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OrganoMetallurgy/Drafts/tert-Butyl hypochlorite
Identifiers
CAS Number	507-40-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	454718;
EC Number	208-072-7;
PubChem CID	521297;
UNII	LS2JTI16JZ ;
UN number	3255
	SMILES CC(C)(C)OCl;
Properties
Appearance	slightly yellowish liquid
Density	0.9583 g cm–3
Boiling point	79.6 °C (175.3 °F; 352.8 K) at 750 mmHg
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H250, H271, H314, H334
	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 yellowish photosensitive liquid that is used as a chlorinating or oxidizing agent in organic chemistry. ^[1]

Properties

Reacts violently with rubber

Structure

Synthesis/Preparation

Tert-butyl hypochlorite can be prepared by the reaction of a solution of tert-butyl alcohol with a sodium hypochlorite solution and acetic acid under low light conditions.^[2]

Applications/Uses/Reactions

Chlorination Radical chlorination Chloramines Oxidation Oxidizes secondary alcohols to ketones in the presence of pyridine (in the absence of pyridine, α-chloro ketones also tend to be produced) Sulfides to sulfoxides Selenides to seleoxides Tellerides to telluroxides Addition Adds to electron rich alkenes Adds to isocyanides

References

^ Simpkins, Nigel S.; Cha, Jin K. (2001). Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289x.rb388.pub2. ISBN 9780470842898.
^ "t-BUTYL HYPOCHLORITE". Organic Syntheses. 49. doi:10.15227/orgsyn.049.0009.

Category:Reagents for organic chemistry Category:Hypochlorites

[1] Simpkins, Nigel S.; Cha, Jin K. (2001). Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons, Ltd. doi:10.1002/047084289x.rb388.pub2. ISBN 9780470842898.

[2] "t-BUTYL HYPOCHLORITE". Organic Syntheses. 49. doi:10.15227/orgsyn.049.0009.

[1]

[2]