tert-Butyl nitrite

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.

tert-Butyl nitrite
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.962
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).
Infobox references

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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