*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
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.
Indole-3-carboxaldehyde (3-Formylindole) is a compound in Radix Isatidis extract that enhances intestinal epithelial barrier function and has anti-inflammatory activity.
Synonyms: 3-Formylindole; Indole-3-formaldehyde; NSC 10118
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
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'.
CAS No. : | 487-89-8 |
Formula : | C9H7NO |
M.W : | 145.16 |
SMILES Code : | O=CC1=CNC2=C1C=CC=C2 |
Synonyms : |
3-Formylindole; Indole-3-formaldehyde; NSC 10118
|
MDL No. : | MFCD00005622 |
InChI Key : | OLNJUISKUQQNIM-UHFFFAOYSA-N |
Pubchem ID : | 10256 |
GHS Pictogram: |
![]() |
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 |
---|---|---|
88%Chromat. | With sodium hydroxide; In isopropyl alcohol; at 82℃; for 2h; | General procedure: In a typical procedure, a 5 mg (0.77 mol%) of RuO2/MWCNT and 80 mg (2 mmol) of NaOH were stirred with 5 mL of i-PrOH taken in an ace pressure tube equipped with a stirring bar. Then the substrate (1 mmol) was added to the stirring solution and then the mixture was heated at 82C. The completion of the reaction was monitored by GC. After the reaction, the catalyst was separated out from the reaction mixture by simple centrifugation and the products and unconverted reactants were analyzed by GC without any purification. Selectivity of the product for each reaction was alsocalculated. Finally, the separated RuO2/MWCNT was washed well with diethyl ether followed by drying in an oven at 60C for 5 h and it was reused for the subsequent transfer hydrogenation of carbonyl compounds to investigate the reusability of the RuO2/MWCNT. |
With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 20℃; for 3h; | General procedure: To a solution of a compound 11a-11d (10 mmol) in 20 mL of DMF, phosphorus oxychloride (1.4 mL, 15 mmol) was added dropwise at 0C. Upon 2 h of the process at 55C, the mixture was poured into 150 mL of ice water. Then 20 % NaOH solution was added to adjust pH at 8.0. The crude product was filtered off and recrystallized from anhydrous ethanol to give the corresponding product. Compounds 12a-12d (10 mmol) were dissolved in 20 mL of EtOH/THF (1: 1), and sodium boron hydride was added to the reaction mixture in portions. Upon stirring the mixture for 3 h, 20 mL of saturated Na2CO3solution was added to quench the reaction. In 10 min the mixture was extracted by 30 mL of ethyl acetate, then the organic layer was washed with 30 mL of saturated sodium chloride solution. The organic layer was concentrated in vacuum to give the corresponding solid product 13a-13d. (1H-Indol-3-yl)methanol (13a). White solid, yield 91 %, mp 97-98C (lit. 99-100C). 1H NMR spectrum, delta, ppm: 4.64 d (J = 5.0 Hz, 2H, CH2), 4.74 t (J = 5.0 Hz, 1H, OH), 6.98 t (J = 7.5 Hz, 1H, ArH), 7.07 t (J = 7.5 Hz, 1H, ArH), 7.23 s (1H, CH-N), 7.35 d (J = 8.5 Hz, 1H, ArH), 7.59 d (J = 7.5 Hz, 1H, ArH), 10.90 s (1H, NH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Indole-3-carboxaldehyde (189 mg, 1.3 mmol) and NH4OH .bul. HCl (113 mg, 1.63 mmol) were dissolved in a Parr flask with 15 mL of MeOH, which was previously saturated with anhydrous ammonia. The flask was stoppered and placed on a Parr shaker for 5 hours. To the resulting solution was added 200 mg of Raney Nickel (50percent slurry in H2O) and the flask was pressurized to 60 psi with H2 and allowed to shake overnight. The next day, the resulting mixture was filtered through celite and volatiles were removed to yield a yellow solid, 190 mg (100percent yield). The product was unstable, so it was used immediately in subsequent reactions without further purification. 1H NMR (CDCl3/CD3OD) delta 8.04 (br s, 1H, NH), 7.67 (d, 1H, ArH, J=7.8), 7.39 (d, 1H, ArH, J=7.1), 7.16 (3H, ArH), 4.07 (d, 2H, ArCH2 J=7.4 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With LACTIC ACID; dihydrogen peroxide; at 30℃; for 7h; | General procedure: A mixture of alcohol (1 mmol) and lactic acid (1 mL) was charged in 25 mL round bottom flask subjected to constant magnetic stirring at room temperature (30C). The reaction mixture was further activated by addition of 30% H2O2 (1.07 equiv.). The reaction progress was monitored by GC. After completion of the reaction, Dichloromethane (2×6 mL) was added to the reaction mixture and then washed with distilled water (2×2mL). The organic layer was separated and dried over Na2SO4 and removed under reduced pressure. The crude product was obtained by evaporation method and again purified by column chromatography using ethyl acetate and n-hexane as eluting system. |
82% | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate; In water; acetonitrile; at 20℃; for 6h;Green chemistry; | General procedure: A mixture of alcohol (5.0 mmol), Cu(OAc)2 (9.1 mg, 0.05 mmol), and TEMPO (7.8 mg, 0.05 mmol) in CH3CN/H2O (5/10 mL) was stirred at room temperature for specified time. After completion of the reaction (monitored by TLC, eluents: petroleum ether/ethyl acetate = 4/1), dichloromethane (10 mL) was added to the resulting mixture. The dichloromethane phase was separated, and the aqueous phase was further extracted with dichloromethane (10 mL × 2). The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give a residue, which was purified by column chromatography (eluents: petroleum ether/ethyl acetate = 10/1) to provide the desired product. |
72% | With magnetic polydopamine-wrapped Fe3O4 core-shell submicrosphere-supported nano-palladium; air; In o-xylene; at 120℃; for 24h;Sonication; | General procedure: Approximately 0.1 g of Fe3O4(at)PDAPd catalyst (2 mol% of Pd) was used. The aforementioned solidand liquor were separated using a magnet and placed under ultrasonic washing using 10 mL 3O-xylene. Then, 1 mmol of benzyl alcohol derivative and 5 mL of O-xylene were successively added and blended under ultrasonic conditions. The mixture was then magnetically stirred for 24 h under 120 C. After the reaction ended, the solid and liquor were separated using a magnet. The liquor wasconcentrated, and the dehydrogenation product could be obtained after purification through column chromatography (petroleum ether/ethyl acetate). |
43% | With 4,5,6,7-tetrachloro-2',4',5',7'-tetraiodofluorescein disodium salt; oxygen; ammonium thiocyanate; In acetonitrile; at 20℃; for 20h;Irradiation; | General procedure: A glass vial fitted with magnetic stirrer and a magnetic bar containing a reaction mixture of alcohol (0.1 mmol), NH4SCN (3 eq.), catalyst (5 mol%) and 2 ml of solvent. The vial was closed with rubber septum and O2 was bubbling for 15 minutes using needles. The reaction mixture was irradiated under a 23W CFL lamp for a certain time period. Reaction progress was monitored by TLC. After, completion of the reaction, a yellow solid was formed. The reaction mixture of three vials with the same content were combined and filter it through whatman filter paper. The mixture was evaporated under reduced pressure and purified by column chromatography using hexane/ethyl acetate as eluent. Further, the reaction mixture was run on a GC-MS instrument for characterisation. Yield, conversion and selectivity were calculated using following equations. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In ethanol; acetone; | EXAMPLE 71 (E)-1-(4-Benzyloxy-3,5-dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-one (Compound 71) 4'-Hydroxy-3',5'-dimethoxyacetophenone (1.57 g) and benzyl bromide (1.35 g) were dissolved in acetone (50 ml), and potassium carbonate (1.70 g) was added thereto, followed by heating under reflux for 24 hours. Insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was washed with hexane and collected by filtration. The obtained crystals (1.96 g) and indole-3-carboxaldehyde (0.99 g) were dissolved in ethanol (10 ml), and piperidine (0.85 g) was added thereto, followed by heating under reflux for 32 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 71 (0.17 g). 1 H-NMR (270 MHz, DMSO-d6) delta3.92 (s, 6H), 5.03 (s, 2H), 7.21-7.25 (m, 2H), 7.31-7.41 (m, 5H), 7.45-7.52 (m, 3H), 7.63 (d, J=15.3 Hz, 1H), 8.05 (m, 1H), 8.06 (d, J=15.3 Hz, 1H), 8.15 (d, J=3.0Hz, 1H), 11.91 (s, 1H) EI-MS m/z=413 (M+) Elemental analysis: C26 H23 NO4 Calcd.(%): C, 75.53; H, 5.61; N, 3.39 Found (%): C, 75.41; H, 5.45; N, 3.38 | |
With potassium carbonate; In ethanol; acetone; | Example 3 (E)-1-(4-Benzyloxy-3,5-dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-one (Compound 3) 4'-Hydroxy-3',5'-dimethoxyacetophenone (1.57 g) and benzyl bromide (1.35 g) were dissolved in acetone (50 ml), and potassium carbonate (1.70 g) was added thereto, followed by heating under reflux for 24 hours. Insoluble matters were filtered off, and the filtrate was concentrated under reduced pressure. The residue was washed with hexane and collected by filtration. The obtained crystals (1.96 g) and indole-3-carboxaldehyde (0.99 g) were dissolved in ethanol (10 ml), and piperidine (0.85 g) was added thereto, followed by heating under reflux for 32 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from a mixed solvent of ethyl acetate and hexane to give Compound 3 (0.17 g). 1H-NMR (270 MHz, DMSO-d6) delta 3.92 (s, 6H), 5.03 (s, 2H), 7.21-7.25 (m, 2H), 7.31-7.41 (m, 5H), 7.45-7.52 (m, 3H), 7.63 (d, J = 15.3 Hz, 1H), 8.05 (m, 1H), 8.06 (d, J = 15.3 Hz, 1H), 8.15 (d, J = 3.0Hz, 1H), 11.91 (s, 1H) EI-MS m/z = 413 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; | EXAMPLE 70 (E)-1-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-one (Compound 70) 4'-Hydroxy-3',5'-dimethoxyacetophenone (1.96 g) and indole-3-carboxaldehyde (1.45 g) were dissolved in ethanol (20 ml), and piperidine (0.85 g) was added thereto, followed by heating under reflux for 32 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from ethyl acetate to give Compound 70 (0.62 g). 1 H-NMR (270 MHz, DMSO-d6) delta3.91 (s, 6H), 7.19-7.26 (m, 2H), 7.40 (s, 2H), 7.48 (m, 1H), 7.65 (d, J=15.6 Hz, 1H), 8.02 (d, J=15.6 Hz, 1H), 8.05 (m, 1H), 8.11 (d, J=2.5 Hz, 1H), 9.26 (s, 1H), 11.91 (s, 1H) EI-MS m/z=323 (M+) Elemental analysis: C19 H17 NO4 Calcd.(%): C, 70.57; H, 5.30; N, 4.33 Found (%): C, 70.56; H, 5.34; N, 4.38 | |
In ethanol; | Example 2 (E)-1-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(indol-3-yl)-2-propen-1-one (Compound 2) 4'-Hydroxy-3',5'-dimethoxyacetophenone (1.96 g) and indole-3-carboxaldehyde (1.45 g) were dissolved in ethanol (20 ml), and piperidine (0.85 g) was added thereto, followed by heating under reflux for 32 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The obtained crude crystals were recrystallized from ethyl acetate to give Compound 2 (0.62 g). 1H-NMR (270 MHz, DMSO-d6) delta 3.91 (s, 6H), 7.19-7.26 (m, 2H), 7.40 (s, 2H), 7.48 (m, 1H), 7.65 (d, J = 15.6 Hz, 1H), 8.02 (d, J = 15.6 Hz, 1H), 8.05 (m, 1H), 8.11 (d, J = 2.5 Hz, 1H), 9.26 (s, 1H), 11.91 (s, 1H) EI-MS m/z = 323 (M+) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium sulfate; triethylamine; In tetrahydrofuran; at 80℃; for 33h;Microwave irradiation; | General procedure: In a 20 mL glass tube equipped with septa, the aldehyde, dry Na2SO4 (2.81 equiv) and triethylamine (2 equiv) were suspended in dry THF. Then, the hydroxylamine hydrochloride (2 equiv) was added. The mixture was stirred for 30 s, and then exposed to MWI (250 W) at 80 °C during the time indicated for each compound. When the reaction was over (TLC analysis), the reaction mixture was diluted with water, extracted with CH2Cl2, dried over anhydrous sodium sulphate, filtered and the solvent was evaporated. The resultant solid was purified by column chromatography to give pure compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67.8% | In ethanol;Reflux; | General procedure: solutionof acid hydrazide (0.01 mol) and appropriate benzaldehyde/acetophenone (0.01 mol) in ethanol was refluxed for 5-6 h. The precipitated title compounds were then filtered off, washed with water and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium ethanolate; In ethanol; at 20℃; | General procedure: Various aldehydes (1.0 equiv) were added to stirred solutions of indolin-2-one, 5-chloroindolin-2-one or <strong>[5654-97-7]7-azaoxindole</strong> (1.0equiv) in absolute ethanol. After stirring at room temperature for 5 min NaOEt/EtOH (0.5 mL) was added and the mixture was then stirred at room temperature overnight. The solvent was then removed under vacuum. The residue was washed with saturated sodium chloride solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under vacuum. The solid part was purified by chromatography over silica gel using ethyl acetate/petroleum ether as the eluent to afford desired compounds 1a-1g, 2a, 3a. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With sodium hydroxide; In methanol; at 20℃; | General procedure: To a solution of indol-3-carboxaldehyde 5 (1 mmol) and appropriate acetophenone 4 (1 mmol) in anhydrous methanol (20 mL) was added 10%-40% sodium hydroxide (2 mL) and stirred the reaction mixture at RT for 2-8 h. The contents of reaction mixture were poured into ice-cold water and neutralized with dilute hydrochloric acid. The solid so obtained was filtered, column chromatographed and recrystallized from ethanol to afford pure 1(a-j) viz Trans-3-(1H-indol-3-yl)-1-(benzofuran)-2-propen-1-one (1a), Trans-3-(1H-indol-3-yl)-1-(2?-hydroxyphenyl)-2-propen-1-one (1b), Trans-3-(1H-indol-3-yl)-1-(2?-chlorophenyl)-2-propen-1-one (1c), Trans-3-(1H-indol-3-yl)-1-(4?-allyloxyphenyl)-2-propen-1-one (1d), Trans-3-(1H-indol-3-yl)-1-(4?-allyloxy-2?-hydroxyphenyl)-2- propen-1-one (1e), Trans-3-(1H-indol-3-yl)-1-(4?-flouro-3?-methylphenyl)-2-propen-1-one (1f), Trans- 3-(1H-indol-3-yl)-1-(4?-benzyloxyphenyl)-2-propen-1-one (1g), Trans-3-(1H- indol-3-yl)-1-(3?- allyloxyphenyl)-2-propen-1-one (1h), Trans-3-(1H-indol-3-yl)-1-(4?-chlorophenyl)-2-propen-1-one(1i) and Trans-3-indolyl-3-(anthracenyl)-2-propen-1-one (1j) . Spectral data of the compounds 1(a-j) was compared with the reported data in the literature by Gaur et al 2015. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With hydrogen trititanate; In neat (no solvent); at 20℃; for 0.25h;Green chemistry; | General procedure: Dialkyl/diaryl phosphite (1.0 mmol) was added portion wise over a period of 5 min to the stirred mixture of heterocyclic aldehyde (1.0 mmol) and benzothiazole amine (1.0 mmol) at room temperature. Further 5 mol percent of TNT was added to the reaction mixture and the stirring was continued for 15 min. After the completion of the reaction as monitored through TLC, the reaction mixture was dissolved in EtOAc (2 mL) and the catalyst was separated by centrifugation followed by subsequent washings with EtOAc. The recovered catalyst was reused for the next cycle. The filtrate was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated on a rotary evaporator and the resulting residue was purified by silica gel column chromatography (70:30, hexane/EtOAc) to afford the corresponding pure alpha-aminophosphonate. The novel alpha-aminophosphonates were structurally assigned by their IR, NMR (1H, 13C & 31P), and mass spectral (HRMS) analyses. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.9 mg; 1.3 mg; 1.1 mg; 0.8 mg; 5.9 mg; 2.0 mg; 1.0 mg; 2.1 mg; 2.3 mg; 1.1 mg; 1.1 mg; 0.9 mg; 1.1 mg; 1.2 mg; 1.7 mg | With Angelica sinensis (Oliv.) Diels callus; In methanol; for 168.0h; | General procedure: Isofraxetin-6-O-beta-D-glucopyranoside (859 mg) was dissolved in CH3OH (86.0 mL) and distributed into 59 bottles of the suspension cultures of A. sinensis callus equally. The mixture was co-cultured for 7 days, then the cells and medium were separated by filtration. The medium was concentrated to 200 mL and partitioned by the same volume of EtOAc (ethylacetate) and n-BuOH (n-butyl alcohol) successively for three times. Next, the organic phase was collected and concentrated under the reduced pressure toyield EtOAc extract (Fr. 1, 0.25 g) and n-BuOH extract (Fr. 2, 1.20 g) respectively. The cells were dried under 50C, and then were extracted in an ultrasonic bath with CH3OH for 30 min. After that, the extract was further partitioned by EtOAc and n-BuOH respectively to afford EtOAc extract (Fr. 3,0.62 g) and n-BuOH extract (Fr. 4, 1.46 g). Compared with the experimental group, cultures and medium without isofraxetin-6-O-b-D-glucopyranoside act as control group and was processed to get Fr. 5-8 by the same procedures. The combination of Fr. 1 and Fr. 3 (EE, 0.87 g) was subjected on ODS column chromatography (CC) with gradient elution CH3OH/H2O (from 0:100 to 100:0) to get five subfractions (Fr. 1a-5a). Next, Fr. 1a was separated by HPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) eluted with CH3OH/H2O(49: 51) to afford compounds 5 (2.1 mg, tR = 14 min), 6 (2.3 mg, tR = 18 min)and 3 (5.9 mg, tR = 39 min). Fr. 2a was firstly fractioned by silica gel CC(3 50 cm) with gradient elution petroleum/acetone (0:100-100:0) to get substraction 2a-1 and 2a-2. Then Fr. 2a-1 was purified by HPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) with CH3CN/H2O (37: 63) to provide compounds 8 (1.0 mg, tR = 22 min), 10 (1.1 mg, tR = 27 min) and 14(1.2 mg, tR = 35 min). While compound 15 (0.9 mg, tR = 25 min) was purifiedfrom substration Fr. 2a-2, using HPLC with ODS column (250 mm 10 mm,flow rate 3 mL/min) eluted with CH3CN/H2O (39: 61). And Fr. 3a was chromatographied on HPLC with ODS column (250 mm 10 mm, flow rate3 mL/min) to yield compounds 9 (1.1 mg, tR = 40 min) and 11 (0.9 mg,tR = 56 min) using CH3OH/H2O (35: 65) as elute. However, compounds 12(0.8 mg, tR = 37 min) and 13 (1.3 mg, tR = 49 min) were obtained from Fr. 4a byHPLC with ODS column (250 mm 10 mm, flow rate 3 mL/min) using CH3CN/H2O (8:92) as eluting solvent. Equally, Fr. 2 and Fr. 4 was combined as BE(2.66 g) to subject on ODS CC with CH3OH/H2O (from 0:100 to 100:0) to getseven fractions (Fr. 1b-7b). Fr. 1b was isolated using HPLC with ODS column(250 mm 10 mm, flow rate 3 mL/min) eluted by CH3OH/H2O (20: 80) andthen purified by Sephadex LH-20 chromatography eluted with CH3OH to afford compounds 1 (1.1 mg) and 2 (1.7 mg). Furthermore, compound 4 (2.0 mg) wasobtained from Fr. 3b by recrystallization in CH3OH. Next, Fr. 4b was subjectedon silica gel CC (3 50 cm) with gradient elution CH2Cl2/CH3OH (0:100-100:0)to get substraction Fr. 4b-1 and Fr. 4b-2. Then Fr. 4b-1 was purified by HPLCwith ODS column (250 mm 10 mm, flow rate 3 mL/min) with CH3CN/H2O(13: 87) to provide compounds 7 (1.1 mg, tR = 19 min) and 16 (1.8 mg,tR = 39 min). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With chitosan; In neat (no solvent); at 75℃; for 0.05h;Microwave irradiation; Green chemistry; | General procedure: An equimolar mixture of <strong>[54396-44-0]2-methyl-3-(trifluoromethyl)aniline</strong> (0.351 g, 0.002 mol), corresponding aldehyde (0.002 mol), dimethyl phosphite (0.18 ml, 0.002 mol) and chitosan catalyst (10 molpercent) were taken in a reaction glass tube, degassed for 10 min and microwave irradiated at 180 W for 2 min at 60 °C. The progress of the reaction was monitored by TLC using petroleum ether and ethyl acetate (3:7) as solvent. After completion of the reaction, the mixture was diluted with ethyl acetate, washed with water (2 x 15 ml) followed by brine (1 x 10 ml), dried over Na2SO4 and evaporated to dryness. The crude mass was purified by column chromatography on silicagel (100-200 mesh) by using a 7:3 mixture of ethyl acetate in hexane to afford the pure alpha-aminophosphonates. |
Tags: Indole-3-carboxaldehyde | 3-Formylindole | Aldehydes | Indoles | Organic Building Blocks | Heterocyclic Building Blocks | 487-89-8
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