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158496

Proton-sponge®

99%

Synonym(s):

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

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Size/SKUAvailabilityPrice
10 g
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$58.80
50 g
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$171.00

About This Item

Linear Formula:
C10H6[N(CH3)2]2
CAS Number:
Molecular Weight:
214.31
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
244-001-6
Beilstein/REAXYS Number:
396782
MDL number:
Assay:
99%
Form:
solid

$58.80


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Quality Segment

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

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

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This Item
14795105139S3256
description

99%

description

purum, ≥99.0% (NT)

description

99%

description

≥97%

assay

99%

assay

≥99.0% (NT)

assay

99%

assay

≥97%

solubility

chloroform: soluble 50 mg/mL, clear (faint yellow to dark yellow to dark red)

solubility

-

solubility

-

solubility

water: 50 mg/mL, clear, colorless

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

solid

form

solid

form

-

form

-

mp

49-51 °C (lit.)

mp

45-49 °C

mp

-

mp

28-30 (lit.)

functional group

amine

functional group

amine

functional group

-

functional group

-


pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves



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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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