2,3-Butanediol
BUTANE-2,3-DIOL · Dimethylethylene glycol · 2,3-Butandiol · 2,3-BUTYLENE GLYCOL · OMEGA-BUTYLENE GLYCOL · 2,3-Butanediol, 98%, mixture of racemic and meso forms, tech. · 2,3-Butaneiol · 2,3-butanodiol
Identifiers & Physical Properties
| CAS No. | 35007-63-7 |
|---|---|
| Molecular formula | C4H10O2 |
| Average molar mass | 90.12 g/mol |
| Monoisotopic mass | 90.06807956 g/mol |
| SMILES | CC(O)C(C)O |
| InChIKey | OWBTYPJTUOEWEK-UHFFFAOYSA-N |
| PubChem CID | 262 |
| ChEMBL | CHEMBL2312529 |
| ChEBI | CHEBI:62064 |
| EC No. | 208-173-6 |
| DTXSID | DTXSID8041321 |
Chemical & Physical Properties
| XLogP | -0.9 |
|---|---|
| Topological polar surface area | 40.5 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 6 |
| Formal charge | 0 |
| Complexity | 30 |
| LogP (partition coefficient) | log Kow = -0.92 |
| Odor | Odorlessat 0.10 % in dipropylene glycol. fruity creamy buttery |
| Taste | Sweet taste |
| Density | 1.045 at 20 °C/20 °C1.002 g/mL at 20 °C (lit.) |
| Viscosity | 0.121 sq m/sec at 25 °C |
| Color/Form | Nearly colorless, crystalline solid or liquid |
| Solubility | In water, miscible at 20 °CMiscible with waterEasily soluble in low molecular mass alcohols and ketones.Soluble in alcohol, ether1000 mg/mL at 20 °CChloroform, Methanol |
| Flash point | 85 °C85 °C (185 °F) - closed cup185 °F - open cup |
| Boiling point | BP: 182 °C at 1 atm182.00 °C. @ 760.00 mm Hg183-184 °C (lit.) |
| Decomposition | Hazardous decomposition products formed under fire conditions - Carbon oxides.When heated to decomposition it emits acrid smoke and fumes. |
| Melting point | 19 °C25 °C25 °C (lit.) |
| Vapor density | 3.1 (Air = 1) |
| Vapor pressure | <1 hPa (20 °C) |
| Refractive index | n20/D 1.433(lit.) |
| FLAVIS Number | 02.133 | Butane-2,3-diol |
| Storage conditions | Store below +30°C. |
| pKa (acidity coefficient) | 14.67±0.20(Predicted) |
| Physical state | Viscous Liquid |
| Color | Colorless to pale yellow |
| pH | 7 (H2O, 20℃)Aqueous solution |
| Explosive limits | 3.1-11.4%(V) |
| Odor type | creamy |
| Specific heat capacity | Cp(liquid): 2.36 J/(g·K), at 25℃ |
| Sensitivity | Hygroscopic |
| Merck | 14,1568 |
| BRN | 969165 |
| Henry's law constant | 1.1×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, acid anhydrides, acid chlorides, chloroformates, reducing agents. |
| Cosmetics Ingredients Functions | HUMECTANTSOLVENTSKIN CONDITIONINGFRAGRANCE |
| Cosmetic Ingredient Review (CIR) | 2,3-Butanediol (513-85-9) |
| InChI | 1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3 |
| InChIKey | OWBTYPJTUOEWEK-UHFFFAOYSA-N |
| SMILES | CC(O)C(C)O |
| LogP (partition coefficient) | -0.92 at 25℃ |
| CAS DataBase Reference | 513-85-9(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 45427ZB5IJ |
| NIST Chemistry Reference | 2,3-Butanediol(513-85-9) |
| EPA Substance Registry System | 2,3-Butanediol (513-85-9) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H227 |
| GHS precautionary statements | P210-P280-P403+P235-P501-P210e-P280a-P370+P378a-P501a |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Safety statements (S) | 24/25 |
| Water hazard class (WGK) | 1 |
| RTECS number | EK0532000 |
| Autoignition temperature | 395 °C DIN 51794 |
| TSCA inventory status | TSCA listed |
| Customs code | 29053980 |
| Storage class | 10 - Combustible liquids |
| Hazardous substances data | 513-85-9(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 94.5% (208 of 220) of all reports.Not ClassifiedReported as not meeting GHS hazard criteria by 208 of 220 companies (only 5.5% companies provided GHS information). For more detailed information, please visit ECHA C&L website.Aggregated GHS information provided per 220 reports by companies from 3 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 208 of 220 reports by companies.There are 2 notifications provided by 12 of 220 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.WarningH227: Combustible liquid [Warning Flammable liquids]P210, P280, P370+P378, P403, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatory information | Chemical: 2,3-ButanediolCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 15-08-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/100602,3-Butylene glycol: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Fire potential | Flammable when exposed to heat or flame. |
| Hazards summary | Emergency treatment: Glycols[HSDB] Intraperitoneal dose of 3920 mg/kg was lowest dose to produce ataxia in rats[RTECS] May cause irritation[MSDSonline] |
| EPA Safer Chemical | Chemical: 2,3-ButanediolGreen circle - The chemical has been verified to be of low concern based on experimental and modeled data. |
Applications & Uses
Description
2,3-Butanediol(23BD) is the organic compound with the formula (CH3CHOH). It is classified as a vic-diol (glycol). It exists as three stereoisomers, a chiral pair and the meso isomer. All are colorless liquids. Applications include precursors to various plastics and pesticides.2,3-Butanediol is a commodity chemical usually produced from oil. It can be used as a precursor in the manufacture of a range of chemical products, including the solvents methyl ethyl ketone (MEK), gamma-butyrolactone (GBL), and 1,3-butadiene.
Uses
2,3-Butanediol (2,3-BD) is a promising bulk chemical with a potentially wide range of applications e.g., in the manufacture of printing inks, perfumes, synthetic rubber, fumigants, antifreeze agents, fuel additives, foodstuffs and pharmaceuticals. Its high heating value and ability to increase the octane number of fuels make 2,3-BD a promising drop-in fuel. It can also be converted to methyl-ethyl ketone (MEK), which is considered an effective liquid fuel additive. After combination with MEK and hydrogenation reaction, 2,3-BD can be converted to octane, which is used to produce high-quality aviation fuel.
General Description
2,3-Butanediol is a chiral compound which is extensively utilized in chemical feedstocks and liquid fuels.
Preparation & Synthesis
Preparation
2,3-Butanediol is prepared by hydrolysis of 2,3-epoxybutane:(CH3CH)2O + H2O → CH3(CHOH)2CH3