N,N,N',N'-Tetramethylnaphthalin-1,8-diamin

Proton sponge

HCID 88675CAS 20734-58-1

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Grundinformationen

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
ChEMBL: CHEMBL1574733
ChEBI: CHEBI:194986
UNII: 6S79D2P9H8
EC Number: 244-001-6
Nikkaji: J83.008I

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,4
Polarare Oberfläche (TPSA): 6,5 Å²
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
pka: 12.1 · 12.1(at 25℃)
Farbe: Pale brownish-pink
Wasserlöslichkeit: insoluble
Merck: 14 · 14,3388
BRN: 396782 · 396782
InChI: 1S/C14H18N2/c1-15(2)12-9-5-7-11-8-6-10-13(14(11)12)16(3)4/h5-10H,1-4H3
InChIKey: GJFNRSDCSTVPCJ-UHFFFAOYSA-N
SMILES: CN(C)c1cccc2cccc(N(C)C)c12
CAS Datenbank: 20734 · 20734-58-1(CAS DataBase Reference)
NIST chemische Informationen: 1 · 1,8-Naphthalenediamine, N,N,N',N'-tetramethyl-(20734-58-1)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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 · 2 Einträge

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
safety_code: 26-45-36/37/39
hazard_class: 8
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

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 · 2 Einträge

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.