Home > Community > Is chlorophenylmethane the correct IUPAC name rather than chloromethylbenzene?
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Ketan Badwe

Is chlorophenylmethane the correct IUPAC name rather than chloromethylbenzene?

BWAMBALE JORAM  Follow

The preferred IUPAC name is, indeed, (chloromethyl)benzene, built from substitutive prefix chloromethyl. The parentheses around "chloromethyl" are required because it is a compound substituent (a simple substituent attached to another simple substituent, specifically, methyl and chloro in this case). The Blue Book [1, p. 66] has plenty of examples similar to yours:

$$\begin{array}{lll}\ce{C6H5-CH2-NCS} &\quad &\text{benzyl isothiocyanate} \\ & &\text{(isothiocyanatomethyl)benzene (PIN)} \\ & & \\\ce{C6H5-NC} &\quad &\text{phenyl isocyanide} \\ & &\text{isocyanobenzene (PIN)}\end{array}$$

Note that common names for this molecule also include: benzyl chloride and α-chlorotoluene.

References

  1. Favre, H. A.; Powell, W. H. IUPAC “Blue Book” Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names; IUPAC Recommendations; Royal Society of Chemistry: Cambridge, England, 2013. ISBN 978-0-85404-182-4.

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John Staples  Follow
The remark about the use of parentheses is correct. However, the actual question was whether the preferred name is chloro(phenyl)methane or (chloromethyl)benzene.More
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Emil Bode  Follow
@Loong You are right. I was (and still am) too lazy to look up the relevant rules so just decided to edit in a brief line about the parentheses; I leave it to you if you want to expand further or write another answer.More
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Douglas Sucy  Follow
Is 1-phenyl methyl chloride possible?More
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