Tert-butyl acetoacetate

Base Information

• Chemical Name: Tert-butyl acetoacetate
• CAS No.: 1694-31-1
• Molecular Formula: C8H14O3
• Molecular Weight: 158.197
• Hs Code.: 29183000
• European Community (EC) Number: 216-904-5
• NSC Number: 42869
• UNII: 1D3DOS61GX
• DSSTox Substance ID: DTXSID4044402
• Nikkaji Number: J100.916H
• Wikidata: Q27252262
• ChEMBL ID: CHEMBL3187029
• Mol file: 1694-31-1.mol

Synonyms:tert-butyl acetoacetate;1694-31-1;tert-Butyl 3-oxobutanoate;t-Butyl acetoacetate;Butanoic acid, 3-oxo-, 1,1-dimethylethyl ester;Acetoacetic acid, tert-butyl ester;tert-Butyl 3-oxobutyrate;Acetoacetic Acid tert-Butyl Ester;t-butylacetoacetate;MFCD00008811;TBAA;tert-butylacetoacetate;tert-Butyl Oxobutyrate;Butyl acetoacetate, tert-;UNII-1D3DOS61GX;1D3DOS61GX;1,1-dimethylethyl acetoacetate;DTXSID4044402;EINECS 216-904-5;NSC-42869;EC 216-904-5;t-butyl acetoaceate;tertbutylacetoacetate;ter'-Butylacetoacetate;t-Butyl-3-oxobutyrate;tert.-butyl acetoacetate;tert-Butyl acetoacetate;tert-Butyl-3-oxobutyrate;acetoacetate t-butyl ester;tertiary butyl acetoacetate;acetoacetic tert-butyl ester;SCHEMBL82881;tert-Butyl 3-oxobutanoate #;T-BUTYL 3-OXOBUTANOATE;CHEMBL3187029;DTXCID2024402;acetoacetic acid tert.butyl ester;acetoacetic acid-tert. butylester;TERT-BUTYL ACETYLACETONATE;1,1-dimethylethyl 3-oxobutanoate;3-oxobutyric acid tert-butyl ester;AMY40220;NSC42869;3-oxo-butyric acid tert-butyl ester;Tox21_302057;NSC 42869;AKOS000119489;DS-3420;NCGC00255936-01;CAS-1694-31-1;A0816;CS-0006847;FT-0621781;tert-Butyl acetoacetate, reagent grade, 97%;tert-Butyl acetoacetate, reagent grade, 98%;EN300-20336;Butanoic acid,3-oxo-,1,1-diMethylethyl ester;D70417;A811105;J-010541;J-524564;Q27252262;F0001-0773;tert-Butyl acetoacetate, Vetec(TM) reagent grade, 97%;tert-Butyl acetoacetate, Lonza quality, >=98.0% (w/w) (GC);tert-Butyl acetoacetate, produced by Wacker Chemie AG, Burghausen, Germany, >=98.0% (GC)

Chemical Property of Tert-butyl acetoacetate

Chemical Property:

• Appearance/Colour: Clear yellow liquid
• Vapor Pressure: 0.749mmHg at 25°C
• Melting Point: -38 °C
• Refractive Index: n20/D 1.419
• Boiling Point: 184 °C at 760 mmHg
• PKA: 10.71±0.46(Predicted)
• Flash Point: 66.5 °C
• PSA: 43.37000
• Density: 0.981 g/cm³
• LogP: 1.30720
• Storage Temp.: ?20°C
• Solubility.: 9g/l
• Water Solubility.: Soluble in water (9g/L).
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 158.094294304
• Heavy Atom Count: 11
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

beta-actin ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CC(=O)CC(=O)OC(C)(C)C
• Description: Tert-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.
• Uses: Intermediate for the syntheses of different organic chemicals. Product Data Sheet tert-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.

Technology Process of Tert-butyl acetoacetate

There total 36 articles about Tert-butyl acetoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.8%

cycl-isopropylidene malonate (2033-24-1) + acetyl chloride (75-36-5) + tert-butyl alcohol (75-65-0) → tert-butyl acetoacetate (1694-31-1)

Guidance literature:

cycl-isopropylidene malonate; acetyl chloride; With pyridine; In dichloromethane; at -5 - 20 ℃; for 3h;

tert-butyl alcohol; at 70 ℃; for 5h;

Reference yield: 94.4%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + tert-butyl alcohol (75-65-0) → tert-butyl acetoacetate (1694-31-1)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; tributyl-amine; at 60 - 150 ℃; for 0.5h; Concentration; Temperature;

Reference yield: 89.0%

2-bromo-pyridine (109-04-6) + tert-butyl sodioacetate → tert-butyl acetoacetate (1694-31-1) + tert-butyl 2-(pyridin-2-yl)acetate (150059-62-4) + Di-pyridin-2-yl-acetic acid tert-butyl ester

Guidance literature:

With iron(II) sulfate; In ammonia; for 0.75h; Yields of byproduct given;

upstream raw materials:

4-methyleneoxetan-2-one

tert-butyl alcohol

diethyl ether

acetic acid tert-butyl ester

Downstream raw materials:

tert-butyl 3,5-dimethyl-4-acetyl-2-pyrrolecarboxylate

3,5-dimethyl-pyrrole-2,4-dicarboxylic acid 4-tert-butyl ester 2-ethyl ester

tert-butyl 6-methyl-2,4-dioxocyclohexane-1-carboxylate

6-γ-Carboaethoxy-propyl-2.4-dioxo-cyclohexancarbonsaeure-tert.-butylester

Refernces

• 1、 Hauser,Walker. "-". . p. 295. Retrieved 1947.
• 2、 Renfrow,Walker. "-". . p. 3957. Retrieved 1948.
• 3、 Sidhom, Peter A.,El-Bastawissy, Eman,Salama, Abeer A.,El-Moselhy, Tarek F.. "Revisiting ageless antiques; synthesis, biological evaluation, docking simulation and mechanistic insights of 1,4-Dihydropyridines as anticancer agents". supporting information. . Retrieved 2021/06/21.
• 4、 Chityala, Yadaiah,Duguta, Govardhan,Kamatala, Chinna Rajanna,Muddam, Bhooshan,Mukka, Satish Kumar. "N, N’-dimethyl formamide (DMF) mediated Vilsmeier–Haack adducts with 1,3,5-triazine compounds as efficient catalysts for the transesterification of β-ketoesters". supporting information. p. 1641 - 1655. Retrieved 2020/05/25.