Ethyl nitrite

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Ethyl nitrite
Names
Preferred IUPAC name
Ethyl nitrite
Other names
1-Nitrosooxyethane
Ethyl alcohol nitrite
Nitrous acid
Nitrous ether
Ethyl ester
Nitrethyl
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.385 Edit this at Wikidata
UNII
  • InChI=1S/C2H5NO2/c1-2-5-3-4/h2H2,1H3 checkY
    Key: QQZWEECEMNQSTG-UHFFFAOYSA-N checkY
  • InChI=1/C2H5NO2/c1-2-5-3-4/h2H2,1H3
    Key: QQZWEECEMNQSTG-UHFFFAOYAU
  • O=NOCC
Properties
C2H5NO2
Molar mass 75.067 g·mol−1
Boiling point 17 °C (63 °F; 290 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 [1]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2
4
4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

The chemical compound ethyl nitrite is an alkyl nitrite. It may be prepared from ethanol.[2]

It is used as a reagent with butanone to yield the dimethylglyoxime end product.

Ethyl nitrite is the main ingredient in a traditional ethanol-based South African remedy for colds and flu known as Witdulsies and sold in pharmacies. It is known as a traditional Afrikaans remedy and may have Dutch roots, as the same remedy is apparently made by the Germano-Dutch Amish people in the USA. However FDA has blocked over-the-counter sales of this same remedy, known in the USA as sweet nitrite or sweet spirit of nitre since 1980.[3] Its use has been associated with fatal methemoglobinemia.[4]

References

  1. ^ "NFPA 704 Ratings for Common Chemicals".
  2. ^ Semon, W. L.; Damerell, V. R. (1943). "Dimethylglyoxime". Organic Syntheses; Collected Volumes, vol. 2, p. 204.
  3. ^ "Rulemaking History for OTC Sweet Spirits of Nitre Drug Products". fda.gov. Retrieved 2016-12-26.
  4. ^ "ETHYL NITRITE - National Library of Medicine HSDB Database". toxnet.nlm.nih.gov. Retrieved 2017-11-18.[dead link]

External links

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