759-58-0

Basic information

• Product Name: ETHYL 2-CYANO-3-METHYLCROTONATE
• Synonyms: Crotonic acid, 2-cyano-3-methyl-, ethyl ester;Ethyl isopropylidene(cyano)acetate;TIMTEC-BB SBB007715;ETHYL 2-CYANO-3-METHYLCROTONATE;ETHYL 2-CYANO-3-METHYL-2-BUTENOATE;Ethyl 2-cyano-3-methylbutanoate;2-cyano-3-methylcrotonic acid ethyl ester;Ethyl 2-cyano-3-methyl-2-butanoate
• CAS NO: 759-58-0
• Molecular Formula: C₈H₁₁NO₂
• Molecular Weight: 153.18
• Product Categories: Small molecule;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 759-58-0.mol

Chemical Properties

• Melting Point: ca 20℃
• Boiling Point: 98-99 °C1 mm Hg(lit.)
• Flash Point: 224 °F
• Appearance: clear colorless to slightly yellow liquid
• Density: 1.014 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00386mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• BRN: 507839
• CAS DataBase Reference: ETHYL 2-CYANO-3-METHYLCROTONATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-CYANO-3-METHYLCROTONATE(759-58-0)
• EPA Substance Registry System: ETHYL 2-CYANO-3-METHYLCROTONATE(759-58-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 759-58-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
ETHYL 2-CYANO-3-METHYLCROTONATE is used as a highly activated acceptor for chemical reactions, particularly in the phospha-Michael reaction. Its unique chemical properties make it a valuable component in the synthesis of various organic compounds and pharmaceuticals.
Used in Pharmaceutical Industry:
ETHYL 2-CYANO-3-METHYLCROTONATE is used as a key intermediate in the synthesis of pharmaceutical compounds. Its ability to undergo the phospha-Michael reaction allows for the creation of new and innovative drug molecules with potential therapeutic applications.
Used in Research and Development:
ETHYL 2-CYANO-3-METHYLCROTONATE is used as a research compound in the development of new chemical reactions and processes. Its unique properties and reactivity make it an important tool for chemists and researchers working to advance the field of organic chemistry.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3418, 1949 DOI: 10.1021/ja01178a044

InChI:InChI=1/C8H11NO2/c1-4-11-8(10)7(5-9)6(2)3/h4H2,1-3H3

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 67-64-1 acetone 
• 186581-53-3 diazomethane 
• 686-33-9 ethyl 2-cyanobut-2-enoate 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 25468-53-5 ethyl (2Z)-2-cyano-3-ethoxypent-2-enoate 
• 593-51-1 methylamine hydrochloride 
• 62-53-3 aniline 
• 109-89-7 diethylamine 
• 110-89-4 piperidine 

Downstream Products

• 3213-49-8 ethyl 2-isopropylcyanoacetate 
• 91690-68-5 2-cyano-3,3-dimethyl-heptanoic acid ethyl ester 
• 24543-06-4 ethyl 1,2,2-tricyano-3,3-dimethylcyclopropane-1-carboxylate 
• 597-43-3 2,2-dimethylsuccinic acid 
• 52119-01-4 ethyl 2,3-dicyano-3-methylbutanoate 
• 56264-36-9 2-cyano-3-methyl-3-phenyl-butyric acid ethyl ester 
• 61193-04-2 3-(R,S),5-(R,S)-3,5-dicyano-4,4-dimethyl-2,6-dioxopiperidine 
• 6333-05-7 2-cyano-3,3-dimethyl-4-phenyl-butyric acid ethyl ester 
• 3302-16-7 3,3-dimethyl-butyronitrile 
• 141-82-2 malonic acid 
• 759-21-7 2-cyano-3-methylbut-2-enoic acid 
• 65996-11-4 1-carbethoxy-1-cyano-2-methyl-4-dimethylamino-1,4-butadiene 
• 25380-95-4 4-(3-methoxyphenyl)-3,3-dimethylbutanoic acid 
• 143661-10-3 (2-Methyl-2H-chromen-2-yl)-acetonitrile 

Relevant articles and documents

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes: Scope and limitations

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes utilizing S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate is an efficient approach to obtain a range of monofluorocyclopropane derivatives. So far, fluoromethylsulfonium salts have displayed the broadest scope for direct fluoromethylene transfer. In contrast to more commonly used fluorohalomethanes or freon derivatives, diarylfluoromethylsulfonium salts are bench stable, easy-to use reagents useful for the direct transfer of a fluoromethylene group to alkenes giving access to the challenging products-fluorocyclopropane derivatives. Interplay between the reactivity of the starting materials and stability of the fluorocyclopropanes formed determines the outcome of the process.

ISOINDOLINES AS HDAC INHIBITORS

The present disclosure relates to inhibitors of zinc-dependent histone deacetylases (HDACs), having the formula: (I) wherein Z, X1, X2, Y1, Y2, Y3, L, Z, and R are described herein.

Vanadium-Catalyzed Condensation of Ethyl Cyanoacetate with Ketones

Vanadium compounds and complexes activated by pyridine or morpholine catalyze condensation of ethyl cyanoacetate with ketones and aldehydes leading to alkylidenecyanoacetates in 75–100% yield.

Copper-Mediated, Heterogeneous, Enantioselective Intramolecular Buchner Reactions of α-Diazoketones Using Continuous Flow Processing

Enantioselective intramolecular Buchner reactions of α-diazoketones can be effected using heterogeneous copper-bis(oxazoline) catalysts in batch or using continuous flow processing in up to 83% ee. The catalyst can be reused up to 7 times without loss of activity. For α-diazoketones 3 and 4, the enantioselection achieved in flow with the immobilized catalyst was comparable with the standard homogeneous catalyzed process.

PIPERIDINE COMPOUNDS AS PCSK9 INHIBITORS

One aspect of the invention relates to a series of new PCSK9 inhibitor compounds comprising piperidine ring structures, including compounds of formula (I) and/or pharmaceutically acceptable salts thereof. Another aspect of the invention relates to methods of treating PCSK9 receptor related diseases comprising administration of one or more compounds of formula (I) or a pharmaceutically acceptable salt thereof.

Flash preparation of carbenoids: A different performance of cyanogen bromide

Cyanogen halides are known substances for the cyanating reaction. There are a few evidences for bromination reaction too. On the other hand carbenes are known as very important substances due to their remarkable reactions. Unfortunately carbenes at room temperature are very unstable and there is not a simple method for preparation of them. In most cases the isolation is not possible. We have reported a new reliable and fast preparation method of almost stable carbenoids. The mechanism of the formation has been discussed.

HETEROCYCLIC COMPOUNDS AND USES THEREOF

Compounds and pharmaceutical compositions of formulae (I), (XI) and (XII) as PI3 kinase modulators and their use in the treatment of diseases such as cancer.

HETEROCYCLIC COMPOUNDS AND USES THEREOF

Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.

Efficient protocol for knoevenagel condensation in presence of the diazabicyclo[5.4.0]undec-7-ene-water complex

A simple and efficient protocol for Knoevenagel condensation has been developed in the presence of diazabicyclo[5.4.0]undec-7-ene (DBU)/water complex. A widely range of carbonyl compounds (aliphatic and aromatic aldehydes, ketones) could react smoothly with methylene active ingredients (malononitrile, ethyl cyanoacetate, diethyl malonate and acetylacetone), which can not proceed by conven- tional catalyst. Other significant features of this method include readily work-up, good recyclability of catalytic system and short reaction time.

Schiff base structured acid-base cooperative dual sites in an ionic solid catalyst lead to efficient heterogeneous knoevenagel condensations

An acid-base bifunctional ionic solid catalyst [PySaIm]3PW was synthesized by the anion exchange of the ionic-liquid (IL) precursor 1-(2-salicylaldimine)pyridinium bromide ([PySaIm]Br) with the Keggin-structured sodium phosphotungstate (Na