:2-Chloro-m-cresol

{{DISPLAYTITLE:2-Chloro-m-cresol}}

{{Chembox

| Verifiedfields = changed

| verifiedrevid = 477212990

|Name=2-Chloro-m-cresol

|ImageFile=2-chloro-m-cresol.png

|ImageClass = skin-invert-image

|ImageSize=120px

|PIN= 2-Chloro-3-methylphenol

|OtherNames= 2-Chloro-hydroxytoluene; 2-Chloro-m-cresol

|Section1= {{Chembox Identifiers

| CASNo=608-26-4

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = XZT2VD3JL6

| PubChem = 14852

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 14162

| SMILES = Clc1c(cccc1O)C

| InChI = 1/C7H7ClO/c1-5-3-2-4-6(9)7(5)8/h2-4,9H,1H3

| InChIKey = HKHXLHGVIHQKMK-UHFFFAOYAK

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C7H7ClO/c1-5-3-2-4-6(9)7(5)8/h2-4,9H,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HKHXLHGVIHQKMK-UHFFFAOYSA-N

| MeSHName=

}}

|Section2= {{Chembox Properties

| Formula=C₇H₇ClO

| MolarMass =142.5829

| Appearance=

| Density= 1.228 g/cm³

| MeltingPt =

| BoilingPt =

}}

|Section3= {{Chembox Hazards

| FlashPtC =78.1

}}

}}

2-Chloro-m-cresol is a chlorinated cresol. The compound is difficult to synthesise as chlorination of m-cresol yields the para-product (4-chloro-3-methylphenol). Historically synthesis has been achieved via a para-selective nitration, followed by conversion to a diazonium compound and a Sandmeyer reaction to insert the chlorine into the 2-position.{{cite journal |last1=Huston |first1=Ralph C. |last2=Chen |first2=Philip S. |title=The Chloro Derivatives of m-Cresol |journal=Journal of the American Chemical Society |date=October 1933 |volume=55 |issue=10 |pages=4214–4218 |doi=10.1021/ja01337a056}}