tert-Butyl nitrite

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tert-Butyl nitrite
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.962 Edit this at Wikidata
EC Number
  • 208-757-0
UNII
  • InChI=1S/C4H9NO2/c1-4(2,3)7-5-6/h1-3H3
    Key: IOGXOCVLYRDXLW-UHFFFAOYSA-N
  • CC(C)(C)ON=O
Properties
C4H9NO2
Molar mass 103.121 g·mol−1
Appearance colorless liquid
Boiling point 61–63 °C (142–145 °F; 334–336 K)
Hazards
GHS labelling:[1]
GHS02: FlammableGHS07: Exclamation mark
Danger
H225, H302, H332
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P303+P361+P353, P304+P312, P304+P340, P312, P330, P370+P378, P403+P235, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

tert-Butyl nitrite is an organic compound with the formula (CH3)3CONO. A colorless liquid, it is the tert-butyl ester of nitrous acid. It is typically employed as a solution with tert-butyl alcohol.

Use

The compound is used as a reagent in organic synthesis.[2] It reacts with secondary amides to give N-nitroso amides:[3]

RC(O)N(H)R + (CH3)3CONO → RC(O)N(NO)R + (CH3)3COH

See also

References

  1. ^ "tert-Butyl nitrite". pubchem.ncbi.nlm.nih.gov. Retrieved 2 February 2022.
  2. ^ Di Qiu, He Meng, Liang Jin, Shengbo Tang, Shuai Wang, Fangyang Mo, Yan Zhang, Jianbo Wang (2014). "Synthesis of Arylboronic Pinacol Esters from Corresponding Arylamines". Organic Syntheses. 91: 106. doi:10.15227/orgsyn.091.0106.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Yedage, Subhash L.; Bhanage, Bhalchandra M. (2017). "Tert-Butyl Nitrite-Mediated Synthesis of N-Nitrosoamides, Carboxylic Acids, Benzocoumarins, and Isocoumarins from Amides". The Journal of Organic Chemistry. 82 (11): 5769–5781. doi:10.1021/acs.joc.7b00570. PMID 28472882.
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