| Revision as of 14:35, 14 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit |
Latest revision as of 19:23, 8 November 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers75,027 edits link |
| (123 intermediate revisions by 50 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
|Verifiedfields = changed |
|
| verifiedrevid = 398779413 |
|
|
|
|Watchedfields = changed |
|
| Name = Diethylamine |
|
|
|
|verifiedrevid = 407845259 |
|
| ImageFile = diethylamine.png |
|
|
|
|Reference = <ref>''Merck Index'', 12th Edition, '''3160'''</ref> |
|
<!-- | ImageSize = 120px --> |
|
|
|
|ImageFile = Et2NH.svg |
|
| ImageFile2 = Diethylamine-3D-balls.png |
|
|
|
|ImageFile_Ref = {{chemboximage|correct|??}} |
|
| ImageName = Diethylamine |
|
|
|
|ImageSize = 230 |
|
| IUPACName = Diethylamine |
|
|
|
|ImageAlt = Skeletal formula of diethylamine |
|
| Section1 = {{Chembox Identifiers |
|
|
|
|ImageFile2 = Diethylamine 3D ball.png |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
|
|ImageFile2_Ref = {{chemboximage|correct|??}} |
|
| ChemSpiderID = 7730 |
|
|
| PubChem = 8021 |
|
|ImageSize2 = 160 |
|
|
|ImageAlt2 = Ball and stick model of the diethylamine molecule |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
|
|PIN = ''N''-Ethylethanamine |
|
| UNII = B035PIS86W |
|
|
|
|OtherNames = (Diethyl)amine<br>Diethylamine (deprecated<ref>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 671 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>) |
|
| InChI = 1/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3 |
|
|
|
|Section1={{Chembox Identifiers |
|
| InChIKey = HPNMFZURTQLUMO-UHFFFAOYAD |
|
|
| ChEMBL = 1189 |
|
|CASNo = 109-89-7 |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|CASNo_Ref = {{cascite|correct|CAS}} |
|
|
|PubChem = 8021 |
|
| StdInChI = 1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3 |
|
|
|
|ChemSpiderID = 7730 |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| StdInChIKey = HPNMFZURTQLUMO-UHFFFAOYSA-N |
|
|
|
|UNII = B035PIS86W |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|
|
|UNII_Ref = {{fdacite|correct|FDA}} |
|
| CASNo = 109-89-7 |
|
|
|
|EINECS = 203-716-3 |
|
| SMILES = N(CC)CC |
|
|
|
|UNNumber = 1154 |
|
|
|MeSHName = diethylamine |
|
|
|ChEMBL = 1189 |
|
|
|ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
|
|ChEBI_Ref = {{ebicite|correct|EBI}} |
|
|
|ChEBI = 85259 |
|
|
|RTECS = HZ8750000 |
|
|
|Beilstein = 605268 |
|
|
|SMILES = CCNCC |
|
|
|StdInChI = 1S/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3 |
|
|
|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|StdInChIKey = HPNMFZURTQLUMO-UHFFFAOYSA-N |
|
|
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
}} |
|
|
|Section2={{Chembox Properties |
|
|
|C=4 | H=11 | N=1 |
|
|
|Appearance = Colourless liquid |
|
|
|Odor = fishy, ammonical |
|
|
|Density = 0.7074 g mL<sup>−1</sup> |
|
|
|MeltingPtK = 223.35 |
|
|
|BoilingPtK = 327.9 to 329.5 |
|
|
|Solubility = Miscible |
|
|
|LogP = 0.657 |
|
|
|VaporPressure = 24.2–97.5 kPa |
|
|
|HenryConstant = 150 μmol Pa<sup>−1</sup> kg<sup>−1</sup> |
|
|
|pKa = 10.98 (of ammonium form) |
|
|
|RefractIndex = 1.385 |
|
|
|MagSus = -56.8·10<sup>−6</sup> cm<sup>3</sup>/mol |
|
|
}} |
|
|
|Section3={{Chembox Thermochemistry |
|
|
|DeltaHf = −131 kJ mol<sup>−1</sup> |
|
|
|DeltaHc = −3.035 MJ mol<sup>−1</sup> |
|
|
|HeatCapacity = 178.1 J K<sup>−1</sup> mol<sup>−1</sup> |
|
|
}} |
|
|
|Section4={{Chembox Hazards |
|
|
|ExternalSDS = |
|
|
|GHSPictograms = {{gHS flame}} {{gHS corrosion}} {{gHS exclamation mark}} |
|
|
|GHSSignalWord = '''DANGER''' |
|
|
|HPhrases = {{h-phrases|225|302|312|314|332}} |
|
|
|PPhrases = {{p-phrases|210|280|305+351+338|310}} |
|
|
|NFPA-H = 3 |
|
|
|NFPA-F = 3 |
|
|
|NFPA-R = 1 |
|
|
|FlashPtC = -23 |
|
|
|AutoignitionPtC = 312 |
|
|
|ExploLimits = 1.8–10.1% |
|
|
|PEL = TWA 25 ppm (75 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0209}}</ref> |
|
|
|REL = TWA 10 ppm (30 mg/m<sup>3</sup>) ST 25 ppm (75 mg/m<sup>3</sup>)<ref name=PGCH/> |
|
|
|IDLH = 200 ppm<ref name=PGCH/> |
|
|
|LC50 = 4000 ppm (rat, 4 hr)<ref name=IDLH>{{IDLH|109897|Diethylamine}}</ref> |
|
|
|LD50 = 540 mg/kg (rat, oral)<br/>500 mg/kg (mouse, oral)<ref name=IDLH/> |
|
|
}} |
|
|
|Section5={{Chembox Related |
|
|
|OtherFunction_label = amines |
|
|
|OtherFunction = {{unbulleted list|]|]|]||]|]}} |
|
|
|OtherCompounds = |
|
}} |
|
}} |
|
| Section2 = {{Chembox Properties |
|
|
| Formula = C<sub>4</sub>H<sub>11</sub>N |
|
|
| MolarMass = 73.14 g/mol |
|
|
| Density = 0.7074 g/cm<sup>3</sup> |
|
|
| MeltingPt = -50 °C |
|
|
| BoilingPt = 55.5 °C |
|
|
| pKa=10.98<ref>Hall, H.K., ''J. Am. Chem. Soc.'', '''1957''', ''79'', 5441.</ref> |
|
|
}} |
|
|
| Section7 = {{Chembox Hazards |
|
|
| ExternalMSDS = |
|
|
| EUClass = |
|
|
| EUIndex = |
|
|
| MainHazards = |
|
|
| NFPA-H = 3 |
|
|
| NFPA-F = 3 |
|
|
| NFPA-R = 1 |
|
|
| NFPA-O = |
|
|
| RPhrases = |
|
|
| SPhrases = |
|
|
| RSPhrases = |
|
|
| FlashPt = -28 °C (-18 °F) |
|
|
| Autoignition = 312 °C (594 °F) |
|
|
| ExploLimits = 1.8-10.1% |
|
|
| PEL = 25 ppm |
|
|
}} |
|
|
}} |
|
}} |
|
|
|
|
|
'''Diethylamine''' is a ] with the molecular structure CH<sub>3</sub>CH<sub>2</sub>NHCH<sub>2</sub>CH<sub>3</sub>. It is a flammable, strongly alkaline liquid. It is miscible with water and ]. It is a colorless liquid which often appears brown due to impurities. It is volatile and has a strong ]. |
|
'''Diethylamine''' is an ] with the formula (CH<sub>3</sub>CH<sub>2</sub>)<sub>2</sub>NH. It is classified as a ]. It is a flammable, volatile weakly alkaline liquid that is ] with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor. |
|
|
|
|
|
|
==Production and uses== |
|
Diethylamine is manufactured from ethanol and ] and is obtained together with ] and ]. It is used as a corrosion inhibitor and in the production of rubber, resins, dyes and pharmaceuticals. |
|
|
|
The ]-catalyzed reaction makes diethylamine from ethanol and ]. Diethylamine is obtained together with ] and ]. Annual production of the three ethylamines was estimated in 2000 to be 80,000,000 kg.<ref name=Ullmann>{{Ullmann|author=Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke|title=Amines, Aliphatic|year=2005|DOI=10.1002/14356007.a02_001}}</ref> |
|
|
|
|
|
|
Diethylamine is used in the production of corrosion inhibitor ''N'',''N''-], by reaction with ]. It is also a precursor to a wide variety of other commercial products. It is also sometimes used in the illicit production of ].<ref>{{cite web |last1=Shulgin |first1=Alexander |title=Erowid Online Books:"TIHKAL" - #26 LSD-25 |url=https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml |website=www.erowid.org |access-date=12 August 2019}}</ref> |
|
Diethylamine is a corrosive chemical and contact with skin may cause irritation or burns. |
|
|
|
|
|
|
==Organic chemistry== |
|
|
As the most abundantly available secondary amine that is liquid at room temperature, diethylamine has been extensively deployed in chemical synthesis. Its reactions illustrate the pattern seen for many other dialkylamines. It participates in ]s involving the installation of diethylaminomethyl substituents.<ref>{{cite journal |doi=10.15227/orgsyn.023.0030 |author=Charles E. Maxwell|title=β-Diethylaminomethylacetophenone Hydrochloride |journal=Organic Syntheses |date=1943 |volume=23 |page=30 }}</ref><ref>{{cite journal |doi=10.15227/orgsyn.027.0020 |author=C. F. H. Allen and J. A. VanAllan |
|
|
|title=Diethylaminoacetonitrile |journal=Organic Syntheses |date=1947 |volume=27 |page=20 }}</ref><ref>{{cite journal |doi=10.15227/orgsyn.037.0018 |author=Alfred L. Wilds, Robert M. Nowak, Kirtland E. McCaleb|title=1-Diethylamino-3-Butanone |journal=Organic Syntheses |date=1957 |volume=37 |page=18 }}</ref> Alkylation gives the tertiary amine.<ref>{{cite journal |author=W. W. Hartman|doi=10.15227/orgsyn.014.0028 |title=β-Diethylaminoethyl Alcohol |journal=Organic Syntheses |date=1934 |volume=14 |page=28 }}</ref> With ], it reacts to give the silylamide.<ref>{{cite journal |author=W. J. Middleton, E. M. Bingham|doi=10.15227/orgsyn.057.0050 |title=Diethylaminosulfur Trifluoride |journal=Organic Syntheses |date=1977 |volume=57 |page=50 }}</ref> |
|
|
|
|
|
==Supramolecular structure== |
|
|
] |
|
|
Diethylamine is the smallest and simplest molecule that features a ] ] as its lowest energy aggregate. Other similarly sized ] molecules favor cyclic structures.<ref>{{cite journal |author1=Felix Hanke |author2=Chloe J. Pugh |author3=Ellis F. Kay |author4=Joshua B. Taylor |author5=Stephen M. Todd |author6=Craig M. Robertson |author7=Benjamin J. Slater |author8=Alexander Steiner | title = The simplest supramolecular helix | journal = ] | year = 2018 | volume = 54 |issue=47 |pages=6012–6015 | doi = 10.1039/C8CC03295E|pmid=29796532 }}</ref> |
|
|
|
|
|
==Safety== |
|
|
Diethylamine has low toxicity, but the vapor causes transient impairment of vision.<ref name=Ullmann/> |
|
|
|
|
|
==References== |
|
==References== |
|
|
{{Reflist}} |
|
*''Merck Index'', 12th Edition, '''3160'''. |
|
|
<references/> |
|
|
|
|
|
|
==External links== |
|
==External links== |
|
* |
|
* |
|
|
* |
|
|
|
|
|
] |
|
] |
|
] |
|
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|