tert-Butyl hypochlorite

*tert*-Butyl hypochlorite
Names
	Preferred IUPAC name tert-Butyl hypochlorite
Identifiers
CAS Number	507-40-4;
3D model (JSmol)	Interactive image;
ChemSpider	454718;
ECHA InfoCard	100.007.339
EC Number	208-072-7;
PubChem CID	521297;
UNII	LS2JTI16JZ;
UN number	3255
CompTox Dashboard (EPA)	DTXSID3074941 ;
	InChI InChI=1S/C4H9ClO/c1-4(2,3)6-5/h1-3H3 Key: IXZDIALLLMRYOU-UHFFFAOYSA-N;
	SMILES ClOC(C)(C)C;
Properties
Chemical formula	C4H9ClO
Molar mass	108.57 g·mol−1
Appearance	Yellow liquid
Density	0.9583 g/cm3
Boiling point	79.6 °C (175.3 °F; 352.8 K) explosive
Solubility in water	Sparingly
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H250, H251, H271, H314, H334
Precautionary statements	P210, P220, P221, P222, P233, P235+P410, P240, P241, P242, P243, P260, P261, P264, P280, P283, P285, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P306+P360, P310, P321, P342+P311, P363, P370+P378, P371+P380+P375, P403+P235, P405, P407, P413, P420, P422, 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 hypochlorite is the organic compound with the formula (CH₃)₃COCl. A yellow liquid, it is a rare example of an organic hypochlorite, i.e. a compound with an O-Cl bond. It is a reactive material that is useful for chlorinations. It can be viewed as a lipophilic version of sodium hypochlorite (bleach).[1]

Synthesis and reactions

It is produced by chlorination of tert-butyl alcohol in the presence of base:[2][3]

(CH₃)₃COH + Cl₂ + NaOH → (CH₃)₃COCl + NaCl + H₂O

tert-Butyl hypochlorite is useful in the preparation of organic chloramines:[4]

R₂NH + t-BuOCl → R₂NCl + t-BuOH

References

Simpkins, Nigel S.; Cha, Jin K. (2006). "t-Butyl Hypochlorite". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb388.pub2. ISBN 0471936235.
Teeter, H. M.; Bell, E. W. (1952). "tert-Butyl Hypochlorite". Org. Synth. 32: 20. doi:10.15227/orgsyn.032.0020.
Mintz, H. M.; Walling, C. (1969). "t-Butyl Hypochlorite". Org. Synth. 49: 9. doi:10.15227/orgsyn.049.0009.
Herranz, Eugenio; Sharpless, K. Barry (1983). "Osmium-catalyzed Vicinal Oxyamination of Olefins by N-chloro-N-Argentocarbamates: Ethyl Threo-[1-(2-hydroxy-1,2-diphenylethyl)]carbamate". Org. Synth. 61: 93. doi:10.15227/orgsyn.061.0093.

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[1] Simpkins, Nigel S.; Cha, Jin K. (2006). "t-Butyl Hypochlorite". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb388.pub2. ISBN 0471936235.

[2] Teeter, H. M.; Bell, E. W. (1952). "tert-Butyl Hypochlorite". Org. Synth. 32: 20. doi:10.15227/orgsyn.032.0020.

[3] Mintz, H. M.; Walling, C. (1969). "t-Butyl Hypochlorite". Org. Synth. 49: 9. doi:10.15227/orgsyn.049.0009.

[4] Herranz, Eugenio; Sharpless, K. Barry (1983). "Osmium-catalyzed Vicinal Oxyamination of Olefins by N-chloro-N-Argentocarbamates: Ethyl Threo-[1-(2-hydroxy-1,2-diphenylethyl)]carbamate". Org. Synth. 61: 93. doi:10.15227/orgsyn.061.0093.