diazodinitrophenol

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 427437931

| ImageFileL1 = 2-Diazo-4,6-dinitrophenol.svg

| ImageSizeL1 = 150

| ImageAltL1 = Skeletal formula

| ImageFileR1 = Diazodinitrophenol-3D-balls-2.png

| ImageSizeR1 = 160

| ImageAltR1 = Ball-and-stick model

| ImageFile2 = Diazodinitrophenol.jpg

| ImageSize2 = 300

| PIN=6-Diazo-2,4-dinitrocyclohexa-2,4-dien-1-one

| OtherNames=

|Section1={{Chembox Identifiers

| Abbreviations = DDNP

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=4682-03-5

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = CV76O0RICT

| PubChem=5463880

| SMILES= [N]=[N]=C(C=C([N+]([O-])=O)C=C1[N+]([O-])=O)C1=O

| EINECS = 225-134-9

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4576415

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C6H2N4O5/c7-8-4-1-3(9(12)13)2-5(6(4)11)10(14)15/h1-2H

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = IUKSYUOJRHDWRR-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=6|H=2|N=4|O=5

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=Insoluble

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

Diazodinitrophenol (DDNP) was the first diazo compound produced; it was subsequently used to make dyes and explosives. It forms yellow crystals in pure form; however, the color of impure forms may vary from dark yellow to green to dark brown.Robert Matyáš and Jiří Pachman, Primary Explosives (Berlin, Germany: Springer Verlag, 2013), [https://books.google.com/books?id=wfJHAAAAQBAJ&pg=PA157 Chapter 6: Diazodinitrophenol, pp. 157-166]; see p. 159. It is soluble in acetic acid, acetone, concentrated hydrochloric acid, like most non-polar solvents and is slightly soluble in water.Tadeusz Urbański with Marian Jurecki and Sylvia Laverton, trans., Chemistry and Technology of Explosives (Oxford, England: Permagon Press, 1967), vol. 3, [https://archive.org/stream/ChemistryAndTechnologyOfExplosives-VolumeIii/ChemistryAndTechnologyOfExplosives-VolumeIii-TadeuszUrbanski#page/n211/mode/2up pp. 201-204]; see especially p. 202.

A solution of cold sodium hydroxide may be used to destroy it.(Urbański, 1967), p. 202. DDNP may be desensitized by immersing it in water, as it does not react in water at normal temperature. It is less sensitive to impact but more powerful than mercury fulminate and almost as powerful as lead azide.(Urbański, 1967), p. 204. The sensitivity of DDNP to friction is much less than that of mercury fulminate and lead azide.

{{multiple image

| align = center

| direction =

| width = 238

| image1 =

| alt1 = 2

| caption1 =

| image2 =

| alt2 = 3

| caption2 =

| image3 =

| alt3 = 4

| footer = Sensitivity of DDNP compared to other primary explosives and PETN.

}}

DDNP is used with other materials to form priming mixtures, particularly where a high sensitivity to flame or heat is desired. DDNP is often used as an initiating explosive in propellant primer devices and is a substitute for lead styphnate in what are termed "green" or "non-toxic" (lead free) priming explosive compositions. Lead free primers have been judged as inadequate for service use in firearms due to weak and uneven initiation compared to lead based primers.{{cite arXiv |eprint=1410.6390|ref=Courtney|last1=Courtney|first1=Elya|title=Performance testing of lead free primers: Blast waves, velocity variations, and environmental testing|last2=Courtney|first2=Amy|author3=Peter David Summer|last4=Courtney|first4=Michael|class=physics.pop-ph|year=2014}}