Basic information
- Standard SMILES
CCOC(=O)C(C)C- InChIKey
WDAXFOBOLVPGLV-UHFFFAOYSA-N- Molecular formula
- C6H12O2
- Average molar mass
- 116.16 g/mol
- Monoisotopic mass
- 116.08372962
Overview
Ethyl isobutyrate appears as a colorless volatile liquid with a fruity, aromatic odor. Less dense than water and insoluble in water. Vapors heavier than air. May irritate skin and eyes. Used to make flavoring extracts and other chemicals.
Names & identifiers
- Preferred name
- Ethyl isobutyrate
- IUPAC
- ethyl 2-methylpropanoate
- English name
- Ethyl isobutyrate
- Molecular formula
- C6H12O2
- Molecular weight
- 116.16
Names & synonyms
ETHYL ISOBUTYRATE97-62-1Ethyl 2-methylpropanoateEthyl isobutanoatePropanoic acid, 2-methyl-, ethyl esterEthyl 2,2-dimethylacetateEthyl 2-methylpropionateIsobutyric acid, ethyl esterFEMA No. 24289A9661LN4HNSC-97194DTXSID7047728
Show more names
Ethyl methylpropanoateFEMA 2428Ethyl-2-methylproanoateEthylisobutyrat
CHEBI:87303RefChem:138960DTXCID6027717202-595-4Isobutyric acid ethyl esterEthylisobutyratePropionic acid, 2-methyl-, ethyl esterEthyl iso-butyrate
Database identifiers
- CAS
97-62-1- PubChem CID
- 7342
- DTXSID
DTXSID7047728- ChEMBL
CHEMBL295870- ChEBI
CHEBI:87303- UNII
- 9A9661LN4H
- EC Number
- 202-595-4
- Nikkaji
- J3.222K
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 76.6
Experimental & physicochemical properties
Chemical Classes
Other Classes -> Esters, Other
Flammable agents - 3rd degree
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710]
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Ethyl isobutyrate) -> IFRA transparency List
LogP1.55
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.862-0.868
Flavoring AgentsEU Flavoring substances
Solubility
very soluble in ether
1 ml in 1 ml 95% alcohol (in ethanol)
Flash Pointless than 70 °F (NFPA, 2010)
Boiling Point
112.00 to 113.00 °C. @ 760.00 mm Hg
112-113 °C
Melting Point-88.2 °C
Physicochemical properties
- Melting point
- -88 °C · -88°C
- Boiling point
- 112 · 112-113 °C (lit.)
- Density
- 0.865 g/mL · 0.865 g/mL at 25 °C (lit.)
- vapor density
- 4.01 · 4.01 (vs air)
- vapor pressure
- 40 mm · 40 mm Hg ( 33.8 °C)
- refractive index
- 20 · n20/D 1.387(lit.)
- FEMA
- 2428 · 2428 | ETHYL ISOBUTYRATE
- FLAVIS Number
- 9.413 · 09.413 | Ethyl isobutyrate
- Flash point
- 57 °F · 57 °F
- storage temp.
- Flammables area
- solubility
- alcohol: miscible(lit.)
- form
- Liquid
- color
- Clear colorless
- Odor
- 10 % · at 10.00 % in dipropylene glycol. sweet ethereal fruity alcoholic fusel rummy
- Odor Type
- fruity
- biological source
- synthetic
- Odor Threshold
- 0.000022 ppm · 0.000022ppm
- Water Solubility
- Not miscible or difficult to mix in water. Soluble in alcohol.
- Merck
- 14 · 14,3814
- JECFA Number
- 186 · 186
- BRN
- 773846 · 773846
- Henry's Law Constant
- 1.5 · 1.5×10-2 mol/(m3Pa) at 25℃, Brockbank (2013)
- Stability
- Volatile
- Major Application
- flavors and fragrances
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C6H12O2/c1-4-8-6(7)5(2)3/h5H,4H2,1-3H3
- InChIKey
- WDAXFOBOLVPGLV-UHFFFAOYSA-N
- SMILES
- CCOC(=O)C(C)C
- LogP
- 1.8 at · 1.8 at 22.9℃
- CAS DataBase Reference
- 97 · 97-62-1(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- ETHYL ISOBUTYRATE
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 9 A9661LN4H · 9A9661LN4H
- NIST Chemistry Reference
- 2 · Propanoic acid, 2-methyl-, ethyl ester(97-62-1)
- EPA Substance Registry System
- Ethyl isobutyrate (97-62-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 315 · H315-H225
- Precautionary statements
- 501 · P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P362+P364-P303+P361+P353-P332+P313-P403+P235
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-36/37/38
- Safety Statements
- 16 · 16-26-36-36/37/39
- RIDADR
- 2385 · UN 2385
- WGK Germany
- 2 · 2
- RTECS
- 4675000 · NQ4675000
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29156000 · 29156000
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 · Flam. Liq. 2
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (> 99.9%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1699 reports by companies from 10 notifications to the ECHA C&L Inventory.
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
Hazard information
Regulatory Information
Chemical: Propanoic acid, 2-methyl-, ethyl ester
Regulation (EC) No 1831/2003 (amended)
Status: Active Update: 29-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20388
Ethyl isobutyrate: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Other Safety InformationIMAP assessments - Propanoic acid, 2-methyl-, ethyl ester: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· May cause toxic effects if inhaled or absorbed through skin.
Hazards SummaryA moderate skin irritant; Intraperitoneal LD50 (mouse) = 800 mg/kg; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Alfa Aesar MSDS]
DOT ID and Guide2385 129
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity AlertsHighly Flammable
Reactivity Profile
An ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
DOT Hazard Classification
Ethyl isobutyrate
UN2385
Class 3 Flammable and combustible liquid (49 eCFR § 173.120)
PG II: the degree of danger presented by the material is medium
Air and Water ReactionsHighly flammable. Insoluble in water.
Safety & protection
Fire FightingExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
General First Aid:
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Nonfire Spill ResponseExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Isolation and Evacuation
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Immediate precautionary measure
Personal Protective Equipment (PPE)Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Emergency Response Planning GuidelinesCAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- NQ4675000
- ridadr
- UN 2385
- hs_code
- 29156000
- risk_code
- 11-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xi
- safety_code
- 16-26-36-36/37/39
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H315-H225
- 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
- Hazard Classifications
- Flam. Liq. 2
- Precautionary statements
- P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P362+P364-P303+P361+P353-P332+P313-P403+P235
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
Used to make flavoring compounds and essences; [Merck Index] Used as a flavoring agent; [FDA] Used to flavor animal feeds; [ExPub: EFSA - FEEDAP]
Farming (Feed Additives) [Category: Industry]
Household ProductsInformation on 2 consumer products that contain Ethyl Isobutyrate in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
General Manufacturing InformationPropanoic acid, 2-methyl-, ethyl ester: ACTIVE
Applications
UsesUsed as food essence and flavoring, mainly used in the preparation of cream and strawberry, cherry and other fruit essences. It can also be used as raw flavoring in cigarettes, daily chemical products and other products. At the same time, it is also an excellent organic solvent.
OccurrenceReported found in apple juice, banana, chocolate, cognac, Concord grape, honey, apricot, orange, pineapple, rum, strawberry, strawberry oil, watermelon, whiskey, champagne wine, grape wine, beer, port, passion fruit wine, sherry wine, orange juice, papaya, mango, kiwi fruit, quince, spineless monkey orange (Strychnos madagasc.), spearmint oil and Parmesan cheese.
UsesIt is employed to make flavoring compounds and essences, as a flavoring agent and to flavor animal feeds.
UsesEthyl Isobutyrate is a synthetic flavoring agent that is a stable, colorless liquid of dry, fruity odor. it should be stored in tin, glass, or resin-lined containers. it is used to give fruity effects to flavors for applications in candy, baked goods, and beverages at 10–100 ppm.
General DescriptionEthyl isobutyrate appears as a colorless volatile liquid with a fruity, aromatic odor. Less dense than water and insoluble in water. Vapors heavier than air. May irritate skin and eyes. Used to make flavoring extracts and other chemicals.
Preparation methods
PreparationObtained by esterification of isobutyric acid and anhydrous ethanol. After mixing isobutyric acid and anhydrous ethanol, carefully add concentrated sulfuric acid. After refluxing the mixture for 14h, it should be washed by water and saturated sodium bicarbonate solution and dried by anhydrous magnesium sulfate and then go through distillation. Collecting fractions at 109-111℃ and obtain 2- methyl ethyl propionate. The yield is 69 percent.
PreparationBy esterification of ethanol with isobutyric acid under azeotropic conditions.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
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Additional notes
DefinitionChEBI: Ethyl isobutyrate is a fatty acid methyl ester obtained by the formal condensation of isobutyric acid with ethanol. It has a role as a metabolite. It is functionally related to an isobutyric acid.
Related reactions
175 records
Linked notes
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