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Sigma-Aldrich

4-(Dimethylamino)pyridine, polymer-bound

extent of labeling: ~3.0 mmol/g "DMAP" loading, matrix crosslinked with 2% DVB

Synonym(s):

4-(Dimethylamino)pyridine on Polystyrene, DMAP on PS, polymer bound DMAP

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About This Item

Empirical Formula (Hill Notation):
C8H8
CAS Number:
82942-26-5
Molecular Weight:
104.15
MDL number:
MFCD04041220
UNSPSC Code:
12352128
PubChem Substance ID:
57649897
NACRES:
NA.22

reaction suitability

reaction type: solution phase peptide synthesis

extent of labeling

~3.0 mmol/g "DMAP" loading

matrix

crosslinked with 2% DVB

anion traces

chloride (Cl-): ≤5000 mg/kg

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General description

Polymer-bound 4-(dimethylamino)pyridine is used for improved derivatization of chiral and achiral aliphatic amines, amino alcohols and amino acids.

Application

Polymer-bound 4-(dimethylamino)pyridine is used as a supported base in the Michael addition and nitrous acid elimination process step involved in the synthesis of thiophene-2-carboxylates using β-nitroacrylates as starting materials, under a general and efficient continuous flow-based protocol. It also serves as a supported catalyst in the preparation of ω-nitro esters starting from cyclic 2-nitro ketones under solid heterogeneous catalysis.(5)

Other Notes

Polymer supported, recyclable acylation catalyst

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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$\beta$-Nitroacrylates as Starting Materials of Thiophene-2-Carboxylates Under Continuous Flow Conditions
Chiurchiu E, et al.
advanced synthesis and catalysis, 361(9), 2042-2047 (2019)
$\beta$-Nitroacrylates as Starting Materials of Thiophene-2-Carboxylates Under Continuous Flow Conditions
Chiurchiu E, et al.
Advanced Synthesis & Catalysis, 361(9), 2042-2047 (2019)
A new, low impact and efficient synthesis of $\omega$-nitro esters under solid heterogeneous catalysis
Chiurchiu E, et al.
Green Chemistry, 19(20), 4956-4960 (2017)
Szu-Yuan Chou et al.
Scientific reports, 10(1), 18519-18519 (2020-10-30)
Cell development and behavior are driven by internal genetic programming, but the external microenvironment is increasingly recognized as a significant factor in cell differentiation, migration, and in the case of cancer, metastatic progression. Yet it remains unclear how the microenvironment
S. Shinkai et al.
Bulletin of the Chemical Society of Japan, 54, 631-631 (1981)
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