Safer and Convenient Synthesis of 3,4-Dicyanofuroxan
Publication type: Journal Article
Publication date: 2019-06-12
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A safer, convenient, cost-effective, and scalable synthesis for 3,4-dicyanofuroxan (C4N4O2) is described. Dropwise treatment of a well-stirred suspension of cyanoacetic acid in dichloromethane with concentrated mixed acid (HNO3/H2SO4) affords dicyanofuroxan in 72% yield and in 84% purity after liquid chromatography analysis. Single crystal X-ray diffraction studies further confirm the product and yield its molecular conformation and crystal packing. During the dropwise addition of mixed acid, self-heating occurs, and this event is necessary for the reaction to adequately proceed. However, such self-heating is limited to the refluxing temperature of dichloromethane. This new method supersedes the previous methods used to synthesize dicyanofuroxan, which were low-yielding and of significantly lower purity, irreproducible, relied on expensive reagents, and suffered from dangerous exothermic profiles.
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18
Total citations:
18
Citations from 2024:
1
(5.56%)
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GOST
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Johnson E. C. et al. Safer and Convenient Synthesis of 3,4-Dicyanofuroxan // Organic Process Research and Development. 2019. Vol. 23. No. 6. pp. 1275-1279.
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Johnson E. C., Bukowski E. J., Sausa R. C., Sabatini J. J. Safer and Convenient Synthesis of 3,4-Dicyanofuroxan // Organic Process Research and Development. 2019. Vol. 23. No. 6. pp. 1275-1279.
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RIS
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TY - JOUR
DO - 10.1021/acs.oprd.9b00186
UR - https://doi.org/10.1021/acs.oprd.9b00186
TI - Safer and Convenient Synthesis of 3,4-Dicyanofuroxan
T2 - Organic Process Research and Development
AU - Johnson, Eric C.
AU - Bukowski, Eric J
AU - Sausa, Rosario C.
AU - Sabatini, Jesse J.
PY - 2019
DA - 2019/06/12
PB - American Chemical Society (ACS)
SP - 1275-1279
IS - 6
VL - 23
SN - 1083-6160
SN - 1520-586X
ER -
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BibTex (up to 50 authors)
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@article{2019_Johnson,
author = {Eric C. Johnson and Eric J Bukowski and Rosario C. Sausa and Jesse J. Sabatini},
title = {Safer and Convenient Synthesis of 3,4-Dicyanofuroxan},
journal = {Organic Process Research and Development},
year = {2019},
volume = {23},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.oprd.9b00186},
number = {6},
pages = {1275--1279},
doi = {10.1021/acs.oprd.9b00186}
}
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MLA
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Johnson, Eric C., et al. “Safer and Convenient Synthesis of 3,4-Dicyanofuroxan.” Organic Process Research and Development, vol. 23, no. 6, Jun. 2019, pp. 1275-1279. https://doi.org/10.1021/acs.oprd.9b00186.
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