158496

Proton-sponge^®

99%

• Synonym(s): 1,8-Bis(dimethylamino)naphthalene, N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine
• Linear Formula: C₁₀H₆[N(CH₃)₂]₂
• CAS Number: 20734-58-1
• Molecular Weight: 214.31
• Beilstein: 396782
• EC Number: 244-001-6
• MDL number: MFCD00003920
• PubChem Substance ID: 24849762
• NACRES: NA.22

Properties

• Quality Level: 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)
• 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 also referred 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 Sigma-Aldrich Co. LLC

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315 - H319 - H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): 235.4 °F
• Flash Point(C): 113 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves