lauroyl chloride

{{Chembox

| ImageFile = Lauroyl chloride.svg

| ImageSize =

| ImageAlt =

| IUPACName = Dodecanoyl chloride

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 112-16-3

| CASNo_Ref = {{Cascite|correct|CAS}}

| ChEMBL = 3561663

| ChemSpiderID = 7874

| EC_number = 203-941-7

| PubChem = 8166

| UNII = 9LHL10777I

| StdInChI=1S/C12H23ClO/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3

| StdInChIKey = NQGIJDNPUZEBRU-UHFFFAOYSA-N

| SMILES = CCCCCCCCCCCC(=O)Cl

}}

|Section2={{Chembox Properties

| C=12|H=23|Cl=1|O =1

| MolarMass =

| Appearance = colorless liquid

| Density = 0.93 g/cm³

| MeltingPtC = -17

| BoilingPtC = 145

| BoilingPt_notes = 18 torr

| Solubility = }}

|Section3={{Chembox Hazards

| GHS_ref={{cite web |title=Lauroyl chloride |url=https://pubchem.ncbi.nlm.nih.gov/compound/8166#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=26 March 2022 |language=en}}

| GHSPictograms = {{GHS05}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|290|314|317}}

| PPhrases = {{P-phrases|234|260|261|264|264+265|272|280|301+330+331|302+352|302+361+354|304+340|305+354+338|316|317|321|333+313|362+364|363|390|405|406|501}}

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Lauroyl chloride is the organic compound with the formula CH₃(CH₂)₁₀COCl. It is the acid chloride of lauric acid. Lauroyl chloride is a standard reagent for installing the lauroyl group.{{cite journal |doi=10.1016/j.carres.2008.08.023|title=Rapid homogeneous lauroylation of wheat straw hemicelluloses under mild conditions|year=2008|last1=Peng|first1=Feng|last2=Ren|first2=Jun-Li|last3=Peng|first3=Bai|last4=Xu|first4=Feng|last5=Sun|first5=Run-Cang|last6=Sun|first6=Jin-Xia|journal=Carbohydrate Research|volume=343|issue=17|pages=2956–2962|pmid=18793765}} It is mainly produced as a precursor to dilauroyl peroxide, which is widely used in free-radical polymerizations.{{Ullmann |doi=10.1002/14356007.a19_199.pub2|title=Peroxy Compounds, Organic|year=2018|last1=Uhl|first1=Agnes|last2=Bitzer|first2=Mario|last3=Wolf|first3=Hanno|last4=Hermann|first4=Dominik|last5=Gutewort|first5=Sven|last6=Völkl|first6=Matthias|last7=Nagl|first7=Iris|pages=1–45|isbn=9783527306732}}

Lauroyl chloride is a substrate for diverse reactions characteristic of acid chlorides. With base, it converts to laurone, a ketone with the formula [CH₃(CH₂)₁₀]₂CO.{{cite journal |doi=10.15227/orgsyn.031.0068|title=Laurone|journal=Organic Syntheses|year=1951|volume=31|page=68|author=J. C. Sauer}} With sodium azide, it reacts to give undecyl isocyanate via a Curtius rearrangement of the acyl azide.{{cite journal |doi=10.15227/orgsyn.024.0094|title=Undecyl Isocyanate|first1=C. F. H.|last1=Allen|first2=Alan|last2=Bell|journal=Organic Syntheses|year=1944|volume=24|page=94}}