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Chemical Structure| 762-42-5 Chemical Structure| 762-42-5
Chemical Structure| 762-42-5

Dimethyl acetylenedicarboxylate

CAS No.: 762-42-5

4.5 *For Research Use Only !

Cat. No.: A401572 Purity: 98% GC

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Product Details of Dimethyl acetylenedicarboxylate

CAS No. :762-42-5
Formula : C6H6O4
M.W : 142.11
SMILES Code : O=C(OC)C#CC(OC)=O
MDL No. :MFCD00008456
InChI Key :VHILMKFSCRWWIJ-UHFFFAOYSA-N
Pubchem ID :12980

Safety of Dimethyl acetylenedicarboxylate

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H302-H314
Precautionary Statements:P210-P264-P270-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P370+P378-P403+P235-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of Dimethyl acetylenedicarboxylate

* 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.

  • Upstream synthesis route of [ 762-42-5 ]
  • Downstream synthetic route of [ 762-42-5 ]

[ 762-42-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 762-42-5 ]
  • [ 164254-26-6 ]
  • [ 73406-50-5 ]
  • [ 164254-30-2 ]
References: [1] Journal of Organic Chemistry, 1994, vol. 59, # 18, p. 5347 - 5357.
  • 2
  • [ 118493-85-9 ]
  • [ 762-42-5 ]
  • [ 878158-18-0 ]
References: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 23, p. 6646 - 6649.
  • 3
  • [ 518047-98-8 ]
  • [ 762-42-5 ]
  • [ 519032-08-7 ]
YieldReaction ConditionsOperation in experiment
58%
Stage #1: at 20℃; for 2 h;
Stage #2: With xylene In methanol at 90 - 120℃; for 16 h; Inert atmosphere
Benzyl 2-amino-2-(hydroxyimino)-1,1-dimethylethylcarbamate (2.0 g, 8.0 mmol) was dissolved in 30 mL MeOH, dimethyl acetylenedicarboxylate (DMAD, 1.1 mL, 9.0 mmol) was added slowly. The mixture was stirred for 2 h at room temperature, and then concentrated under reduced pressure to give a white oil. The mixture of the oil and 80 mL xylene was stirred at 90 °C for 2 h and 120 °C for 2 h, then refluxed for 12 h under nitrogen, concentrated to yield the crude product. The crude product was recrystallized with 2 mL MeOH and 10 mL tert-butyl methyl ether to afford 5 as a yellow solid (1.7 g, 58 percent): 1H-NMR (DMSO-d6) δ: 7.35 (m, 5H), 5.00 (s, 2H), 3.83 (s, 3H), 1.48 (s, 6H); ESI-MS m/z 360 (M), 384 (M+Na) +.
References: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7114 - 7118.
 

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