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(2E)-3-phenyl-2-(phenylcarbonyl)prop-2-enenitrile, also known as benzylidene malononitrile, is a chemical compound with the molecular formula C17H11N. It is a yellow solid that is widely used in organic synthesis as a reactant in the preparation of various compounds, including heterocycles and pharmaceuticals. Benzylidene malononitrile is known for its ability to undergo various chemical reactions, such as Knoevenagel condensation and Michael addition, which makes it a versatile building block in organic chemistry. It is also used as a fluorescent probe for the detection of cysteine in biological samples, making it useful in biochemical research. However, benzylidene malononitrile is a hazardous chemical and should be handled with care due to its toxicity and potential health hazards.

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  • 20413-05-2 Structure
  • Basic information

    1. Product Name: (2E)-3-phenyl-2-(phenylcarbonyl)prop-2-enenitrile
    2. Synonyms: (2E)-2-Benzoyl-3-phenylacrylonitrile; 2-Benzoyl-3-phenylacrylonitrile; benzenepropanenitrile, beta-oxo-alpha-(phenylmethylene)-, (alphaE)-
    3. CAS NO:20413-05-2
    4. Molecular Formula: C16H11NO
    5. Molecular Weight: 233.2646
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 20413-05-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 397.4°C at 760 mmHg
    3. Flash Point: 194.1°C
    4. Appearance: N/A
    5. Density: 1.169g/cm3
    6. Vapor Pressure: 1.6E-06mmHg at 25°C
    7. Refractive Index: 1.635
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: (2E)-3-phenyl-2-(phenylcarbonyl)prop-2-enenitrile(CAS DataBase Reference)
    11. NIST Chemistry Reference: (2E)-3-phenyl-2-(phenylcarbonyl)prop-2-enenitrile(20413-05-2)
    12. EPA Substance Registry System: (2E)-3-phenyl-2-(phenylcarbonyl)prop-2-enenitrile(20413-05-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 20413-05-2(Hazardous Substances Data)

20413-05-2 Usage

Uses

Used in Organic Synthesis:
(2E)-3-phenyl-2-(phenylcarbonyl)prop-2-enenitrile is used as a reactant in the preparation of various compounds, including heterocycles and pharmaceuticals, for its ability to undergo various chemical reactions such as Knoevenagel condensation and Michael addition.
Used in Biochemical Research:
(2E)-3-phenyl-2-(phenylcarbonyl)prop-2-enenitrile is used as a fluorescent probe for the detection of cysteine in biological samples, making it useful in biochemical research.
Used in Pharmaceutical Industry:
(2E)-3-phenyl-2-(phenylcarbonyl)prop-2-enenitrile is used as a building block in the synthesis of pharmaceuticals due to its versatility in undergoing various chemical reactions.
Used in Hazardous Chemical Handling:
(2E)-3-phenyl-2-(phenylcarbonyl)prop-2-enenitrile is used as a reference for proper handling and safety measures due to its toxicity and potential health hazards.

Check Digit Verification of cas no

The CAS Registry Mumber 20413-05-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,4,1 and 3 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 20413-05:
(7*2)+(6*0)+(5*4)+(4*1)+(3*3)+(2*0)+(1*5)=52
52 % 10 = 2
So 20413-05-2 is a valid CAS Registry Number.

20413-05-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-2-benzoyl-3-phenylprop-2-enenitrile

1.2 Other means of identification

Product number -
Other names VOMBBXQRJHALLY-RVDMUPIBSA

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:20413-05-2 SDS

20413-05-2Relevant articles and documents

Magnesium Halide-Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes

Ogura, Kazuki,Shibata, Ikuya,Shimazu, Jun-ya,Suzuki, Itaru

supporting information, p. 2785 - 2787 (2021/06/26)

MgX2-catalyzed annulation of methylenecyclopropanes with acyl cyanoalkenes was accomplished to give oxaspiro[2.5]octenes in excellent yields. The reaction proceeded through a rare intramolecular oxa-Michael addition of Mg enolate. The oxaspiro

Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles

Chang, Weixing,Kong, Jingyang,Li, Jing,Liu, Lingyan,Wang, Hongkai,Zeng, Tianlong

supporting information, p. 4024 - 4032 (2021/07/12)

Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).

Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures

Delost, Michael D.,Njardarson, Jon T.

supporting information, p. 6121 - 6125 (2021/08/16)

We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Development of Tyrphostin Analogues to Study Inhibition of the Mycobacterium tuberculosis Pup Proteasome System**

Janssen, Guido V.,Zhang, Susan,Merkx, Remco,Schiesswohl, Christa,Chatterjee, Champak,Darwin, K. Heran,Geurink, Paul P.,van der Heden van Noort, Gerbrand J.,Ovaa, Huib

, p. 3082 - 3089 (2021/09/14)

Tuberculosis is a global health problem caused by infection with the Mycobacterium tuberculosis (Mtb) bacteria. Although antibiotic treatment has dramatically reduced the impact of tuberculosis on the population, the existence and spreading of drug resist

HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE INCLUDING SAME

-

Paragraph 0142; 0143, (2018/03/10)

The present specification relates to a hetero-cyclic compound and an organic light emitting device comprising the same.

Dienamine-Mediated Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Linear Deconjugated Enones: Diversity-Oriented Synthesis of 3,4-Dihydropyrans

Maity, Rajendra,Pan, Subhas Chandra

supporting information, p. 871 - 874 (2017/02/15)

The first organocatalytic asymmetric inverse-electron-demand Diels–Alder reaction of deconjugated enones by using a linear dienamine was explored. Electron-poor oxadienes having a cyano group were found to be suitable in this reaction. With a 20 mol-% loa

Organocatalytic Asymmetric [4+2] Cycloaddition of 1-Acetylcyclopentene and 1-Acetylcyclohexene for the Synthesis of Fused Carbocycles

Nath, Utpal,Pan, Subhas Chandra

supporting information, p. 6457 - 6461 (2017/12/01)

The first organocatalytic asymmetric [4+2]-cycloaddition reaction of 1-acetylcyclopentenes and 1-acetylcyclohexenes was developed. Enones having cyano groups were used as the dienophiles in this method. The reaction provides a useful practical route to th

Development of 1H-Pyrazolo[3,4-b]pyridines as Metabotropic Glutamate Receptor 5 Positive Allosteric Modulators

Hill, Matthew D.,Fang, Haiquan,Brown, Jeffrey M.,Molski, Thaddeus,Easton, Amy,Han, Xiaojun,Miller, Regina,Hill-Drzewi, Melissa,Gallagher, Lizbeth,Matchett, Michele,Gulianello, Michael,Balakrishnan, Anand,Bertekap, Robert L.,Santone, Kenneth S.,Whiterock, Valerie J.,Zhuo, Xiaoliang,Bronson, Joanne J.,Macor, John E.,Degnan, Andrew P.

supporting information, p. 1082 - 1086 (2016/12/18)

The metabotropic glutamate receptor 5 (mGluR5) is an attractive target for the treatment of schizophrenia due to its role in regulating glutamatergic signaling in association with the N-methyl-d-aspartate receptor (NMDAR). We describe the synthesis of 1H-pyrazolo[3,4-b]pyridines and their utility as mGluR5 positive allosteric modulators (PAMs) without inherent agonist activity. A facile and convergent synthetic route provided access to a structurally diverse set of analogues that contain neither the aryl-acetylene-aryl nor aryl-methyleneoxy-aryl elements, the predominant structural motifs described in the literature. Binding studies suggest that members of our new chemotype do not engage the receptor at the MPEP and CPPHA mGluR5 allosteric sites. SAR studies culminated in the first non-MPEP site PAM, 1H-pyrazolo[3,4-b]pyridine 31 (BMT-145027), to improve cognition in a preclinical rodent model of learning and memory.

One-pot highly diastereoselective annulation to N-unprotected tetrasubstituted 2-pyrrolines

Meninno, Sara,Capobianco, Amedeo,Peluso, Andrea,Lattanzi, Alessandra

supporting information, p. 2137 - 2140 (2015/04/27)

A one-pot DABCO-catalysed Michael addition of glycine imine-derived esters to trans-2-aroyl-3-arylacrylonitriles followed by a deprotection/cyclization/tautomerization sequence afforded tetrasubstituted N-unprotected trans-2-pyrrolines in up to 96% yield.

Reduced graphene oxide supported piperazine in aminocatalysis

Rodrigo, Eduardo,García Alcubilla, Beatriz,Sainz, Raquel,Fierro, J. L. García,Ferritto, Rafael,Cid, M. Belén

supporting information, p. 6270 - 6273 (2014/06/09)

Reduced graphene oxide (rGO) has been used as a support for piperazine to provide a heterogeneous bifunctional organocatalyst (rGO-NH) that is able to efficiently promote vintage organic transformations such as Knoevenagel, Michael and aldol reactions. The obtained results suggest a significant role of the support in the course of these reactions. This journal is the Partner Organisations 2014.

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