CAS 1694-31-1 Tert-butyl acetoacetate (HCID 15538)

Names & identifiers

Preferred name: Tert-butyl acetoacetate
IUPAC: tert-butyl 3-oxobutanoate
English name: tert-Butyl acetoacetate
Molecular formula: C8H14O3
Molecular weight: 158.2

Names & synonyms

tert-butyl acetoacetate1694-31-1tert-Butyl 3-oxobutanoatet-Butyl acetoacetateButanoic acid, 3-oxo-, 1,1-dimethylethyl esterAcetoacetic acid, tert-butyl estertert-Butyl 3-oxobutyrateAcetoacetic Acid tert-Butyl Estertert-Butyl OxobutyrateMFCD00008811t-butylacetoacetateTBAA

Show more names

ACTBBeta-actinbactactbabactzfbactin1CEDI-002

tert-butylacetoacetateDTXSID4044402Sunitinib Impurity 421D3DOS61GX1,1-dimethylethyl acetoacetateNSC-42869Butyl acetoacetate, tert-UNII-1D3DOS61GX

Database identifiers

CAS: 1694-31-1
PubChem CID: 15538
DTXSID: DTXSID4044402
ChEMBL: CHEMBL3187029
UNII: 1D3DOS61GX
EC Number: 216-904-5
Nikkaji: J100.916H

Properties

Computed structural properties

XLogP: 1
Topological polar surface area: 43.4 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 4
Heavy atoms: 11
Formal charge: 0
Complexity: 165

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Esters, Other

Density0.954 @25 °C

Physical Description · 2 items

Liquid

Colorless odorless liquid; [Eastman Chemical MSDS]

Physicochemical properties

Melting point: -38 °C · -38 °C (lit.)
Boiling point: 71 · 71-72 °C/11 mmHg (lit.)
Density: 0.954 g/mL · 0.954 g/mL at 25 °C (lit.)
vapor pressure: 79.32 Pa · 79.32Pa at 25℃
refractive index: 20 · n20/D 1.419
Flash point: 150 °F · 150 °F
storage temp.: -20 °C · -20°C
solubility: 9 g/l · 9g/l
form: Liquid
pka: 10.71 · 10.71±0.46(Predicted)
color: clear
PH: 5.7 · 5.7 (9g/l, H2O, 20℃)
explosive limit: 1.1 % · 1.1%(V)
biological source: rabbit
Water Solubility: Soluble in water (9g/L).
BRN: 1680303 · 1680303
InChI: 1S/C8H14O3/c1-6(9)5-7(10)11-8(2,3)4/h5H2,1-4H3
InChIKey: JKUYRAMKJLMYLO-UHFFFAOYSA-N
SMILES: CC(=O)CC(=O)OC(C)(C)C
LogP: 0.67 · 0.67-1.41 at 20℃
CAS DataBase Reference: 1694 · 1694-31-1(CAS DataBase Reference)
FDA UNII: 1 D3DOS61GX · 1D3DOS61GX
NIST Chemistry Reference: 3 · Butanoic acid, 3-oxo-, 1,1-dimethylethyl ester(1694-31-1)
EPA Substance Registry System: tert-Butyl acetoacetate (1694-31-1)
UNSPSC Code: 12352203 · 12352203
NACRES: 41 · NA.41
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 227 · H227
Precautionary statements: 210 e-P280a-P370+P378a-P501a-P210-P280-P370+P378-P403+P235-P501 · P210e-P280a-P370+P378a-P501a-P210-P280-P370+P378-P403+P235-P501
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Risk Statements: 36 · 36/37/38
Safety Statements: 24 · 24/25
RIDADR: 3272 · 3272
WGK Germany: 1 · 1
TSCA: TSCA listed
HazardClass: 3.2 · 3.2
PackingGroup: III
HS Code: 29183000 · 29183000
Storage Class: 10 · 10 - Combustible liquids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 96.1% (49 of 51) of all reports.

Not Classified

Aggregated GHS information provided per 51 reports by companies from 4 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 5 items

Chemical: Butanoic acid, 3-oxo-, 1,1-dimethylethyl ester

Butanoic acid, 3-oxo-, 1,1-dimethylethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanoic acid, 3-oxo-, 1,1-dimethylethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 07-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/12377

Butanoic acid, 3-oxo-, 1,1-dimethylethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryA slight eye irritant in rabbits; Not irritating or sensitizing to guinea pig skin; [Eastman Chemical MSDS]

Hazard Classes and CategoriesNot Classified

Safety & protection

Protective Action Criteria (PAC) · 3 items

13 [mg/m3]

150 [mg/m3]

890 [mg/m3]

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 1
tsca: TSCA listed
ridadr: 3272
hs_code: 29183000
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
hazard_class: 3.2
Storage Class: 10 - Combustible liquids
packing_group: III
Hazard statements: H227
REACH Registrations: Active
Precautionary statements: P210e-P280a-P370+P378a-P501a-P210-P280-P370+P378-P403+P235-P501

Chemistry & industry

Uses & manufacturing

UsesUsed as a chemical intermediate; [Eastman Chemical MSDS]

U.S. Production2023: 35,274 lb

Industry UsesSurface modifier

General Manufacturing Information · 2 items

All Other Chemical Product and Preparation Manufacturing

Butanoic acid, 3-oxo-, 1,1-dimethylethyl ester: ACTIVE

Applications · 4 items

DescriptionTert-Butyl acetoacetate is a reagent used to acetoacetylate hydroxyl-bearing coatings resins, such as polyesters, acrylics, cellulosics, and epoxies. It can be used as an acetoacetylating reagent in pharmaceutical, agrichemical, and pigment applications. It is used as an intermediate for the syntheses of different organic chemicals. For instance, it may be used to synthesize various acetoacetic acid derivatives, acetoacetates, acetoacetamides, 1-(diethylamino)-2-acetoacetoxypropane, (S)-tert-butyl 3-hydroxybutyrate, benzothiazole β-keto ester derivatives, and 3,4-disubstituted pyrroles.

UsesIntermediate for the syntheses of different organic chemicals. Product Data Sheet

Usestert-Butyl acetoacetate is used as intermediate for the syntheses of different organic chemicals. Raw material in pharmaceutical Industry, In agrochemical industry. Reagent for Acyloin synthesis and ,β - unsaturated ketones synthesis.

General Descriptiontert-Butyl acetoacetate (t-BAA) is a cheap and easy to store commercial reagent. Reaction demonstrated that the more hindered tert-butyl acetoacetate (t-BAA, la) is ca.15-20-fold more reactive than the more commonly used methyl or ethyl analogs. It is widely employed as an acetoacetylating reagent.

Upstream & downstream products

Upstream raw materials

Downstream products

ETHYL 2-AMINO-4-METHYLTHIOPHENE-3-CARBOXYLATE ETHYL 4-CHLORO-3-METHYLTHIENO[2,3-B]PYRIDINE-5-CARBOXYLATE 5-METHYL-3,4-DIHYDROTHIENO[2,3-D]PYRIMIDIN-4-ONE 4-CHLORO-5-METHYLTHIENO[2,3-D]PYRIMIDINE 2,2,6-Trimethyl-4H-1,3-dioxin-4-one 2-(CHLOROMETHYL)-5-METHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE ETHYL 2-(5-FORMYL-2,4-DIMETHYL-1H-PYRROL-3-YL)ACETATE Acetoacetanilide Methyl (R)-(-)-3-hydroxybutyrate 1-(4-NITROPHENYL)-3-METHYL-5-PYRAZOLONE N,N'-(1,4-Phenylene)bis(acetoacetamide)N-Benzylacetoacetamide

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Related reactions

219 records

New reaction record

HRID 11451As reactantuspto-grants-2006_08

HRID 18393As reactantuspto-grants-2010_06

HRID 46541As reactantuspto-grants-1979_11

HRID 59858As reactantuspto-grants-2016_09

HRID 69111As reactantuspto-grants-2014_09

HRID 90807As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)

HRID 91746As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)

HRID 96940As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)

Compound notes

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Basic information