3-Chloropropylamine hydrochloride
[CAS# 6276-54-6]

Identification

• Classification: Organic raw materials >> Amino compound >> Acyclic monoamines, polyamines and their derivatives and salts
• Name: 3-Chloropropylamine hydrochloride
• Synonyms: 1-Amino-3-chloropropane hydrochloride; 3-Chloropropylammonium chloride
• Molecular Formula: C₃H₈ClN.HCl;C₃H₉Cl₂N
• Molecular Weight: 130.02
• CAS Registry Number: 6276-54-6
• EC Number: 228-474-6
• SMILES: C(CN)CCl.Cl

Properties

• Melting point: 145 - 150 °C (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Respiratory sensitization	Resp. Sens.	1	H334
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3-Chloropropylamine hydrochloride is a synthetic organic compound with the molecular formula C₃H₉Cl₂N. It consists of a chlorinated alkyl chain terminated by a primary amine group, with the hydrochloride salt increasing its stability and solubility in water. The compound is a white to off-white crystalline solid and is commonly used as an intermediate in organic synthesis due to its bifunctional nature. It contains both a nucleophilic amine and an electrophilic chlorine, allowing it to participate in a wide variety of substitution and condensation reactions.

The substance is typically produced by the hydrochloride salt formation of 3-chloropropylamine, which itself is obtained through the amination of 1,3-dichloropropane or other halogenated precursors. Industrial production methods are designed to maintain high purity and ensure stability during storage. The hydrochloride form is favored for its improved handling characteristics compared to the free base, which is more volatile and reactive under ambient conditions.

3-Chloropropylamine hydrochloride has found extensive utility as a synthetic building block in chemical and materials research. Its primary amine group can undergo acylation, alkylation, and reductive amination reactions, while the alkyl chloride moiety is commonly used for nucleophilic substitution reactions, such as with alcohols, thiols, or secondary amines. This dual reactivity makes the compound particularly useful in the preparation of functionalized molecules and polymers.

One of the most frequent applications of 3-chloropropylamine hydrochloride is in the synthesis of modified polyacrylamides. By reacting with carboxylic acid groups on polymer backbones, the chloropropylamine moiety can introduce pendant groups that influence solubility, charge density, and thermal or mechanical properties. This has led to its use in the development of star-shaped and comb-like polymer architectures for use in drag reduction, water treatment, and enhanced oil recovery.

The compound is also used to introduce linker arms or functional side chains into pharmaceutical or agrochemical intermediates. Its amine group allows it to be coupled to various acid or ester functionalities, while the chloro group permits further substitution reactions. These properties have made it a useful intermediate in the design of molecules with specific spatial arrangements or reactivity patterns.

In materials science, 3-chloropropylamine hydrochloride has been employed to modify surfaces through covalent attachment. When bound to silanes or other reactive surfaces, it serves as an anchoring group that allows further chemical modification, enhancing the compatibility or reactivity of the surface. Applications in this area include the preparation of functional membranes, resins, and monolayer assemblies.

The compound must be handled with care due to the reactivity of both functional groups. The amine can cause irritation upon inhalation or skin contact, and the alkyl chloride group is capable of alkylating biological molecules. Safety data recommend the use of gloves, protective clothing, and proper ventilation during handling. The hydrochloride form reduces volatility and enhances safety during storage and transfer.

3-Chloropropylamine hydrochloride is not typically found in commercial consumer products but is widely distributed through chemical suppliers for use in academic and industrial research. It serves as a versatile intermediate for chemists seeking to build complex molecules, modify polymers, or functionalize surfaces. The compound’s value lies in its ability to bridge different chemical functionalities in a controlled and predictable manner, making it a foundational reagent in diverse areas of synthetic chemistry.

References

Bhagiyalakshmi M, Lee J Y, Anuradha R, Jang H T (2009) Synthesis of chloropropylamine grafted mesoporous MCM‑41, MCM‑48 and SBA‑15 from rice husk ash: their application to CO₂ chemisorption J Porous Mater 16 4 525–533 DOI: 10.1007/s10934-009-9310-7

Qiao L‑Z, Yu C‑M, Sun R‑T (2021) Preparation of amino‑functionalized guanidinium ionic liquid‑modified magnetic materials and application in solid‑phase extraction of pollutants in water J Anal Test 5 2 129–137 DOI: 10.1007/s41664-021-00188-7

Yue C, Su D, Zhang X, Wu W, Xiao L (2014) Amino‑functional imidazolium ionic liquids for CO₂ activation and conversion to form cyclic carbonate Catal Lett 144 5 857–864 DOI: 10.1007/s10562-014-1241-5