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Allyl isothiocyanate
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==Production and applications== Allyl isothiocyanate is produced commercially by the reaction of [[allyl chloride]] and [[potassium thiocyanate]]:<ref name=Ullmann/> :CH<sub>2</sub>=CHCH<sub>2</sub>Cl + KSCN β CH<sub>2</sub>=CHCH<sub>2</sub>NCS + KCl The product obtained in this fashion is sometimes known as ''synthetic mustard oil''. Allyl thiocyanate isomerizes to the isothiocyanate:<ref name=JCE>{{cite journal |doi=10.1021/ed048p81 |title=The Preparation and Isomerization of Allyl Thiocyanate. An Organic Chemistry Experiment |date=1971 |last1=Emergon |first1=David W. |journal=Journal of Chemical Education |volume=48 |issue=1 |page=81 |bibcode=1971JChEd..48...81E }}</ref> :{{chem2|CH2\dCHCH2SCN -> CH2\dCHCH2NCS}} Allyl isothiocyanate can also be liberated by dry [[distillation]] of the seeds. The product obtained in this fashion is known as [[mustard oil|volatile oil of mustard]]. It is used principally as a [[flavoring]] agent in foods. Synthetic allyl isothiocyanate is used as an [[insecticide]], as an anti-mold agent <ref>US Patent No. 8691042</ref> <!--as an [[animal repellent]], to [[denatured alcohol|denature alcohol]], and as a [[topical anesthetic]].--> [[antibacterial|bacteriocide]],<ref>{{cite journal |last1=Masuda |first1=Shuichi |last2=Masuda |first2=Hideki |last3=Shimamura |first3=Yuko |last4=Sugiyama |first4=Chitose |last5=Takabayashi |first5=Fumiyo |title=Improvement Effects of Wasabi (Wasabia japonica) Leaves and Allyl Isothiocyanate on Stomach Lesions of Mongolian Gerbils Infected with Helicobacter pylori |journal=Natural Product Communications |date=April 2017 |volume=12 |issue=4 |pages=595β598 |doi=10.1177/1934578X1701200431 |pmid=30520603|s2cid=54567566 |doi-access=free }}</ref> and [[nematicide]], and is used in certain cases for crop protection.<ref name=Ullmann/> It is also used in fire alarms for the deaf.<ref>{{US patent reference|number= 20100308995A1|issue-date= 2015-06-24 |inventor= Hideaki Goto, Tomo Sakai, Koichiro Mizoguchi, Yukinobu Tajima, Makoto Imai| title= Odor generation alarm and method for informing unusual situation}}</ref><ref>{{cite web |last1=Phillipson |first1=Tacye |title=Why would you want a wasabai fire alarm? |url=https://blog.nms.ac.uk/2018/08/29/why-would-you-want-a-wasbai-fire-alarm/ |website=National Museums Scotland Blog |date=29 August 2018 |access-date=10 March 2022}}</ref> Hydrolysis of allyl isothiocyanate gives [[allylamine]].<ref>{{OrgSynth | author = Leffler, M. T. | title = Allylamine | volume = 18 | pages = 5 | collvol = 2 | collvolpages = 24 | year = 1938 | prep = CV2P0024 }}</ref>
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