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Send EmailDimethyl Indanone, Dimethylindanone, 66309-83-9
Product Name: 2,6-Dimethyl-1-indanone
Chemical Name: 2,6-Dimethyl-1-indanone
CAS No: 66309-83-9
EC No (EINECS): 266-351-9
Chemical Formula: C₁₁H₁₂O
Molecular Weight: 160.22 g/mol
REACH Status: Registered
| Parameter | Description |
|---|---|
| Chemical Name (IUPAC) | 2,6-Dimethyl-2,3-dihydro-1H-inden-1-one |
| Other Names | 2,6-Dimethyl-1-indanone, 2,6-Dimethyl-1-indanone, 2,6-Dimethylindan-1-one |
| CAS Number | 66309-83-9 |
| EC Number (EINECS) | 266-351-9 |
| Molecular Formula | C₁₁H₁₂O |
| Molecular Weight | 160.22 g/mol |
| Chemical Class | Aromatic ketone, indanone derivative, cyclic ketone |
| Appearance | Light yellow crystalline solid |
| Odor | Mild characteristic, aromatic |
| Taste | Not determined as technical product |
| REACH Status | Registered |
CHEMICAL STRUCTURE AND DESCRIPTION:
2,6-Dimethyl-1-indanone is an aromatic ketone with an indanone (2,3-dihydro-1H-inden-1-one) skeleton. Its structure contains a five-membered cyclopentanone ring fused to a benzene ring. It contains methyl groups at the 2 and 6 positions. This structure gives the compound both ketone reactivity and aromatic substitution properties.
Structural Formula (Open Structure):
O
||
C
/
CH₂ CH-CH₃
| |
C₆H₃(CH₃)
(Benzene ring with 6-methyl, cyclopentanone with 2-methyl)
(2,6-Dimethyl-2,3-dihydro-1H-inden-1-one)
These structural features:
Give the compound a ketone functional group; allow reduction, condensation, and Grignard reactions.
Allow electrophilic substitution reactions on the aromatic ring.
Methyl groups increase lipophilic character and influence molecular interactions.
Indanone derivatives are important building blocks in the synthesis of pharmaceutical and biologically active molecules.
2,6-Dimethyl-1-indanone is an indanone derivative used as an intermediate in organic syntheses, particularly in pharmaceutical and fine chemical applications.
| Property | Value |
|---|---|
| Molecular Formula | C₁₁H₁₂O |
| Molecular Weight | 160.22 g/mol |
| Appearance | Light yellow crystalline solid |
| Odor | Mild characteristic, aromatic |
| Density | ~1.0 g/cm³ (20 °C, estimated) |
| Melting Point | 65–70 °C |
| Boiling Point | ~280 °C (760 mmHg) |
| Flash Point | >110 °C (closed cup, estimated) |
| Vapor Pressure | Low (<0.01 mmHg at 20 °C) |
| Solubility | Soluble in organic solvents; low solubility in water |
| Stability | Stable under recommended storage conditions |
| pH (aqueous solution) | Neutral |
| Volatility | Low |
| Hygroscopicity | Not hygroscopic |
2,6-Dimethyl-1-indanone is a light yellow crystalline solid. Its melting point is 65–70 °C, boiling point ~280 °C. Its density is about 1.0 g/cm³. It is soluble in organic solvents and has low solubility in water. It has low volatility and is not hygroscopic.
| Solvent | Solubility | Conditions |
|---|---|---|
| Water | Low (<0.1 g/L) | 20 °C |
| Methanol | Soluble | - |
| Ethanol | Soluble | - |
| Isopropanol | Soluble | - |
| Acetone | Soluble | - |
| Ethyl acetate | Soluble | - |
| Dichloromethane | Soluble | - |
| Toluene | Soluble | - |
| Hexane | Partially soluble | - |
| Dimethyl sulfoxide (DMSO) | Soluble | - |
The compound is readily soluble in polar and non-polar organic solvents. It is not miscible with water and shows very low solubility in water. This property makes it useful in organic syntheses and extraction processes.
| Property | Description |
|---|---|
| Chemical Class | Aromatic ketone, cyclic ketone |
| Reactivity | Nucleophilic addition, condensation, reduction, oxidation, electrophilic aromatic substitution |
| Hydrolytic Stability | High |
| Thermal Stability | Good |
| Oxidation Resistance | Moderate |
| Polymerization | Does not undergo hazardous spontaneous polymerization |
| Compatibility | Organic solvents, reducing agents, Grignard reagents, amines |
| Substances to Avoid | Strong oxidizing agents, strong acids, strong bases |
| Hazardous Decomposition Products | Carbon monoxide (CO), carbon dioxide (CO₂), aromatic compounds |
Due to its ketone group, the compound undergoes nucleophilic addition (Grignard, hydride reduction), condensation (aldol, Knoevenagel), and reduction reactions. The aromatic ring is open to electrophilic substitution (nitration, sulfonation, halogenation). The methyl groups can be functionalized under appropriate conditions.
| Parameter | Specification |
|---|---|
| Purity (GC) | ≥ 98.0% |
| Appearance | Light yellow crystalline solid |
| Color (Pt-Co) | ≤ 100 Hazen |
| Melting Range | 65–70 °C |
| Water Content | ≤ 0.5% |
| Ash | ≤ 0.1% |
| Heavy Metals | ≤ 10 ppm |
| Solubility (Ethanol) | Clear solution |
| Shelf Life | 24 months (under proper storage) |
The product is produced in technical grade with high purity. In industrial applications, batch-to-batch consistency, color stability, and low impurity content are important.
| Application | Description |
|---|---|
| Pharmaceutical Intermediate | Building block in the synthesis of drug active ingredients |
| Fine Chemicals | Intermediate in the production of specialty chemicals |
| Biologically Active Molecules | In the synthesis of various biologically active compounds |
| Aromatic Compound Synthesis | In the production of indanone derivatives and aromatic molecules |
2,6-Dimethyl-1-indanone is used as an intermediate in organic syntheses, particularly in pharmaceutical and fine chemical applications.
| Application | Description |
|---|---|
| Indanone Derivatives | Synthesis of various indanone-based compounds |
| Biologically Active Molecules | Pharmaceutical and agrochemical active ingredients |
| Functional Aromatics | Production of specialty aromatic compounds |
The compound is used in the production of indanone derivatives and various aromatic/biologically active molecules.
| Application | Description |
|---|---|
| Laboratory Synthesis | Raw material in the development of new compounds |
| Model Compound | In the study of reaction mechanisms |
| Catalyst Research | Substrate in catalytic reactions |
The compound is preferred as a raw material in the development of new compounds in laboratory settings.
| Application | Description |
|---|---|
| Agrochemical Synthesis | Pesticide and herbicide intermediates |
| Dyes and Pigments | Specialty dyestuff synthesis |
| Photographic Chemicals | Intermediate in photographic chemicals |
| Property | Description |
|---|---|
| Structural Class | Aromatic ketone, indanone derivative |
| Functional Groups | Ketone (-C=O), methyl groups |
| Aromatic Ring | Open to electrophilic substitution |
| Ketone Reactivity | Nucleophilic addition, condensation, reduction |
| Lipophilic Character | Increased due to methyl groups |
| Molecular Structure | Bicyclic system (benzene + cyclopentanone) |
| Polarity | Medium polarity |
The indanone skeleton gives the compound both aromatic and ketone reactivity. The methyl groups increase lipophilic character and influence molecular interactions.
| Application | Description |
|---|---|
| Condensation Reactions | Aldol, Knoevenagel, and Claisen-Schmidt reactions |
| Grignard Reaction | Addition of organomagnesium to the ketone group |
| Reduction | Reduction to alcohol (NaBH₄, LiAlH₄) |
| Oxidation | Oxidation of the ketone group |
| Electrophilic Substitution | Nitration, sulfonation, halogenation on the aromatic ring |
| Functionalization | Modification of methyl groups |
| Parameter | Value |
|---|---|
| GHS Classification | Generally not classified as a hazardous substance; however, good laboratory practices are required |
| Oral LD50 (Rat) | > 2000 mg/kg (estimated) |
| Dermal LD50 (Rabbit) | > 2000 mg/kg (estimated) |
| Skin Irritation | May be mildly irritating |
| Eye Irritation | May be mildly irritating |
| Respiratory Irritation | Dust/vapor inhalation may cause discomfort |
| Skin Sensitization | Not expected |
| Mutagenicity | Not classified |
| Carcinogenicity | Not classified |
| Bioaccumulation | Not likely |
| WGK Germany | 1 (slightly hazardous to water) |
The compound is generally classified as a laboratory chemical. It may not have a standard GHS classification; however, due to general organic ketone properties, it may cause eye and skin irritation, may be harmful if swallowed, and its vapors may cause discomfort if inhaled.
| Parameter | Information |
|---|---|
| UN Number | Not applicable (not a hazardous substance) |
| Hazard Class | Not a hazardous substance |
| Packing Group | Not applicable |
| Proper Shipping Name | 2,6-Dimethyl-1-indanone |
| Marine Pollutant | No |
| ADR/RID Label | Not applicable |
The compound must be transported in accordance with general ADR/RID rules for organic chemicals. It is not classified as a hazardous substance.
| Region | Status |
|---|---|
| EU | REACH registered |
| USA (TSCA) | Listed |
| EINECS | 266-351-9 |
| Turkey (KKDİK) | Should be evaluated within compliance and registration requirements |
| Food Contact | Not suitable for technical grade |
| Hazardous Substance | No |
| Parameter | Information |
|---|---|
| Storage Conditions | Store in a cool, dry, and well-ventilated area |
| Temperature | 15–25 °C |
| Container Requirements | Tightly closed containers |
| Moisture Control | Dry environment; protect from moisture |
| Substances to Avoid | Strong oxidizing agents, strong acids, strong bases, heat sources |
| Shelf Life | 24 months (under proper storage) |
| Handling Notes | Avoid breathing dust; use PPE |
| Packaging Options | 25 kg fiber drum, 50 kg drum; custom packaging upon request |
Handling Notes:
Avoid dust formation.
Use appropriate personal protective equipment (gloves, goggles, laboratory coat).
Avoid contact with skin and eyes.
Keep away from heat sources.
| Parameter | Information |
|---|---|
| Fire Hazard | Combustible solid; may burn at high temperatures |
| Flash Point | >110 °C (closed cup, estimated) |
| Extinguishing Media | Foam, CO₂, dry chemical, water spray |
| Special Hazards | Combustion may release carbon monoxide and carbon dioxide |
| Protective Equipment | Self-contained breathing apparatus (SCBA), full protective clothing |
In case of fire, appropriate extinguishing media should be used, and firefighting personnel should wear protective equipment.
| Parameter | Information |
|---|---|
| Personal Protection | Dust mask, protective goggles, gloves, laboratory coat |
| Ventilation | Ventilate the area |
| Containment | Contain the spill |
| Cleaning Methods | Carefully sweep or vacuum; place in suitable disposal container |
| Environmental Precautions | Prevent entry into drains, sewers, and water sources |
| Waste Disposal | Dispose of according to local regulations |
In case of a spill, clean up while preventing dust formation. Dispose of waste properly. Prevent environmental release.
| Exposure Route | Action |
|---|---|
| Inhalation | Move to fresh air; seek medical attention if symptoms persist |
| Skin Contact | Wash with plenty of water and soap |
| Eye Contact | Rinse with water for at least 15 minutes |
| Ingestion | Rinse mouth, seek medical attention |
| Raw Material | Description |
|---|---|
| Indanone | Precursor in synthesis |
| Methylating agents | For the addition of methyl groups |
| Catalysts | Used in synthesis reactions |
| Solvents | For reaction medium |
| By-Product | Application |
|---|---|
| Indanone Derivatives | Pharmaceutical and biologically active molecules |
| Pharmaceutical Intermediates | Drug synthesis |
| Aromatic Compounds | Dyes, pigments, fine chemicals |
| Alcohols | Reduction products |
| Industry | Application Area | Example Use | Suitability |
|---|---|---|---|
| Pharmaceutical | Intermediate | Drug synthesis | High |
| Fine Chemicals | Intermediate | Specialty chemicals | High |
| Research | Laboratory synthesis | New compound development | High |
| Agrochemical | Intermediate | Pesticide synthesis | Suitable |
| Dyes and Pigments | Intermediate | Dyestuff synthesis | Suitable |
| Photographic Chemicals | Intermediate | Photographic chemicals | Limited |
The compound can undergo many chemical reactions due to its ketone and aromatic ring:
| Reaction | Description |
|---|---|
| Nucleophilic Addition | Grignard, hydride reduction |
| Condensation | Aldol, Knoevenagel, Claisen-Schmidt |
| Reduction | Reduction to alcohol (NaBH₄, LiAlH₄) |
| Oxidation | Oxidation of the ketone group |
| Electrophilic Substitution | Nitration, sulfonation, halogenation |
| Methyl Functionalization | Modification of methyl groups |
The compound derivatives are widely used in pharmaceutical, fine chemical, and research applications.
| Compound | Description |
|---|---|
| 2,6-Dimethylindanol | Reduction product; alcohol |
| 2,6-Dimethylindanone Oxime | Oxime derivative |
| 2,6-Dimethylindanone Hydrazone | Hydrazone derivative |
| 1-Indanone | Parent skeleton; indanone |
| 2-Methyl-1-indanone | Similar structure; single methyl group |
| 6-Methyl-1-indanone | Similar structure; single methyl group |
SUMMARY:
2,6-Dimethyl-1-indanone is a light yellow crystalline solid with the formula C₁₁H₁₂O and CAS number 66309-83-9. It is an aromatic ketone with an indanone skeleton. It is used as an intermediate in organic syntheses, particularly in pharmaceutical and fine chemical applications. It is used in aromatic compound synthesis, in the production of indanone derivatives and biologically active molecules. It is preferred as a raw material in research laboratory syntheses. It is soluble in organic solvents and has low solubility in water. It is generally not classified as a hazardous substance; however, good laboratory practices are required. It should be stored in a cool, dry, and well-ventilated area in tightly closed containers.
Key Properties:
| Property | Value |
|---|---|
| Appearance | Light yellow crystalline solid |
| Chemical Formula | C₁₁H₁₂O |
| Molecular Weight | 160.22 g/mol |
| CAS Number | 66309-83-9 |
| Melting Point | 65–70 °C |
| Boiling Point | ~280 °C |
| Density | ~1.0 g/cm³ |
| Solubility | Soluble in organic solvents; low in water |
| Chemical Class | Aromatic ketone, indanone derivative |
| Primary Use | Pharmaceutical and fine chemical intermediate |
Main Applications:
| Industry | Applications |
|---|---|
| Pharmaceutical | Intermediate, drug synthesis |
| Fine Chemicals | Specialty chemicals, aromatic compounds |
| Research | Laboratory synthesis, new compound development |
| Agrochemical | Pesticide intermediates |
| Dyes and Pigments | Dyestuff synthesis |
| Photographic Chemicals | Photographic chemicals |
Key Safety Points:
LOW TOXICITY: Generally not a hazardous substance; LD50 > 2000 mg/kg (estimated)
MILD IRRITATION: May cause mild irritation to eyes and skin
DUST CONTROL: Inhalation of dust should be avoided
STORAGE: 15–25 °C, cool, dry, well-ventilated
PPE RECOMMENDED: Gloves, protective goggles, laboratory coat
INCOMPATIBLE: Strong oxidizing agents, strong acids, strong bases
CRITICAL WARNINGS:
The compound is an aromatic ketone with an indanone skeleton. It shows ketone and aromatic ring reactivity.
It is used as an intermediate in pharmaceutical and fine chemical applications.
It is a building block in the synthesis of indanone derivatives and biologically active molecules.
It is soluble in organic solvents; it has low solubility in water.
It is generally not classified as a hazardous substance; however, good laboratory practices are required.
It may cause mild irritation on contact with eyes and skin; contact should be avoided.
Dust inhalation may cause discomfort; good ventilation should be provided.
It is a combustible solid; it should be kept away from heat sources.
It should be protected from moisture; store in tightly closed containers.
Important Statement: This Technical Data Sheet (TDS) is for informational purposes only. The information provided is based on available data and is believed to be accurate. However, the user is solely responsible for determining the suitability of the product for their own specific applications and for complying with all applicable regulations and safety requirements. For complete safety, use, storage, and regulatory compliance information, always refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Users are obligated to test the product in their own processes and applications. All local, national, and international regulations must be followed when working with 2,6-Dimethyl-1-indanone.