4-Dimethylaminopyridine - ≥99% , CAS No.1122-58-3

CAS: 1122-58-3 Cat. No.: D109207 Formula: C₇H₁₀N₂ Molecular Weight: 122.17 Beilstein Registry Number: 3539759 EC Number: 214-353-5

GRADE & PURITY ≥99%

Synonyms

N,N-dimethyl 4-pyridinamine | p-dimethylamino pyridine | (4-DMAP);4-Dimethylaminopyridine | 4-di methylaminopyridine | 4-Dimethylaminepyridine | N,N-dimethyl-N-(4-pyridinyl)amine | dimethyl-pyridin-4-yl-amine | dimethyl-pyridin-4yl-amine | dimethylpyridin

Storage

Protected from light,Room temperature

Shipped In

Normal

Overview

A highly efficient catalyst for acylation reactions

4-Dimethylaminopyridine (DMAP) is a versatile nucleophilic catalyst used in acylation and esterification reactions. It can also be used in various organic transformations such as Baylis-Hillman reaction, Dakin-West reaction, protection of amines, C-acylation, silylation, and applications in natural product chemistry.
Application
4-Dimethylaminopyridine can be used as a catalyst for the following reactions:
Synthesis of 3,5-substituted 2,6-dicyanoanilines by reaction with malononitrile, aldehydes and β-nitroolefins.
Acylation of alcohols with anhydrides to synthesize the corresponding esters in the absence of auxiliary bases and solvents.
Baylis-Hillman reaction to generate carbon-carbon bonds by coupling of activated alkenes with aldehydes or ketones.
Efficient catalyst for acylation reactions.

Specifications

Synonyms

N,N-dimethyl 4-pyridinamine | p-dimethylamino pyridine | (4-DMAP);4-Dimethylaminopyridine | 4-di methylaminopyridine | 4-Dimethylaminepyridine | N,N-dimethyl-N-(4-pyridinyl)amine | dimethyl-pyridin-4-yl-amine | dimethyl-pyridin-4yl-amine | dimethylpyridin

Specifications & Purity

≥99%

Storage

Protected from light,Room temperature

Shipped In

Normal

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504752548
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504752548
• Canonical Smiles: CN(C)C1=CC=NC=C1
• IUPAC Name: N,N-dimethylpyridin-4-amine
• InChIKey: VHYFNPMBLIVWCW-UHFFFAOYSA-N
• INCHI: 1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3
• Isomeric SMILES: CN(C)C1=CC=NC=C1
• WGK Germany: 3
• RTECS: US9230000
• UN Number: 2811
• Molecular Weight: 122.17
• Beilstein: 3539759
• Reaxy-Rn: 110354
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=110354&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines
        • Level5 Tertiary amines
          • Level6 Tertiary alkylarylamines
            • Level7 Dialkylarylamines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Tertiary amines - Tertiary alkylarylamines
• Direct Parent: Dialkylarylamines
• Alternative Parents: Aminopyridines and derivatives Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Dialkylarylamine - Aminopyridine - Pyridine - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Organopnictogen compound - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in methanol, benzene, ethyl acetate, chloroform, methylene chloride, acetone, and acetic acid. Slightly soluble in ether, diisopropyl ether, cyclohexane, hexane, and water.
• Sensitivity: light sensitive
• Flash Point(°F): 230 °F
• Flash Point(°C): 110 ℃
• Boil Point(°C): 162°C
• Melt Point(°C): 110°C
• Molecular Weight: 122.170 g/mol
• XLogP3: 1.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 122.084 Da
• Monoisotopic Mass: 122.084 Da
• Topological Polar Surface Area: 16.100 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 75.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1122-58-3, the molecular formula is C7H10N2, and the molecular weight is 122.17 g/mol. InChIKey VHYFNPMBLIVWCW-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.