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ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE, also known as ethyl 1-cyanocyclopropanecarboxylate, is an alkyl 1-cyanocyclopanecarboxylate compound. It is synthesized by reacting ethyl cyanoacetate, 1,2-dibromoethane, potassium carbonate, and DMSO. This organic compound is characterized by its unique structure and reactivity, which makes it suitable for various applications in different industries.

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  • 1558-81-2 Structure
  • Basic information

    1. Product Name: ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE
    2. Synonyms: ETHYL 1-CYANO-1-CYCLOPROPANECARBOXYLATE;ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE;1-CYANO-CYCLOPROPANECARBOXYLIC ACIDETHYL ESTER;Cyclopropanecarboxylic acid, 1-cyano-, ethyl ester;Ethyl 1-cyano-1-cyclopropanecarboxylate 96%;ethyl 1-cyanocyclopropane-1-carboxylate;1-cyano-1-cyclopropanecarboxylic acid ethyl ester;1-cyanocyclopropane-1-carboxylic acid ethyl ester
    3. CAS NO:1558-81-2
    4. Molecular Formula: C7H9NO2
    5. Molecular Weight: 139.15
    6. EINECS: N/A
    7. Product Categories: C6 to C7;Carbonyl Compounds;Esters;Building Blocks;C6 to C7;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
    8. Mol File: 1558-81-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 217 °C(lit.)
    3. Flash Point: 211 °F
    4. Appearance: /
    5. Density: 1.077 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.0996mmHg at 25°C
    7. Refractive Index: n20/D 1.445(lit.)
    8. Storage Temp.: Sealed in dry,Room Temperature
    9. Solubility: N/A
    10. CAS DataBase Reference: ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE(1558-81-2)
    12. EPA Substance Registry System: ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE(1558-81-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: 36/37/38
    3. Safety Statements: 26-37
    4. WGK Germany: 3
    5. RTECS:
    6. TSCA: No
    7. HazardClass: IRRITANT
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1558-81-2(Hazardous Substances Data)

1558-81-2 Usage

Uses

Used in Polymer Industry:
ETHYL 1-CYANOCYCLOPROPANECARBOXYLATE is used as a monomer for the preparation of poly(ethyl trimethylene-1-cyano-1-carboxylate)s. Its incorporation into polymers enhances their properties, such as strength, flexibility, and durability, making them suitable for a wide range of applications, including packaging materials, automotive components, and consumer goods.

Check Digit Verification of cas no

The CAS Registry Mumber 1558-81-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,5 and 8 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1558-81:
(6*1)+(5*5)+(4*5)+(3*8)+(2*8)+(1*1)=92
92 % 10 = 2
So 1558-81-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H9NO2/c1-2-10-6(9)7(5-8)3-4-7/h2-4H2,1H3

1558-81-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 1-cyanocyclopropanecarboxylate

1.2 Other means of identification

Product number -
Other names ethyl 1-cyanocyclopropane-1-carboxylate

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:1558-81-2 SDS

1558-81-2Relevant articles and documents

Electrosynthesis of cyclopropane derivatives by a Perkin-type reaction

Petrosyan, V. A.,Vasil'ev, A. A.,Tatarinova, V. I.

, p. 84 - 88 (1994)

Electrolysis of active methylene compounds at a Pt cathode in MeCN in the presence of vicinal dihaloalkanes leads to cyclopropane derivatives in yields up to 90percent.In the cases of CH-acids with low pKa it is expedient to apply more active dihaloalkanes, while for CH-acids with higher pKa the desired product yields may be raised using electrogenerated bases. - Key words: CH-acids; 1,2-dihaloalkanes; cyclopropanes; electrosynthesis; electroreduction; electronegative bases; azobenzene.

Anionic ring-opening polymerization of alkyl 1- cyanocyclopropanecarboxylates

Kagumba, Lawino C.,Penelle, Jacques

, p. 4588 - 4594 (2005)

Poly(alkyl 1-cyanotrimethylene-1-carboxylate)s (CH2CH 2C(CN)(COOR))n are the next higher chain homologues of poly(α-cyanoacrylate)s. They were synthesized via the anionic ring-opening polymerization of the corresponding alkyl 1-cyanocyclopropanecarboxylate monomers initiated with thiophenolate salts (PhSM, with M = Li, Na, K, and NBu4) and at temperatures above 50°C. Precipitation of the growing polymer chains at an early stage during the polymerization did not prevent further propagation, probably via polymerization in the solid or at the solid surface. The propagating cyanoacetate carbanion is very stable in a normal air atmosphere, surviving for long periods of time in the absence of strong acids. Although monodisperse polymers were obtained in most experiments (M w/Mn + and NBu 4+ counterions were used. Nonquantitative initiations characterized polymerizations initiated by PhSLi and PhSNa. Attempted polymerizations of ethyl 1-cyanocyclobutanecarboxylate failed under similar or slightly more energetic experimental conditions, with the thiophenolate initiator attacking the pendant ester rather than the cyclic methylene group.

Synthesis, bioactivity, theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor

Liu, Xing-Hai,Chen, Pei-Quan,Wang, Bao-Lei,Li, Yong-Hong,Wang, Su-Hua,Li, Zheng-Ming

, p. 3784 - 3788 (2007)

Ketol-acid reductoisomerase (KARI; EC 1.1.1.86) catalyzes the second common step in branched-chain amino acid biosynthesis. The catalyzed process consists of two stages, the first of which is an alkyl migration from one carbon atom to its neighbouring ato

CATHODIC SYNTHESIS OF CYCLOPROPANE DERIVATIVES BY THE ELECTROLYSIS OF COMPOUNDS WITH AN ACTIVATED METHYLENE GROUP IN 1,2-DICHLOROETHANE

Vasil'ev, A. A.,Tatarinova, V. I.,Petrosyan, V. A.

, p. 631 - 633 (1990)

The cathodic electrolysis of compounds with an activated methylene group in 1,2-dichloroethane leads to 1,1-disubstituted cyclopropanes.The current yield of these cyclopropane derivatives depends on the CH-acidity of the starting compounds and has a maximum at pKa ca.13.

A new synthesis of bicyclic N,O- and N,S-enaminals by the anionic cyclization of alk-4-ynals with amino alcohols and amino thiols

Gvozdev,Shavrin,Nefedov

, p. 409 - 415 (2014)

A reaction of alk-4-ynals with aliphatic amino alcohols or 2-aminoethanethiol in the system DMSO - KOH gives bicyclic N,O- and N,S-enaminals: 6-methylidenehexahydro-2H-pyrrolo[2,1-b][1,3]oxazines, 5-methylidenehexahydropyrrolo[2,1-b]oxazoles, or 5-methyl-

MACROCYCLIC COMPOUNDS AS STING AGONISTS AND METHODS AND USES THEREOF

-

Paragraph 0306-0307, (2021/01/29)

Disclosed are macrocyclic compounds having the general Formula (I) or (II) and their tautomeric forms, stereoisomers, pharmaceutically acceptable salts, hydrates, solvates and prodrugs thereof, and their combination with suitable medicament, corresponding processes for the synthesis and pharmaceutical compositions and uses of compounds disclosed herein.

A class of chiral beta-hydroxyamide compounds, preparation method and applications thereof,

-

Paragraph 0167; 0178, (2020/03/12)

The invention discloses a chiral beta-hydroxyamide compound and a preparation method thereof, wherein the compound is represented by a formula I. According to the invention, the raw material for preparing a non-natural chiral amino acid compound is obtained by carrying out catalytic hydrolysis on a prochiral diamide compound II with different substituents by using a Rhodococcus erythropolis AJ270microbial system, wherein the use amount of the Rhodococcus erythropolis can be adjusted according to the use amount of a substrate, the reaction solvent is a common buffer solution with the pH valueof 6.0-8.0, the temperature is 20-37 DEG C, the reaction time is 3-120 h, and the Rhodococcus erythropolis microbial catalytic system can be cultured through fermentation and conveniently stored; andwith the application of the biotransformation to prepare chiral monoamide carboxylic acid and dicarboxylic acid, the characteristics of simplicity and convenience in operation, high reaction efficiency, mild reaction conditions, high enantioselectivity, easiness in product separation and high product purity are achieved, and the application prospect is god.

Quinazolinone Compound and Application Thereof

-

Paragraph 0760-0762, (2020/11/27)

The present invention relates to a series of quinazolinone compounds and applications thereof as PI3Kα inhibitors. In particular, the present invention relates to a compound shown in formula (I) and a tautomer or pharmaceutically acceptable salt thereof.

PARTIALLY SATURATED NITROGEN-CONTAINING HETEROCYCLIC COMPOUND

-

Paragraph 0289; 0290, (2015/06/17)

There are provided compounds having a superior PHD2 inhibitory effect that are represented by general formula (I'): (in the above-mentioned general formula (I'), W, Y, R2, R3, R4, and Y4 are as described hereinabove), or pharmaceutically acceptable salts thereof.

NOVEL COMPOUNDS

-

Page/Page column 66, (2015/12/17)

Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.

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