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[ CAS No. 25055-82-7 ]

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type HazMat fee
Excepted Quantity Free
Inaccessible (Haz class 6.1), Domestic USD 41.00
Inaccessible (Haz class 6.1), International USD 64.00
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Chemical Structure| 25055-82-7
Chemical Structure| 25055-82-7
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Product Details of [ 25055-82-7 ]

CAS No. :25055-82-7 MDL No. :MFCD22683730
Formula : C4H8N2O Boiling Point : 133.2±32.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :100.12 g/mol Pubchem ID :14859129
Synonyms :

Safety of [ 25055-82-7 ]

Signal Word:Danger Class:3,8
Precautionary Statements:P210-P240-P242-P243-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P370+P378-P403+P233-P501 UN#:2924
Hazard Statements:H226-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 25055-82-7 ]

  • Upstream synthesis route of [ 25055-82-7 ]
  • Downstream synthetic route of [ 25055-82-7 ]

[ 25055-82-7 ] Synthesis Path-Upstream   1~2

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YieldReaction ConditionsOperation in experiment
304 mg at 0℃; for 0.5 h; Inert atmosphere 4-hydroxy-2-butanone (20, 1.00 g, 11.35 mmol) was pipetted into a dry flask and cooled to 0°C under nitrogen atmosphere. 7N methanolic ammonia (11.2 mL, 79 mmol) was added via syringe, and the solution was allowed to stir at 0°C for 3 hours. A solution of hydroxylamine-O-sulfonic acid (1.476 g, 13.05 mmol) in methanol (9.7 mL) was added dropwise, then was allowed to stir for an additional 16 hours while slowly warming to room temperature. The reaction was filtered through a sintered glass funnel, then transferred to a reaction vessel and re-cooled to 0°C. Triethylamine (1.58 mL,11.35 mmol) was added, then molecular iodine (2.88 g, 11.35 mmol) was added slowly in 10 equal portions until the purple/brown color of iodine persisted in the reaction vessel. The solvent was removed under reduced pressure, and purification of the crude isolate via Kugelrohr distillation (60°C, 1-3 torr) delivered the 2,2-diazirinyl intermediate as a clear oil (304 mg, 27percent yield). A portion of this intermediate (300 mg, 3.00 mmol) was dissolved in dry pyridine (6 mL) and cooled to 0°C in an ice bath. To this solution was added p-toluenesulfonyl chloride (628 mg, 3.30 mmol). The reaction mixture was allowed to stir for 24 hours at 0-4°C, then was poured into a mixture of 37percentw/v HCl (15 mL) and ice (80 mL). The resulting suspension was extracted 3x with ether, then the pooled organic layers were washed with 1N HCl solution, 1N NaOH solution, water, and brine. The organic extract was dried over MgSO4, vacuum filtered, and concentrated to a clear oil (428 mg, 15percent yield over 3 steps) used without further purification.
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7363 - 7374
[2] Patent: WO2013/36866, 2013, A1, . Location in patent: Paragraph 0234; 0284
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 6, p. 1538 - 1544
[4] Molecules, 2017, vol. 22, # 8,
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Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 3, p. 870 - 873[2] Angew. Chem., 2017, vol. 129, # 3, p. 888 - 891,4
[3] Journal of the American Chemical Society, 2017, vol. 139, # 17, p. 6078 - 6081
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5716 - 5726
[5] Angewandte Chemie - International Edition, 2008, vol. 47, # 1, p. 90 - 93
[6] Journal of the American Chemical Society, 2014, vol. 136, # 30, p. 10777 - 10782
[7] Synthesis, 2010, # 17, p. 2997 - 3003
[8] Angewandte Chemie - International Edition, 2017, vol. 56, # 10, p. 2744 - 2748[9] Angew. Chem., 2017, vol. 129, # 10, p. 2788 - 2792,5
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