HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pinacolone
3,3-DIMETHYLBUTAN-2-ONE · 3,3-DIMETHYL-2-BUTANONE · PINACOLIN · 2,2-Dimethyl-3-butanone · TERT-BUTYL METHYL KETONE · t-Butyl methyl ketone · Methyl t-butyl ketone · Pinakolin
Identifiers & Physical Properties
| CAS No. | 75-97-8 |
|---|---|
| Molecular formula | C6H12O |
| Average molar mass | 100.16 g/mol |
| Monoisotopic mass | 100.088815 g/mol |
| SMILES | CC(=O)C(C)(C)C |
| InChIKey | PJGSXYOJTGTZAV-UHFFFAOYSA-N |
| PubChem CID | 6416 |
| ChEMBL | CHEMBL3183565 |
| ChEBI | CHEBI:197349 |
| EC No. | 200-920-4 |
| DTXSID | DTXSID5021752 |
Chemical & Physical Properties
| XLogP | 1.2 |
|---|---|
| Topological polar surface area | 17.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 1 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 76.7 |
| Chemical classes | Other Classes -> Aliphatic Ketones, Other |
| SpringerMaterials Properties | Boiling point |
| LogP (partition coefficient) | log Kow = 1.20 |
| Odor | Peppermint or camphor-like odorethereal-minty-camphoraceous,warm-sweet odor |
| Density | 0.7229 at 25 °C/25 °C0.7229 @25 °C0.801 g/mL at 25 °C(lit.) |
| Viscosity | 2.47X10-03 Pa-sec at melting point |
| Color/Form | Colorless liquid |
| Solubility | Soluble in ethanol, ether, acetone, carbon tetrachlorideSol in water (2.44% at 15 °C)soluble in alcohol, ether, acetoneIn water, 1.9X10+4 mg/L at 25 °C19g/l2.44 g/100 mL (15 ºC) |
| Flash point | 23 °C5 °C (41 °F) - closed cup75 °F |
| Boiling point | 106.1 °C106.1 °C @760 [mm Hg]106 °C(lit.) |
| Melting point | -52.5 °C |
| Vapor pressure | 31.5 [mmHg]31.5 mm Hg at 25 °C31.5 [mm Hg] @25 °C33 hPa ( 20 °C) |
| Refractive index | n20/D 1.396(lit.) |
| Storage conditions | Flammables area |
| Physical state | Liquid |
| Color | Clear colorless to light yellow |
| Odor threshold | 0.043ppm |
| Merck | 14,7440 |
| BRN | 1209331 |
| Henry's law constant | 4.3×10-2 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielectric constant | 12.8(17℃) |
| Stability | Stable. Incompatible with strong oxidizing agents. Flammable. |
| InChI | 1S/C6H12O/c1-5(7)6(2,3)4/h1-4H3 |
| InChIKey | PJGSXYOJTGTZAV-UHFFFAOYSA-N |
| SMILES | O=C(C(C)(C)C)C |
| CAS DataBase Reference | 75-97-8(CAS DataBase Reference) |
| FDA UNII | 3U1AAG3528 |
| NIST Chemistry Reference | 2-Butanone, 3,3-dimethyl-(75-97-8) |
| EPA Substance Registry System | Pinacolone (75-97-8) |
| UNSPSC Code | 12352115 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS07 |
| Signal word | Warning |
| GHS hazard statements | H225-H302-H332-H412 |
| GHS precautionary statements | P210-P233-P240-P241-P242-P243-P280-P264-P270-P261-P271-P273-P303+P361+P353-P370+P378-P301+P312-P330-P304+P340-P312-P403+P235-P501 |
| Hazard symbols | F,Xn,Xi |
| Risk statements (R) | 11-22-10 |
| Safety statements (S) | 9-16-29-33-20/21 |
| UN transport number | UN 1224 3/PG 2 |
| Water hazard class (WGK) | 2 |
| RTECS number | EL7700000 |
| Hazard Note | Irritant/Highly Flammable |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Acute Tox. 4 OralFlam. Liq. 2 |
| Packing group | II |
| Customs code | 29141990 |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 75-97-8(Hazardous Substances Data) |
| REACH registrations | Active |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 3.6% (5 of 137) of reports.DangerH225 (68.6%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P330, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 137 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: 2-Butanone, 3,3-dimethyl-Status: Active Update: 11-01-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/27273 |
| Fire potential | Highly flammable liquid and vapor. |
| Hazards summary | An irritant[MSDSonline] See 2-Butanone. |
| DOT Emergency Guidelines | /GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water./GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution./GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering./GUIDE 127: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.For more DOT Emergency Guidelines (Complete) data for 3,3-DIMETHYL-2-BUTANONE (8 total), please visit the HSDB record page. |
| Hazard Classes and Categories | Flam. Liq. 2 (68.6%)Flammable liquids - Category 2 |
| State drinking water guidelines | (FL) FLORIDA 210 ug/L |
| Explosive Limits and Potential | Vapors may form explosive mixture with air. |
| Critical Temperature and Pressure | Critical temp = 564 KCritical pressure = 3.32E+06 Pa |
| Fire fighting procedures | Use water spray to cool unopened containers.Wear self contained breathing apparatus for fire fighting if necessary.For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spraysolid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. |
| Storage conditions | Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Store in cool place. |
| Cleanup methods | Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. |
| Disposal methods | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. |
| Preventive Measures | Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Use explosion-proof equipment. Keep away from sources of ignition. No smoking. Take measures to prevent the build up of electrostatic charge.ACCIDENTAL RELEASE MEASURES Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. |
| Protective Action Criteria (PAC) | 1.8 [mg/m3]20 [mg/m3]120 [mg/m3] |
| Personal Protective Equipment (PPE) | Complete suit protecting against chemicals, Flame retardant antistatic protective clothing, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). |
| Body burden | In an analysis of expired human air collected from 28 normal, healthy, non-smoking humans, 3,3-dimethyl-2-butanone was detected at concns ranging from approximately 0.12 to 2 ng/L of expired air(1)positive identifactions of 3,3-dimethyl-2-butanone were made in approximately 10% of all samples. In a similar study of 54 humans (387 expired air samples collected), 3,3-dimethyl-2-butanone was detected in 8.3% of all samples with a mean concn of 0.184 ng/L(2). |
| Ecotoxicity values | LC50 Pimephales promelas (fathead minnow) 87 mg/L/96 hr flow-through bioassay, wt 0.12 g, water hardness 45.5 mg/L CaCO3, temp: 25 + or - 1 °C, pH 7.5, dissolved oxygen greater than 60% of saturation |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 110(SRC), determined from a log Kow of 1.2(2) and a regression-derived equation(3), indicates that 3,3-dimethyl-2-butanone is expected to have high mobility in soil(SRC). Volatilization of 3,3-dimethyl-2-butanone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 31.5 mm Hg(4), and water solubility, 19,000 mg/L(5). 3,3-Dimethyl-2-butanone is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data were not available(SRC, 2007).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 110(SRC), determined from a log Kow of 1.2(2) and a regression-derived equation(3), indicates that 3,3-dimethyl-2-butanone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.2X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 31.5 mm Hg(4), and water solubility, 19,000 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7 hours and 5.2 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 2(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,3-dimethyl-2-butanone, which has a vapor pressure of 31.5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,3-dimethyl-2-butanone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 14 days(SRC), calculated from its rate constant of 1.21X10-12 cu cm/molecule-sec at 25 °C(3). 3,3-Dimethyl-2-butanone contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(4). |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Effluent Concentrations | In an analysis of 63 chemical manufacturing effluent discharges collected from across the US, 3,3-dimethyl-2-butanone was detected in one effluent at a concn of <10 ug/L(1). It has been reported that 3,3-dimethyl-2-butanone can be released to the atmosphere through auto emissions and solvents(2). |
| Soil Adsorption/Mobility | The Koc of 3,3-dimethyl-2-butanone is estimated as 110(SRC), using a log Kow of 1.2(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3,3-dimethyl-2-butanone is expected to have high mobility in soil. |
| Natural Pollution Sources | 3,3-Dimethyl-2-butanone has been detected in expired human air (breath) collected from healthy, non-smoking humans(1,2). |
| Artificial Pollution Sources | 3,3-Dimethyl-2-butanone's production and use as an intermediate in the production of fungicides and herbicides(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Bioconcentration | An estimated BCF of 2 was calculated in fish for 3,3-dimethyl-2-butanone(SRC), using a log Kow of 1.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 3,3-dimethyl-2-butanone is estimated as 2.2X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 31.5 mm Hg(1), and water solubility, 19,000 mg/L(2). This Henry's Law constant indicates that 3,3-dimethyl-2-butanone is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 7 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 5.2 days(SRC). 3,3-Dimethyl-2-butanone's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 3,3-dimethyl-2-butanone from dry soil surfaces may exist(SRC) based upon its vapor pressure(1). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Sprague-Dawley rats were given 15, 70 and 140 min exposures to 15 mg/L 3,3-dimethyl-2-butanol, pinacolyl alcohol (PA), or 6-hour exposures to 0.2, 1.0 and 5.0 mg/L PA (1 mg/L = 240 ppm). A 50% mortality rate was obtained at the longest exposure to 15 mg/L. Sex related differences in the blood levels of PA and pinacolone were noted, and the surviving male rats failed to gain weight normally in the first week after exposure. In rats exposed to 5.0 mg/L for 6 hours, there were reductions in horizontal and vertical activity and the minute volume was 55% of controls at the end of exposure. Like many secondary alcohols, PA poses only a possible inhalation hazardhowever, male rats may be somewhat more susceptible than females. /Pinacolyl alcohol//ALTERNATIVE and IN VITRO TESTS/ Following the pretreatment of guinea pigs with 90% LD50 soman, enhancement of microsomal esterase activity was noted 12 and 24 hr after pretreatment. Using Michaelis-Menten enzyme kinetic studies, enhancement was found to occur with liver carboxylesterase and procaine esterase, but not with aniline hydroxylase. Since the soman-enzyme complex was known to undergo aging with the release of pinacolyl alcohol and the subsequent formation of pinacolone, the effects of these metabolites on the activity of liver microsomal enzymes in vitro were explored. Pinacolone and pinacolyl alcohol produced enzyme enhancement in vitro in a manner similar to that produced by soman pretreatment. These effects were compared with those made by acetone in the same incubations, since the enhancing influence of acetone has already been well documented. Similarity was found between the in vitro effects of acetone and the effects of pinacolone and pinacolyl alcohol. Lastly, the in vivo effects of pinacolone on the activities of the same liver microsomal enzymes were studied following pretreatment of the guinea pigs with 90% LDLo (lowest published lethal dose) pinacolone. Pretreating guinea pigs with pinacolone prior to killing them enhanced liver microsomal carboxylesterase and procaine esterase activities, but had no effect on microsomal aniline hydroxylase activity. This pattern of enzyme enhancement was similar to that observed after soman pretreatment. Therefore, soman was found to enhance hepatic microsomal esterase activity in the guinea pig in a manner similar to that seen with its metabolites, as well as acetone. ... |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 3,3-dimethyl-2-butanone with photochemically-produced hydroxyl radicals has been measured as 1.21X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 14 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 3,3-Dimethyl-2-butanone is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 3,3-Dimethyl-2-butanone contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight(2). |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | EL7700000 |
| UN transport number | UN 1224 3/PG 2 |
| Customs code | 29141990 |
| Risk statements (R) | 11-22-10 |
| Signal word | Warning |
| GHS pictogram | GHS02,GHS07 |
| Hazard symbols | F,Xn,Xi |
| hazard_note | Irritant/Highly Flammable |
| Safety statements (S) | 9-16-29-33-20/21 |
| Hazard class | 3Acute Tox. 4 OralFlam. Liq. 2 |
| Storage class | 3 - Flammable liquids |
| Packing group | II |
| GHS hazard statements | H225-H302-H332-H412 |
| Limited quantities | 1.0 L (0.3 gallon) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| GHS precautionary statements | P210-P233-P240-P241-P242-P243-P280-P264-P270-P261-P271-P273-P303+P361+P353-P370+P378-P301+P312-P330-P304+P340-P312-P403+P235-P501 |
| Hazardous substances data | 75-97-8(Hazardous Substances Data) |
Applications & Uses
Uses
Pinacolone is a precursor to triazolylpinacolone, triadimefon, paclobutrazol, uniconazole and metribuzin. Furthermore, it acts as an intermediate for biologically active products such as antibacterial, antifungal, antiviral and antituberculous products. It is an important ketone in organic chemistry and participates in condensation, hydrogenation and reductive amination reactions.
Preparation & Synthesis
Preparation
Pinacolone is prepared by distillation of Pinacolhydrate with diluted Sulfuric acid.