Chinese Name: 3-(1-Naphthyloxy)-1,2-Epoxypropane
English Name: α-Naphthyl Glycidyl Ether
English Other Names: 2-[(1-Naphthyloxy)methyl]oxirane; Naphthyl Glycidyl Ether; 1-naphthylglycidylether; Propranolol Epoxide; Propranolol Impurity 7; Naftopidil Impurity 1
CAS Number: 2461-42-9
EINECS Number: 219-555-7
Chemical Formula: C₁₃H₁₂O₂
Molecular Weight: 200.23 g/mol
InChI InChI=1/C₁₃H₁₂O₂/c1-2-6-12-10(4-1)5-3-7-13(12)15-9-11-8-14-11/h1-7,11H,8-9H₂/t11-/m0/s1
Density 1.192 g/cm³ (20℃)
Boiling point 338.6℃ (760 mmHg); 161-167℃ (2 mmHg); 148-150℃ (272 Pa)
Flash point 152℃
Water solubility Slightly soluble/insoluble in water
Vapor pressure 0.000191 mmHg (25℃)
Refractive index 1.628
Storage conditions Refrigerate, keep away from fire
Sensitivity Sensitive to air and light; skin sensitization; suspected carcinogen
Appearance Pale yellow to pale purple oily liquid
Specific gravity 1.162-1.192
Color Pale yellow/pale purple/orange-yellow oily
BRN 128232
MDL No. MFCD00079026
Hazard Symbols Xn (Hazardous); Xi (Irritating); N (Environmentally hazardous)
Risk Terms R20/21/22 (Hazardous if inhaled, contact with skin, or ingested); R36/37/38 (Irritating to eyes, respiratory system, and skin); R43 (May cause sensitization upon skin contact); R45 (May be carcinogenic)
Safety Terms S26 (Eye contact: Immediately flush with plenty of water and seek medical attention); S36/37/39 (Wear appropriate protective clothing, gloves, and eye/face protection); S45 (In case of accident or discomfort, seek medical attention immediately); S53 (Avoid contact; obtain special instructions before use)
Customs Number 29109000 (Epoxy Compounds)
Properties: 3-(1-Naphthoxy)-1,2-epoxypropane is an aromatic ether compound containing an epoxy group. It is a pale yellow to pale purple oily liquid at room temperature and pressure. Its molecular structure contains a naphthalene ring linked to an epoxypropane group via an ether bond, exhibiting high chemical reactivity, particularly the epoxy group, which can participate in ring-opening reactions. This compound has a low vapor pressure (0.000191 mmHg at 25℃), indicating low volatility, but it can still produce harmful vapors at high temperatures. Its density is approximately 1.192 g/cm³, higher than that of water, and its refractive index is 1.628, indicating high optical density. This substance is sensitive to light and air and must be stored under low-temperature, light-protected conditions.
Uses
3-(1-Naphthoxy)-1,2-epoxypropane is an important pharmaceutical intermediate, mainly used in the synthesis of cardiovascular drugs:
Propranolol intermediate: Propranolol is a non-selective β-receptor blocker, widely used to treat cardiovascular diseases such as hypertension, angina pectoris, and arrhythmia.
Naftopidil intermediate: Naaftopidil is an α1-receptor blocker used to treat benign prostatic hyperplasia and hypertension.
Standards/Impurity Reference Standards: Used as impurity standards in drug quality control (e.g., Propranolol Impurity 7, Naftopidil Impurity 1).
Organic Synthesis Raw Materials: Can be used to synthesize other fine chemicals containing naphthalene ring structures.
Preparation Methods
Main Synthetic Routes (One-Step/Two-Step):
Method 1: Phase Transfer Catalysis (One-Step)
Using α-naphthol and epichlorohydrin as raw materials
Under alkaline conditions (15%) Method 1: Reaction with NaOH aqueous solution
Using polyethylene glycol 400 as a phase transfer catalyst
Reaction temperature: 95℃, reaction time: 10 hours
Overall yield: 83%, purity: 98%
Method 2: Two-step method
Etherification reaction: α-naphthol reacts with epichlorohydrin upon heating to produce 1-chloro-3-(1-naphthoxy)-2-propanol
Cyclization reaction: Hydrogen chloride is removed under the action of sodium hydroxide, resulting in cyclization to produce 3-(1-naphthoxy)-1,2-epoxypropane
Method 3: Transesterification method
Using (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester reacting with 1-naphthol, the yield can reach 99%
Safety Information
GHS Hazard Classification:
Skin sensitization (Category 1): H317 – May cause allergic skin reactions
Germ cell mutagenicity (Category 2): H341 – Possibly causes genetic defects
Carcinogenicity (Category 2): H351 – Suspected carcinogen
Safety Precautions:
Personal Protection: Wear protective gloves, safety glasses, and protective clothing. Avoid direct skin contact.
Ventilation: Operate in a well-ventilated environment. Avoid inhaling vapors/dust.
Storage: Refrigerate (2-8℃), keep away from fire and oxidizers, and seal containers.
Spill Handling: Absorb with inert material (such as sand or vermiculite). Avoid drainage.
First Aid: For skin contact, immediately flush with plenty of water; for eye contact, flush with saline solution for at least 15 minutes; for inhalation, move to fresh air.
Environmental Hazards: May be harmful to aquatic life. Avoid release into the environment.
Waste should be disposed of in accordance with local regulations.
Post time: Mar-23-2026
