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39405

4-(Dimethylamino)pyridine

purum, ≥98.0% (NT)

Synonym(s):

N,N-Dimethylpyridin-4-amine, DMAP

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About This Item

Empirical Formula (Hill Notation):
C7H10N2
CAS Number:
Molecular Weight:
122.17
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
214-353-5
Beilstein/REAXYS Number:
110354
MDL number:
Assay:
≥98.0% (NT)
Form:
crystals, pellets
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grade

purum

Quality Level

assay

≥98.0% (NT)

form

crystals, pellets

mp

108-110 °C (lit.), 111-114 °C

solubility

methanol: 0.1 g/mL, clear, colorless to almost colorless

functional group

amine

SMILES string

CN(C)c1ccncc1

InChI

1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3

InChI key

VHYFNPMBLIVWCW-UHFFFAOYSA-N

General description

4-(Dimethylamino)pyridine is generally employed as a catalyst in the acylation of amines, alcohols, enolates, and phenols. It can also be used in the esterification of carboxylic acids. It is known to exhibit good catalytic activity in non-polar solvents.

Application

4-(Dimethylamino)pyridine can be used:
  • As a capping agent in the preparation of water-soluble gold nanoparticles.
  • As an initiator in the polymerization of epoxy monomers.
  • As an auxiliary reagent in the electroless preparation of gold nanotubes applicable in catalysis.[1]
  • As a catalyst in the preparation of γ- and δ-lactones via iodolactonization of γ,δ-unsaturated carboxylic acids.

A highly efficient catalyst for acylation reactions

Other Notes

Hypernucleophilic acylation catalyst.

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This Item
8.204998.51055107700
grade

purum

grade

-

grade

-

grade

-

assay

≥98.0% (NT)

assay

≥99.0% (GC)

assay

≥99.0% (GC)

assay

≥99%

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

crystals, pellets

form

solid

form

powder

form

chips, crystalline powder, flakes

solubility

methanol: 0.1 g/mL, clear, colorless to almost colorless

solubility

60 g/L

solubility

-

solubility

H2O: 50 mg/mL

mp

108-110 °C (lit.), 111-114 °C

mp

110-112 °C

mp

110-112 °C

mp

108-110 °C (lit.)


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Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 1

target_organs

Nervous system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

255.2 °F

flash_point_c

124 °C

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges



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4-(Dimethylamino) pyridine-catalysed iodolactonisation of γ, δ-unsaturated carboxylic acids
Meng C, et al.
Organic & Biomolecular Chemistry, 13(24), 6766-6772 (2015)
4-Dimethylamino-pyridine (DMAP)
Grondal C
Synlett, 2003(10), 1568-1569 (2003)
E.F. Scriben
Chemical Society Reviews, 13, 129-129 (1983)



Global Trade Item Number

SKUGTIN
39405-1KG04061826714614
39405-10G04061831982190
39405-50G04061831982213
39405-250G04061831982206

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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