1-Chloro-3-phenylpropane
[CAS# 104-52-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic hydrocarbon reagent
• Name: 1-Chloro-3-phenylpropane
• Synonyms: (3-Chloropropyl)benzene
• Molecular Formula: C₉H₁₁Cl
• Molecular Weight: 154.64
• CAS Registry Number: 104-52-9
• EC Number: 203-210-2
• SMILES: C1=CC=C(C=C1)CCCCl

Properties

• Water solubility: SLIGHTLY SOLUBLE
• Density: 1.0±0.1 g/mL, Calc.^*, 1.045 g/mL (Expl.)
• Melting point: -27 °C
• Index of Refraction: 1.515, Calc.^*, 1.521 (Expl.)
• Boiling Point: 220.2±9.0 °C (760 mmHg), Calc.^*, 219 °C (Expl.)
• Flash Point: 87.2 °C, Calc.^*, 87 °C (Expl.)

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

Safety Data

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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

1-Chloro-3-phenylpropane is an organic compound with the chemical formula C9H11Cl. It is a chloroalkyl derivative, where a chlorine atom is attached to the third carbon of a phenylpropane backbone. The compound is a colorless liquid at room temperature and has a characteristic aromatic odor.

The synthesis of 1-chloro-3-phenylpropane typically involves the chlorination of 3-phenylpropene, which is a precursor compound obtained through the alkylation of benzene with propylene or by other methods such as the Friedel-Crafts reaction. Chlorine is introduced into the 3-position of the phenylpropane chain, leading to the formation of 1-chloro-3-phenylpropane.

1-Chloro-3-phenylpropane has applications primarily in the field of organic synthesis. It is commonly used as an intermediate in the preparation of other chemicals, including pharmaceuticals and agrochemicals. The compound's structure makes it a useful building block for the synthesis of various functionalized aromatic compounds. It is used in reactions that involve nucleophilic substitution, where the chlorine atom is replaced by various nucleophiles, such as amines or alcohols, leading to the formation of substituted derivatives.

In the context of pharmaceuticals, 1-chloro-3-phenylpropane and its derivatives may be used in the synthesis of biologically active compounds. Some of these derivatives have been investigated for potential antimicrobial and anticancer activities, though further studies are required to establish their clinical applications.

In addition to its use in pharmaceutical and agrochemical synthesis, 1-chloro-3-phenylpropane can also serve as a reagent in the preparation of various polymer materials, where it is incorporated into polymer chains to alter their properties.

The compound is relatively stable under normal conditions but should be handled with care due to its chlorinated nature, as exposure to chlorine compounds can lead to health hazards. Safety measures should be taken to avoid inhalation or skin contact with the substance.

1-chloro-3-phenylpropane is not commonly used in consumer products but plays an essential role in industrial and synthetic chemistry, primarily as an intermediate in the synthesis of other compounds. The compound's practical applications highlight its importance in various chemical synthesis pathways.

References

1979. Telomerization of ethylene by benzyl chloride. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 28(6), 47386.
DOI: 10.1007/bf00947386

2019. Photocatalytic activation of alkyl chlorides by assembly-promoted single electron transfer in microheterogeneous solutions. Nature Catalysis, 2(11), 369.
DOI: 10.1038/s41929-019-0369-5

2019. Synthesis, in vitro antifungal evaluation and docking studies of novel derivatives of imidazoles and benzimidazoles. Medicinal Chemistry Research, 28(8), 2369.
DOI: 10.1007/s00044-019-02369-7