Editing Dichloromethane (section)

==Chemical reactions==
Dichloromethane is widely used as a solvent in part because it is relatively inert.  It does participate in reactions with certain strong nucleophiles however. [[Tert-butyllithium]] deprotonates DCM:<ref>{{cite journal |doi=10.1021/om50005a008|title=Homologation of boronic esters to .alpha.-chloro boronic esters |year=1983 |last1=Matteson |first1=Donald S. |last2=Majumdar |first2=Debesh |journal=Organometallics |volume=2 |issue=11 |pages=1529–1535 }}</ref>
:{{Chem2|H2CCl2  +  RLi  ->  HCCl2Li  +  RH}}
[[Methyllithium]] reacts with methylene chloride to give [[chlorocarbene]]:{{cn|date=May 2024}}
:{{chem2|CH2Cl2  +  CH3Li  ->  CHCl  +  CH4  +  LiCl}}

Although DCM is a common solvent in organic chemistry laboratories and is commonly assumed to be inert, it does react with some amines and triazoles.<ref>{{Cite journal |last1=Mills |first1=John E. |last2=Maryanoff |first2=Cynthia A. |last3=Cosgrove |first3=Robin M. |last4=Scott |first4=Lorraine |last5=McComsey |first5=David F. |title=The Reaction of Amines with Methylene Chloride. A Brief Review |date=1984 |url=http://www.tandfonline.com/doi/abs/10.1080/00304948409356172 |journal=Organic Preparations and Procedures International |language=en |volume=16 |issue=2 |pages=97–114 |doi=10.1080/00304948409356172 |issn=0030-4948|url-access=subscription }}</ref> Tertiary amines can react with DCM to form quaternary chloromethyl chloride salts via the [[Menshutkin reaction]].<ref>{{Cite journal |last1=Dunlap |first1=Lee E. |last2=Olson |first2=David E. |date=2018-05-31 |title=Reaction of N , N -Dimethyltryptamine with Dichloromethane Under Common Experimental Conditions |journal=ACS Omega |language=en |volume=3 |issue=5 |pages=4968–4973 |doi=10.1021/acsomega.8b00507 |issn=2470-1343 |pmc=5981293 |pmid=29876537}}</ref> Secondary amines can react with DCM to yield an equilibrium of iminium chlorides and chloromethyl chlorides, which can react with a second equivalent of the secondary amine to form [[aminal]]s.<ref>{{Cite journal |last1=Mills |first1=John E. |last2=Maryanoff |first2=Cynthia A. |last3=McComsey |first3=David F. |last4=Stanzione |first4=Robin C. |last5=Scott |first5=Lorraine |date=1987 |title=Reaction of amines with methylene chloride. Evidence for rapid aminal formation from N-methylenepyrrolidinium chloride and pyrrolidine |url=https://pubs.acs.org/doi/abs/10.1021/jo00385a038 |journal=The Journal of Organic Chemistry |language=en |volume=52 |issue=9 |pages=1857–1859 |doi=10.1021/jo00385a038 |issn=0022-3263|url-access=subscription }}</ref> At increased temperatures, [[pyridine]]s including [[4-Dimethylaminopyridine|DMAP]], react with DCM to form methylene bispyridinium dichlorides.<ref>{{Cite journal |last1=Rudine |first1=Alexander B. |last2=Walter |first2=Michael G. |last3=Wamser |first3=Carl C. |date=2010-06-18 |title=Reaction of Dichloromethane with Pyridine Derivatives under Ambient Conditions |url=https://pubs.acs.org/doi/10.1021/jo100276m |journal=The Journal of Organic Chemistry |language=en |volume=75 |issue=12 |pages=4292–4295 |doi=10.1021/jo100276m |pmid=20469919 |issn=0022-3263|url-access=subscription }}</ref> [[Hydroxybenzotriazole]] and related reagents used in peptide coupling react with DCM in the presence of [[triethylamine]], forming [[acetal]]s.<ref>{{Cite journal |last1=Ji |first1=Jian-guo |last2=Zhang |first2=De-yi |last3=Ye |first3=Yun-hua |last4=Xing |first4=Qi-yi |date=1998 |title=Studies on the reactions of HOBt, HOOBt, HOSu with dichloroalkane solvents |url=https://linkinghub.elsevier.com/retrieve/pii/S0040403998014063 |journal=Tetrahedron Letters |language=en |volume=39 |issue=36 |pages=6515–6516 |doi=10.1016/S0040-4039(98)01406-3|url-access=subscription }}</ref>