tert-Butyl nitrite

*tert*-Butyl nitrite
Identifiers
CAS Number	540-80-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	10444;
ECHA InfoCard	100.007.962
EC Number	208-757-0;
PubChem CID	10906;
UNII	4780H7U8LU;
CompTox Dashboard (EPA)	DTXSID10202316 ;
	InChI InChI=1S/C4H9NO2/c1-4(2,3)7-5-6/h1-3H3 Key: IOGXOCVLYRDXLW-UHFFFAOYSA-N;
	SMILES CC(C)(C)ON=O;
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H332
Precautionary statements	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

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

References

^ "tert-Butyl nitrite". pubchem.ncbi.nlm.nih.gov. Retrieved 2 February 2022.
^ 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)
^ 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.

[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.

[1]

[2]

[3]

Use

See also

References