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Names | |||
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IUPAC name
(benzene)tricarbonylchromium
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Other names
benzene tricarbonyl chromium, (benzene)chromium tricarbonyl, Benchrotrene, pi-benzenetricarbonylchromium
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Identifiers | |||
3D model (JSmol)
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ChemSpider | |||
ECHA InfoCard | 100.031.939 | ||
EC Number |
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PubChem CID
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Properties | |||
Cr(C6H6)(CO)3 | |||
Molar mass | 214.14 g/mol | ||
Appearance | solid yellow crystals | ||
Melting point | 163 to 166 °C (325 to 331 °F; 436 to 439 K) | ||
nonsoluble | |||
Solubility | THF, ether, benzene | ||
Structure | |||
tetrahedral, "piano stool" | |||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Harmful through inhalation, contact with skin, or swallowed | ||
GHS labelling: | |||
Warning | |||
H302, H312, H332 | |||
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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(Benzene)chromium tricarbonyl is an organometallic compound with the formula Cr(C6H6)(CO)3. This yellow crystalline solid compound is soluble in common nonpolar organic solvents. The molecule adopts a geometry known as “piano stool” because of the planar arrangement of the aryl group and the presence of three CO ligands as "legs" on the chromium-bond axis.[1]
(Benzene)tricarbonylchromium was first reported in 1957 by Fischer and Öfele, who prepared the compound by the carbonylation of bis(benzene)chromium.[2] They obtained mainly chromium carbonyl (Cr(CO)6) and traces of Cr(C6H6)(CO)3. The synthesis was optimized through the reaction of Cr(CO)6 and Cr(C6H6)2. For commercial purposes, a reaction of Cr(CO)6 and benzene is used:
Complexes of the type (Arene)Cr(CO)3 have been well investigated as reagents in organic synthesis..[3] The aromatic ring of (benzene)tricarbonylchromium is substantially more electrophilic than benzene itself, allowing it to undergo nucleophilic addition reactions.[4]
It is also more acidic, undergoing lithiation upon treatment with n-butyllithium. The resulting organolithium compound can then be used as a nucleophile in various reactions, for example, with trimethylsilyl chloride:
(Benzene)tricarbonylchromium is a useful catalyst for the hydrogenation of 1,3-dienes. The product alkene results from 1,4-addition of hydrogen. The complex does not hydrogenate isolated double bonds.
Chromium(0) |
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Chromium(I) |
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Chromium(II) |
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Chromium(II, III) | |||
Chromium(III) | |||
Chromium(IV) | |||
Chromium(V) | |||
Chromium(VI) |
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Polyatomic ion |