Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 18514-52-8 | MDL No. : | MFCD00064109 |
Formula : | C4H4N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 108.10 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
0.18 mg | With ferric sulfate nonahydrate In water at 80℃; for 24 h; | General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.18 mg | With ferric sulfate nonahydrate In water at 80℃; for 24 h; | General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.01 mg | at 80℃; for 24 h; | General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.9 mg | at 80℃; for 24 h; | General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1,2-diamino-1,2-dicyanoethylene (25 g) and glyoxylic acid monohydrate (21.3 g) were dissolved in 2N-hydrochloric acid (240 ml), and the solution was stirred at room temperature for 4 hours and then concentrated under reduced pressure. To the residue, an aqueous 10% sodium hydroxide solution (600 ml) was added and, after heating at reflux for 13 hours, the reaction solution was ice-cooled and neutralized with concentrated hydrochloric acid. The resulting ocher precipitate was collected by filtration and then washed with water and acetone. The crude product was suspended in acetic acid (800 ml) and heated at reflux at 120C for 2 hours. The reaction mixture was returned to room temperature and filtered, and then the filtrate was concentrated. The resulting precipitate was collected by filtration and washed with ether. After ice cooling methanol (600 ml), thionyl chloride (60 ml) was added dropwise, followed by stirring at room temperature for one hour, the addition of the crude product and further stirring at 80C. The reaction solution was concentrated and then purified by silica gel column chromatography (chloroform:methanol = 10:1 to 5:1) to obtain the objective product (8.0 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In ethanol; water at 60℃; for 3h; | To a solution of ninhydrin (18,58 g, 104.3 mmol) in H2O/EtOH/AcOH (130:195:9.1; 167 ml) a solution of diaminomaleodinitrile (11.27 g, 104.3 mmol) in H2O/EtOH/AcOH (130:195:9.1; 167 ml) was added and the mixture was stirred at 60° C. After 3 hours, the precipitate was collected by filtration, washed with EtOH (100 ml) and dried under vacuum, affording 1 (23.64 g, 98%) as yellow-brown solid. 1H NMR (300 MHz, CDCl3): δ 8.07 (d, 1H), 7.98 (d, 1H), 7.87 (dd, 1H), 7.77 (dd, 1H). ESI+MS: calcd for C13H4N4O: 232.20; found: 233.0 (MH+). |
57% | With acetic acid In ethanol; water at 0 - 20℃; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In acetonitrile at 20℃; for 16.1667h; | 5.1.112.A A. (Z)-l-(2-Amino-l,2-dicyanovinyl)-3-(biphenyl-2-yl)urea.; In a round bottom flask, 2,3-diaminomaleonitrile (1.0 g, 9.25 mmol) was dissolved in acetonitrile (35 mL) and stirred at room temperature. 2-Biphenyl isocyanate (1.80 g, 9.25 mmol) in acetonitrile (5 mL) was added dropwise over 10 minutes and the reaction stirred at room temperature. After 16 hours, the solution was condensed under reduced pressure and the resultant solid purified using Biotage silica chromatography (0-100% ethyl acetate in hexanes) to afford the title compound (1.48 g, 53%). MS (ESI) m/z 304.3 [M+l]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In acetonitrile at 20℃; for 16h; | 5.1.19.A A. (Z)-l-(2-Amino-l,2-dicyanovinyl)-3-(2,4-dichlorophenyl)urea.; In a round bottom flask, 2,3-diaminomaleonitrile (1.0 g, 9.26 mmol) was dissolved in acetonitrile (20 mL) and stirred at room temperature. 2,4-Dichlorophenylisocyanate (1.82 g, 9.72 mmol) was added and the solution was stirred at room temperature for 16 hours. The resultant urea product was collected by filtration, washed with small portions of acetonitrile followed by diethyl ether. The filtered material was dried under high vacuum at 60 0C overnight to yield the title compound (2.15 g, 79%). 1H NMR (300 MHz, DMSO-J6) δ 8.41 (d, J=4.8, 2H), 8.14 (d, 8. 7, IH), 7.63 (d, J=27, IH), 7.39 (dd, IH), 7.32 (bs, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With trifluoroacetic acid | |
With trifluoroacetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With acetic acid at 150℃; for 12h; | |
88% | In ethanol for 6h; Reflux; | |
85% | In neat (no solvent) at 20℃; for 5h; Green chemistry; | 2.1. Preparation of Pyrazine Derivative General procedure: 1 mmol of recrystallised benzil and 2mmol of ethylenediamine were added to a mortar. The mixture was grinded for a few minutes and transferred to a 50 ml round bottom flask and was kept stirring with a magnetic spinning bar for 6 hrs.The reaction was checked by TLC (ethylacetate and pet-ether). The product was extracted by ethylacetate, washed by water and filtered through Na2SO4. Product was purified by column chromatography using Silica-gel. Petroleum ether-Ethylacetate(PE-EA)mixtures were used as eluent. All the products were characterized by IR, 1H NMR and 13C NMR. |
85% | With silica gel In water at 20℃; for 5h; Green chemistry; | Preparation of 2, 3-disubstituted pyrazines Typical procedure General procedure: Ethylenediamine (1 mmol), benzil (1 mmol), and the silica gel (1 g) were mixed in a mortar and the mixture was grinded for a few minutes in the presence of 2-3 drops of water. Finally, the mixture was transferred to a 50 mL round bottom bottle and was kept under magnetic stirrer at room temperature for 6 h. The completion of reaction was monitored by TLC. Ethyl acetate (3×15 ml) was added to the reaction mixture and the extract was filtered through anhydrous Na2SO4. Finally, 2,3-diphenylpyrazine was isolated by column chromatography over silica gel (60-120 mesh) where pet ether and ethyl acetate mixture was used as eluent. |
85% | With acetic acid at 80 - 90℃; for 3h; | |
83.72% | With toluene-4-sulfonic acid In ethanol for 5h; Reflux; | 1 Synthesis of α-dicyano derivatives (1-5): a general procedure General procedure: A solution of benzil (0.036 mol), DAMN (4.73 g, 0.044 mol) and p-toluenesulfonic acid (0.02 g) in EtOH (50 ml) was refluxed for 5 h. In the end of reaction a dark cream colored suspension was achieved. The crude mixture was filtered off and washed with MeOH. The crude product was recrystallized from mixture solution of CCl4/CHCl3; 1:1 to lead pure compound 1. The other dicyano compounds 2-5 were synthesized via similar manner from phenanthraquinone, dinitrobenzil, dinitro phenanthraquinone and 1,4-benzodialdehyde respectively, the recrystallization solution for compound 2 was o-dichlorobenzene and for compounds 3-5 was 96% EtOH. |
80% | With silica gel at 20 - 100℃; for 2h; Neat (no solvent); | |
Acidic conditions; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.9% | With piperidine In benzene for 8h; Reflux; Dean-Stark trap; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.7% | With piperidine In benzene for 8h; Reflux; Dean-Stark trap; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium fluoride on basic alumina at 20℃; for 5h; | General procedure for condensation and substitution of α-bromo ketone with o-phenylenediamine: General procedure: A mixture of 1,2-diamine (1 mmol) and α-bromo ketone (1 mmol) was intimately mixed with pre-activated KF-alumina (1:4) (0.5 g) (Basic; Grade: Brockmann 1, and activated by heating under vacuum at 150 °C until bubbling ceases and then cooled to room temperature under vacuum) and stirred the solid mixture with a magnetic spin bar at room temperature for hours as indicated in refPreviewPlaceHolderTable 3. After the reaction was complete, the solid mixture washed with diethyl ether (3 × 10 mL) and the solid was filtered off. The filtrate was concentrated and passed through a short column of silica gel to afford the quinoxalines. The desired product was pure on TLC and characterized by spectral (1H and 13C NMR) data and compared to those reported. |
84% | With polymeric resin-bound hexafluorophosphate ion In methanol; water at 20℃; for 5h; | General procedure for quinoxalines General procedure: In a typical experimental procedure, o-phenlylenediamine and α-bromo ketone in 1:1 molar ratios was taken in a 100 mL round bottom flask. To this water-methanol (1:1) and 100 mg PHP was admixed. The reaction mixture was then allowed to stir with magnetic spinning bar, after some time a yellowish mass appeared which settles down like a precipitate after the completion of the reaction (checked by TLC). It was then filtered; the solid reaction mixture was dissolved with dichloromethane (25 mL) and evaporated under vacuum. The crude product was then crystallised from ethanol. The desired product was pure on TLC and characterized by spectral (IR, 1H and 13C NMR) data and compared to those reported in literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | General procedure: A mixture of oxalaldehyde (1 mmol) 2,3-diaminomaleonitrile (1 mmol), sodium azide (3 mmol) in DMSO (2 mL) was stirred at 100 C for 6 h. After completion of the reaction confirmed by TLC (eluent: EtOAc/n-hexane, 1:1), the solvent was evaporated under reduced pressure. To the participate was added 20 mL of 2 N HCl with vigorous stirring causing the 2,3-di(1H-tetrazole-5-yl) pyrazine to precipitate. The precipitate was filtered and dried in a drying oven to furnish the 2,3-di(1H-tetrazole-5-yl) 5a as white powder (0.20 g, yield 93%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: phenylglyoxal hydrate; 2,3-diaminomaleonitrile With sodium azide In dimethyl sulfoxide at 100℃; for 3h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide | 4.1.6. Typical procedure for the preparation of 2,3-di(1H-tetrazole-5-yl)pyrazine (5a) General procedure: A mixture of oxalaldehyde (1 mmol) 2,3-diaminomaleonitrile (1 mmol), sodium azide (3 mmol) in DMSO (2 mL) was stirred at 100 °C for 6 h. After completion of the reaction confirmed by TLC (eluent: EtOAc/n-hexane, 1:1), the solvent was evaporated under reduced pressure. To the participate was added 20 mL of 2 N HCl with vigorous stirring causing the 2,3-di(1H-tetrazole-5-yl) pyrazine to precipitate. The precipitate was filtered and dried in a drying oven to furnish the 2,3-di(1H-tetrazole-5-yl) 5a as white powder (0.20 g, yield 93%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 1,2-bis(4-methoxyphenyl)-1,2-ethanedione; 2,3-diaminomaleonitrile With sodium azide In dimethyl sulfoxide at 100℃; for 3h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide | 4.1.1. Typical procedure for the preparation of 3-(1H-tetrazole-5-yl) pyrazine-2-carbonitrile (3a) General procedure: A mixture of oxalaldehyde (1 mmol), 2,3-diaminomaleonitrile (1 mmol), and sodium azide (1.5 mmol) in DMSO (2 mL) was stirred at 100 °C for 3 h. After completion of the reaction confirmed by TLC (eluent: EtOAc/n-hexane, 1:1), the solvent was removed. To the residue was added 10 mL of 2 N HCl with vigorous stirring causing the 3-(1H-tetrazole-5-yl) pyrazine-2-carbonitrile 3a as cream powder (0.16 g, yield 91%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: 1,2-bis(4-methoxyphenyl)-1,2-ethanedione; 2,3-diaminomaleonitrile With sodium azide In dimethyl sulfoxide at 100℃; for 3h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide | 4.1.6. Typical procedure for the preparation of 2,3-di(1H-tetrazole-5-yl)pyrazine (5a) General procedure: A mixture of oxalaldehyde (1 mmol) 2,3-diaminomaleonitrile (1 mmol), sodium azide (3 mmol) in DMSO (2 mL) was stirred at 100 °C for 6 h. After completion of the reaction confirmed by TLC (eluent: EtOAc/n-hexane, 1:1), the solvent was evaporated under reduced pressure. To the participate was added 20 mL of 2 N HCl with vigorous stirring causing the 2,3-di(1H-tetrazole-5-yl) pyrazine to precipitate. The precipitate was filtered and dried in a drying oven to furnish the 2,3-di(1H-tetrazole-5-yl) 5a as white powder (0.20 g, yield 93%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hydrogenchloride In ethanol; water for 0.5h; Reflux; | Pyrazine-2,3-dicarbonitrile (1) Pyrazine-2,3-dicarbonitrile (1)DAMN (20 g, 185 mmol) was dissolved in boiling EtOH (120 mL)and 40% aq glyoxal solution (30 mL, 2 mmol) was added. After stirringthe mixture, concd HCl (3 mL) was added and the refluxing was continued for 30 min. The mixture was cooled to r.t. and the precipitated crystalline solid was collected by filtration, washed with EtOH (30 mL), hexane (30 mL), and dried on air to give 1 as acolorless solid; yield: 22 g (91%); mp 133-134 °C (Lit.14a,31 mp130-135 °C). |
82% | In neat (no solvent) at 20℃; for 6.5h; Green chemistry; | 2.1. Preparation of Pyrazine Derivative General procedure: 1 mmol of recrystallised benzil and 2mmol of ethylenediamine were added to a mortar. The mixture was grinded for a few minutes and transferred to a 50 ml round bottom flask and was kept stirring with a magnetic spinning bar for 6 hrs.The reaction was checked by TLC (ethylacetate and pet-ether). The product was extracted by ethylacetate, washed by water and filtered through Na2SO4. Product was purified by column chromatography using Silica-gel. Petroleum ether-Ethylacetate(PE-EA)mixtures were used as eluent. All the products were characterized by IR, 1H NMR and 13C NMR. |
82% | With silica gel In water at 20℃; for 6.5h; Green chemistry; | Preparation of 2, 3-disubstituted pyrazines Typical procedure General procedure: Ethylenediamine (1 mmol), benzil (1 mmol), and the silica gel (1 g) were mixed in a mortar and the mixture was grinded for a few minutes in the presence of 2-3 drops of water. Finally, the mixture was transferred to a 50 mL round bottom bottle and was kept under magnetic stirrer at room temperature for 6 h. The completion of reaction was monitored by TLC. Ethyl acetate (3×15 ml) was added to the reaction mixture and the extract was filtered through anhydrous Na2SO4. Finally, 2,3-diphenylpyrazine was isolated by column chromatography over silica gel (60-120 mesh) where pet ether and ethyl acetate mixture was used as eluent. |
76% | With acetic acid at 80 - 90℃; for 3h; | |
Acidic conditions; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.71% | With acetic acid In ethanol at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In water; at 50℃; for 4h; | [0151j To a solution of 2,3-diaminomaleonitrile (20 g, 185.013 mmol) in water (400 mL) heated at 50 C was added <strong>[3952-66-7]methyl 2-oxobutanoate</strong> (21.48 g, 185.013 mmol) dropwise and the reaction mixture was stirred at the same temperature for 4 h. The reaction mixture was cooled to room temperature and allowed to precipitate for overnight. The solid formed was filtered, washed with n-pentane and dried to afford the title compound 5-ethyl-6-oxo-1,6- dihydropyrazine-2,3-dicarbonitrile (27 g, 84% yield) as a brown solid. Calculated M-H:173.16; FoundM-H: 173.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With acetic acid at 50℃; for 3h; | |
41.7% | With toluene-4-sulfonic acid In methanol for 3h; Reflux; | 1 Synthesis of 5,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-methanoquinoxaline-2,3-dicarbonitrile (Compound 3) To a solution of camphorquinone (Compound 2) (16.6 g, 0.1 mol), DAMN (10.8 g, 0.1 mol) in methanol (40 ml)The solution containing p-toluenesulfonic acid was refluxed for 3 hours. The crude product was recrystallized from ethanol,Water 3 was obtained (yellow solid, 41.7%); |
With acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Hexaketocyclohexane octahydrate(8 g, 12.6 mmol) and diaminomaleonitrile (22 g, 100.8 mmol) were refluxed in AcOH (300 mL) for 2 h. The black suspension was filtered off while hot and washed with hot AcOH (3 25 mL),resulting in a black solid. The solid was suspended in 30% HNO3(60 mL) and heated at 100 C for 3 h. The hot dark brown suspension was poured into ice water (200 mL) and cooled overnight. The suspension was filtered and the solid was refluxed in MeCN(500 mL) for 2 h and was filtered. The filtrate was then evaporated in vacuo to yield an orange solid (4.5 g, yield 50%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With acetic acid for 8h; Reflux; | |
75% | With acetic acid for 8h; Reflux; | 7,10-dibromo-2,3-dicyanopyrazino phenanthrene The mixture of 3,6-dibromophenanthrene-9,10-dione (2.20 g, 6 mmol) and diaminomaleonitrile(0.64 g, 6 mmol) in acetic acid (20 mL) was heated to refluxfor 8 h. After cooling to room temperature, the resulting mixture was poured into ice water (200 mL), and then filtered. The solid was washed with water several times. The crude product was purified by column chromatography on silica gel (eluent: dichloromethane) and dried under vacuum to give the desired compound as a light yellow solid in a75% yield. 1H NMR (600 MHz, CDCl3, δ): 9.04 (d, J=8.7 Hz, 1H), 8.69(s, 1H), 8.07 (d, J=6.0 Hz, 2H), 7.67 (d, J=8.3 Hz, 2H). |
75% | With acetic acid In ethanol for 12h; Reflux; |
75% | With acetic acid for 12h; Reflux; | 2. Synthesis of Photocatalysts General procedure: A suspension of 9,10-phenanthrenequinone (1.25 g, 6 mmol), 2,3-diaminomaleonitrile(commercially available, 0.65 g, 6 mmol) in ethanol (60 mL) and acetic acid (1 mL)was refluxed with stirring for 12 h. After cooling to room temperature, the resultingsolid product was collected and recrystallized from DMF to give compound DCPP1(1.4 g, 83%).A suspension of 3,6-dibromo-9,10-phenanthrenequinone (2.2 g, 6.0 mmol) and 2,3-diaminomaleonitrile (0.65 g, 6.0 mmol) in acetic acid (20 mL) was refluxed withstirring for 12 h. After cooling to room temperature, the resulting mixture was poured into ice water (200 mL), and then filtered. The solid was washed with water severaltimes. The crude product was collected and recrystallized from DMF to give yellowsolid DCPP2 (1.97 g, 75%).A suspension of 2,7-dibromo-9,10-phenanthrenequinone (2.2 g, 6.0 mmol) and 2,3-diaminomaleonitrile (0.65 g, 6.0 mmol) in acetic acid (20 mL) was refluxed withstirring for 12 h. After cooling to room temperature, the resulting mixture was pouredinto ice water (200 mL), and then filtered. The solid was washed with water severaltimes. The crude product was collected and recrystallized from DMF to give yellowsolid DCPP3 (1.99 g, 76%). |
With hydrogenchloride In ethanol | ||
85 % | With acetic acid Reflux; | 7,10-dibromo-2,3-dicyanopyrazino phenanthrene (1) Synthesis of 7,10-dibromo-2,3-dicyanopyrazino phenanthrene is the second step of the reaction scheme which was obtained ac- cording to the reported procedure [28] . Herein a mixture of 3,6- dibromophenanthrene-9,10-dione (1.30 g, 3.5 mmol) and diamino- maleonitrile (0.38 g, 3.5 mmol) in acetic acid (20 mL) was refluxed for 3 h. The reaction mixture cooled to room temperature and then poured over crushed ice to obtained a light yellow solid. The ob- tained solid was filtered, dried under vacuum and purified using column chromatography. Molecule was characterized by IR, mass spectrum and elemental analysis. It is hard to perform 1 H and 13 C NMR spectral analysis of this molecule due to its less solubility in organic solvents. Eluent- chloroform, light yellow solid, yield 1.30 g (85.00%), mp. > 200 °C, FTIR (solid, max /cm -1 ): 3089, 2928, 2855 (Ar. = C -H str.), 2237 (Ar. -C N str.), 1586, 1505 (Ar. -C = C str.), 1350 (C -N str.), 1266, 1091, 1022 (Ar. -C -H bend), 833, 561 (C-Br), MALDI-TOF: mass calcd. for C 18 H 6 Br 2 N 4 [M] + : 438.08; found [M] + : 436.6 8, [M + 2]: 438.6 8, [M + 4]: 440.67, elemental anal. calcd. for C 18 H 6 Br 2 N 4 : C, 49.35; H, 1.38; N, 12.79%; found: C, 49.28; H, 1.45; N, 12.74%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: trifluoroacetic anhydride; 2,3-diaminomaleonitrile In 1,4-dioxane Inert atmosphere; Reflux; Stage #2: With lithium carbonate In water | 1 Example 1 2.42 g of trifluoroacetic anhydride were introduced into a reactor comprising a solution of 1.14 g of DAMN in 11 ml of dioxane. The mixture was maintained under argon and stirred under reflux until the reactants had completely disappeared. After removing the solvent and the trifluoroacetic acid under vacuum, the solid residue was dissolved in 50 ml of ether. The ether solution was extracted 4 times with a suspension comprising 1 g of lithium carbonate in 90 ml of water and then the aqueous solution of the lithium salt was washed with ether. After removing the water in a rotary evaporator, the dark residue was dried under vacuum at 100° C. The dark-colored solid was subsequently extracted with acetonitrile (4×10 ml) and the resulting solution was filtered. The acetonitrile was subsequently removed and the crude salt was purified by chromatography on alumina using an acetonitrile/benzene 21 mixture as eluent. After drying, 1.45 g (yield 71%) of lithium 2-trifluoromethyl-4,5-dicyanoimidazole were obtained in the form of a colorless solid. The lithium salt (LiTDCI) is obtained in the form of a disolvate after recrystallization. The pure product is obtained, by treatment under vacuum at 150° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With C5H14N3O3S(1+)*Cl(1-) In water at 20℃; for 1.25h; | General procedure for the preparation of products 4a-l and 6a-e General procedure: The catalyst (0.01 g, 5 mol%) was added to a solution of diamines (1 mmol),carbonyl compounds (1 mmol), and isocyanides (1 mmol) in 3 ml of water. The reaction mixture was allowed to stir for an appropriate time until the precipitate appeared. After completion of the reaction, as indicated by TLC (EtOAc:n-hexane,1:2), the reaction mixture was filtered off and the residue was washed with water and then crystallized from ethanol or acetone to give pure products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogenchloride; In ethanol; water; at 60℃; for 3h;Inert atmosphere; | Diamino maleonitrile (0.88 g, 8.2 mmol), 1,2-bis (4-bromophenyl) ethane-1,2-dione (3.0 g, 8.2 mmol) and hydrochloric acid (36%, 1.5 g) were reacted in 60 ml of ethanol at 60 C. for 3 hours in a nitrogen atmosphere. After cooling to room temperature, the reaction product was extracted with 100 ml of dichloromethane and 100 ml of water. The separated organic phase was dried over anhydrous magnesium sulfate and then filtered and evaporated to obtain 5,6-bis (4-bromophenyl) pyrazine-2,3-dicarbonitrile (3.2 g, yield of 90%), which is a mauve solid. 1H NMR (500 MHz, CDCl3, delta): 7.58 (dd, 4H), 7.46 (dd, 4H); MS (MALDI-TOF) m/z: [M]+ calcd for C18H8Br2N4, 437.91. found, 437.70. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.18 mg; 0.07 mg; 0.03 mg; 1.9 mg; 0.21 mg; 0.11 mg; 0.18 mg; 0.18 mg; 0.73 mg; 0.22 mg; 0.01 mg; 0.57 mg; 0.27 mg; 0.02 mg | With ferric sulfate nonahydrate; In water; at 80℃; for 24h;pH 7.57; | General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 muL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0% w/w) at 80 C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 muL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0% w/w ofthe corresponding salt?s pellet) at 80 C for 24 h. For the innerenvironment, NH2CHO (200 muL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0% w/w) at80 C for 24 h. The reaction of NH2CHO (10% v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 muL) at 60C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 C, detector temperature 280 C, gradient 100 C for 2min, and 10 C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98% compared to that of the reference standards.The analysis was limited to products of ?1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.16 mg; 0.02 mg; 0.009 mg; 0.096 mg; 0.38 mg; 0.9 mg; 0.15 mg; 0.015 mg; 0.13 mg | With ferric sulfate nonahydrate; at 80℃; for 24h;pH 12.0; | General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 muL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0% w/w) at 80 C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 muL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0% w/w ofthe corresponding salt?s pellet) at 80 C for 24 h. For the innerenvironment, NH2CHO (200 muL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0% w/w) at80 C for 24 h. The reaction of NH2CHO (10% v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 muL) at 60C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 C, detector temperature 280 C, gradient 100 C for 2min, and 10 C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98% compared to that of the reference standards.The analysis was limited to products of ?1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.11 mg; 0.005 mg; 0.0023 mg; 0.071 mg; 0.12 mg; 0.01 mg; 0.09 mg | With magnesium sulfate; at 80℃; for 24h;pH 12.0; | General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 muL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0% w/w) at 80 C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 muL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0% w/w ofthe corresponding salt?s pellet) at 80 C for 24 h. For the innerenvironment, NH2CHO (200 muL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0% w/w) at80 C for 24 h. The reaction of NH2CHO (10% v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 muL) at 60C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 C, detector temperature 280 C, gradient 100 C for 2min, and 10 C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98% compared to that of the reference standards.The analysis was limited to products of ?1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol at 70℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
49% | With toluene-4-sulfonic acid; In methanol; for 3.0h;Reflux; | 3,3-Dimethyl-2-oxobutanal 4 (17.12 g, 0.15 mol) wasrefluxed with diaminomaleonitrile (12.5 g, 0.17 mol) in thepresence of p-toluenesulfonic acid as catalyst for 3 h. Aftercooling, the mixture was passed through a pad of Celiteand the filtrate was evaporated under reduced pressure.The residue was purified by column chromatography onsilica gel using using ethyl acetate/hexane (1:3) as eluent toproduce a yellowish brown solid (15.0 g). Yield 49%. Mp160-162 C. 1H NMR (d-chloroform), delta: 1.45 (9 H, s); 8.94(1 H, s). Anal. Calcd. (%) for C10H10N7:C, 64.50; H, 5.41;N, 30.09. Found (%): C, 64.56; H, 5.39; N, 30.02. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In neat (no solvent) at 20℃; for 6h; Green chemistry; | 2.1. Preparation of Pyrazine Derivative General procedure: 1 mmol of recrystallised benzil and 2mmol of ethylenediamine were added to a mortar. The mixture was grinded for a few minutes and transferred to a 50 ml round bottom flask and was kept stirring with a magnetic spinning bar for 6 hrs.The reaction was checked by TLC (ethylacetate and pet-ether). The product was extracted by ethylacetate, washed by water and filtered through Na2SO4. Product was purified by column chromatography using Silica-gel. Petroleum ether-Ethylacetate(PE-EA)mixtures were used as eluent. All the products were characterized by IR, 1H NMR and 13C NMR. |
75% | With silica gel In water at 20℃; for 6h; Green chemistry; | Preparation of 2, 3-disubstituted pyrazines Typical procedure General procedure: Ethylenediamine (1 mmol), benzil (1 mmol), and the silica gel (1 g) were mixed in a mortar and the mixture was grinded for a few minutes in the presence of 2-3 drops of water. Finally, the mixture was transferred to a 50 mL round bottom bottle and was kept under magnetic stirrer at room temperature for 6 h. The completion of reaction was monitored by TLC. Ethyl acetate (3×15 ml) was added to the reaction mixture and the extract was filtered through anhydrous Na2SO4. Finally, 2,3-diphenylpyrazine was isolated by column chromatography over silica gel (60-120 mesh) where pet ether and ethyl acetate mixture was used as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In neat (no solvent) at 20℃; for 7h; Green chemistry; | 2.1. Preparation of Pyrazine Derivative General procedure: 1 mmol of recrystallised benzil and 2mmol of ethylenediamine were added to a mortar. The mixture was grinded for a few minutes and transferred to a 50 ml round bottom flask and was kept stirring with a magnetic spinning bar for 6 hrs.The reaction was checked by TLC (ethylacetate and pet-ether). The product was extracted by ethylacetate, washed by water and filtered through Na2SO4. Product was purified by column chromatography using Silica-gel. Petroleum ether-Ethylacetate(PE-EA)mixtures were used as eluent. All the products were characterized by IR, 1H NMR and 13C NMR. |
86% | With silica gel In water at 20℃; for 7h; Green chemistry; | Preparation of 2, 3-disubstituted pyrazines Typical procedure General procedure: Ethylenediamine (1 mmol), benzil (1 mmol), and the silica gel (1 g) were mixed in a mortar and the mixture was grinded for a few minutes in the presence of 2-3 drops of water. Finally, the mixture was transferred to a 50 mL round bottom bottle and was kept under magnetic stirrer at room temperature for 6 h. The completion of reaction was monitored by TLC. Ethyl acetate (3×15 ml) was added to the reaction mixture and the extract was filtered through anhydrous Na2SO4. Finally, 2,3-diphenylpyrazine was isolated by column chromatography over silica gel (60-120 mesh) where pet ether and ethyl acetate mixture was used as eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In neat (no solvent) at 20℃; for 7h; Green chemistry; | 2.1. Preparation of Pyrazine Derivative General procedure: 1 mmol of recrystallised benzil and 2mmol of ethylenediamine were added to a mortar. The mixture was grinded for a few minutes and transferred to a 50 ml round bottom flask and was kept stirring with a magnetic spinning bar for 6 hrs.The reaction was checked by TLC (ethylacetate and pet-ether). The product was extracted by ethylacetate, washed by water and filtered through Na2SO4. Product was purified by column chromatography using Silica-gel. Petroleum ether-Ethylacetate(PE-EA)mixtures were used as eluent. All the products were characterized by IR, 1H NMR and 13C NMR. |
72% | With silica gel In water at 20℃; for 7h; Green chemistry; | Preparation of 2, 3-disubstituted pyrazines Typical procedure General procedure: Ethylenediamine (1 mmol), benzil (1 mmol), and the silica gel (1 g) were mixed in a mortar and the mixture was grinded for a few minutes in the presence of 2-3 drops of water. Finally, the mixture was transferred to a 50 mL round bottom bottle and was kept under magnetic stirrer at room temperature for 6 h. The completion of reaction was monitored by TLC. Ethyl acetate (3×15 ml) was added to the reaction mixture and the extract was filtered through anhydrous Na2SO4. Finally, 2,3-diphenylpyrazine was isolated by column chromatography over silica gel (60-120 mesh) where pet ether and ethyl acetate mixture was used as eluent. |
Acidic conditions; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 80℃; for 23h; | The 2 mmol 1st product I and 2 mmol diamino malaya nitrile dissolved in 35 ml of ethanol, in 80 C heating and stirring, the reflux condensation of the reaction 23 hours, cooling to room temperature. Column chromatography purification, eluting agent is n-hexane/dichloromethane, is separated to obtain a yellow solid, HL is the ligand (four-styrene - diamino malaya nitrile derivatives). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With NiO39PW11(5-)*5C8H15N2(1+)*3H2O In methanol at 20℃; for 3h; | General procedure for the synthesistetrazolyldiazepines (5a-o) using[bmim]5[PW11NiO39]·3H2O General procedure: A solution of 1,2-diamine (1 mmol), ketone (2.2 mmol), isocyanide (1 mmol) and trimethylsilylazide (1.2 mmol) and [bmim]5[PW11NiO39]·3H2O (5 mol%) in MeOH (5 mL) was stirred for 2-4 h at room temperature. After completion of the reaction, as indicated by TLC, the precipitate and catalyst was filtered off. The residue of products and catalyst was separated by washing with acetone. Then the product was crystallized from acetone:ethanol to give pure products 5a-o. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With NiO39PW11(5-)*5C8H15N2(1+)*3H2O In methanol at 20℃; for 4h; | General procedure for the synthesistetrazolyldiazepines (5a-o) using[bmim]5[PW11NiO39]·3H2O General procedure: A solution of 1,2-diamine (1 mmol), ketone (2.2 mmol), isocyanide (1 mmol) and trimethylsilylazide (1.2 mmol) and [bmim]5[PW11NiO39]·3H2O (5 mol%) in MeOH (5 mL) was stirred for 2-4 h at room temperature. After completion of the reaction, as indicated by TLC, the precipitate and catalyst was filtered off. The residue of products and catalyst was separated by washing with acetone. Then the product was crystallized from acetone:ethanol to give pure products 5a-o. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In ethanol; for 4h;Reflux; | <strong>[103854-64-4]8-methoxyquinoline-2-carbaldehyde</strong> (0.5 g, 1.7 mmol) was taken in ethanol (15 ml) and 1,2-diaminomaleonitrile was added to it with continuous stirring. The reaction mixture was then refluxed for 4 h. A yellow precipitation occurred was filtered and washed with cold ethanol. Finally the compound was purified through column chromatography using 1% CH3OH in CHCl3 (v/v) as eluent to get yellow crystalline solid. Yield = (0.46 g) 92%. 1H NMR (300 MHz, DMSO-d6): δ 3.98 (s, 3H), 5.73 (s, 2H), 7.22 (d, J = 6.9 Hz, 1H), 7.54 (m, 2H), 8.30 (s, 1H), 8.36 (d, J = 9.0 Hz, 1H), 8.52 (d, J = 9.0 Hz, 1H). 13C NMR (75 MHz, DMSO-d6): δ 56.2, 102.4, 109.4, 113.8, 114.5, 118.5, 119.8, 128.9, 129.8, 133.0, 136.7, 139.7, 153.0, 155.2, 155.8. TOF MS (ESI, positive): calcd for C15H12N5O [M + H]+ (m/z): 278.1042; found: 278.0272. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.1% | With sulfuric acid In methanol at 20℃; for 2h; | Compound 3 (PHC1): compound 2 (50 mg, 0.14 mmol) and diaminomaleonitrile (15 mg, 0.14 mmol) were dissolved in 8 mL MeOH, 1 drop of conc. H2SO4 was added, and then the mixture solution was stirred for 2 h in room temperature until all the starting material was consumed, which was monitored by TLC analysis. Water (20 mL) was added to the reaction mixture. The resulting solution was extracted with dichloromethane (3 20 mL). The extract was dried over sodium sulfate and then concentrated under vacuum to give 3 as a dark-red solid (61 mg, 97.1%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With sulfuric acid In ethanol at 20℃; for 0.166667h; | 3.1.1. General Procedure for the Synthesis of the 1-amino-2-arylidenamine-1,2-(dicyano)ethenes(3a-3e) General procedure: One drop of concentrated sulphuric acid (0.01 mL) was added to a suspension ofdiaminomaleonitrile 1 and benzaldehyde 2 (1 molar equivalent) in ethanol. The reaction was stirredfor 10 minutes at room temperature. The yellow solid was filtered, washed with cold diethyl ether,and identified as the title compound 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sulfuric acid; In methanol; at 20℃; for 0.5h; | 2,2'-Bisthiophene-5-carboxaldehyde (0.1 mg. 1 eq.) and diaminomaleonitrile (0.055 mg. 1 eq.) were dissolved in 5 mL of methanol; then add a few drops of Conc. H2SO4. The reaction mixture was furthers tirred for 30 min. at room temperature until to afford the precipitate. A yellowish-orange colored solid was obtained, filtered and washed with cold ethanol, followed by diethyl ether, then dried to obtain the solid (yield=85%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.1% | With toluene-4-sulfonic acid; In ethanol; for 5h;Reflux; | 2,7-dibromophenanthrene (36.6 g, 0.1 mol), diaminomaleonitrile (13 g, 0.12 mol), p-toluenesulfonic acid(51.2g) was added to 500ml of ethanol, added to reflux reaction for 5h, TLC monitoring reaction was complete, filtered after cooling, filter cakeAfter methanol washing twice, toluene: ethanol = 1:1 recrystallization gave 28.5 g of a yellow solid, yield: 65.1%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.3% | With potassium acetate In N,N-dimethyl-formamide at 120℃; for 24h; | 7.1 (1) NDI-01-B (11.68 g, 20.0 mmol) was added to DMF (300 mL),Add 2,3-diaminomaleonitrile(4.32 g, 40.0 mmol),Potassium acetate (3.92 g, 40.0 mmol) was added and the reaction was stirred at 120 °C for 24 hours.Cool to room temperature, spin dry DMF with oil pump, add a small amount of water (100 mL), filter, Washed (100mL * 2), the crude product was beaten twice with PE: DCM = 1:1 (50mL: 50mL), filtered, The product is baked at 80 degrees for 16 hours.The product NDI-18-A (8.58 g, yield 90.3%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; for 15h; Inert atmosphere; | 4.11.2. Representative procedure a for the synthesis of 8-oxopurine-6-carboxamides (Scheme 1) General procedure: A mixture of diaminomaleonitrile (2) (217mg, 2.0mmol) and2-methoxyphenyl isocyanate (3a) (0.28mL, 2.1mmol) in anhydrousTHF (15mL) was stirred at room temperature for 24 h underan argon atmosphere. The mixture was concentrated underreduced pressure. The residual solids were filtered and rinsedwith cold EtOH and Et2O to yield the urea compound 4a (310 mg,60% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at 20℃; for 20h; Inert atmosphere; | 4.11.2. Representative procedure a for the synthesis of 8-oxopurine-6-carboxamides (Scheme 1) General procedure: A mixture of diaminomaleonitrile (2) (217mg, 2.0mmol) and2-methoxyphenyl isocyanate (3a) (0.28mL, 2.1mmol) in anhydrousTHF (15mL) was stirred at room temperature for 24 h underan argon atmosphere. The mixture was concentrated underreduced pressure. The residual solids were filtered and rinsedwith cold EtOH and Et2O to yield the urea compound 4a (310 mg,60% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | at 40℃; for 4h;Inert atmosphere; | In a 500 ml three-necked bottle,Compound N3 (16.80 g, 1 equivalent) was added under nitrogen protection,Compound M9 (21.60 g, 2 eq), acetic acid (150 ml),Reaction at 40 C for 4 hours,After cooling to room temperature, it was quenched by adding 150 ml of water, extracted with ethyl acetate (150 ml * 3), dried over anhydrous sodium sulfate, and dried. The crude product was purified by chromatography (ethyl acetate / hexane, 1/10) ,Intermediate 1-9 was obtained (10.93 g, 35% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With acetic acid at 40℃; for 4h; Inert atmosphere; | 3.1; 8.1 Synthesis of intermediate 1 ' In a 250 ml three-necked bottle,Under nitrogen protection, 4,5-dihydroxycyclopent-4-ene-1,2,3-trione (14.21 g, 1 equivalent),2,3-diamino-2-butenedinitrile (10.80 g, 1 eq), acetic acid (100 ml),The reaction was carried out at 40 ° C for 4 hours. After cooling to room temperature, 150 ml of water was added to quench it.Extracted with ethyl acetate (150 ml x 3), the organic phase was dried over anhydrous sodium sulfate,The organic solvent was spin-dried to obtain a crude product.The crude product was purified by chromatography (ethyl acetate / hexane volume ratio 1/10),Got intermediate 1 ’(14.98 g, yield 70%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With trifluoroacetic acid In acetonitrile for 48h; Reflux; | 2.5.1. BDM (2-amino-3-(BODIPYmethyleneamino)maleonitrile) BY-CHO (600 mg, 1.7 mmol) and diaminomaleonitrile (216 mg,2.0 mmol) were dissolved in acetonitrile (40 mL). One drop oftrifluoroacetic acid was added, and the mixture was heated to refluxfor 48 h. Then, it was cooled to 0 °C until the dark-red solid fully precipitatedfrom the solution. The crystalline BDM was isolated in 82% yield(615 mg).M.p.: 288-289 °C; IR (KBr, υ, cm-1): 488, 500, 676, 822, 880, 976,1022, 1216, 1438, 1460, 1508, 1578, 1601, 1941, 2198, 2225, 2924,2958, 3370, 3477; 1H NMR (600 MHz, CDCl3) δ: 8.40 (s, 1H), 7.53 (s,3H), 7.29 (s, 2H), 6.13 (s, 2H), 4.83 (s, 2H), 2.82 (s, 3H), 2.61 (s, 3H),1.58 (s, 3H), 1.41 (s, 3H); 13C NMR (150 MHz, CDCl3) δ: 160.9, 159.4,155.7, 153.1, 143.0, 138.1, 134.5, 133.8, 129.7, 129.6, 128.0, 123.9,122.6, 117.3, 114.0, 112.3, 110.5, 15.2, 15.0, 14.5, 12.5; HRMS (ESI):C24H21BF2N6Na [M + Na] requires 465.1787; found: 465.1809. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With acetic acid Heating; | 12 Synthesis of compound A37: Compound A2 (3.37 g, 10 mmol), maleonitrile diamine (1.08 g, 10 mmol) and 10 ml of acetic acid were heated overnight, and the reaction mixture was cooled to room temperature,The resulting solid was filtered and washed with ethanol and water to give A37 (3.97 g, 97%), |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In ethanol for 4h; Reflux; | 2.2 Synthesis of compound YXF Compounds 1 and 2 were synthesized according to the reported method [51]. As illustrated in Scheme 1, compound 2 (163mg, 1.0mmol) and diaminomaleonitrile (108mg, 1.0mmol) were completely dissolved in 10mL of EtOH, respectively. Then, the solution of compound 2 was added dropwise into the diaminomaleonitrile solution. After the reaction mixture was stirred with refluxing for 4h, a yellow-green solid was precipitated, collected, and washed with EtOH to afford compound YXF (164mg, yield 65%). 1H NMR (400MHz, acetone-d6), δ H 8.54 (s, 1H), 8.12 (t, J=6.4Hz, 2H), 7.74 (br, 2H), 7.64-7.54 (m, 2H) ppm (Fig. S1); 13C NMR (100MHz, Acetone-d6), δ C 165.77, 154.19, 149.17, 135.71, 128.91, 127.14, 126.85, 124.23, 122.21, 113.21, 112.17, 103.67ppm (Fig. S2); HR-MS: m/zcalcd for C12H8N5S+ [M+H]+: 254.0495, found: 254.0491 (Fig. S3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With silver hexafluoroantimonate; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In dichloromethane at 60℃; for 12h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With acetic acid for 3h; Reflux; | Synthesis of [(CN)2ppz]: 2,3-Dicyanopyrazino[2,3-f][4,7]phenanthroline, [(CN)2ppz]: This ligand was synthetized as precursor of L1. 0.2 g (0.9 mmol) of 4,7-phenanthroline-5,6-dione were dissolved in 30 mL of acetic acid with 0.1 g (0.9 mmol) of Diaminomaleonitrile. The solution was refluxed during 3 h., followed by the addition of drops of ethyl ether; finally, the solid was repeatedly washed with ethyl ether, obtaining a yellow-brown solid. (0.26 g,88 %). IR-KBr (cm-1): 2983 n(CH aromatic); 2240 n(CN); 1587 n(CN). 1H NMR (400 MHz, d6-DMSO) δ/ppm 9.41 (d, J = 8.1 Hz, 2Hc), 9.26 (d, J = 3.7 Hz, 2Hb), 8.09 (dd, J = 8.3, 4.3 Hz, 2Ha). MS m/z (%): Calcd for C16H6N6 m/z 282.26. ([M + H]+) Found: m/z 283.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With acetic acid In ethanol at 80℃; for 19h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With acetic acid Heating; | 13 Synthesis of compound A26: Heat compound A3 (4.17g, 10mmol), diaminomaleonitrile (2.16g, 20mmol) and 10ml of acetic acid overnight,The reaction mixture was cooled to room temperature, the resulting solid was filtered, and washed with ethanol and water to obtain A26 (2.63 g, 47%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In acetic acid Reflux; | 2.2.1. Synthesis of compound 1 Camphoroquinone (0.30 g, 1.8 mmol), diaminomaleonitrile(0.22 g, 2 mmol) were dissolved in acetic acid (99.7%, 15 mL),and the solution was refluxed for 3-4 h (monitored by TLC). Afterfinishing the reaction, acetic acid was first removed from resultantsolution, and extracted with CH2Cl2. The organic phase waswashed to neutrality, dried over anhydrous Na2SO4, and evaporatedto remove CH2Cl2. The residue was subjected to flash columnchromatography on silica gel (using petroleum ether : ethyl acetate = 1:1, v/v) to give compound 1 as white solid (0.24 g, yield79%), melting point: 134.9-135.3 C. 1H NMR (600 MHz, CDCl3) d(ppm): 3.17 (d, J = 4.5 Hz, 1H), 2.39 (td, J = 9.9, 4.4 Hz, 1H), 2.14(dd, J = 10.7, 9.1 Hz, 1H), 1.38 (s, 3H), 1.33 (t, J = 9.7 Hz, 2H),1.13 (s, 3H), 0.62 (s, 3H).13C NMR (150 MHz, CDCl3) d (ppm):168.78, 149.30, 130.59, 113.86, 54.18 (d, J = 269.6 Hz), 30.89,23.89, 20.02, 18.39. HRMS (m/z) [M + H]+: calculated forC14H15N4 + H+: 239.1297, found: 239.1291. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2,3-diaminomaleonitrile With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 0.333333h; Stage #2: 1,4-dibromonaphthalene-2, 3-diamine In acetonitrile | 2 In the second step, the compound represented by structural formula (II-b) is synthesized using the following method. 0.59 g of diamine maleonitrile (5.5 mmol) and 20 mL of acetonitrile were added to the round bottom flask at room temperature to obtain a dark brown solution. Further, 1.25 g of2,3-dichloro-5,6-dicyano-1,4-benzoquinone was added into a round bottom flaskin several portions and stirred for 20 minutes to obtain a light brown solution. The above light brown solution was filtered to obtain a light brown solid. Then, the light brown solid and 1.58 g of 1,4-dibromo-2,3-diaminenaphthalene (5.0 mmol) were mixed to obtain a mixedsolid. Then, the mixed solid was divided into several portions and added to 30 mL of trifluoroacetic acid to obtain a mixture. After the mixture was stirred overnight, the mixture was diluted with water; and the precipitate of the mixture was collected by filtration and acetonitrile washing. The precipitate was further purified by column chromatography (DCM/Hex=1/1) to obtain the compound represented by the structural formula (II-b). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With acetic acid In ethanol at 50℃; for 12h; | 2.2. Synthesis of probe TPB-CN The intermediate of 40-(diphenylamino)-[1,10-biphenyl]-4-carbaldehyde (TPB-CHO) was synthesized by our group in previouswork [48]. The synthetic procedure for 2amino3(((E)(4 0-(diphenylamino)-[1,10biphenyl]4yl)methylene) amino)maleonitrile(TPB-CN) was described as follows: TPB-CHO (0.36 g, 1.0 mmol)and 2,3-diaminomaleonitrile (0.112 g, 1.0 mmol) were added toan ethanol solution (20.0 mL), followed by addition of 5 lL aceticacid. Then, the solution was stirred at 50 C for 12 h and formedthe precipitation. After cooling to 25 C, the precipitates were filtered,washed and recrystallized twice with methanol. Finally,brownish red solid was obtained with a yield of 68% (Scheme 1).1H NMR (600 MHz, CDCl3) (Fig. S1, HRMS): 7.43 (d, J = 1.92 Hz1H), 8.35 (d, J = 8.80 Hz, 2H), 8.18 (s, 1H), 8.89 (d, J = 8.72 Hz,2H), 7.69 (d, J = 2.14 Hz, 1H), 7.52 (d, J = 8.70 Hz, 2H), 7.30 (d,J = 7.98 Hz, 3H), 7.17 (m, 6H), 7.54 (t, J = 7.54 Hz, 3H). 13C NMR(150 MHz, CDCl3) (Fig. S2, HRMS): 148.23, 147.35, 144.67,133.09, 132.96, 129.78, 129.41, 127.82, 126.92, 124.84, 124.16,123.49, 123.44, 123.22, 113.60, 112.37, 108.64. High resolutionmass spectrometry (Fig. S3, HRMS): m/z = 440.1867 [M + H]+, calculatedfor [M + H]+ =440.1870. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogenchloride; NaNO2 In lithium hydroxide monohydrate at 0 - 20℃; for 1.5h; | Preparation of H3BTT: (1) Weigh 7.0 g of sodium nitrite and dissolve it in 125 mL of distilled water for use. Weigh 10.8g of diaminomaleonitrile and dissolve it in 100mL of dilute hydrochloric acid (1mol L-1). Under strict temperature control at 0 to 5°C, slowly add sodium nitrite solution dropwise (the reaction emits a lot of heat). , react at low temperature for 30 min, and then slowly heat up to 20 °C and continue the reaction for 1 h. The orange filtrate was obtained by suction filtration, extracted with ether, the ether phase was taken, the ether was distilled off (the temperature did not exceed 30°C), and then dried under vacuum to obtain a bright yellow powder with a yield of 90%. |
82% | With hydrogenchloride; NaNO2 In lithium hydroxide monohydrate at 0 - 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With acetic acid In ethanol at 50℃; for 6h; | 1.1.2; 1.2.2; 1.3.2 (2) Synthesis of multifunctional fluorescent dyes. The specific steps are as follows: compound (II) (350 mg, 1 mmol)Dissolve in absolute ethanol (15ml), add diaminomaleonitrile (130mg, 1.2mmol), add 2 drops of glacial acetic acid,Stir at 50°C for 6h, after the reaction, cool to room temperature, filter the precipitate,Washed with absolute ethanol for several times, and dried to obtain 370 mg of light yellow product with a yield of 84%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With glacial acetic acid at 25 - 70℃; for 4h; | 1-5; 1-6 Example 1 Take 2.16g (0.02mol) of 2,3-diamino-2-butenedicarbonitrile, 2.27g (0.01mol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone for subsequent use, 27mL of anhydrous acetic acid was added to the 100mL four-necked flask equipped with mechanical stirring, thermometer and reflux condenser, 2,3-diamino-2-butenedionitrile and 2,3-dichloro-5,6-dicyano-p-benzoquinone were added in batches at room temperature (25°C), and 2,3-diamino-2-butenedinitrile is dissolved in anhydrous acetic acid, under stirring conditions, Then add 2,3-dichloro-5,6-dicyano-p-benzoquinone, 0.3 g each time, every 5 minutes, after the addition is completed, stir the reaction at room temperature for 2 hours, and then heat the water bath to 70 ° C and stir the reaction for 2 hour, after stopping stirring and cooling to room temperature, filter, wash the filter cake with water (15mL*3 times), put the filter cake into a round-bottomed beaker with a reflux condenser, add 27mL of toluene, heat to 90°C and stir for 30min, filter with filter paper and collect the filtrate, repeat this operation for 5 times, and obtain a white solid after rotary evaporation under reduced pressure, which is pure 2,3,5,6-pyrazine tetranitrile. The yield is 72.0 %. |
Tags: 18514-52-8 synthesis path| 18514-52-8 SDS| 18514-52-8 COA| 18514-52-8 purity| 18514-52-8 application| 18514-52-8 NMR| 18514-52-8 COA| 18514-52-8 structure
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 :