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39410

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000351062
0000323967
0000327656
0000300199
0000323967

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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)
$\beta$-Nitroacrylates as Starting Materials of Thiophene-2-Carboxylates Under Continuous Flow Conditions
Chiurchiu E, et al.
Advanced Synthesis & Catalysis, 361(9), 2042-2047 (2019)
$\beta$-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)
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
E.F. Scriven
Chemical Society Reviews, 12, 129-129 (1983)
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