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Ethyl 2-cyano-3-(dimethylamino)acrylate, with the molecular formula C9H12N2O2 and IUPAC name Ethyl 2-cyano-3-dimethylaminoprop-2-enoate, is a chemical compound that belongs to the categories of acrylates and nitriles. It is derived from acrylic acid and contains a -C≡N functional group. Ethyl 2-cyano-3-(dimethylamino)acrylate is known for its reactivity, making it a valuable component in various chemical synthesis processes. It is also used as a laboratory reagent for the preparation of polymerizable monomers. However, due to its potential hazards on skin contact, inhalation, or ingestion, it requires careful handling and storage.

16849-87-9

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16849-87-9 Usage

Uses

Used in Chemical Synthesis:
Ethyl 2-cyano-3-(dimethylamino)acrylate is used as a reagent for various chemical synthesis processes due to its reactivity. It plays a crucial role in the production of different compounds, contributing to the advancement of the chemical industry.
Used in Laboratory Research:
As a laboratory reagent, Ethyl 2-cyano-3-(dimethylamino)acrylate is used in the preparation of polymerizable monomers. This application is essential for the development of new materials and the study of polymer chemistry.
Used in Pharmaceutical Industry:
Ethyl 2-cyano-3-(dimethylamino)acrylate is used as an intermediate in the synthesis of certain pharmaceutical compounds. Its unique structure and reactivity make it a valuable component in the development of new drugs and therapeutic agents.
Used in Material Science:
In the field of material science, Ethyl 2-cyano-3-(dimethylamino)acrylate is used as a precursor for the development of new polymers and materials with specific properties. Its versatility in chemical reactions allows for the creation of materials with tailored characteristics for various applications.

Check Digit Verification of cas no

The CAS Registry Mumber 16849-87-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,8,4 and 9 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 16849-87:
(7*1)+(6*6)+(5*8)+(4*4)+(3*9)+(2*8)+(1*7)=149
149 % 10 = 9
So 16849-87-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H12N2O2/c1-4-12-8(11)7(5-9)6-10(2)3/h6H,4H2,1-3H3/b7-6+

16849-87-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 2-cyano-3-(dimethylamino)acrylate

1.2 Other means of identification

Product number -
Other names Dimethylaminomethylen-cyan-essigsaeure-aethylester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16849-87-9 SDS

16849-87-9Relevant academic research and scientific papers

X-ray crystallographic, spectroscopic and quantum chemical studies on ethyl 2-cyano-3-N,N-dimethyl amino acrylate

Gupta,Sharma, Archna,Dinesh,Rajnikant

, p. 237 - 243 (2007)

Structural and spectral characteristics of ethyl 2-cyano-3-N,N-dimethyl amino acrylate have been studied by methods of X-ray crystallography, infrared spectroscopy and quantum chemistry. The compound crystallizes in monoclinic space group P21/n

Synthesis method of N-hydroxyethyl-5-amino-1H pyrazole

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Paragraph 0023-0025; 0030-0032, (2021/07/21)

The invention discloses a synthesis method of N-hydroxyethyl-5-amino-1H pyrazole. The synthesis method comprises the following steps: by taking N, N-dimethylformamide as a raw material, carrying out one-pot reaction on the N, N-dimethylformamide, dimethyl sulfate and cyanoacetic acid R ester to prepare 2-cyano-3-(dimethylamino) acrylic acid R ester; carrying out cyclization and hydrolysis on the 2-cyano-3-(dimethylamino) acrylic acid R ester and beta-hydroxyethylhydrazine to prepare N-hydroxyethyl-5-amino-1H pyrazole-4-formic acid; and carrying out decarboxylation on N-hydroxyethyl-5-amino-1H pyrazole-4-formic acid, so as to prepare N-hydroxyethyl-5-amino-1H pyrazole, wherein R is an alkane group below C4. The synthesis method provided by the invention has the advantages of strong operability, high economic benefit and high yield.

SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS

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Page/Page column 75, (2018/12/03)

The present application relates to substituted fused heteroaryl and heterocyclic compounds, useful as nicotinamide adenine dinucleotide phosphate oxidase inhibitors (NADPH oxidase inhibitors), processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by NADPH oxidase. (Formula I)

ACETALS OF LACTAMS AND AMIDES. 42. REACTIONS OF ENAMINO AMIDES AND ENAMINO ESTERS WITH SOME FORMYLATING AGENTS. SYNTHESIS OF DERIVATIVES OF 2-PYRIDONE AND OF PYRIMIDIN-4- AND -6-ONES

Granik, V. G.,Ershov, L. V.,Grizik, S. I.,Chistyakov, V. V.

, p. 1026 - 1031 (2007/10/02)

The reactions of enamino esters and enamino amides with the diethyl acetal of dimethylformamide and with orthoformic ester have been investigated and it has been shown that the process takes place in two directions - with the formation of pyrimidone or 2-

REACTION OF GOLD'S REAGENT WITH ACTIVATED METHYLENE GROUPS DERIVED FROM ESTERS AND NITROARENES

Gupton, John T.,Lizzi, Michael J.,Polk, Dale

, p. 939 - 946 (2007/10/02)

A series of esters and nitrotoluenes were reacted with Gold's reagent under basic conditions and were found to produce the corresponding dimethylamino methyleneated product in both cases.

Preparation and Reaction of Trimethoxyacetamide and Trimethoxyacetamide Derivates

Kantlehner, Willi,Kapassakalidis, Joannis J.,Maier, Thomas

, p. 1448 - 1454 (2007/10/02)

Trimethoxyacetamide (2a) can be prepared from either trimethoxyacetonitrile (3) or from methyltrimethoxyacetate (1a).Similarly triethoxyacetamide can be obtained from 1b and ammonia.The synthesis of pure 1a is described.Hydrazine hydrate reacts with 1a to form trimethoxyacetohydrazide (6).The compounds 2a and 6 are formylated by tert-butoxy-N,N,N',N'-tetramethylmethanediamine ("aminal ester") at the NH2 group to furnish the formamidine 8 and the formamidrazone 9, respectively. 8 has also been prepared by reaction of N,N-dimethylformamide dimethylacetal with 2a.Reaction of 8 with phenylhydrazine affords the tetrazine 11.CH-acidic compounds such as malonodinitrile and ethyl cyanoacetate are formylated by 8 at the CH2 groups to yield the enamines 12a,b .

Orthoamides, XXXIII.-Contributions to the Chemistry of Bis(dialkylamino)acetonitriles

Kantlehner, Willi,Baur, Richard,Bredereck, Hellmut

, p. 358 - 371 (2007/10/02)

Bis(dialkylamino)acetonitriles 2a-d react with acetyl chloride and antimony pentachloride to give N,N,N',N'-tetraalkylformamidinium hexachloroantimonates 5a-d.Reaction of p-nitrophenol with 2a,b affords N,N,N',N'-tetraalkylformamidinium salts 8a,b, while reaction of aromatic aldehydes 11 with compounds 2 gives aryl(dialkylamino)acetonitriles 12.Phenyl isothiocyanate reacts with the nitriles 2a-c to give 1:1 adducts for which the structure of N,N,N',N'-tetraalkylformamidinium cyano-N-(phenyl)thioformamidates 19 is proposed.N,N,N',N'-Tetraalkylformamidinium p-toluenesulfonates 30a,b have been prepared from nitriles 2a,b and methyl p-toluoenesulfonate (28).Alkylation of 2c with 28 at higher temperatures affords 1,1-dimethylpiperidinium p-toluoenesulfonate (34) and a small amount (1-piperidinyl)malonodinitrile (33).The nitrile 2a reacts with CH acidic compounds such as ethyl cyanoacetate, malonodinitrile and benzyl cyanide to form the enamines 38.

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