Lauroyl chloride

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.[2] It is mainly produced as a precursor to dilauroyl peroxide, which is widely used in free-radical polymerizations.[3]

Lauroyl chloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.583
EC Number
  • 203-941-7
UNII
  • InChI=1S/C12H23ClO/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3
    Key: NQGIJDNPUZEBRU-UHFFFAOYSA-N
  • CCCCCCCCCCCC(=O)Cl
Properties
C12H23ClO
Molar mass 218.77 g·mol−1
Appearance colorless liquid
Density 0.93 g/cm3
Melting point −17 °C (1 °F; 256 K)
Boiling point 145 °C (293 °F; 418 K) 18 torr
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H290, H314, H317
P234, P260, P261, P264, P264+P265, P272, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P333+P313, P362+P364, P363, P390, P405, P406, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[4] With sodium azide, it reacts to give undecyl isocyanate via a Curtius rearrangement of the acyl azide.[5]

References
  1. "Lauroyl chloride". pubchem.ncbi.nlm.nih.gov. Retrieved 26 March 2022.
  2. Peng, Feng; Ren, Jun-Li; Peng, Bai; Xu, Feng; Sun, Run-Cang; Sun, Jin-Xia (2008). "Rapid homogeneous lauroylation of wheat straw hemicelluloses under mild conditions". Carbohydrate Research. 343 (17): 2956–2962. doi:10.1016/j.carres.2008.08.023. PMID 18793765.
  3. Uhl, Agnes; Bitzer, Mario; Wolf, Hanno; Hermann, Dominik; Gutewort, Sven; Völkl, Matthias; Nagl, Iris (2018). "Peroxy Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–45. doi:10.1002/14356007.a19_199.pub2.
  4. J. C. Sauer (1951). "Laurone". Organic Syntheses. 31: 68. doi:10.15227/orgsyn.031.0068.
  5. Allen, C. F. H.; Bell, Alan (1944). "Undecyl Isocyanate". Organic Syntheses. 24: 94. doi:10.15227/orgsyn.024.0094.
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