{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,31]],"date-time":"2026-10-31T14:21:26Z","timestamp":1793456486309,"version":"4.5.0"},"reference-count":148,"publisher":"American Chemical Society (ACS)","issue":"1","license":[{"start":{"date-parts":[[2020,1,1]],"date-time":"2020-01-01T00:00:00Z","timestamp":1577836800000},"content-version":"vor","delay-in-days":34,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100000266","name":"Research Councils UK","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000266","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000288","name":"Royal Society","doi-asserted-by":"publisher","award":["RG150444"],"award-info":[{"award-number":["RG150444"]}],"id":[{"id":"10.13039\/501100000288","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000288","name":"Royal Society","doi-asserted-by":"publisher","award":["RGFA80031"],"award-info":[{"award-number":["RGFA80031"]}],"id":[{"id":"10.13039\/501100000288","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000288","name":"Royal Society","doi-asserted-by":"publisher","award":["UF140161"],"award-info":[{"award-number":["UF140161"]}],"id":[{"id":"10.13039\/501100000288","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100004330","name":"GlaxoSmithKline","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100004330","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Pharmacat Consortium"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,1,17]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Despite their wide use in academia as metal-carbene precursors, diazo compounds are often avoided in industry owing to concerns over their instability, exothermic decomposition, and potential explosive behavior. The stability of sulfonyl azides and other diazo transfer reagents is relatively well understood, but there is little reliable data available for diazo compounds. This work first collates available sensitivity and thermal analysis data for diazo transfer reagents and diazo compounds to act as an accessible reference resource. Thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and accelerating rate calorimetry (ARC) data for the model donor\/acceptor diazo compound ethyl (phenyl)diazoacetate are presented. We also present a rigorous DSC dataset with 43 other diazo compounds, enabling direct comparison to other energetic materials to provide a clear reference work to the academic and industrial chemistry communities. Interestingly, there is a wide range of onset temperatures (Tonset) for this series of compounds, which varied between 75 and 160 \u00b0C. The thermal stability variation depends on the electronic effect of substituents and the amount of charge delocalization. A statistical model is demonstrated to predict the thermal stability of differently substituted phenyl diazoacetates. A maximum recommended process temperature (TD24) to avoid decomposition is estimated for selected diazo compounds. The average enthalpy of decomposition (\u0394HD) for diazo compounds without other energetic functional groups is \u2212102 kJ mol\u20131. Several diazo transfer reagents are analyzed using the same DSC protocol and found to have higher thermal stability, which is in general agreement with the reported values. For sulfonyl azide reagents, an average \u0394HD of \u2212201 kJ mol\u20131 is observed. High-quality thermal data from ARC experiments shows the initiation of decomposition for ethyl (phenyl)diazoacetate to be 60 \u00b0C, compared to that of 100 \u00b0C for the common diazo transfer reagent p-acetamidobenzenesulfonyl azide (p-ABSA). The Yoshida correlation is applied to DSC data for each diazo compound to provide an indication of both their impact sensitivity (IS) and explosivity. As a neat substance, none of the diazo compounds tested are predicted to be explosive, but many (particularly donor\/acceptor diazo compounds) are predicted to be impact-sensitive. It is therefore recommended that manipulation, agitation, and other processing of neat diazo compounds are conducted with due care to avoid impacts, particularly in large quantities. The full dataset is presented to inform chemists of the nature and magnitude of hazards when using diazo compounds and diazo transfer reagents. Given the demonstrated potential for rapid heat generation and gas evolution, adequate temperature control and cautious addition of reagents that begin a reaction are strongly recommended when conducting reactions with diazo compounds.<\/jats:p>","DOI":"10.1021\/acs.oprd.9b00422","type":"journal-article","created":{"date-parts":[[2019,11,28]],"date-time":"2019-11-28T07:15:19Z","timestamp":1574925319000},"page":"67-84","source":"Crossref","is-referenced-by-count":368,"title":["Thermal Stability\nand Explosive Hazard Assessment\nof Diazo Compounds and Diazo Transfer Reagents"],"prefix":"10.1021","volume":"24","author":[{"given":"Sebastian P.","family":"Green","sequence":"first","affiliation":[{"name":"Imperial College London , , White City Campus, 80 Wood Lane , ,","place":["London, U.K., W12 0BZ"]},{"name":"Imperial College London , , South Kensington Campus, Exhibition Road , ,","place":["London, U.K., SW7 2AZ"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katherine M.","family":"Wheelhouse","sequence":"additional","affiliation":[{"name":"GlaxoSmithKline, GSK Medicines Research Centre , , Gunnels Wood Road , Stevenage, ,","place":["Hertfordshire, U.K., SG1 2NY"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrew D.","family":"Payne","sequence":"additional","affiliation":[{"name":"GlaxoSmithKline, GSK Medicines Research Centre , , Gunnels Wood Road , Stevenage, ,","place":["Hertfordshire, U.K., SG1 2NY"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3431-2371","authenticated-orcid":true,"given":"Jason P.","family":"Hallett","sequence":"additional","affiliation":[{"name":"Imperial College London , , South Kensington Campus, Exhibition Road , ,","place":["London, U.K., SW7 2AZ"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8394-2516","authenticated-orcid":true,"given":"Philip W.","family":"Miller","sequence":"additional","affiliation":[{"name":"Imperial College London , , White City Campus, 80 Wood Lane , ,","place":["London, U.K., W12 0BZ"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3993-5818","authenticated-orcid":true,"given":"James A.","family":"Bull","sequence":"additional","affiliation":[{"name":"Imperial College London , , White City Campus, 80 Wood Lane , ,","place":["London, U.K., W12 0BZ"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2019,11,28]]},"reference":[{"key":"2026101908071710000_cit1a","doi-asserted-by":"publisher","first-page":"2583","DOI":"10.1021\/cr040677v","article-title":"Process Chemistry: The Science, Business, Logic, and\nLogistics","volume":"106","author":"Zhang","year":"2006","journal-title":"Chem. 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Process Res.\nDev."},{"key":"2026101908071710000_cit3b","doi-asserted-by":"publisher","first-page":"4525","DOI":"10.1021\/acs.joc.8b00270","article-title":"Synthesis and Explosion\nHazards of 4-Azido-l-phenylalanine","volume":"83","author":"Richardson","year":"2018","journal-title":"J. Org. Chem."},{"key":"2026101908071710000_cit3c","doi-asserted-by":"publisher","first-page":"12334","DOI":"10.1021\/acs.joc.8b02068","article-title":"Cyclic Hypervalent\nIodine Reagents for Azidation: Safer Reagents and Photoredox-Catalyzed\nRing Expansion","volume":"83","author":"Alazet","year":"2018","journal-title":"J. Org. Chem."},{"key":"2026101908071710000_cit3d","doi-asserted-by":"publisher","first-page":"9614","DOI":"10.1002\/chem.201902036","article-title":"Ranking Oxidant Sensitiveness: A Guide for Synthetic\nUtility","volume":"25","author":"Dallaston","year":"2019","journal-title":"Chem. \u2013 Eur. J."},{"key":"2026101908071710000_cit4a","doi-asserted-by":"crossref","DOI":"10.1515\/9783110439335","volume-title":"Chemistry\nof High-Energy Materials","author":"Klapo\u0308tke","year":"2015","edition":"3"},{"key":"2026101908071710000_cit4b","volume-title":"Primary Explosives","author":"Matya\u0301s\u030c","year":"2012","edition":"1"},{"key":"2026101908071710000_cit5a","doi-asserted-by":"publisher","first-page":"131","DOI":"10.1080\/10629369308028824","article-title":"Predicting the Impact\nSensitivity of Explosive Molecules Using Neuromimetic Networks","volume":"1","author":"Nefati","year":"1993","journal-title":"SAR QSAR Environ. 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News"},{"key":"2026101908071710000_cit6c","first-page":"1037","article-title":"A Review of the Mallet Impact\nTest for Small Scale Explosive Formulations","volume-title":"Proceedings of the 19th Seminar on New Trends in Research of Energetic\nMaterials, Part 2","author":"Weaver","year":"2016"},{"key":"2026101908071710000_cit8a","doi-asserted-by":"publisher","first-page":"101","DOI":"10.1016\/j.jhazmat.2004.06.022","article-title":"Use of ARC in Screening\nfor Explosive Properties","volume":"115","author":"Bodman","year":"2004","journal-title":"J. Hazard. Mater."},{"key":"2026101908071710000_cit9","unstructured":"UN.\n          \n          2015. ISBN 978-92-1-139155-8, link: www.unece.org\/trans\/areas-of-work\/dangerous-goods\/legal-instruments-and-recommendations\/un-manual-of-tests-and-criteria\/rev6-files.html."},{"key":"2026101908071710000_cit10","first-page":"311","article-title":"Prediction of Fire\nand Explosion Hazard for Reactive\nChemicals (I): Estimation of Explosive Properties of Self-Reactive\nChemicals from SC-DSC Data","volume":"48","author":"Yoshida","year":"1987","journal-title":"Kogyo Kayaku"},{"key":"2026101908071710000_cit11","doi-asserted-by":"publisher","first-page":"5893","DOI":"10.1021\/acs.joc.9b00269","article-title":"Diazo Transfer Reagent\n2-Azido-4,6-Dimethoxy-1,3,5-Triazine\n(ADT) Displays Highly Exothermic Decomposition Comparable to Tosyl\nAzide","volume":"84","author":"Green","year":"2019","journal-title":"J. Org. 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Soc."},{"key":"2026101908071710000_cit15","doi-asserted-by":"publisher","first-page":"1393","DOI":"10.1021\/acs.oprd.8b00214","article-title":"The First Kilogram Synthesis of Beclabuvir,\nan HCV NS5B Polymerase Inhibitor","volume":"22","author":"Bien","year":"2018","journal-title":"Org. Process\nRes. Dev."},{"key":"2026101908071710000_cit16a","doi-asserted-by":"publisher","first-page":"9468","DOI":"10.1021\/ja00074a012","article-title":"\u03b1-Hydroxy Esters as Chiral Auxiliaries in Asymmetric\nCyclopropanations by Rhodium(II)-Stabilized Vinylcarbenoids","volume":"115","author":"Davies","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"2026101908071710000_cit16b","doi-asserted-by":"publisher","first-page":"6897","DOI":"10.1021\/ja9604931","article-title":"Asymmetric Cyclopropanations\nby Rhodium(II) N-(Arylsulfonyl)Prolinate Catalyzed\nDecomposition of Vinyldiazomethanes in the Presence of Alkenes. Practical\nEnantioselective Synthesis of the Four Stereoisomers of 2-Phenylcyclopropan-1-Amino\nAcid","volume":"118","author":"Davies","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"2026101908071710000_cit17a","doi-asserted-by":"publisher","first-page":"688","DOI":"10.1039\/C39810000688","article-title":"Transition-Metal-Catalysed\nReactions of Diazoesters.\nInsertion into C\u2013H Bonds of Paraffins by Carbenoids","volume":"14","author":"Demonceau","year":"1981","journal-title":"J. Chem. Soc., Chem. Commun."},{"key":"2026101908071710000_cit17b","doi-asserted-by":"publisher","first-page":"2861","DOI":"10.1021\/cr0200217","article-title":"Catalytic\nEnantioselective C\u2013H Activation by Means of Metal-Carbenoid-Induced\nC\u2013H Insertion","volume":"103","author":"Davies","year":"2003","journal-title":"Chem. 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Lett."},{"key":"2026101908071710000_cit17i","doi-asserted-by":"publisher","first-page":"395","DOI":"10.1038\/s41586-018-0799-2","article-title":"Desymmetrization\nof Cyclohexanes by Site- and Stereoselective C\u2013H Functionalization","volume":"564","author":"Fu","year":"2018","journal-title":"Nature"},{"key":"2026101908071710000_cit18a","doi-asserted-by":"publisher","first-page":"4918","DOI":"10.1039\/c3cs35496b","article-title":"Catalytic\nX\u2013H\nInsertion Reactions Based on Carbenoids","volume":"42","author":"Gillingham","year":"2013","journal-title":"Chem.\nSoc. Rev."},{"key":"2026101908071710000_cit18b","doi-asserted-by":"publisher","first-page":"11483","DOI":"10.1002\/anie.201105485","article-title":"Asymmetric\nN\u2013H Insertion Reaction Cooperatively Catalyzed by Rhodium and\nChiral Spiro Phosphoric Acids","volume":"50","author":"Xu","year":"2011","journal-title":"Angew. Chem.,\nInt. 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Chem."},{"key":"2026101908071710000_cit18d","doi-asserted-by":"publisher","first-page":"2276","DOI":"10.1016\/j.tet.2013.01.020","article-title":"Continuous-Flow Generation of Diazoesters\nand Their Direct Use in S\u2013H and P\u2013H Insertion Reactions:\nSynthesis of \u03b1-Sulfanyl, \u03b1-Sulfonyl, and \u03b1-Phosphono\nCarboxylates","volume":"69","author":"Bartrum","year":"2013","journal-title":"Tetrahedron"},{"key":"2026101908071710000_cit19a","doi-asserted-by":"publisher","first-page":"31","DOI":"10.1016\/S0040-4039(00)93616-5","article-title":"A Novel\nSynthesis of the Carbapen-2-em Ring System","volume":"21","author":"Ratcliffe","year":"1980","journal-title":"Tetrahedron Lett."},{"key":"2026101908071710000_cit19b","doi-asserted-by":"publisher","first-page":"6765","DOI":"10.1021\/ja00412a048","article-title":"Stereospecific\nConversion of Penicillin to Thienamycin","volume":"103","author":"Karady","year":"1981","journal-title":"J.\nAm. Chem. Soc."},{"key":"2026101908071710000_cit20a","doi-asserted-by":"publisher","first-page":"14230","DOI":"10.1002\/anie.201408928","article-title":"Synthesis of Di-,\nTri-, and Tetrasubstituted Oxetanes by Rhodium-Catalyzed O\u2013H\nInsertion and C\u2013C Bond-Forming Cyclization","volume":"53","author":"Davis","year":"2014","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026101908071710000_cit20b","doi-asserted-by":"publisher","first-page":"15446","DOI":"10.1039\/C5CC05740J","article-title":"Synthesis of Diversely Functionalised 2,2-Disubstituted\nOxetanes: Fragment Motifs in New Chemical Space","volume":"51","author":"Davis","year":"2015","journal-title":"Chem. Commun."},{"key":"2026101908071710000_cit20c","doi-asserted-by":"publisher","first-page":"11477","DOI":"10.1021\/acs.joc.6b02134","article-title":"Synthesis of Substituted\n1,4-Dioxenes through O\u2013H Insertion and Cyclization Using Keto-Diazo\nCompounds","volume":"81","author":"Davis","year":"2016","journal-title":"J. Org. 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