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158496

Sigma-Aldrich

Proton-sponge®

99%

Synonym(s):

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

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About This Item

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
UNSPSC Code:
12352100
PubChem Substance ID:
24849762
NACRES:
NA.22

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

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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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - 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 - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD9416
BCCJ1184
BCCJ2766
BCCH3472
BCCD9879

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Mario Bakardjiev et al.
Dalton transactions (Cambridge, England : 2003), 39(17), 4186-4190 (2010-04-15)
Treatment of C-substituted nido dicarbadecaboranes 5,6-R',R-5,6-C(2)B(8)H(10) (1) (where R',R = H,H (1a); H,Me, (1b); Me,Me, (1c); H,Ph, (1d) and Ph,Ph, (1e) with 1,8-bis-(dimethylamino)naphthalene (proton sponge = PS) and t-BuNC in CH(2)Cl(2), followed by acidification, generated a series of pure neutral
Unusual Reactivity of ?Proton Sponge? as a Hydride Donor to Transition Metals: Synthesis and Structural Characterization of Fluoroalkyl (hydrido) Complexes of Iridium (III) and Rhodium (III).
Hughes RP, et al.
Organometallics, 20(14), 3190-3197 (2014)
Mario Bakardjiev et al.
Inorganic chemistry, 52(15), 9087-9093 (2013-07-28)
Reactions between arachno-6,9-C2B8H14 (1) and selected acyl chlorides, RCOCl, in the presence of PS (PS = "proton sponge", 1,8-dimethylamino naphthalene) in CH2Cl2 for 24 h at reflux, followed by in situ acidification with concentrated H2SO4 at 0 °C, generate a
1, 8-Bis (dimethylamino) naphthalene
Barner BA
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Nanocluster Formation and Stabilization Fundamental Studies. 2. Proton Sponge as an Effective H^+ Scavenger and Expansion of the Anion Stabilization Ability Series.
Ozkar S and Finke RG.
Langmuir, 18(20), 7653-7662 (2002)
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