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158496 Aldrich

Proton-sponge®

99%

Synonym: 1,8-Bis(dimethylamino)naphthalene, N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine

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Properties

Related Categories Acids & Bases, Bases, Building Blocks, Chemical Synthesis, Nitrogen Compounds,
InChI Key   GJFNRSDCSTVPCJ-UHFFFAOYSA-N
assay   99%
mp   49-51 °C(lit.)
solubility   chloroform: soluble50 mg/mL, clear, faintly yellow to greenish-yellow

Description

Packaging

10, 50 g in glass bottle

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.

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.

Legal Information

Proton-sponge is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

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Peer-Reviewed Papers
15

References

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