Di-tert-butyl chromate

*tert*-Butyl chromate
Names
	IUPAC name tert-Butyl chromate
	Other names Di-tert-butyl ester of chromic acid; Bis(tert-butyl)chromate
Identifiers
CAS Number	1189-85-1;
3D model (JSmol)	Interactive image;
ChemSpider	11649895;
PubChem CID	102059956 wrong formula;
RTECS number	GB2900000;
	InChI InChI=1S/2C4H9O.Cr.2O/c21-4(2,3)5;;;/h21-3H3;;;/q2-1;+2;; Key: PNWJTIFZRHJYLK-UHFFFAOYSA-N; InChI=1/2C4H9O.Cr.2O/c21-4(2,3)5;;;/h21-3H3;;;/q2-1;+2;;/rC8H18CrO4/c1-7(2,3)12-9(10,11)13-8(4,5)6/h1-6H3 Key: PNWJTIFZRHJYLK-PZTLRDNSAU;
	SMILES O([Cr](OC(C)(C)C)(=O)=O)C(C)(C)C;
Properties
Chemical formula	[(CH3)3CO]2CrO2
Molar mass	230.3 g/mol[1]
Appearance	red oil
Melting point	−2.8 °C (27.0 °F; 270.3 K) [2]
Solubility in water	Miscible[2]
Hazards
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 0.005 mg CrO3/m3 [skin][1]
REL (Recommended)	Ca TWA 0.001 mg Cr(VI)/m3[1]
IDLH (Immediate danger)	Ca [15 mg/m3 {as Cr(VI)}][1]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Di-tert-butyl chromate is an alkoxide with the formula CrO₂(OC(CH₃)₃)₂. It is prepared by treatment of t-butanol with chromic anhydride. It forms red crystals at temperatures below –5 °C, above which it melts to give a red oil.[3][4] The complex, which is diamagnetic, is of fundamental interest as a model for the intermediates in oxidations of alcohols by chromium(VI). This complex is stable because as a t-butyl groups lack beta-hydrogens. This complex and its analogues have tetrahedral geometry at chromium, as established by X-ray crystallography of its analogues.[5][6]

Applications

It is used as a precursor to chromium-based catalysts, such as the Phillips catalyst, which are employed for the polymerization of ethylene.[7]

Safety

Like other forms of hexavalent chromium, di-tert-butyl chromate is classified as a potential carcinogen by the United States National Institute for Occupational Safety and Health.[1][2]

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References

NIOSH Pocket Guide to Chemical Hazards. "#0080". National Institute for Occupational Safety and Health (NIOSH).
"Tert-butyl chromate". International Chemical Safety Cards. NIOSH. July 1, 2014.
Freeman, Fillmore (2001-04-15), "Di-tert-butyl Chromate", Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Ltd, doi:10.1002/047084289x.rd059m, ISBN 978-0471936237
Richer, Jean-Claude; Hachey, Jean-Marie (1975). "Esters Chromiques Dérivés d'Alcools Tertiaires". Canadian Journal of Chemistry. 53 (20): 3087–3093. doi:10.1139/v75-438.
Amirthalingam, V.; Grant, D. F.; Senol, A. (1972). "The crystal structure and absolute configuration of cedryl chromate". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 28 (5): 1340–1345. doi:10.1107/S0567740872004261.
Stavropoulos, Pericles; Bryson, Nathan; Youinou, Marie Therese; Osborn, John A. (1990). "Chromyl complexes with aryloxy and siloxy ligands". Inorganic Chemistry. 29 (10): 1807–1811. doi:10.1021/ic00335a009.
McDaniel, M. (2009). "Influence of porosity on PE molecular weight from the Phillips Cr/Silica catalyst". Journal of Catalysis. 261: 34–49. doi:10.1016/j.jcat.2008.10.015.

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[NPG-1] NIOSH Pocket Guide to Chemical Hazards. "#0080". National Institute for Occupational Safety and Health (NIOSH).

[ICSC-2] "Tert-butyl chromate". International Chemical Safety Cards. NIOSH. July 1, 2014.

[3] Freeman, Fillmore (2001-04-15), "Di-tert-butyl Chromate", Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Ltd, doi:10.1002/047084289x.rd059m, ISBN 978-0471936237

[4] Richer, Jean-Claude; Hachey, Jean-Marie (1975). "Esters Chromiques Dérivés d'Alcools Tertiaires". Canadian Journal of Chemistry. 53 (20): 3087–3093. doi:10.1139/v75-438.

[5] Amirthalingam, V.; Grant, D. F.; Senol, A. (1972). "The crystal structure and absolute configuration of cedryl chromate". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 28 (5): 1340–1345. doi:10.1107/S0567740872004261.

[6] Stavropoulos, Pericles; Bryson, Nathan; Youinou, Marie Therese; Osborn, John A. (1990). "Chromyl complexes with aryloxy and siloxy ligands". Inorganic Chemistry. 29 (10): 1807–1811. doi:10.1021/ic00335a009.

[7] McDaniel, M. (2009). "Influence of porosity on PE molecular weight from the Phillips Cr/Silica catalyst". Journal of Catalysis. 261: 34–49. doi:10.1016/j.jcat.2008.10.015.