Tert-Butyl nitrite

tert-Butyl nitrite

Identifiers
CAS Number	540-80-7  Y
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
Density	0.867 g/mL
Boiling point	61–63 °C (142–145 °F; 334–336 K)
Hazards
GHS labelling: [1]
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 and 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

• Butyl nitrite

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 .
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.