Shandong Huashang Chemical Co., Ltd. is a high-tech enterprise specializing in the research and development, manufacturing, and sales of fine chemicals. Headquartered in Jinan, Shandong, China, we are committed to delivering high-quality products to our global partners. Currently, over 90% of our products are exported to developed markets, including North America, Europe, Japan, South Korea, and the Middle East.
Product Description
3-Acetylpyridine (CAS: 350-03-8), also known as methyl 3-pyridyl ketone or 1-(3-pyridinyl)ethanone, is an aromatic ketone with the molecular formula C?H?NO. It appears as a colorless to pale yellow transparent liquid at room temperature, with a powerful, nutty, popcorn-like aroma and a sweet taste. The compound is miscible with most organic solvents (e.g., ethanol, acetone, ether) and soluble in hot water and dilute acids, but insoluble in petroleum ether. Industrially, it is primarily produced by the dry distillation of calcium nicotinate and calcium acetate, or via the condensation of ethyl nicotinate with ethyl acetoacetate followed by hydrolysis. As a versatile aromatic intermediate, it is widely used in pharmaceutical synthesis, flavor and fragrance formulation, and chemical research.
Uses
Pharmaceutical Intermediate: Key raw material for synthesizing risedronate sodium, a drug for treating osteoporosis and inhibiting bone resorption. It also serves as a critical intermediate in the production of various clinical drugs, including imatinib mesylate, metyrapone, telithromycin, and ridogrel.
Flavor & Fragrance Agent: Approved as a food flavoring (FEMA 3424), it is mainly used to formulate popcorn, peanut, meat, and tobacco-type fragrances. It imparts a rich, nutty aroma to tobacco products and enhances the flavor of roasted foods, and is also used in beverage and confectionery formulations to add a characteristic sweet-nutty note.
Biochemical & Chemical Research: An analog of nicotinamide that competes for incorporation into NAD (nicotinamide adenine dinucleotide), used in biochemical studies of enzyme inhibition, cellular metabolism, and vitamin B3-related biological processes. It is also employed as a research reagent in organic synthesis, a reference standard in analytical chemistry, and a tool for studying pyridine-based reaction mechanisms.
Other Applications: Used as a corrosion inhibitor additive in industrial coatings and as a component in synthetic lubricants to improve anti-oxidation performance. It also acts as a key building block for preparing pyridine-based derivatives, including dyes, pigments, and agrochemical intermediates.
Molecular Formula & Structure
- Molecular Formula: C?H?NO
- Molecular Weight: 121.14 g/mol (121.052765 g·mol?1, precise value)
- IUPAC Name: 1-(Pyridin-3-yl)ethanone
- Synonyms: Methyl 3-pyridyl ketone; 1-(3-Pyridinyl)ethanone; 3-Acetopyridine; β-Acetylpyridine; FEMA 3424; MFCD00006396; BRN 107751; PubChem Substance ID: 24890625; EC Number: 206-496-7; RTECS Number: UE5250000
- EC Number: 206-496-7
- CAS Number: 350-03-8
- SMILES Code: CC(=O)c1cccnc1
- Chemical Structure: The molecule consists of a pyridine ring with an acetyl group (-COCH?) attached at the 3-position, forming an aromatic ketone structure. The conjugated system of the pyridine ring and the carbonyl group endows it with unique chemical reactivity, enabling nucleophilic addition, condensation, and oxidation reactions. The pyridine nitrogen atom also provides basicity, allowing it to form salts with acids, which enhances its solubility in aqueous solutions.
Physical & Chemical Properties
- Appearance: Colorless to pale yellow transparent liquid; powerful, nutty, popcorn-like aroma; sweet taste; slightly hygroscopic.
- Melting Point: 11–13 °C; Boiling Point: 220 °C (760 mmHg), 103–105 °C (15 mmHg, vacuum); Flash Point: 104 °C (closed cup); Refractive Index: n??/D 1.534 (lit.); Autoignition Temperature: 420 °C. It is a combustible liquid, and its vapor may form explosive mixtures with air at temperatures above 104 °C.
- Density: 1.102 g/mL at 25 °C; Vapor Pressure: 0.3 Pa at 20 °C, 1.33 kPa at 83 °C; Solubility: Miscible with ethanol, acetone, ether, chloroform, and DMSO; soluble in hot water (≥60 °C) and dilute acids; insoluble in petroleum ether and hexane; LogP: 0.52 (25 °C); pKa: 5.2 (25 °C, pyridine nitrogen).
- Stability: Stable under normal temperature and pressure; sensitive to strong light and high temperature, which may cause discoloration (turning pale yellow to brown) and degradation. Incompatible with strong oxidizing agents, strong bases, and reducing agents; avoid prolonged exposure to air to prevent oxidation. It may undergo hydrolysis under strong acid or base conditions, generating nicotinic acid derivatives.
- Toxicity: Acute toxicity; oral LD?? (rats) = 460 mg/kg (corrected from 46 μL/kg, standard unit); dermal LD?? (rabbits) = >2000 mg/kg. May cause skin irritation (H315) and serious eye irritation (H319); inhalation of high-concentration vapor may cause respiratory discomfort and dizziness. GHS Labeling: Signal word "Danger"; Hazard statements H301 (Toxic if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation); Precautionary statements P264, P280, P301+P310, P302+P352, P305+P351+P338, P337+P313.
Synthesis & Storage
- Synthesis: Industrial production mainly adopts two routes: (1) Dry distillation of calcium nicotinate and calcium acetate: The mixture is heated to 300–350 °C for dry distillation, and the distillate is collected and rectified to obtain the product. (2) Condensation of ethyl nicotinate with ethyl acetoacetate followed by hydrolysis: The condensation reaction is carried out under alkaline catalysis, and the resulting intermediate is hydrolyzed and decarboxylated to obtain 3-acetylpyridine. The crude product is purified by vacuum distillation (15 mmHg, 103–105 °C) to obtain high-purity (≥98.0%) product.
- Storage: Store in a cool, dry, well-ventilated warehouse at ≤15 °C; keep containers tightly sealed to prevent moisture absorption, volatilization, and contamination. Packed in clean, dry glass bottles (1 kg/bottle) or HDPE plastic drums (25 kg/200 kg per container). Avoid direct sunlight, high temperature (>30 °C), and open flames; keep away from strong oxidizing agents, strong acids, strong bases, and food materials. Shelf life: 12 months when unopened and stored properly; use promptly after opening to prevent discoloration and degradation.
- Safety: Operate in a well-ventilated fume hood; wear nitrile gloves, safety goggles, and protective clothing during handling to avoid skin and eye contact. In case of skin contact, rinse with plenty of water for 15 minutes; in case of eye contact, rinse cautiously with water for several minutes and seek medical attention immediately. In case of ingestion, do not induce vomiting and seek medical attention promptly. In case of fire, use dry sand, carbon dioxide, or alcohol-resistant foam to extinguish; avoid using water to prevent splashing. Dispose of waste and contaminated containers in accordance with local environmental regulations.
