 | |
| Names | |
|---|---|
| Preferred IUPAC name (1-Chloro-2-methylpropan-2-yl)benzene | |
| Other names (Chloro-tert-butyl)benzene | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChemSpider |
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| ECHA InfoCard | 100.007.453 |
| EC Number |
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| UNII | |
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| Properties | |
| C10H13Cl | |
| Molar mass | 168.663 g/mol |
| Appearance | colorless liquid |
| Density | 1.047 g/cm3 |
| Boiling point | 223 °C (433 °F; 496 K) |
| organic solvents | |
| Hazards | |
| GHS labelling:[1] | |
 | |
| Warning | |
| H315,H319,H335 | |
| P261,P264,P264+P265,P271,P280,P302+P352,P304+P340,P305+P351+P338,P319,P321,P332+P317,P337+P317,P362+P364,P403+P233,P405,P501 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Neophyl chloride, C6H5C(CH3)2CH2Cl, is a halogenatedorganic compound with unusual nucleophilic substitution properties. Neophyl chloride is used to form a versatileorganolithium reagent, neophyl lithium, by reaction with lithium.[2][3]
Neophyl chloride was first synthesized by Haller and Ramart fromneophyl alcohol by anucleophilic substitution reaction, usingthionyl chloride as the chlorinating agent:[4]
It is easily prepared on a large scale frombenzene andmethallyl chloride by anelectrophilic aromatic substitution reaction, usingsulfuric acid as thecatalyst:[4] The reaction is an example of anelectrophilic aromatic substitution reaction.
It can also be prepared byfree radical halogenation oftert-butylbenzene, using various chlorine donors.[4]
Neophyl chloride can be used to form an organolithium reagent, neophyl lithium, by reaction withlithium. Organolithium reagents are useful due to theirnucleophilic properties and their ability to form carbon-to-carbon bonds, like in reactions withcarbonyls.
Neophyl chloride is of interest to organic chemists due to its substitution properties. Neophyl chloride is aneopentylhalide which means it is subject to theneopentyl effect. This effect makesSN2nucleophilic substitution highly unlikely because ofsteric interactions due to the branching of the β-carbon. Norotamer of the molecule would allow a backside attack of the α carbon.
β-Hydride elimination also does not occur with neophyl derivatives as this group lacks hydrogens at the β positions. These factors make neophyl chloride a precursor to intermediates that resist common substitution andelimination reactions.
