N,N,N',N'-Tetramethylnaphthalin-1,8-diamin
Proton sponge
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Grundinformationen
- CAS
20734-58-1- Standard-SMILES
CN(C)c1cccc2cccc(N(C)C)c12- InChIKey
GJFNRSDCSTVPCJ-UHFFFAOYSA-N- Summenformel
- C14H18N2
- Durchschnittliche Molmasse
- 214,31 g/mol
- Monoisotopische Masse
- 214,14699858
Überblick
N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine is a member of naphthalenes.
Namen und Bezeichner
- Bevorzugter Name
- Proton sponge
- IUPAC
- 1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine
- Lokaler Name
- N,N,N',N'-Tetramethylnaphthalin-1,8-diamin
- Englischer Name
- 1,8-Bis(dimethylamino)naphthalene
- Summenformel
- C14H18N2
- Molmasse
- 214.31
Namen und Synonyme
20734-58-11,8-Bis(dimethylamino)naphthaleneProton spongeDMAN cpd6S79D2P9H8DTXSID10174807RefChem:73727DTXCID5097298244-001-6N1,N1,N8,N8-tetramethylnaphthalene-1,8-diamine1,8-Bis(dimethylamino)naphtaleneN,N,N',N'-Tetramethyl-1,8-naphthalenediamine
Weitere Namen anzeigen
N,N,N',N'-tetramethyl-1,8-diaminonaphthalenePROTON-SPONGE(R)proton-sponge tmLABOTEST-BB LT004539821, 8-dimethylaminonaphthalene
1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-Proton-spongeMFCD00003920N,N,N',N'-Tetramethylnaphthalene-1,8-diamine1,8-Naphthalenediamine, N1,N1,N8,N8-tetramethyl-Maybridge1_002116N,N,N',N'-Tetramethyl-1,8-naphthalene diamine
Datenbank-Bezeichner
- CAS
20734-58-1- PubChem CID
- 88675
- DTXSID
DTXSID10174807
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 3,4
- Polarare Oberfläche (TPSA)
- 6,5 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 16
- Formalladung
- 0
- Komplexität
- 203
Experimentelle und physikochemische Eigenschaften
PolymersNitrogen Compounds -> Amines, Polyaromatic
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Solubility31.2 [ug/mL] (The mean of the results at pH 7.4)
Physical DescriptionPale cream crystalline powder; [Alfa Aesar MSDS]
Physikochemische Eigenschaften
- Schmelzpunkt
- 49 · 49-51 °C(lit.)
- Siedepunkt
- 144 · 144-145°C (3.7505 mmHg)
- Dichte
- 1.12 · 1.12
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- Löslichkeit
- Soluble in organic solvents.
- Aggregatzustand
- Crystalline Powder
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 95 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: 1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-
1,8-Bis(dimethylamino)-naphthalene: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses burns; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxikologische Informationen
Adverse EffectsDermatotoxin - Skin burns.
Sicherheitsdaten
- F
- 8-10-23
- wgk
- 3
- ridadr
- 3259
- hs_code
- 29215900
- risk_code
- 22-36/37/38-34
- hazard_code
- Xn,C
Chemie und Industrie
Verwendung und Herstellung
UsesPrototype of a group of very high alkalinity aromatic diamines known as proton sponges; Used in organic synthesis and catalysis; [Merck Index]
Anwendungen
BeschreibungSignificant attention in organic chemistry has been given to the so-called proton sponges, which are bi-center nitrogen bases that show spectacularly high basicity and very low nucleophilic character. The first member of this class of compounds 1,8-bis(dimethylamino)naphthalene or DMAN dragged attention due to its unexpectedly high basicity (pKa: DMAN 12.1; 1,8-diaminonaphthalene: 4.6) after its discovery in 1941[1]. It is prepared with an 82% yield from 1,8-diaminonaphthalene, dimethyl sulfate, and sodium hydride.
Verwenden1,8-Bis(dimethylamino)naphthalene, also referred to as protone sponge, is a lipophilic proton trapping agent. 1,8-Bis(dimethylamino)naphthalene is used in the matrix for mass spectroscopy analysis of lipids and fatty acids.
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