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CAS No. : | 81386-30-3 | MDL No. : | MFCD00085801 |
Formula : | C10H10N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 174.20 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 9 |
Precautionary Statements: | P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 | UN#: | 3077 |
Hazard Statements: | H302-H319-H372-H410 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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 |
---|---|---|
83% | General procedure: In 10 mL of dichloromethane 2 mmol of amidoxime 2 was dissolved and 2 mmol of anhydride 3 was added.The reaction mixture was stirred at room temperaturefor 2 h, then it was washed with 10 mL of NaHCO3 solution and 10 mL of water, the organic layer was dried with Na2SO4 and evaporated at a reduced pressure. The residue was dissolved in 1.52 mL of DMSO and 80 mg (2 mmol) of preliminary ground NaOH was added. The reaction mixture was stirred at room temperature for 1 h and diluted with 20 mL of cold water. The formed precipitate was filtered off. | |
for 1.5h;Heating / reflux; | 2.00 g of N'-hydroxy-4-methylbenzenecarboxyimidamide was dissolved in 40 ML of acetic anhydride, and this solution was stirred for 1.5 hours while heating it under reflux.. After the reaction mixture was cooled to room temperature, the solvent was distilled out thereof under reduced pressure, and then the resultant residue was purified by silica gel column chromatography to yield 1.20 g of 5-methyl-3-(4-methylphenyl)-1,2,4-oxadiazole as yellow solid. NMR(400MHz,CDCl3) delta value: 2.41(3H,s), 2.65(3H,s), 7.28(2H,d,J=8.0Hz), 7.94(2H,d,J=8.0Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 200℃; for 3h; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With basic cobalt(II) carbonate; sodium bromide; In acetic acid; at 95℃; for 11h;Green chemistry;Catalytic behavior; | General procedure: Oxidation process was carried out in an ideal mixing reactor. A starting methylarene 1a-h (13 mmol), cobalt acetate (1.3 mmol), and sodium bromide (1.3 mmol) were dissolved in glacial acetic acid (40 mL). Then, the solution was heated to 95 C and air was fed to the reactor. The reaction mixture was allowed to stand for 11 h at 95 C and cooled to ~20 C, a precipitate formed was filtered. 4-(5-Methyl-1,2,4-oxadiazol-3-yl)benzoic acid (2a). The yield was 94%, m.p. 225-226 C. IR, nu/cm-1: 2670 (OH); 1686 (C=O); 1594 (Ar); 1289 (C-O). MS (70 eV), m/z (I rel (%)): 204 [M]+ (78),187 (3), 163 (100), 146 (31), 118 (14), 102 (5), 90 (9), 88 (9). 1H NMR, delta: 2.70 (s, 3 H, Me); 8.11 (s, 4 H, Ar); 13.26 (br.s, 1 H). 13C NMR, delta: 11.91, 126.99, 129.98, 133.10, 166.51, 166.92, 177.68. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium hydroxide; In dimethyl sulfoxide; at 20℃; for 4h; | General procedure: To a solution of amidoxime 1 (2 mmol) and ester 2 (3 mmol) inDMSO (2 mL) 120 mg (3 mmol) powdered NaOH was rapidlyadded.The reaction mixture was stirred at room temperature for therequired time (TLC or precipitation of the product). The reactionmixture was diluted with cold water (30e50 mL). The resultingprecipitate was ltered off, washed with water (30 mL) and dried inair at 50 C. 4.2.1. 5-Methyl-3-(4-methylphenyl)-1,2,4-oxadiazole8 (3a)White solid; yield 86% (299 mg); mp 77e78 C (lit.8 mp77.6e78.2 C). IR (neat): 1591, 1566, 1481, 1409, 1362, 827, 720, 707,cm1. 1H NMR (DMSO-d6, 400 MHz): d 7.77 (d, J 8.1 Hz, 2H), 7.34(d, J 7.6 Hz, 2H), 2.64 (s, 3H), 2.36 (s, 3H). 13 NMR (DMSO-d6,100 MHz): d 177.2, 167.6, 141.4, 129.8, 126.9, 123.6, 21.1, 12.0. MS(ESI): m/z 175 [MH]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium hydroxide; In dimethyl sulfoxide; at 20℃; for 4h; | General procedure: To a solution of amidoxime 1 (2 mmol) and ester 2 (3 mmol) inDMSO (2 mL) 120 mg (3 mmol) powdered NaOH was rapidlyadded.The reaction mixture was stirred at room temperature for therequired time (TLC or precipitation of the product). The reactionmixture was diluted with cold water (30e50 mL). The resultingprecipitate was ltered off, washed with water (30 mL) and dried inair at 50 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With sodium hydroxide In dimethyl sulfoxide at 20℃; for 4h; | 4.2. General procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles General procedure: To a solution of amidoxime 1 (2 mmol) and ester 2 (3 mmol) inDMSO (2 mL) 120 mg (3 mmol) powdered NaOH was rapidlyadded.The reaction mixture was stirred at room temperature for therequired time (TLC or precipitation of the product). The reactionmixture was diluted with cold water (30e50 mL). The resultingprecipitate was ltered off, washed with water (30 mL) and dried inair at 50 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | General procedure: b. In 10 mL of dichloromethane was dissolved 2 mmol of amidoxime 2, 185 mg (2.2 mmol) of NaHCO3 was added. The reaction mixture was cooled to 0 and by portions maintaining the reaction mixture temperature below 5 2 mmol of acyl chloride 3 was added. The reaction mixture was warmed to room temperature, stirred for 2 h, then it was washed with 10 mL of NaHCO3 solution and 10 mL of water, the organic layer was dried with Na2SO4 and evaporated at a reduced pressure. The residue was dissolved in 1.52 mL of DMSO and 80 mg (2 mmol) of preliminary ground NaOH was added. The reaction mixture was stirred at room temperature for 1 h and diluted with 20 mL of cold water. The formed precipitate was filtered off. |