158496

Proton-sponge^®

99%

• Synonyme(s) : 1,8-Bis(dimethylamino)naphthalene, N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine
• Formule linéaire : C₁₀H₆[N(CH₃)₂]₂
• Numéro CAS: 20734-58-1
• Poids moléculaire : 214.31
• UNSPSC Code: 12352100
• NACRES: NA.22
• PubChem Substance ID: 24849762
• EC Number: 244-001-6
• Beilstein/REAXYS Number: 396782
• MDL number: MFCD00003920
• Assay: 99%
• Form: solid

Propriétés

• Quality Segment: 200
• assay: 99%
• form: solid
• mp: 49-51 °C (lit.)
• solubility: chloroform: soluble 50 mg/mL, clear (faint yellow to dark yellow to dark red)
• functional group: amine
• SMILES string: CN(C)c1cccc2cccc(N(C)C)c12
• 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
• InChI key: GJFNRSDCSTVPCJ-UHFFFAOYSA-N

Description

General description

Proton-sponge is a nucleophilic base used in alkoxycarbonylation, dehydrofluorination, arylation, and intramolecular cyclization reactions.

Proton-sponge is also referred to as 1,8-dimethylamino naphthalene. It is very strong base with weak nucleophilic character due to steric effects. It also participates in the reactions between arachno-6,9-C₂B₈H₁₄ and selected acyl chlorides. It has been tested as an effective H⁺ scavenger.

Application

Proton-sponge can be used in the synthesis of C-substituted t-BuNH-8,9-R,R′-nido-7,8,9-C₃B₈H₉ (R,R′ = H,H; MeH; Me,Me; Ph,H and Ph,Ph) tricarbollide compounds. It was also used in the preparation of saturated fluoroalkyl(hydrido) complexes of Iridium.

Very strong base with weak nucleophilic character due to steric effects.

Legal Information

Proton-sponge is a registered trademark of Merck KGaA, Darmstadt, Germany

Informations sur la sécurité

• Pictogrammes: GHS07
• Mot-clé: Warning
• Codes de danger: H302,H315,H319,H335
• Mentions de précaution: P261 - P264 - P271 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Organes cibles: Respiratory system
• Classe de stockage: 11 - Combustible Solids
• Que se passe-t-il ?: WGK 3
• Point d'éclair (°F): 235.4 °F - closed cup
• Point d'éclair (°C): 113 °C - closed cup
• EPI (équipement de protection individuelle): dust mask type N95 (US), Eyeshields, Faceshields, Gloves