2-Chloropropyldimethylamine
[CAS# 108-14-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: 2-Chloropropyldimethylamine
• Molecular Formula: C₅H₁₂ClN
• Molecular Weight: 121.61
• CAS Registry Number: 108-14-5
• EC Number: 203-554-3
• SMILES: CC(CN(C)C)Cl

Properties

• Solubility: 9.5e+004 mg/L (25 ºC water)
• Density: 0.9±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.432, Calc.^*
• Melting point: -65.08 ºC
• Boiling Point: 108.17 ºC, 81.1±13.0 ºC (760 mmHg), Calc.^*
• Flash Point: 2.9±19.8 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Hazard Statements: H302-H314-H315-H319-H335
• Precautionary Statements: P260-P261-P264-P264+P265-P270-P271-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P330-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Skin corrosion	Skin Corr.	1C	H314

Discovory and Applicatios

2-Chloropropyldimethylamine, also known as 1-(Chloropropan-2-yl)dimethylamine, is an organic compound with the molecular formula C₅H₁₂ClN. It is a secondary amine characterized by a dimethylamino group bonded to a 2-chloropropyl chain. The structure consists of a central nitrogen atom substituted with two methyl groups and a 2-chloropropyl moiety, making it a representative of alkylchlorodialkylamines. This compound is typically encountered as a colorless to pale yellow liquid with a fishy odor, which is common for many low molecular weight aliphatic amines.

The discovery and synthesis of 2-chloropropyldimethylamine can be traced back to developments in the field of alkylamine chemistry during the mid-20th century, when chemists explored various halogenated amines for their reactivity and potential use as intermediates. The compound can be prepared by the alkylation of dimethylamine with 1,2-propylene oxide followed by treatment with hydrogen chloride or by reacting dimethylamine with 1-chloro-2-propanol under appropriate conditions. It can also be synthesized via substitution reactions involving epoxides and amines or by employing chlorinated alcohols in nucleophilic substitution processes.

2-Chloropropyldimethylamine has found significant application as an intermediate in the synthesis of quaternary ammonium compounds, particularly in the production of surfactants and antimicrobial agents. When treated with long-chain alkyl halides or other electrophiles, it readily forms quaternary ammonium salts, which are widely used in household disinfectants, fabric softeners, and industrial biocides. These quaternary compounds exhibit surface-active properties and possess bactericidal and fungicidal activities, making them important in formulations intended for sanitation and hygiene.

In polymer chemistry, 2-chloropropyldimethylamine serves as a functional monomer or comonomer component for modifying resins and polymer backbones. The presence of the chloroalkyl group allows it to participate in nucleophilic substitution reactions with nucleophilic sites on polymers, facilitating the attachment of amine functionalities. Such modifications are used to improve polymer solubility, ionic character, or adhesion properties. It is particularly valuable in the preparation of ion-exchange resins and water-treatment polymers.

The compound has also been employed in the synthesis of pharmaceutical and agrochemical intermediates. Its reactive amine and chloro substituents make it a useful building block for constructing more complex organic molecules. In medicinal chemistry, derivatives of 2-chloropropyldimethylamine have been studied for their biological activity or as linkers in drug conjugates. In agrochemical research, it has been used in the synthesis of herbicides and fungicides where dialkylaminoalkyl moieties are present in the active structure.

Safety and handling of 2-chloropropyldimethylamine require appropriate precautions due to its corrosive and irritant nature. It can cause irritation to the skin, eyes, and respiratory system upon exposure. Proper personal protective equipment, including gloves and eye protection, should be used during handling. As with other chlorinated amines, storage should be in tightly closed containers, in a cool and well-ventilated area, away from incompatible substances such as strong oxidizers and acids.

In industrial applications, this compound is also considered for use in the synthesis of catalysts and phase transfer agents. The ability of the amine group to coordinate with metals or form salts with acids is exploited in various synthetic methodologies where phase transfer catalysis or ionic interaction is beneficial for reaction efficiency. This versatility has ensured its place in a broad range of chemical processes.

Overall, 2-chloropropyldimethylamine is a well-characterized chemical intermediate with established roles in organic synthesis, surfactant development, polymer modification, and functional molecule construction. Its bifunctional nature, incorporating both a nucleophilic amine and an electrophilic alkyl chloride, makes it particularly useful in numerous chemical transformations documented in the literature.

References

2003. Isothipendyl. Pharmaceutical Substances, (2003).

2003. Methadone. Pharmaceutical Substances, (2003).

2003. Promethazine. Pharmaceutical Substances, (2003).