-saturated NaCl solution. After phase separation, the aqueous phase was extracted three times with DCM and the combined organic phases were dried with Na2SO4 and evaporated to dryness. Purification by columnchromatography (gradient of heptanes and EtOAc) gave the corresponding epoxides in the reported yields as a mixture of diastereomers. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ethanol; for 0.0166667h;Sonication; | General procedure: Solutions of <strong>[7504-94-1]2-hydrazinylpyrimidine</strong> (70 mg; 0.64 mmol) in ethanol (3 mL), and the benzaldehyde (0.77 mmol) in ethanol (2 mL) were mixed and ultrasonically irradiated for 1.0-2.5 min. After the ultrasonic irradiation, the resulting mixture was concentrated under reduced pressure; the residue was washed with cold ethanol and water. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With toluene-4-sulfonic acid; In hexane; at 65℃; for 20h; | In a 100 mL three-necked flask, o-methoxybenzaldehyde (3.404 g, 0.025 mol), <strong>[13395-85-2]2-tert-butyl-p-chlorophenol</strong> was added.(8.212 g, 0.05 mol), p-toluenesulfonic acid (0.075 g). The solid was dissolved by stirring with 50 mL of n-hexane. temperature reflexThe temperature was raised from room temperature to 65 oC, and the reaction was continued for 20 h under reflux. Allow the reaction mixture to cool to room temperature and add 15 ml of saturatedAfter washing with a NaHCO3 solution, the organic layer was separated, and the organic layer was dried over anhydrous MgSO? The yield was 88%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With indium(III) chloride; In ethanol; at 120℃; for 0.166667h;Microwave irradiation; | General procedure: A mixture of <strong>[1004-38-2]2,4,6-triaminopyrimidine</strong> 1 (1.0 mmol), 3-(2-cyanoacetyl)indole 2 (1.0 mmol), appropriate aromatic aldehyde (1.0 mmol) and indium chloride (0.05 mmol) in ethanol (5.0 mL) were subjected to microwave irradiation for 10 min at 120 C. After completion of the reaction (monitored by TLC using a dichloromethane-ethanol (9:1) mixture as the mobile phase), the reaction mixture was cooled and filtered. The solid product obtained was initially washed with ethanol, and finally recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.7% | With toluene-4-sulfonic acid; In toluene; at 200℃; for 3h;Molecular sieve; High pressure; Sonication; Autoclave; Sealed tube; | General procedure: General synthetic process was as follows: to a 10mL toluenesolution of <strong>[120068-37-3]Fipronil</strong> (4.37 g, 20 mmol), added a certain amount ofbenzaldehyde derivatives (21 mmol) in toluene (25 mL) and activated4 A molecular sieve (2 g), p-toluenesulfonic acid (1 mmol)was added as a catalyst, ultrasonic stirring for 0.5 h, and thentransferred the reaction mixture into a dried 100mL Teflon-linedautoclave and heated with the rate of 1 C/min to the reactiontemperature in the electric oven and kept for a few hours. Theresulting solution was then cooled to room temperature, andremoved 4 A molecule sieve through filtration, the filtrate waswashed with saturated sodium carbonate solution (50 mL), waterand saturated brine, respectively, and then dried over MgSO4. Thefiltrate was concentrated by rotary evaporation, and adsorbed onactivated silica gel. The crude product was obtained by columnchromatography on silica gel with Vethyl acetate/Vpetroleum ether(1:10e20) as the eluent, which was dried under vacuum. |