14352-65-9

Basic information

• Product Name: 2-(Hydroxyimino)acetoacetic acid tert-butyl ester
• Synonyms: 2-(Hydroxyimino)-3-oxobutanoic acid tert-butyl ester;2-(Hydroxyimino)acetoacetic acid tert-butyl ester;2-Hydroxyimino-3-oxobutyric acid tert-butyl ester;(Z)-tert-butyl 2-(hydroxyiMino)-3-oxobutanoate;tert-Butyl 2-(oxyimino)-3-oxobutyrate;tert-Butyl 2-hydroximino-3-oxobutyrate;tert-Butyl 2-hydroxyimino-3-oxobutanoate
• CAS NO: 14352-65-9
• Molecular Formula: C₈H₁₃NO₄
• Molecular Weight: 187.19
• Mol File: 14352-65-9.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 281℃
• Flash Point: 124℃
• Appearance: /
• Density: 1.12
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.468
• CAS DataBase Reference: 2-(Hydroxyimino)acetoacetic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Hydroxyimino)acetoacetic acid tert-butyl ester(14352-65-9)
• EPA Substance Registry System: 2-(Hydroxyimino)acetoacetic acid tert-butyl ester(14352-65-9)

Safety Data

• Hazardous Substances Data: 14352-65-9(Hazardous Substances Data)

Usage

Appearance

White to off-white solid

Melting point

High

Stability

More stable than its parent compound, 2-(hydroxyimino)acetoacetic acid

Ease of handling

Easier to handle in various chemical reactions due to the presence of the tert-butyl ester group

Uses

Building block in the synthesis of various pharmaceuticals and organic compounds, key intermediate in the production of some pesticides

Hazard classification

Low hazard chemical with no known adverse effects on human health or the environment when used in accordance with recommended guidelines.

InChI:InChI=1/C8H13NO4/c1-5(10)6(9-12)7(11)13-8(2,3)4/h12H,1-4H3

Upstream product

• 326914-14-1 5-(5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic Acid (2-dimethylamino-ethyl)amide 
• 1694-31-1 tert-butyl acetoacetate 

Downstream Products

• 76674-93-6 tert-butyl 2-methoxyimino-3-oxobutyrate 
• 86770-31-2 2-tert-butyl 4-ethyl 3,5-dimethyl-1H-pyrrole-2,4-dicarboxylate 
• 89909-48-8 3,5-dimethyl-1H-pyrrole-2, 4-dicarboxylic acid 2-tert-butyl ester 4-benzyl ester 
• 268544-50-9 C₁₁H₁₇NO₆ 
• 1309134-43-7 tert-butyl 8-(5-benzyloxycarbonyl-3-ethyl-4-methyl-2-pyrrolyl)-3-methylindeno[2,1-b]pyrrole-2-carboxylate 
• 945381-56-6 5-carboxymethyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 
• 527384-78-7 t-butyl 2-(2-chlorophenyl)-5-methyl-1H-imidazole-4-carboxylate 
• 88055-48-5 benzyl 5'-t-butoxycarbonyl-3,3'-di(2-methoxycarbonylethyl)-4-methyl-4'-trideuteriomethylpyrromethane-5-carboxylate 
• 79491-18-2 benzyl 4,3'-di(2-acetoxyethyl)-5'-t-butoxycarbonyl-3,4'-dimethyl-2,2'-dipyrrylmethane-5-carboxylate 
• 590424-04-7 tert-butyl 4-[[[2-(diethylamino)ethyl]amino]carbonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate 
• 60024-89-7 4-(2-methoxycarbonylethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

Synthesis of [18F]SU11248, a new potential PET tracer for imaging cancer tyrosine kinase

N-[2-(Diethylamino)ethyl]-5-[(Z)-(5-[18F]fluoro-2-oxo-1, 2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide, a new potential positron emission tomography tracer for imaging cancer tyrosine kinase, has been prepared by the nucleophilic substitution of the nitro-precursor N-[2-(diethylamino)ethyl]-5-[(Z)-(5-nitro-2-oxo-1,2-dihydro-3H- indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide with K 18F/Kryptofix 2.2.2 followed by a simple chromatography methodology combined solid-phase extraction with high-performance liquid chromatography purification procedures in 15-25% radiochemical yields.

Early amidation approach to 3-[(4-amido)pyrrol-2-yl]-2-indolinones

A new synthesis of 3-[(4-amido)pyrrol-2-yl]-2-indolinones has been developed, where the amide side chain was installed prior to pyrrole formation. This strategy precludes the need to use any coupling reagents to install the amide side chain. This process includes a zinc-free alternative to the Knorr pyrrole synthesis.

5-Hydroxy-7-azaindolin-2-one, a novel hybrid of pyridinol and sunitinib: Design, synthesis and cytotoxicity against cancer cells

Angiogenesis plays important roles in tumor growth and metastasis. Sunitinib (Sutent) is an antitumor agent targeting receptor tyrosine kinases which are involved in angiogenesis as well as cancer cell growth and survival. Using the pyridin-3-ol scaffold, which was previously reported as an excellent antioxidant and antiangiogenic platform, we have synthesized sunitinib mimics 6 by hybridizing bicyclic pyridinol 4 as a key scaffold and pyrrole-2-carbaldehydes 7 as side chains. Cytotoxicity assays showed that compounds 6 have comparable to better anticancer activity than sunitinib against five different cancer cell lines. In addition, compounds 6 showed even lower levels of cytotoxicity against normal cells, resulting in up to 26-fold better safety windows, than sunitinib. Signaling pathway-associated transcription factor reporter assay and western blot analyses revealed that apoptosis induction in MDA-MB-231 human breast cancer cells by 6F is mainly mediated through the p53 increase and down-regulation of phospho-signal transducer and activator of transcription 3 (STAT3) and its target gene products, cyclin D, Bcl-2, and survivin. The data strongly suggest that our hybrid compounds can provide a novel anticancer scaffold with improved and safer cytotoxicity profiles than sunitinib.

One-Photon Excitation Followed by a Three-Step Sequential Energy–Energy–Electron Transfer Leading to a Charge-Separated State in a Supramolecular Tetrad Featuring Benzothiazole–Boron-Dipyrromethene–Zinc Porphyrin–C60

A panchromatic triad, consisting of benzothiazole (BTZ) and BF2-chelated boron-dipyrromethene (BODIPY) moieties covalently linked to a zinc porphyrin (ZnP) core, has been synthesized and systematically characterized by using 1H NMR s

IMPROVED WAVELENGTH CONVERSION FILM

Described herein is an improved wavelength conversion film with composite materials that have improved quantum efficiency and color gamut. The film includes narrow FWHM green and red emitting dyes.