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Revision as of 12:37, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477107895 of page Tetryl for the Chem/Drugbox validation project (updated: '').  Latest revision as of 20:10, 10 November 2024 edit 5.178.188.143 (talk) →History and synthesisTag: Visual edit 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 470605355 | verifiedrevid = 477174205
| ImageFile = Tetryl.png | ImageFile = Tetryl.png
| ImageSize = 150px | ImageSize = 150px
| PIN = Methyl(2,4,6-trinitrophenyl)nitramide <!-- Preferred IUPAC names for amides of nitric acid are now systematically based on nitric amide, in accordance with the seniority order of classes rather than as nitro amines; the latter names can be used in general nomenclature. -->
| IUPACName = ''N''-methyl-''N'',2,4,6-tetranitroaniline
| OtherNames = {{bulletedlist|Nitramine (incorrect)|Tetralite|Tetril|''N''-Methyl-''N'',2,4,6-tetranitroaniline|''N''-Methyl-''N'',2,4,6-tetranitrophenyl-1-amine}}
| OtherNames = nitramine, tetralite, tetril
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 479-45-8
| ChEBI = 28950
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9770 | ChemSpiderID = 9770
⚫ | PubChem = 10178
| RTECS = BY6300000
⚫ | UNNumber = ]
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = GJ18911991
| InChI = 1/C7H5N5O8/c1-8(12(19)20)7-5(10(15)16)2-4(9(13)14)3-6(7)11(17)18/h2-3H,1H3 | InChI = 1/C7H5N5O8/c1-8(12(19)20)7-5(10(15)16)2-4(9(13)14)3-6(7)11(17)18/h2-3H,1H3
| InChIKey = AGUIVNYEYSCPNI-UHFFFAOYAF | InChIKey = AGUIVNYEYSCPNI-UHFFFAOYAF
Line 15: Line 23:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AGUIVNYEYSCPNI-UHFFFAOYSA-N | StdInChIKey = AGUIVNYEYSCPNI-UHFFFAOYSA-N
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 479-45-8
⚫ | PubChem = 10178
⚫ | UNNumber = ]
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | UNII = GJ18911991
| SMILES = CN(c1c(cc(cc1(=O))(=O))(=O))(=O) | SMILES = CN(c1c(cc(cc1(=O))(=O))(=O))(=O)
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=7|H=5|N=5|O=8
| Formula = C<sub>7</sub>H<sub>5</sub>N<sub>5</sub>O<sub>8</sub>
| Appearance = Yellow crystalline solid
| MolarMass = 287.15 g/mol
| Appearance = Odorless yellow crystalline solid | Odor = Odorless
| Density = 1.73 g/cm<sup>3</sup> | Density = 1.73 g/cm<sup>3</sup>
| MeltingPtC = 129.5 | MeltingPtC = 129.5
| BoilingPt = Decomposes at 187 °C | BoilingPtC = 187
| BoilingPt_notes = decomposes
| Solubility = virtually insoluble in H<sub>2</sub>O}} | Solubility = Virtually insoluble
⚫ | Section6 = {{Chembox Explosive
| VaporPressure = <1 mmHg (20°C)<ref name=PGCH/>
}}
⚫ |Section6={{Chembox Explosive
| ShockSens = Sensitive | ShockSens = Sensitive
| FrictionSens = Sensitive | FrictionSens = Sensitive
| ExplosiveV = 7,570 ], or 24,836 ] | DetonationV = 7,570 ] (24,836 ])
| REFactor = 1.25 | REFactor = 1.25
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt =
| IDLH = 750 mg/m<sup>3</sup><ref name=PGCH>{{PGCH|0607}}</ref>
| REL = TWA 1.5 mg/m<sup>3</sup> <ref name=PGCH/>
| PEL = TWA 1.5 mg/m<sup>3</sup> <ref name=PGCH/>
| LDLo = 5000 mg/kg (dog, subcutaneous)<ref>{{IDLH|479458|Tetryl}}</ref>
}}
}} }}

'''2,4,6-Trinitrophenylmethylnitramine''' or '''tetryl''' (]<sub>7</sub>]<sub>5</sub>]<sub>5</sub>]<sub>8</sub>) is an ] compound used to make ]s and ] charges.

Tetryl is a ] booster explosive, though its use has been largely superseded by ]. Tetryl is a sensitive secondary high explosive used as a booster, a small charge placed next to the detonator in order to propagate detonation into the main explosive charge.

==Chemical properties==
Tetryl is a yellow crystalline solid powder material, practically insoluble in water but soluble in ], ] and other solvents. When tetryl is heated, it first melts, then decomposes and explodes. It burns readily and is more easily detonated than ]<ref name=gs-eb>{{Cite web|url=http://www.globalsecurity.org/military/systems/munitions/explosives-booster.htm|title = Booster Explosives}}</ref> or ], being about as sensitive as ]. It is detonated by friction, shock, or spark. It remains stable at all temperatures which may be encountered in storage. It is generally used in the form of pressed pellets, and has been approved as the standard bursting charge for small-caliber projectiles, since it gives much better fragmentation than TNT. It has an ] of 23,600–23,900 feet per second (7200–7300&nbsp;m/s). Tetryl is the basis for the service tetryl ] necessary for positive detonation of TNT. A mixture of ] and ] is included in the cap to ensure detonation of tetryl.<ref name=gs-eb/>

==Environmental effect==
The most toxic ordnance compounds, tetryl and 1,3,5-TNB, are also the most degradable. Therefore, these chemicals are expected to be short-lived in nature, and environmental impacts would not be expected in areas that are not currently subject to chronic inputs of these chemicals. Tetryl decomposes rapidly in ]/water solutions, as well as with heat. All aqueous samples expected to contain tetryl should be diluted with ] prior to ] and acidified to pH < 3. All samples expected to contain tetryl should not be exposed to temperatures above room temperature. In addition, degradation products of tetryl appear as a shoulder on the 2,4,6-TNT peak. Peak heights rather than peak areas should be used when tetryl is present in concentrations that are significant relative to the concentration of 2,4,6-TNT.<ref name=gs-eb/>

== History and synthesis ==
] shells (dating from circa 1945) showing color code for tetryl filling]]
Tetryl was used mainly during ] and ] and later conflicts. Tetryl is usually used on its own, though can sometimes be found in compositions such as ]. Tetryl is no longer manufactured or used in the United States, but can still be found in legacy munitions such as the ] anti-personnel ].<ref>“A Military Guide to Terrorism in the 21st Century.” August 2003. P. 171. U.S. Army Training and Doctrine Command, Fort Leavenworth, Kansas. http://smallwarsjournal.com/documents/terrorismhandbook.pdf. Accessed May 11, 2010.</ref>

Dutch chemist Karel Hendrik Mertens originally synthesized the compound as a part of his doctoral dissertation published in 1877<ref>{{Cite book |last=Mertens |first=Karel Hendrik |url=https://books.google.com/books?id=tlkVAQAAIAAJ&pg=PA24 |title=Over nitroderivaten van dimethylaniline |date=1877 |publisher=S. C. Van Doesburgh |language=nl}}</ref> by slowly mixing ] with concentrated ] in the presence of ], and it's still a viable lab technique. However, in the 1930s a more economical route was commercialized, where ] produced by the Smoleński method (developed after WWI) reacts with ] to make dinitromethylaniline which is then easily nitrated without byproducts.

==Health concerns==

Although tetryl is among the most toxic explosive compounds, it is very short-lived. This combined with the fact that the health impacts of this compound are largely unstudied, not much is known about any health problems that this compound may cause.

Epidemiological data shows that tetryl has most effect on the skin, acting as a strong irritant.<ref></ref> Symptoms of skin sensitization such as dermatitis, itch, erythema, etc. may occur.<ref></ref> Tetryl can also affect mucous membranes, the upper respiratory tract, and possibly the liver.

== See also ==

* ]
* ]
* ]

== References ==
{{Reflist}}

* Cooper, Paul W., ''Explosives Engineering'', New York: Wiley-VCH, 1996. {{ISBN|0-471-18636-8}}

== External links ==
* , ]
* {{Webarchive|url=https://web.archive.org/web/20090227041309/http://www.osha.gov/SLTC/healthguidelines/tetryl/recognition.html |date=2009-02-27 }}, ]

]
]