Editing Acetonitrile

{{Short description|Organic compound (CH3−C≡N); Simplest organic nitrile}}
{{Distinguish|Acetyl cyanide}}
{{Chembox
| Watchedfields  = changed
| verifiedrevid  = 477239538
| ImageFileL1    = Acetonitrile-2D-skeletal.svg
| ImageClassL1 = skin-invert-image
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1    = Skeletal formula of acetonitrile
| ImageFileR1    = Acetonitrile-2D-flat.svg
| ImageClassR1 = skin-invert-image
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1    = Skeletal formula of acetonitrile with all explicit hydrogens added
| ImageFileL2    = Acetonitrile-3D-balls.png
| ImageClassL2 = bg-transparent
| ImageFileL2_Ref = {{chemboximage|correct|??}}
| ImageNameL2    = Ball and stick model of acetonitrile
| ImageFileR2    = Acetonitrile-3D-vdW.png
| ImageClassR2 = bg-transparent
| ImageFileR2_Ref = {{chemboximage|correct|??}}
| ImageNameR2    = Spacefill model of acetonitrile
| ImageFile3 = Asetonitril.png
| ImageSize3 = 100px
| PIN            = Acetonitrile<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 902 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| SystematicName = Ethanenitrile<ref name=iupac2013 />
| OtherNames     = {{Unbulleted list|Cyanomethane<ref name=Pella>{{Cite web|title=Material Safety Data Sheet: Acetonitrile|url=http://www.tedpella.com/MSDS_html/18612%20msds.pdf|website = TedPella.com}}</ref>|Ethyl nitrile<ref name=Pella/>|Methanecarbonitrile<ref name=Pella/>|Methyl cyanide<ref name=Pella/>|MeCN |ACN
}}
| Section1       = {{Chembox Identifiers
| CASNo = 75-05-8
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 6342
| ChemSpiderID = 6102
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = Z072SB282N
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 200-835-2
| UNNumber = 1648
| MeSHName = acetonitrile
| ChEBI = 38472
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 45211
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = AL7700000
| Beilstein = 741857
| Gmelin = 895
| SMILES = CC#N
| StdInChI = 1S/C2H3N/c1-2-3/h1H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WEVYAHXRMPXWCK-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| Section2       = {{Chembox Properties
| C=2 | H=3
| N = 1
| Appearance = Colorless liquid
| Odor = Faint, distinct, fruity
| Density = 0.786 g/cm<sup>3</sup> at 25°C
| MeltingPtK = 227 to 229
| BoilingPtK = 354.4 to 355.2
| Solubility = Miscible
| LogP = −0.334
| MagSus = {{val|-28.0|e=-6|u=cm<sup>3</sup>/mol}}
| VaporPressure = 9.71 kPa (at 20.0&nbsp;°C)
| HenryConstant = 530 μmol/(Pa·kg)
| pKa = 25
| LambdaMax = 195&nbsp;nm
| Absorbance = ≤0.10
| RefractIndex = 1.344
| Dipole = 3.92 D
}}
| Section3       = {{Chembox Thermochemistry
| DeltaHf = 40.16–40.96 kJ/mol
| DeltaHc = −1256.03 – −1256.63 kJ/mol
| Entropy = 149.62 J/(K·mol)
| HeatCapacity = 91.69 J/(K·mol)
}}
| Section4       = {{Chembox Hazards
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}}
| GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|225|302|312|319|332}}
| PPhrases = {{P-phrases|210|280|305+351+338}}
| NFPA-H = 2
| NFPA-F = 3
| NFPA-R = 0
| FlashPtC = 2.0
| AutoignitionPtC = 523.0
| ExploLimits = 4.4–16.0%
| LD50 = {{Unbulleted list|2 g/kg <small>(dermal, rabbit)</small>|2.46 g/kg <small>(oral, rat)</small>}}
| PEL = TWA 40 ppm (70 mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0006}}</ref>
| REL = TWA 20 ppm (34 mg/m<sup>3</sup>)<ref name=NIOSH/>
| IDLH = 500 ppm<ref name=NIOSH/>
| LC50 = 5655 ppm (guinea pig, 4 hr)<br/>2828 ppm (rabbit, 4 hr)<br/>53,000 ppm (rat, 30 min)<br/>7500 ppm (rat, 8 hr)<br/>2693 ppm (mouse, 1 hr)<ref name=IDLH>{{IDLH|75058|Acetonitrile}}</ref>
| LCLo = 16,000 ppm (dog, 4 hr)<ref name=IDLH/>
}}
| Section5       = {{Chembox Related
| OtherFunction_label = alkanenitriles
| OtherFunction = {{Unbulleted list|[[Hydrogen cyanide]]|[[Thiocyanic acid]]|[[Cyanogen iodide]]|[[Cyanogen bromide]]|[[Cyanogen chloride]]|[[Cyanogen fluoride]]|[[Aminoacetonitrile]]|[[Glycolonitrile]]|[[Cyanogen]]|[[Propionitrile]]|[[Aminopropionitrile]]|[[Malononitrile]]|[[Pivalonitrile]]|[[Acetone cyanohydrin]]}}
| OtherCompounds = [[DBNPA]]
}}
}}

'''Acetonitrile''', often abbreviated '''MeCN''' ('''methyl cyanide'''), is the [[chemical compound]] with the [[chemical formula|formula]] {{chem2|CH3CN}} and [[Chemical structure|structure]] {{chem2|H3C\sC\tN}}. This colourless liquid is the simplest organic [[nitrile]] ([[hydrogen cyanide]] is a simpler nitrile, but the [[cyanide]] anion is not classed as [[Organic compound|organic]]). It is produced mainly as a byproduct of [[acrylonitrile]] manufacture. It is used as a [[polar aprotic solvent]] in [[organic synthesis]] and in the purification of [[butadiene]].<ref name="ashford">{{cite web|url=http://www.industrialchemistry.info/100pagesAddict3.pdf |title=Archived copy |access-date=2011-03-31 |url-status=dead |archive-url=https://web.archive.org/web/20110516233056/http://www.industrialchemistry.info/100pagesAddict3.pdf |archive-date=2011-05-16 |work=Ashford's Dictionary of Industrial Chemicals, Third edition |page=76 }}</ref> The {{chem2|N\tC\sC}} skeleton is [[Linear molecular geometry|linear]] with a short {{chem2|C\tN}} [[Bond length|distance]] of 1.16&nbsp;[[angstrom|Å]].<ref>{{cite journal|last1=Karakida|first1=Ken'ichi|last2=Fukuyama|first2=Tsutomu|last3=Kuchitsu|first3=Kozo|year=1974|title=Molecular Structures of Hydrogen Cyanide and Acetonitrile as Studied by Gas Electron Diffraction|journal=Bulletin of the Chemical Society of Japan|volume=47|issue=2|pages=299–304|doi=10.1246/bcsj.47.299|doi-access=free}}</ref>

Acetonitrile was first prepared in 1847 by the French chemist [[Jean-Baptiste Dumas]].<ref>{{cite journal | last1 = Dumas | first1 = J.-B. | year = 1847 | title = Action de l'acide phosphorique anhydre sur les sels ammoniacaux |trans-title=Action of anhydrous phosphoric acid on ammonium salts | url = https://books.google.com/books?id=IWFEAQAAIAAJ&pg=PA384| journal = Comptes rendus | volume = 25 | pages = 383–384 }}</ref>

==Applications==
Acetonitrile is used mainly as a solvent in the purification of [[butadiene]] in refineries. Specifically, acetonitrile is fed into the top of a [[distillation column]] filled with [[hydrocarbon]]s including butadiene, and as the acetonitrile falls down through the column, it absorbs the butadiene which is then sent from the bottom of the tower to a second separating tower. Heat is then employed in the separating tower to separate the butadiene.

In the laboratory, it is used as a medium-polarity [[protic solvent|non-protic]] solvent that is [[Miscibility|miscible]] with water and a range of organic solvents, but not saturated hydrocarbons.  It has a convenient range of temperatures at which it is a liquid, and a high [[dielectric constant]] of 38.8. With a [[Electric dipole moment|dipole moment]] of 3.92&nbsp;[[Debye|D]],<ref>{{cite journal|last1=Steiner|first1=P.&nbsp;A.|last2=Gordy|first2=W.|date=1966|title=Journal of Molecular Spectroscopy|url=http://www.sciencedirect.com/science/journal/00222852/21|volume=21|page=291}}</ref> acetonitrile dissolves a wide range of ionic and nonpolar compounds and is useful as a mobile phase in [[High-performance liquid chromatography|HPLC]] and [[Liquid chromatography–mass spectrometry|LC–MS]].

It is widely used in [[Battery (electricity)|battery]] applications because of its relatively high dielectric constant and ability to dissolve [[electrolyte]]s.  For similar reasons, it is a popular solvent in [[cyclic voltammetry]].

Its ultraviolet transparency [[UV cutoff]], low [[viscosity]] and low [[chemical reactivity]] make it a popular choice for [[high-performance liquid chromatography]] (HPLC).

Acetonitrile plays a significant role as the dominant solvent used in [[oligonucleotide synthesis]] from [[nucleoside phosphoramidite]]s.

Industrially, it is used as a solvent for the manufacture of [[pharmaceutical]]s and [[photographic film]].<ref name="ecb"/>

===Organic synthesis===
Acetonitrile is a common two-carbon building block in [[organic synthesis]]<ref>{{OrgSynth | last1= DiBiase |first1=S.&nbsp;A. |last2=Beadle |first2=J.&nbsp;R. |last3=Gokel |first3=G.&nbsp;W. | title = Synthesis of α,β-Unsaturated Nitriles from Acetonitrile: Cyclohexylideneacetonitrile and Cinnamonitrile | collvol = 7 | collvolpages = 108 | prep = cv7p0108}}</ref> of many useful chemicals, including [[acetamidine hydrochloride]], [[thiamine]], and [[1-naphthaleneacetic acid]].<ref name="encyc-toxic">{{Citation|title=Encyclopedia of Toxicology|editor=Philip Wexler|publisher=Elsevier|year=2005|edition=2nd|volume=1|isbn=0-12-745354-7|pages=28–30}}</ref> Its reaction with [[cyanogen chloride]] affords [[malononitrile]].<ref name = "ashford" />

===As an electron pair donor===
Acetonitrile has a free electron pair at the nitrogen atom, which can form many [[transition metal nitrile complexes]]. Being weakly basic, it is an easily displaceable [[ligand]]. For example, [[bis(acetonitrile)palladium dichloride]] is prepared by heating a suspension of [[palladium chloride]] in acetonitrile:<ref>{{Cite book|title=Organic synthesis : concepts and methods|last=Jürgen-Hinrich.|first=Fuhrhop|date=2003|publisher=Wiley-VCH|others=Li, Guangtao, Dr.|isbn=9783527302727|edition=3rd, completely rev. and enl.|location=Weinheim|oclc=51068223|page=26}}</ref>
:{{chem2|PdCl2 + 2 CH3CN -> PdCl2(CH3CN)2}}
A related complex is [[tetrakis(acetonitrile)copper(I) hexafluorophosphate]] {{chem2|[Cu(CH3CN)4]+}}. The {{chem2|CH3CN}} groups in these complexes are rapidly displaced by many other ligands.

It also forms Lewis adducts with group 13 [[Lewis acid]]s like [[boron trifluoride]].<ref>B. Swanson, D. F. Shriver, J. A. Ibers, "Nature of the donor-acceptor bond in acetonitrile-boron trihalides. The structures of the boron trifluoride and boron trichloride complexes of acetonitrile", Inorg. Chem., 2969., volume 8, pp. 2182-2189, {{doi:10.1021/ic50080a032}}</ref> In [[superacid]]s, it is possible to protonate acetonitrile.<ref name="Christe">{{cite journal|last1 = Haiges|first1=Ralf|last2=Baxter|first2=Amanda F.|last3=Goetz|first3=Nadine R.|last4=Axhausen|first4=Joachim A.|last5=Soltner|first5=Theresa|last6=Kornath|first6=Andreas|last7=Christe|first7=Kalr O.|title=Protonation of nitriles: isolation and characterization of alkyl- and arylnitrilium ions|journal=Dalton Transactions|year=2016|volume=45|issue=20|pages=8494–8499|doi=10.1039/C6DT01301E|pmid=27116374}}</ref>

==Production==
Acetonitrile is a byproduct from the manufacture of [[acrylonitrile]] by catalytic [[ammoxidation]] of [[propylene]]. Most is combusted to support the intended process but an estimated several thousand tons are retained for the above-mentioned applications.<ref name=Ullmann>{{Ullmann| last1 = Pollak | first1 = Peter | last2 = Romeder | first2 = Gérard | last3 = Hagedorn | first3 = Ferdinand | last4 = Gelbke | first4 = Heinz-Peter | title = Nitriles | doi = 10.1002/14356007.a17_363 }}</ref> Production trends for acetonitrile thus generally follow those of [[acrylonitrile]]. Acetonitrile can also be produced by many other methods, but these are of no commercial importance as of 2002. Illustrative routes are by dehydration of [[acetamide]] or by [[hydrogenation]] of mixtures of [[carbon monoxide]] and [[ammonia]].<ref>{{Cite patent
 |country= US
 |number= 4179462
 |status=
 |title=Process for preparing acetonitrile
 |pubdate=1979-12-18
 |gdate=
 |fdate=1978-01-16
 |pridate=
 |invent1=Olive, G.
 |invent2=Olive, S.
 |assign1=[[Monsanto Company]]
}}</ref> In {{as of|1992|alt=1992}}, {{convert|14700|t|ST}} of acetonitrile were produced in the US.

===Acetonitrile shortage in 2008–2009 ===
Starting in October 2008, the worldwide supply of acetonitrile was low because Chinese production was shut down for the [[2008 Olympics|Olympics]].  Furthermore, a U.S. factory was damaged in Texas during [[Hurricane Ike]].<ref>{{Cite web | first = Derek | last = Lowe | author-link = Derek Lowe (chemist) | title = The Great Acetonitrile Shortage | year = 2009 | publisher = [[Science Translational Medicine]] | url = https://www.science.org/content/blog-post/great-acetonitrile-shortage}}</ref>  Due to the  global economic slowdown, the production of acrylonitrile used in acrylic fibers and [[acrylonitrile butadiene styrene]] (ABS) resins decreased.  Acetonitrile is a byproduct in the production of [[acrylonitrile]] and its production also decreased, further compounding the acetonitrile shortage.<ref>{{cite journal | author = A. Tullo | title = A Solvent Dries Up | journal = Chemical & Engineering News | volume = 86 | issue = 47 | pages = 27 | doi = 10.1021/cen-v086n047.p027| year = 2008 }}</ref> The global shortage of acetonitrile continued through early 2009.{{update inline|date=February 2018}}

==Safety==

===Toxicity===
Acetonitrile has only modest toxicity in small doses.<ref name="encyc-toxic" /><ref name="inrs">{{Citation | last = Institut national de recherche et de sécurité (INRS) | author-link = Institut national de recherche et de sécurité | title = Fiche toxicologique no.&nbsp;104&nbsp;: Acétonitrile | year = 2004 | place = Paris | publisher = [[Institut national de recherche et de sécurité|INRS]] | url = http://www.inrs.fr/inrs-pub/inrs01.nsf/IntranetObject-accesParReference/FT%20104/$File/ft104.pdf | isbn = 2-7389-1278-8 | access-date = 2008-08-19 | archive-url = https://web.archive.org/web/20110728102249/http://www.inrs.fr/inrs-pub/inrs01.nsf/IntranetObject-accesParReference/FT%20104/$File/ft104.pdf | archive-date = 2011-07-28 | url-status = dead }}</ref> It can be [[Metabolism|metabolised]] to produce [[hydrogen cyanide]], which is the source of the observed toxic effects.<ref name="ecb">{{Citation|last=Spanish Ministry of Health |author-link=Ministry of Health (Spain) |title=Acetonitrile. Summary Risk Assessment Report |year=2002 |place=[[Ispra|Ispra (VA), Italy]] |publisher=[[European Chemicals Bureau]] |url=http://ecb.jrc.it/DOCUMENTS/Existing-Chemicals/RISK_ASSESSMENT/SUMMARY/acetonitrilesum006.pdf |id=Special Publication I.01.65 |url-status=dead |archive-url=https://web.archive.org/web/20081217020910/http://ecb.jrc.it/DOCUMENTS/Existing-Chemicals/RISK_ASSESSMENT/SUMMARY/acetonitrilesum006.pdf |archive-date=2008-12-17 }}</ref><ref name="who">{{Citation | last = International Programme on Chemical Safety | author-link = International Programme on Chemical Safety | title = Environmental Health Criteria 154. Acetonitrile | year = 1993 | place = Geneva | publisher = [[World Health Organization]] | url = http://www.inchem.org/documents/ehc/ehc/ehc154.htm}}</ref><ref name="epa">{{Citation | first = Mark | last = Greenberg | title = Toxicological Review of Acetonitrile | year = 1999 | place = Washington, DC | publisher = [[United States Environmental Protection Agency|U.S. Environmental Protection Agency]] | url = http://www.epa.gov/iris/toxreviews/0205tr.pdf }}</ref> Generally the onset of toxic effects is delayed, due to the time required for the body to metabolize acetonitrile to cyanide (generally about 2–12 hours).<ref name="encyc-toxic" />

Cases of acetonitrile poisoning in humans (or, to be more specific, of cyanide poisoning after exposure to acetonitrile) are rare but not unknown, by inhalation, ingestion and (possibly) by skin absorption.<ref name="who" /> The symptoms, which do not usually appear for several hours after the exposure, include breathing difficulties, slow [[pulse rate]], [[nausea]], and vomiting. [[Convulsion]]s and [[coma]] can occur in serious cases, followed by death from [[respiratory failure]]. The treatment is as for [[cyanide poisoning]], with [[oxygen]], [[sodium nitrite]], and [[sodium thiosulfate]] among the most commonly used emergency treatments.<ref name="who" />

It has been used in formulations for [[nail polish remover]], despite its toxicity. At least two cases have been reported of accidental poisoning of young children by acetonitrile-based nail polish remover, one of which was fatal.<ref>{{Cite journal | last1 = Caravati | first1 = E. M. |last2= Litovitz |first2= T. | title = Pediatric cyanide intoxication and death from an acetonitrile-containing cosmetic | year = 1988 | journal = [[Journal of the American Medical Association|J. Am. Med. Assoc.]] | volume = 260 | issue = 23 | pages = 3470–73 | pmid = 3062198 | doi = 10.1001/jama.260.23.3470}}</ref> [[Acetone]] and [[ethyl acetate]] are often preferred as safer for domestic use, and acetonitrile has been banned in cosmetic products in the [[European Economic Area]] since March 2000.<ref>{{cite journal|url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2000:065:0022:0025:EN:PDF|title=Twenty-Fifth Commission Directive 2000/11/EC of 10 March 2000 adapting to technical progress Annex II to Council Directive 76/768/EEC on the approximation of laws of the Member States relating to cosmetic products|journal=[[Official Journal of the European Communities]]|volume=L65|date=2000-03-14|pages=22–25}}</ref>

====Metabolism and excretion====
{| class="wikitable" width=30%
|-
! Compound
! Cyanide, concentration in brain (μg/kg)
! Oral {{LD50}} (mg/kg)
|-
| [[Potassium cyanide]]
| align="center" | 700&nbsp;±&nbsp;200
| align="right" | 10
|-
| [[Propionitrile]]
| align="center" | 510&nbsp;±&nbsp;80
| align="right" | 40
|-
| [[Butyronitrile]]
| align="center" | 400&nbsp;±&nbsp;100
| align="right" | 50
|-
| [[Malononitrile]]
| align="center" | 600&nbsp;±&nbsp;200
| align="right" | 60
|-
| [[Acrylonitrile]]
| align="center" | 400&nbsp;±&nbsp;100
| align="right" | 90
|-
| '''Acetonitrile'''
| align="center" | 28&nbsp;±&nbsp;5
| align="right" | 2460
|-
| '''Table salt (NaCl)'''
| align="center" {{n/a}}
| align="right" | 3000
|-
| colspan=3 | <small>Ionic cyanide concentrations measured in the brains of Sprague-Dawley rats one hour after oral administration of an {{LD50}} of various nitriles.</small><ref name="ratdata">{{Citation | last1 = Ahmed | first1 = A.&nbsp;E. |last2= Farooqui |first2=M.&nbsp;Y.&nbsp;H. | title = Comparative toxicities of aliphatic nitriles | journal = Toxicol. Lett. | year = 1982 | volume = 12 | pages = 157–64 | doi = 10.1016/0378-4274(82)90179-5 | issue = 2–3 | pmid=6287676}}</ref>
|-
|}
In common with other [[nitrile]]s, acetonitrile can be [[Metabolism|metabolised]] in [[microsome]]s, especially in the liver, to produce [[hydrogen cyanide]], as was first shown by Pozzani ''et al.'' in 1959.<ref>{{Citation | last1 = Pozzani | first1 = U.&nbsp;C. |last2= Carpenter |first2=C.&nbsp;P.|last3= Palm |first3= P.&nbsp;E.|last4= Weil|first4= C.&nbsp;S.|last5= Nair |first5=J.&nbsp;H. | title = An investigation of the mammalian toxicity of acetonitrile | journal = J. Occup. Med. | year = 1959 | volume = 1 | pages = 634–642 | doi = 10.1097/00043764-195912000-00003 | pmid = 14434606 | issue = 12}}</ref> The first step in this pathway is the oxidation of acetonitrile to [[glycolonitrile]] by an [[NADPH]]-dependent [[cytochrome P450]] [[monooxygenase]]. The glycolonitrile then undergoes a spontaneous decomposition to give hydrogen cyanide and [[formaldehyde]].<ref name="inrs" /><ref name="who" /> Formaldehyde, a toxin and a carcinogen on its own, is further oxidized to [[formic acid]], which is another source of toxicity.

The metabolism of acetonitrile is much slower than that of other nitriles, which accounts for its relatively low toxicity. Hence, one hour after administration of a potentially lethal dose, the concentration of cyanide in the rat brain was {{frac|20}} that for a [[propionitrile]] dose 60 times lower (see table).<ref name="ratdata" />

The relatively slow metabolism of acetonitrile to hydrogen cyanide allows more of the cyanide produced to be detoxified within the body to [[thiocyanate]] (the [[rhodanese]] pathway). It also allows more of the acetonitrile to be excreted unchanged before it is metabolised. The main pathways of excretion are by exhalation and in the urine.<ref name="inrs" /><ref name="who" /><ref name="epa" />

==See also==
*[[Trichloroacetonitrile]] – a derivative of acetonitrile used to [[protecting group|protect]] [[hydroxyl|alcohol groups]], and also used as a reagent in the [[Overman rearrangement]]

==References==
{{reflist|30em}}

==External links==
* [http://webbook.nist.gov/cgi/cbook.cgi?ID=C75058 WebBook page for C<sub>2</sub>H<sub>3</sub>N]
* [http://www.inchem.org/documents/icsc/icsc/eics0088.htm International Chemical Safety Card 0088]
* [https://web.archive.org/web/20060304144216/http://www.npi.gov.au/database/substance-info/profiles/4.html National Pollutant Inventory - Acetonitrile fact sheet]
* [https://www.cdc.gov/niosh/npg/npgd0006.html NIOSH Pocket Guide to Chemical Hazards]
* [http://www.epa.gov/chemfact/s_acenit.txt Chemical Summary for Acetonitrile (CAS No. 75-05-8)], Office of Pollution Prevention and Toxics, U.S. Environmental Protection Agency
* [http://www.layruoru.com/dokuwiki/doku.php/solvents Simulation of acetonitrile]
* [https://scitechdaily.com/how-did-organic-matter-reach-earth-cosmic-detectives-trace-origin-of-complex-organic-molecules/ How Did Organic Matter Reach Earth? Cosmic Detectives Trace Origin of Complex Organic Molecules], on: SciTechDaily. September 10, 2020. Source: Tokyo University of Science: Acetonitrile found in molecular cloud [[Sagittarius B2|Sgr B2(M)]] at the center of [[Milky Way|our galaxy]].

{{Molecules detected in outer space}}

{{Authority control}}

[[Category:Alkanenitriles|2]]
[[Category:Solvents]]
[[Category:Ligands]]
[[Category:Organic compounds with 2 carbon atoms]]