Dimethyl-pyridin-4-yl-amine (DMAP)
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Dimethyl-pyridin-4-yl-amine (DMAP)

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Dimethyl-pyridin-4-yl-amine is a highly efficient catalyst for acylation reactions.

Category
Peptide Synthesis Reagents
Catalog number
BAT-008162
CAS number
1122-58-3
Molecular Formula
C7H10N2
Molecular Weight
122.17
Dimethyl-pyridin-4-yl-amine (DMAP)
IUPAC Name
N,N-dimethylpyridin-4-amine
Synonyms
4-(dimethylamino)-pyridin; 4-Dimethylaminepyridine; gamma-(Dimethylamino)pyridine; N,N-Dimethyl-4-aminopyridine; n,n-dimethyl-4-pyridinamin; p-Dimethylaminopyridine; Pyridine, 4-(dimethylamino)-; AURORA KA-6495; DMAP; 4-dimethylaminopyridine; 4-DMAP; γ-(Dimethylamino)pyridine; USP Valacyclovir Related Compound G; Valaciclovir EP Impurity G; Valacyclovir USP Related Compound G
Appearance
Off-white to White Crystalline Powder
Purity
98%
Density
1.012 g/cm3
Melting Point
83-86 °C
Boiling Point
211.0 °C
Storage
2-8 °C
Solubility
Slightly soluble in Chloroform, Methanol
Application
A highly efficient catalyst for acylation reactions.
InChI
InChI=1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3
InChI Key
VHYFNPMBLIVWCW-UHFFFAOYSA-N
Canonical SMILES
CN(C)C1=CC=NC=C1
1. Bis(azido-κN)bis-[4-(dimethyl-amino)-pyridine-κN]zinc
Fatiha Guenifa, Nasreddine Hadjadj, Ouahida Zeghouan, Lamia Bendjeddou, Hocine Merazig Acta Crystallogr Sect E Struct Rep Online. 2013 Mar 1;69(Pt 3):m169. doi: 10.1107/S1600536813004686. Epub 2013 Feb 23.
In the title complex, [Zn(N3)2(C7H10N2)2], the Zn(II) atom is coordinated by two N atoms from two 4-(dimethyl-amino)-pyridine (DMAP) ligands and by two N atoms from two azide anions in a distorted tetra-hedral coordination geometry. In the crystal, weak C-H⋯N hydrogen bonds between the DMAP and azide ligands link these discrete complex mol-ecules into a three-dimensional supra-molecular network.
2. 2,3;5,6-Di-O-isopropyl-idene-1-O-(2-phenyl-acet-yl)-α-d-mannofuran-ose
Iulia A Sacui, Peter Norris, Matthias Zeller Acta Crystallogr Sect E Struct Rep Online. 2010 Aug 18;66(Pt 9):o2341. doi: 10.1107/S1600536810032368.
The title compound, C(20)H(26)O(7), was prepared by esterification of 2,3;5,6-di-O-isopropyl-idene-α-d-mannofuran-ose with phenyl-acetic acid under standard DCC/DMAP (DCC = dicyclohexylcarbodiimide and DMAP = 4-dimethylaminopyridine) con-ditions. The solid-state structure confirms the retention of the α-configuration at the anomeric C atom. The compound is characterized by a relatively rigid framework with only a few degrees of freedom. Comparison with other di-O-isopropyl-idenemannofuran-ose derivatives shows the main differences to be associated with the flexible dimethyl-dioxolane ring, and that there are only small differences for the 2,3-O-isopropyl-idene-α-d-manno-furan-ose backbone. The packing is marked by a large number of weak C-H⋯O inter-actions.
3. Alcohol-Soluble Zwitterionic 4-(Dimethyl(pyridin-2-yl)ammonio)butane-1-sulfonate Small Molecule as a Cathode Modifier for Nonfullerene Acceptor-Based Organic Solar Cells
Fong-Yi Cao, Yen-Chen Su, Yung-Ching Hsueh, Chia-Cheng Chou, Yen-Ju Cheng ACS Appl Mater Interfaces. 2021 Mar 3;13(8):10222-10230. doi: 10.1021/acsami.0c21449. Epub 2021 Feb 22.
A new zwitterionic small molecule 4-(dimethyl(pyridin-2-yl)ammonio)butane-1-sulfonate (PAS), synthesized from 2-dimethylaminopyrindine (2-DMAP), was developed for the ITO cathode modifier. PAS and 2-DMAP dissolved in methanol can form a thin layer on ITO cathode by a simple spin-coating process. The heteroatom moieties in 2-DMAP (sp2 and sp3 nitrogen) and PAS (sp2 nitrogen and sulfonate ion) can coordinate to the ITO surface and decrease the ITO work function by the induced surface dipoles. The fullerene-based (PBDTT-FTTE:PC71BM) inverted OSCs using PAS and 2-DMAP interlayer can achieve PCEs of 8.95 and 8.26%, respectively, which are superior to the devices without a modifier (PCE = 3.25%) and comparable to the corresponding ZnO-based device (PCE = 8.57%). Nevertheless, 2-DMAP, like other nitrogen-containing polymer interlayer materials, turns out to be not applicable to inverted organic solar cells (I-OSCs) with IT-4F as the n-type electron acceptor because the amino group of 2-DMAP can act as a nucleophile to attack the end-group of IT-4F at the interface. The decomposition of IT-4F by 2-DMAP was carefully proved to be via retro-aldol condensation. As a result, the device (PBDBT-F:IT-4F) modified with 2-DMAP displayed a low PCE of 7.34%. The zwitterionic PAS with reduced nucleophilicity and basicity can modify the ITO surface without decomposing IT-4F. The PBDBT-F:IT-4F-based device modified with PAS maintained a high PCE of 11.41%. Most importantly, the PAS-based device using the well-known Y6 acceptor (PBDBT-F:Y6) can achieve a PCE of 13.82%. This new interfacial material can be universally applied to I-OSCs employing various A-D-A-type acceptors installed with the electrophilic 1,1-dicyanamethylene-5,6-difluoro-3-indanone (FIC) end-group.
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