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Chemical Structure| 68776-60-3 Chemical Structure| 68776-60-3

Structure of 68776-60-3

Chemical Structure| 68776-60-3

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Product Details of [ 68776-60-3 ]

CAS No. :68776-60-3
Formula : C4H2N2O
M.W : 94.07
SMILES Code : N#CC1=NC=CO1
MDL No. :MFCD08669511
InChI Key :UUAXDPHPSHEGQQ-UHFFFAOYSA-N
Pubchem ID :19809513

Safety of [ 68776-60-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H300-H311+H331
Precautionary Statements:P261-P264-P280-P301+P310
Class:6.1
UN#:2810
Packing Group:

Application In Synthesis of [ 68776-60-3 ]

* 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.

  • Downstream synthetic route of [ 68776-60-3 ]

[ 68776-60-3 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 22288-78-4 ]
  • [ 68776-60-3 ]
  • [ 884539-46-2 ]
YieldReaction ConditionsOperation in experiment
43% With potassium tert-butylate; In tetrahydrofuran; at 0℃; for 2h; Example 113: 2-(1,3-Oxazol-2-yl)thieno[3,2-cf|pyrimidin-4-ol; EPO <DP n="133"/>Methyl 3-aminothiophene-2-carboxylate (0.95 g, 6.1 mmol, 1.0 equiv) and 1 ,3-oxazole-2- carbonitrile (0.57 g, 6.1 mmol, 1.0 equiv) were taken up in anhydrous tetrahydrofuran (24 ml_). The resultant solution was cooled to 0 C and treated with potassium terf-butoxide (1.0 g, 9.2 mmol, 1.5 equiv). The resultant yellow slurry was stirred for 2 h, concentrated in vacuo and poured into saturated ammonium chloride (100 mL). An off-white solid was collected by filtration, which was triturated with MTBE, and gave an off-white (0.56 g, 43% yield) product: 1H NMR (400 MHz, DMSO-d6) delta 8.24 (s, 1H), 7.94 (d, J = 5.3Hz, 1 H), 7.41 (s, 1H), 7.70 (br. s, 1H), 7.32 (d, J = 5.3Hz, 1H); LCMS (ESI+) C9H5N3O2S m/z 220 (M + H)+.
  • 2
  • [ 884539-45-1 ]
  • [ 68776-60-3 ]
YieldReaction ConditionsOperation in experiment
74% With pyridine; trichlorophosphate; at 20℃; for 5h; Example 112: 1,3-Oxazole-2-carbonitrile.; 0. prCN1 ,3-Oxazole-2-carboxamide (0.98 g, 8.8 mmol. 1.0 equiv) was dissolved in pyridine (17 mL) and treated with POCI3 (1.2 mL, 12.2 mmol, 1.4 equiv). The resultant beige slurry, which gave a brown solution, was stirred for 5 hours at room temperature. The reaction mixture was diluted with ice and the aqueous layer, which was adjusted to pH 3 with 6M HCI, was extracted with ether. The ether extract was washed with water, brine, dried over magnesium sulfate, filtered, concentrated in vacuo and gave the product as an amber oil (0.61 g, 74% yield): 1H NMR (400 MHz, DMSO-d6) delta 8.608 (s, 1 H), 7.67 (s, 1H).
With pyridine; trichlorophosphate; for 4h; Neat POCI3 (1.12 mL, 12.3 mmol) was added to a pyridine solution (17 mL) of oxazole-2- carboxylic acid amide (982 mg, 8.8 mmol). After 4 h the mixture was cooled to 0 0C and taken to pH 3 with concentrated aqueous HCl. The aqueous mixture was extracted with Et2theta and the combined extracts were washed with water then brine, dried (Mg2SO4), concentrated and used without further purification to give 478 mg of 5-cyclopropyl-furan-2-carbonitrile. The residue contained water, and was therefore dissolved in CH2CI2, dried (Na2SO4), and concentrated to give 573 mg (70% pure, 30% pyridine) that was used without further purification.
With pyridine; trichlorophosphate; for 4h; Neat POCI3 (1.12 mL, 12.3 mmol) was added to a pyridine solution (17 mL) of oxazole- 2-carboxylic acid amide (982 mg, 8.8 mmol). After 4 h the mixture was cooled to 0 0C and taken to pH 3 with concentrated aqueous HCl. The aqueous mixture was extracted with Et2O and the combined extracts were washed with water then brine, dried (Mg2SO4), concentrated and used without further purification to give 478 mg of 5-cyclopropyl- furan-2-carbonitrile. The residue contained water, and was therefore dissolved in CH2Cl2, dried (Na2SO4), and concentrated to give 573 mg of the title compound that was used without further purification.
With pyridine; trichlorophosphate; for 4h; Neat POCI3 (1.12 mL, 12.3 mmol) was added to a pyridine solution (17 mL) of oxazole-2- carboxylic acid amide (982 mg, 8.8 mmol). After 4 h the mixture was cooled to 0 0C and taken to pH 3 with concentrated aqueous HCl. The aqueous mixture was extracted with Et2theta and the combined extracts were washed with water then brine, dried (Mg2SO4), concentrated and used without further purification to give 478 mg of 5-cyclopropyl-furan-2-carbonitrile. The residue contained water, and was therefore dissolved in CH2Cl2, dried (Na2SO4), and concentrated to give 573 mg of the title compound that was used without further purification.

YieldReaction ConditionsOperation in experiment
EXAMPLE 9 A solution of N-tert-butyl oxazoleamide (18.2 g, 0.1 mole) and phosphorus pentachloride (25.0 g, 0.12 mole) in chloroform (150 ml) was heated at reflux for 30 hours. The solvent was removed by distillation at atmospheric pressure and the residue was distilled rapidly without fractionation at approximately 0.1 mm. The distillate was redistilled with fractionation through a Vigreux column giving 9.25 g of a mixture of cyanooxazole and phosphorus oxychloride in one fraction and 6.3 g of recovered N-tert-butyl oxazoleamide in another. The fraction containing the cyanooxazole was analyzed qualitatively by infrared and nmr spectroscopy and quantitatively by ultraviolet spectroscopy.
  • 4
  • [ 1221405-30-6 ]
  • [ 68776-60-3 ]
  • [ 1221431-75-9 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In 1,4-dioxane; at 150℃; for 0.166667h;microwave irradiation; Solid t-BuOK (7 mg, 0.06 mmol) was added to a dioxane suspension (0.20 mL) of 2- amino-5-pyrazin-2-ylmethyl-thiophene-3-carbonitrile (68 mg, 0.32 mmol) and oxazole-2- carbonitrile (33 mg, 0.35 mmol) and the mixture was heated by microwave irradiation (150 0C, 10 min, 300 W). The reaction mixture was diluted with dichloromethane and methanol, dry packed onto silica gel, and purified via column chromatography to give 77 mg of the title compound. 1H NMR (DMSO-d6, 300MHz): delta (ppm) 8.76 (s, IH), 8.65 (s, IH), 8.59 (s, IH), 8.26 (s, IH), 7.75 (br s, 2H), 7.42 (s, IH), 7.39 (s, IH), 4.47 (s, 2H); MS m/e 311 (M+H).
  • 5
  • [ 1221405-33-9 ]
  • [ 68776-60-3 ]
  • [ 1221431-77-1 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; In 1,4-dioxane; at 130℃; for 0.166667h;microwave irradiation; Solid t-BuOK (6 mg, 0.05 mmol) was added to a dioxane suspension (0.20 mL) of 2- amino-5-(l-methyl-l-pyridin-2-yl-ethyl)-thiophene-3-carbonitrile (63 mg, 0.26 mmol) and <strong>[68776-60-3]oxazole-2-carbonitrile</strong> (27 mg, 0.28 mmol, prepared as an intermediate in Example 2) and the mixture was heated by microwave irradiation (130 0C, 10 min, 300 W). The reaction mixture was diluted with dichloromethane and methanol, dry packed onto silica gel, and purified via column chromatography to give 44 mg of the title compound. 1H NMR (DMSO-de, 300MHz): delta (ppm) 8.57 (ddd, J=4.7, 1.1, 0.9 Hz, IH), 8.25 (s, IH), 7.69 - 7.80 (m, 3H), 7.53 (s, IH), 7.42 (s, IH), 7.40 (d, J=7.9 Hz, IH), 7.24 - 7.29 (m, IH), 1.83 (s, 6H); MS m/e 338 (M+H).
  • 6
  • [ 1221432-10-5 ]
  • [ 68776-60-3 ]
  • 2-oxazol-2-yl-6-pyridin-2-ylmethyl-thieno[2,3-d]pyrimidin-4-ylamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Solid t-BuOK (9 mg, 0.08 mmol) was added to a dioxane suspension (0.20 mL) of 2- amino-5-pyridin-2-ylmethyl-thiophene-3-carbonitrile (87 mg, 0.40 mmol) and oxazole-2- carbonitrile (46 mg, 0.49 mmol, prepared as an intermeduiate in Example 2) and the mixture was heated by microwave irradiation (130 0C, 10 min, 300 W). The reaction mixture was diluted with dichloromethane and methanol, dry packed onto silica gel, and purified via column chromatography to give 107 mg of the title compound. The free base was dissolved in CH2Cl2 containing a minimal amount of methanol to achieve solution and the solution was added to 1 M HCl in Et2O. The precipitated hydrochloride salt was collected by vacuum filtration to give 112 mg of the title compound. 1H NMR (300 MHz, DMS0-D6) delta ppm 8.89 (d, J=4.9 Hz, 1 H), 8.53 (t, J=I .1 Hz, 1 H), 8.31 (s, 1 H), 7.92 - 8.18 (m, 4 H), 7.51 (s, 1 H), 7.48 (s, IH), 4.80 (s, 2 H); MS m/e 310 (M+H).
  • 7
  • [ 79-42-5 ]
  • [ 68776-60-3 ]
  • [ 1279105-98-4 ]
YieldReaction ConditionsOperation in experiment
51% With pyridine; at 100℃; for 3h; 5-Methyl-2-oxazol-2-yl-thiazol-4-ol : To a mixture of <strong>[68776-60-3]2-<strong>[68776-60-3]cyanooxazole</strong></strong> (500 mg, 5.32 mmol) and thiolactic acid (564 mg, 5.32 mmol) was added pyridine (0.1 ml, 1.32 mmol). The mixture was heated to 100 C. for 3 h, after which it was cooled to rt, EtOH (3 ml) was added, and the suspension stirred for 10 min, filtered, and the solid dried. Further purification by column chromatography (30% EtOAc /Hexane) gave 5-Methyl-2-oxazol-2-yl-thiazol-4-ol (492 mg, 51%) as an off white solid.
51% With pyridine; at 100℃; for 3h; 5-Methyl-2-oxazol-2-yl-thiazol-4-ol: To a mixture of <strong>[68776-60-3]2-<strong>[68776-60-3]cyanooxazole</strong></strong> (500 mg, 5.32 mmol) and thiolactic acid (564 mg, 5.32 mmol) was added pyridine (0.1 ml, 1.32 mmol). The mixture was heated to 100 C. for 3 h, after which it was cooled to rt, EtOH (3 ml) was added, and the suspension stirred for 10 min, filtered, and the solid dried. Further purification by column chromatography (30% EtOAc/Hexane) gave 5-Methyl-2-oxazol-2-yl-thiazol-4-ol (492 mg, 51%) as an off white solid.
51% With pyridine; at 100℃; for 3h; 5-Methyl-2-oxazol-2-yl-thiazol-4-ol: To a mixture of <strong>[68776-60-3]2-<strong>[68776-60-3]cyanooxazole</strong></strong> (500 mg, 5.32 mmol) and thiolactic acid (564 mg, 5.32 mmol) was added pyridine (0.1 ml, 1.32 mmol). The mixture was heated to 100 C. for 3 h, after which it was cooled to rt, EtOH (3 ml) was added, and the suspension stirred for 10 min, filtered, and the solid dried.Further purification by column chromatography (30% EtOAc/Hexane) gave 5-Methyl-2-oxazol-2-yl-thiazol-4-ol (492 mg, 51%) as an off white solid.
51% With pyridine; at 100℃; for 3h; To a mixture of <strong>[68776-60-3]2-<strong>[68776-60-3]cyanooxazole</strong></strong> (500 mg, 5.32 mmol) and thiolactic acid (564 mg, 5.32 mmol) was added pyridine (0.1 ml, 1.32 mmol). The mixture was heated to 100 C. for 3 h, after which it was cooled to rt, EtOH (3 ml) was added, and the suspension stirred for 10 min, filtered, and the solid dried. Further purification by column chromatography (30% EtOAc/Hexane) gave 5-Methyl-2-oxazol-2-yl-thiazol-4-ol (492 mg, 51%) as an off white solid.

  • 8
  • [ 364596-21-4 ]
  • [ 68776-60-3 ]
  • [ 1431558-33-6 ]
  • 9
  • [ 68776-60-3 ]
  • [ 1571216-65-3 ]
  • 10
  • [ 352-13-6 ]
  • [ 68776-60-3 ]
  • C16H12F2N2O [ No CAS ]
 

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