Neophyl chloride

Source: Wikipedia, the free encyclopedia.
Neophyl chloride
Names
Preferred IUPAC name
(1-Chloro-2-methylpropan-2-yl)benzene
Other names
(Chloro-tert-butyl)benzene
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.007.453 Edit this at Wikidata
EC Number
  • 208-197-7
UNII
  • InChI=1S/C10H13Cl/c1-10(2,8-11)9-6-4-3-5-7-9/h3-7H,8H2,1-2H3 checkY
    Key: DNXXUUPUQXSUFH-UHFFFAOYSA-N checkY
  • InChI=1/C10H13Cl/c1-10(2,8-11)9-6-4-3-5-7-9/h3-7H,8H2,1-2H3
    Key: DNXXUUPUQXSUFH-UHFFFAOYAJ
  • ClCC(c1ccccc1)(C)C
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]
GHS07: Exclamation mark
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 their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Neophyl chloride, C6H5C(CH3)2CH2Cl, is a halogenated organic compound with unusual nucleophilic substitution properties. Neophyl chloride is used to form a versatile organolithium reagent, neophyl lithium, by reaction with lithium.[2][3]

Preparation

Neophyl chloride was first synthesized[citation needed] by Haller and Ramart from neophyl alcohol by a nucleophilic substitution reaction, using thionyl chloride as the chlorinating agent:[4]

C6H5C(CH3)2CH2OH + SOCl2 → C6H5C(CH3)2CH2Cl + HCl + SO2

It is easily prepared on a large scale from

catalyst:[4] The reaction is an example of an electrophilic aromatic substitution
reaction.

H2C=C(CH3)CH2Cl + C6H6 → C6H5C(CH3)2CH2Cl

It can also be prepared by

tert-butylbenzene, using various chlorine donors.[4]

Reactions and applications

Neophyl chloride can be used to form an organolithium reagent, neophyl lithium, by reaction with

carbonyls
.

C6H5C(CH3)2CH2Cl + 2Li → C6H5C(CH3)2CH2Li + LiCl

Neophyl chloride is of interest to organic chemists due to its substitution properties. Neophyl chloride is a neopentyl halide which means it is subject to the neopentyl effect. This effect makes SN2 nucleophilic substitution highly unlikely because of steric interactions due to the branching of the β-carbon. No rotamer 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 and elimination reactions.

References

  1. ^ "Neophyl chloride". pubchem.ncbi.nlm.nih.gov. Retrieved 27 December 2021.
  2. ISBN 0-8493-0595-0
    .
  3. ISBN 0-02-946720-9
    .
  4. ^ a b c W. T. Smith, Jr. and J. T. Sellas (1963). "Neophyl chloride". Organic Syntheses.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Neophyl_chloride&oldid=1157898179"