tert-Butyl hypochlorite

*tert*-Butyl hypochlorite
Names
	IUPAC name 2-Methyl-2-propanyl 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	Colorless liquid
Density	0.9583 g/cm3
Boiling point	79.6 °C (175.3 °F; 352.8 K) explosive
Solubility in water	Sparingly
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H250, H251, H271, H314, H318, H334
GHS precautionary statements	P210, P220, P221, P222, P233, P235+410, P240, P241, P242, P243, P260, P261, P264, P280, P283, P285, P301+330+331, P302+334, P303+361+353, P304+340, P304+341, P305+351+338, P306+360, P310, P321
	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 colorless 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.[1] 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.