Mesityl oxide CAS 141-79-7
Introduction：Basic information about Mesityl oxide CAS 141-79-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Mesityl oxide Basic informationDescription References
| Product Name: | Mesityl oxide |
| Synonyms: | The propyl acetone;Mesityloxide 0;Cilastatin Impurity D (Mesityl Oxide);Mesityl oxide technical grade, 90%;Isopropylideneacetone4-Methyl-3-penten-2-one;4-Methyl-3-penten-2-one, 9CI;Cilastatin sodium impurity D;Mesity oxide |
| CAS: | 141-79-7 |
| MF: | C6H10O |
| MW: | 98.14 |
| EINECS: | 205-502-5 |
| Product Categories: | Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Acetone series |
| Mol File: | 141-79-7.mol |
Mesityl oxide Chemical Properties
| Melting point | −53 °C(lit.) |
| Boiling point | 129 °C(lit.) |
| density | 0.858 g/mL at 25 °C(lit.) |
| vapor pressure | 10.5 hPa (20 °C) |
| refractive index | n |
| FEMA | 3368 | 4-METHYL-3-PENTEN-2-ONE |
| Fp | 87 °F |
| storage temp. | Store below +30°C. |
| solubility | 30g/l |
| form | Liquid, Free Of Suspended Matter |
| color | Clear |
| Specific Gravity | 0.86 |
| Odor | Strong; peppermint; honeylike. |
| Odor Type | vegetable |
| biological source | synthetic |
| explosive limit | 1.4-10.1%(V) |
| Water Solubility | 28 G/L (20 ºC) |
| Merck | 14,5908 |
| JECFA Number | 1131 |
| BRN | 1361550 |
| Henry's Law Constant | (x 10-6 atm?m3/mol):4.01 at 20 °C (approximate - calculated from water solubility and vapor pressure) |
| Exposure limits | TLV-TWA 60 mg/m3 (15 ppm) (ACGIH),10-h TWA 40 mg/m3 (10 ppm) (NIOSH);STEL 100 mg/m3 (25 ppm); IDLH 5000ppm. |
| Dielectric constant | 15.4（20℃） |
| Stability: | Light Sensitive |
| Major Application | flavors and fragrances |
| Cosmetics Ingredients Functions | PERFUMING |
| InChI | 1S/C6H10O/c1-5(2)4-6(3)7/h4H,1-3H3 |
| InChIKey | SHOJXDKTYKFBRD-UHFFFAOYSA-N |
| SMILES | C\C(C)=C\C(C)=O |
| LogP | 1.37 at 20℃ |
| CAS DataBase Reference | 141-79-7(CAS DataBase Reference) |
| NIST Chemistry Reference | 3-Penten-2-one, 4-methyl-(141-79-7) |
| EPA Substance Registry System | Mesityl oxide (141-79-7) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 10-20/21/22-36/37/38 |
| Safety Statements | 25 |
| RIDADR | UN 1229 3/PG 3 |
| OEB | A |
| OEL | TWA: 10 ppm (40 mg/m3) |
| WGK Germany | 1 |
| RTECS | SB4200000 |
| Autoignition Temperature | 344 °C |
| TSCA | TSCA listed |
| HS Code | 2914 19 90 |
| HazardClass | 3 |
| PackingGroup | III |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 3 Inhalation Acute Tox. 4 Dermal Acute Tox. 4 Oral Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 STOT SE 3 |
| Hazardous Substances Data | 141-79-7(Hazardous Substances Data) |
| Toxicity | LD50 in mice (mg/kg): 710 ±85 intragastric; LC50 in mice (2 hr), rats (4 hr) (mg/m3): 10000 ±270, 9000 ±600 (Ismerov) |
| IDLA | 1,400 ppm [10% LEL] |
| Description | Mesity oxide(141-79-7) is a tri-functional intermediate of considerable utility in the synthesis of a number of different types of organic compounds, such as mesityl oxide can be hydrogenated to methyl isobutyl ketone and other flavor ingredients in foods, such as 4- methyl-pentanone. Mesityl oxide can be used as a solvent for resins, gums, nitrocellulose, oils, lacquers, and inks. It is also used as an insect repellant and used in ore flotation. |
| References | [1] Pradyot Patnaik, A Comprehensive Guide to the Hazardous Properties of Chemical Substances, 3rd Edition, 2007 [2] Klaus Weissermel, and Hans-Jürgen Arpe, Industrial Organic Chemistry, 3rd Edition, 1997 [3] George A. Burdock, Fenaroli’s Handbook of Flavor Ingredients, 4th Edition, 2001 |
| Description | The commercial grade of 4-methyl-3-penten-2-one exhibits an unpleasant grassy-green or pungent, acrylic odor. The pure material has a pleasant, honey-like odor. This substance may be prepared by reacting acetone or diacetone alcohol with iodine or other dehydrating agent; by condensation of acetone over sulfonated polystyrene-divinylbenzene resin used as an ion exchange catalyst. |
| Chemical Properties | Mesityl oxide is a clear, pale yellow, or colorless liquid with a strong peppermint odor. The odor threshold is 0.05 ppm. |
| Physical properties | Clear, pale yellow liquid with a strong, peppermint, or honey-like odor. Experimentallydetermined detection and recognition odor threshold concentrations were 70 μg/m3 (17 ppbv) and200 μg/m3 (50 ppbv), respectively (Hellman and Small, 1974). |
| Occurrence | Reported found in orange juice, baked potato, bell pepper, sauerkraut, tomato, crisp bread, parmesan cheese,milk, chicken fat, hop oil, rum, coffee, tea, peanut, passion fruit, mushroom, tamarind, prickly pear, buckwheat, basil, elder flower,rosemary, shrimp, nectarine, clam and maté |
| Uses | 4-Methyl-4-penten-2-one is used to asmall extent as an intermediate in synthesis. Mostof it is converted to 4-methyl-2-pentanone byselective hydrogenation. Although 4-methyl-2-pentanone has excellent solvent properties fornitrocellulose, cellulose esters and ethers, copolymers of vinyl chloride – vinyl acetate andother synthetic resins, as well as natural andsynthetic rubber, its use as a solvent is limitedas a result of its toxicity and chemical instability.The fraction of 4-methyl-4-penten-2-one permitted in solvent systems has been set at 5 vol%(Rule 66 of the Los Angeles, California, AirPollution Control District).Some of the numerous possible reactions thatmesityl oxide may undergo have been used forthe synthesis of products such as Budralazine, anantihypertensive agent. |
| Uses | Solvent for nitrocellulose, many gums and resins, particularly vinyl resins. In lacquers, varnishes and enamels. In making methyl isobutyl ketone. |
| Preparation | 4-Methyl-4-penten-2-one is the precursor of methyl isobutyl ketone (see Section 2.2) and can be produced from acetone in a single- or a two-step process . Pure mesityl oxide is obtained by azeotropic distillation of the crude watercontaining product. Subsequent purification by removal of the accompanying impurities, such as mesitylene and phorone [504-20-1], is effected by distillation. |
| Definition | ChEBI: 4-Methyl-3-penten-2-one, 9CI is an olefinic compound. It is functionally related to an acrylic acid. |
| Synthesis Reference(s) | Tetrahedron Letters, 27, p. 3733, 1986 DOI: 10.1016/S0040-4039(00)83866-6 |
| General Description | Mesityl oxide appears as a colorless, oily liquid with a pungent honey-like odor. Flash point 87 °F. Less dense than water and slightly soluble in water. Vapors heavier than air. Used in paint removers, as a solvent for plastics, and as an insect repellent. |
| Air & Water Reactions | Highly flammable. Slightly soluble in water |
| Reactivity Profile | Mixing MESITYL OXIDE in equal molar proportions with any of the following substances in a closed container caused the temperature and pressure to increase: 2-aminoethanol, chlorosulfonic acid, ethylene diamine, nitric acid, oleum, or sulfuric acid [NFPA 1991]. |
| Hazard | Flammable, moderate fire risk. Toxic byingestion, inhalation, and skin absorption. Eye andupper respiratory tract irritant, central nervous system impairment. |
| Health Hazard | Inhalation causes irritation of nose and throat, headache, dizziness, difficult breathing. Contact with liquid or concentrated vapor causes severe eye irritation. Liquid irritates skin. Ingestion causes irritation of mouth and stomach. |
| Health Hazard | Mesityl oxide is a moderately toxic substance, more toxic than the saturated ketones.Inhalation of its vapors can cause irritationto the eyes, skin, and mucous membranes. Inhumans, the irritation effect on the eyes andnose are reported to be 25 and 50 ppm. Athigh concentrations narcosis can result. Otherthan narcosis, prolonged exposure to highconcentrations can injure the lungs, liver, and kidney. A concentration of 2500 ppm waslethal to rats. LD50 value, oral (rats): 1120 mg/kg. |
| Fire Hazard | Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. |
| Safety Profile | Poison by intraperitoneal route. Moderately toxic by ingestion. Mildly toxic by inhalation and skin contact. Human systemic effects by inhalation: conjunctiva irritation. This compound is highly irritating to all tissues on contact; its vapors also are irritating. High concentrations are narcotic. It is readdy absorbed through intact skin. Single exposures tend to indicate that ths ketone has greater acute and narcotic action than isophorone. It can have harmful effects upon the hdneys and liver, and may damage the eyes and lungs to a serious degree. Prolonged exposure can injure liver, kidneys, and lungs. It can cause opaque cornea, keratoconus, and extensive necrosis of cornea. Dangerous fire hazard when exposed to heat, sparks, or flame; can react with oxidzing materials. Reacts violently with 2-amino ethanol, chlorosulfonic acid, ethylene diamine, HNO3, oleum, H2SO4. An insect repellent. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES. |
| Potential Exposure | Mesityl oxide is used as a solvent forcellulose esters and ethers and other resins in lacquers andinks. It is used in paint and varnish removers and as aninsect repellent |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove fromexposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. |
| storage | Color Code—Red: Flammability Hazard: Store in a flammable liquid storage area or approved cabinet away from ignition sources and corrosive and reactive materials. Mesityl oxide 1715 Prior to working with this chemical you should be trained on its proper handling and storage. Before entering confined space where this chemical may be present, check to make sure that an explosive concentration does not exist. Store in tightly closed containers in a cool, well-ventilated area away from oxidizers, strong acids. See incompatibilities above. Where possible, automatically pump liquid from drums or other storage containers to process containers. |
| Shipping | UN1229 Mesitly oxide, Hazard Class: 3; Labels:3-Flammable liquid. |
| Purification Methods | Purify it by distillation, preferably in a vacuum or via the semicarbazone (m 165o) which is decomposed to pure ketone. The 2,4-dinitrophenylhydrazone (m 205-206o) crystallises from EtOH. [Johnson J Am Chem Soc 73 5888 1951, Johnson J Am Chem Soc 75 2720 1953, Erskine & Waight J Chem Soc 3425 1960, Beilstein 1 H 736, 1 I 382, 1 II 793, 1 III 2995, 1 IV 3471.] |
| Incompatibilities | May form explosive mixture with air.May be able to form explosive peroxides. May reactviolently with nitric acid; aliphatic amines; alkanolamines, 2-aminoethanol, ethylene diamine; chlorosulfonic acid; oleum(fuming sulfuric acid). Not compatible with oxidizers, strongacids; strong bases; reducing agents; halogens. Dissolvessome forms of plastics, resins and rubber. Attacks copper. |
| Toxics Screening Level | The initial threshold screening level for mesityl oxide is 400 μg/m3 based on an 8-hour averaging time. |
| Waste Disposal | Dissolve or mix the materialwith a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,state, and local environmental regulations must be observed. |
Mesityl oxide Preparation Products And Raw materials
| Raw materials | Diacetone Alcohol-->2,6-Dimethyl-4-heptanone-->4-Methyl-3-penten-2-one oxime-->2-Pentanone, 4-chloro-4-methyl--->3,4-epoxy-4-methylpentan-2-one-->2-Heptanone, 4-hydroxy--->4-Methyl-4-(methylnitrosoamino)-2-pentanone-->4-METHYL-3-PENTEN-2-OL-->Ethoxyquin-->Phenetidine-->Cyclopropane, 2-bromo-1,1-dimethyl-3-methylene- |
| Preparation Products | ADS-->4,4-DIMETHYL-2-PENTANONE-->Delta Damascone-->Damascenone-->4-AMINO-4-METHYL-2-PENTANONE HYDROGENOXALATE-->2,2,3,3-tetramethylhexane-->2,2,4,4,6-pentamethyl-hexahydropyrimidine-->7-Quinolinol, 1-ethyl-1,2-dihydro-2,2,4-trimethyl- |
