3-Dimethylaminopropylchloride hydrochloride
[CAS# 5407-04-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Oxy-containing amino compound
• Name: 3-Dimethylaminopropylchloride hydrochloride
• Synonyms: 3-Chloropropyldimethylammonium chloride; 3-Chloro-N,N-dimethylpropylamine hydrochloride; DMPC
• Molecular Formula: C₅H₁₂ClN.HCl;C₅H₁₃Cl₂N
• Molecular Weight: 158.07
• CAS Registry Number: 5407-04-5 (1281-00-1)
• EC Number: 226-467-2
• SMILES: CN(C)CCCCl.Cl

Properties

• Melting point: 140-143 °C (Expl.)
• Water solubility: soluble (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335-H412
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin corrosion	Skin Corr.	1B	H314
Eye irritation	Eye Irrit.	2A	H319
Germ cell mutagenicity	Muta.	2	H341

Discovery and Applications

3-Dimethylaminopropylchloride hydrochloride, often abbreviated as DMAP-Cl, is a chemical compound with the formula C6H15Cl2N. It is a quaternary ammonium salt that features a dimethylamino group attached to a propyl chain, with a chloride counterion. This compound is widely utilized in chemical synthesis, particularly in the field of organic chemistry, due to its role as a versatile reagent and catalyst in various reactions.

The discovery of 3-dimethylaminopropylchloride hydrochloride can be traced back to the search for efficient catalysts in organic synthesis. Researchers identified that tertiary amines, especially those possessing a long alkyl chain, could significantly accelerate certain types of chemical reactions. Specifically, DMAP-Cl became known for its ability to enhance nucleophilic substitution reactions and other processes involving the activation of electrophilic compounds. The presence of the dimethylamino group facilitates the coordination of the reagent to the electrophile, thereby increasing its reactivity.

One of the primary applications of 3-dimethylaminopropylchloride hydrochloride is in the synthesis of various organic molecules. It is commonly used as a catalyst in acylation reactions, where it facilitates the formation of amide or ester bonds. In these reactions, DMAP-Cl serves as a nucleophilic catalyst that accelerates the transfer of acyl groups from acyl donors, such as acyl chlorides or anhydrides, to nucleophilic acceptors like amines or alcohols. This property makes it invaluable in the synthesis of peptides, pharmaceuticals, and other biologically active compounds.

Another significant application of DMAP-Cl is in peptide synthesis, where it plays a crucial role in the activation of carboxyl groups. It is used to enhance the formation of peptide bonds by facilitating the coupling of amino acids. This application is of particular importance in the field of medicinal chemistry, where peptides serve as precursors for drug development. By increasing the efficiency and yield of peptide bond formation, DMAP-Cl has made a substantial impact on the synthesis of therapeutic peptides and proteins.

Furthermore, 3-dimethylaminopropylchloride hydrochloride is utilized in the preparation of various other chemical intermediates. It is involved in the synthesis of N-alkylated amines, which are essential in the production of surfactants, plasticizers, and other industrial chemicals. In addition to its role in organic synthesis, DMAP-Cl is also used in the modification of natural products, where it can be employed to introduce functional groups into molecular structures. This functionality is important for the creation of novel compounds with potential applications in materials science and biotechnology.

The use of DMAP-Cl is not limited to organic synthesis alone. It has also found applications in the development of polymer materials, where it is used as a chain-transfer agent in certain polymerization processes. In these applications, it helps control the molecular weight and polydispersity of the resulting polymers, making it useful in the production of high-performance materials.

In conclusion, 3-dimethylaminopropylchloride hydrochloride is a highly versatile chemical compound with a broad range of applications in organic synthesis, peptide chemistry, and materials science. Its discovery as a catalyst and reagent has greatly contributed to the efficiency of various chemical processes, especially in the synthesis of complex organic molecules. As research continues, the compound's applications are likely to expand, further solidifying its importance in modern chemical and pharmaceutical industries.

References

2022. Dynole 34-2 and Acrylo-Dyn 2-30, Novel Dynamin GTPase Chemical Biology Probes. Methods in Molecular Biology (Clifton, N.J.).
DOI: 10.1007/978-1-0716-1916-2_17

2016. Surface-modified polyacrylonitrile nanofibres as supports. Polymer Bulletin, 73(10).
DOI: 10.1007/s00289-016-1830-0

2015. A Nucleus-Imaging Probe That Selectively Stabilizes a Minor Conformation of c-MYC G-quadruplex and Down-regulates c-MYC Transcription in Human Cancer Cells. Scientific Reports, 5.
DOI: 10.1038/srep13183