Basic information
- Standard SMILES
CC(=O)CC(=O)OCC(C)C- InChIKey
ZYXNLVMBIHVDRH-UHFFFAOYSA-N- Molecular formula
- C8H14O3
- Average molar mass
- 158.19 g/mol
- Monoisotopic mass
- 158.09429431
Overview
2-Methylpropyl 3-oxobutanoate is an oxo carboxylic acid.
Names & identifiers
- Preferred name
- Isobutyl acetoacetate
- IUPAC
- 2-methylpropyl 3-oxobutanoate
- English name
- Isobutyl acetoacetate
- Molecular formula
- C8H14O3
- Molecular weight
- 158.2
Names & synonyms
Isobutyl acetoacetateIsobutyl 3-oxobutanoate2-Methylpropyl 3-oxobutanoateButanoic acid, 3-oxo-, 2-methylpropyl esterAcetoacetic acid, isobutyl esterIsobutyl 3-ketobutyrateIsobutyl 3-ketobutanoate2-Methyl-1-propyl acetoacetate5HI9DAL68ZFEMA No. 2177UNII-5HI9DAL68ZAI3-36524
Show more names
ACIBIsobutyl Acetoacetate >Isobutyl acetoacetate(IBAA)2-Methylpropyl acetoacetateACETOACETIC ACID ISOBUTYL ESTERIsobutyl acetoacetate USP/EP/BPIsobutyl Acetoacetate, 98.0%(GC)
EINECS 231-937-5DTXSID3064805ZYXNLVMBIHVDRH-UHFFFAOYSA-ISOBUTYL ACETOACETATE [FHFI]RefChem:149074DTXCID0048004231-937-5InChI=1/C8H14O3/c1-6(2)5-11-8(10)4-7(3)9/h6H,4-5H2,1-3H3
Database identifiers
- CAS
7779-75-1- PubChem CID
- 522677
- DTXSID
DTXSID3064805- ChEBI
CHEBI:173674- UNII
- 5HI9DAL68Z
- EC Number
- 231-937-5
- Nikkaji
- J133.554E
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 149
Experimental & physicochemical properties
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.97
Flavoring AgentsEU Flavoring substances
Solubility
insoluble in water; soluble in alcohol and oil
(in ethanol)
Boiling Point
196.00 °C. @ 760.00 mm Hg
196 °C; 84.5 °C (11 mm Hg)
Refractive Index1.422-1.432
Physical Descriptioncolourless liquid; fruity taste; sweet, fruity odour of brandy
Physicochemical properties
- Melting point
- 177 · 177-179 °C(Solv: ethyl ether (60-29-7))
- Boiling point
- 100 °C/22 · 100 °C/22 mmHg (lit.)
- Density
- 0.98 g/mL · 0.98 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.424(lit.)
- FEMA
- 2177 · 2177 | ISOBUTYL ACETOACETATE
- FLAVIS Number
- 9.404 · 09.404 | Isobutyl acetoacetate
- Flash point
- 173 °F · 173 °F
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- form
- liquid
- pka
- 10 · 10+-.0.46(Predicted)
- color
- clear
- Odor
- 10 % · at 10.00 % in dipropylene glycol. sweet wine brandy fruity
- Odor Type
- fruity
- JECFA Number
- 597 · 597
- BRN
- 1761405 · 1761405
- InChI
- 1S/C8H14O3/c1-6(2)5-11-8(10)4-7(3)9/h6H,4-5H2,1-3H3
- InChIKey
- ZYXNLVMBIHVDRH-UHFFFAOYSA-N
- SMILES
- CC(C)COC(=O)CC(C)=O || CC(C)COC(=O)CC(C)=O
- LogP
- 1.6 · 1.60
- CAS DataBase Reference
- 7779 · 7779-75-1(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- ISOBUTYL ACETOACETATE
- FDA 21 CFR
- 172.515 · 172.515
- FDA UNII
- 5 HI9DAL68Z · 5HI9DAL68Z
- NIST Chemistry Reference
- 3 · Butanoic acid, 3-oxo-, 2-methylpropyl ester(7779-75-1)
- EPA Substance Registry System
- 3 · Butanoic acid, 3-oxo-, 2-methylpropyl ester (7779-75-1)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 227 · H227-H315-H319
- Precautionary statements
- 210 · P210-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- WGK Germany
- 3 · 3
- TSCA
- TSCA listed
- HS Code
- 2918.3 · 2918.30.9000
- Storage Class
- 10 · 10 - Combustible liquids
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 85.7% (12 of 14) of all reports.
Warning
H315 (14.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
Aggregated GHS information provided per 14 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Butanoic acid, 3-oxo-, 2-methylpropyl ester
Butanoic acid, 3-oxo-, 2-methylpropyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (14.3%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 2918.30.9000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H227-H315-H319
- Precautionary statements
- P210-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501
Chemistry & industry
Uses & manufacturing
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationButanoic acid, 3-oxo-, 2-methylpropyl ester: ACTIVE
Applications
DescriptionIsobutyl acetoacetate has a sweet, winey, brandy-like odor and a sweet and slightly fruity flavor. May be prepared from isobutyl acetate by heating in the presence of sodium isobutylate.
UsesIsobutyl acetoacetate is used as intermediate for the production of pharmaceuticals (e.g. Nisoldipine). Product Data Sheet
UsesIsobutyl Acetoacetate is a building block that has been used as a reactant in the preparation of b-annulated 1,4-dihydropyridine derivatives as TGFβ signaling inhibitors.
Preparation methods
PreparationFrom isobutyl acetate by heating in the presence of sodium isobutylate. Or by Claisen condensation of iso-ButyI acetate with Ethylacetate, using Sodium ethoxide catalyst.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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Additional notes
DefinitionChEBI: 2-Methylpropyl 3-oxobutanoate is an oxo carboxylic acid.
Related reactions
6 records
Linked notes
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