10432-44-7

Basic information

• Product Name: 2-[1-(2-THIENYL)ETHYLIDENE]MALONONITRILE
• Synonyms: 2-[1-(2-THIENYL)ETHYLIDENE]MALONONITRILE;(1-(2-Thienyl)ethylidene)malononitrile;α-Cyano-β-(2-thienyl)crotononitrile;2-(1-(Thiophen-2-yl)ethylidene)malononitrile
• CAS NO: 10432-44-7
• Molecular Formula: C₉H₆N₂S
• Molecular Weight: 174.22
• Mol File: 10432-44-7.mol

Chemical Properties

• Melting Point: 88-90°C
• Boiling Point: 296.3 °C at 760 mmHg
• Flash Point: 133 °C
• Appearance: /
• Density: 1.219 g/cm³
• Vapor Pressure: 0.00144mmHg at 25°C
• Refractive Index: 1.588
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 2-[1-(2-THIENYL)ETHYLIDENE]MALONONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[1-(2-THIENYL)ETHYLIDENE]MALONONITRILE(10432-44-7)
• EPA Substance Registry System: 2-[1-(2-THIENYL)ETHYLIDENE]MALONONITRILE(10432-44-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 10432-44-7(Hazardous Substances Data)

Usage

Uses

Used in Dye Industry:
TTME is used as a dye intermediate for its ability to contribute to the color and stability of dyes, enhancing the performance of dye products in various applications.
Used in Pharmaceutical Industry:
TTME is utilized in the synthesis of pharmaceuticals, serving as a key component in the development of new drugs, due to its chemical properties that can be manipulated to create a range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, TTME is employed in the synthesis of agrochemicals, potentially contributing to the development of more effective and targeted pesticides or other agricultural chemicals.
Used in Organic Electronics and Optoelectronics:
TTME is used in the research and development of organic electronics and optoelectronic devices, where its unique properties may be leveraged to improve device performance or create new types of electronic components.
Used in Chemical Research:
TTME's sensitivity to Diels-Alder reactions makes it a valuable subject for chemical research, where understanding and controlling these reactions can lead to advancements in synthetic chemistry and material science.

InChI:InChI=1/C9H6N2S/c1-7(8(5-10)6-11)9-3-2-4-12-9/h2-4H,1H3

Upstream product

• 88-15-3 2-Acetylthiophene 
• 109-77-3 malononitrile 

Downstream Products

• 143644-43-3 1-amino-2-nitro-3-phenyl-5-(2'-thienyl)-6-benzenecarbonitrile 
• 112906-28-2 2-amino-4,6-di(thiophen-2-yl)isophthalonitrile 
• 133405-30-8 2-Amino-4-benzo[1,3]dioxol-5-yl-6-thiophen-2-yl-isophthalonitrile 
• 112906-25-9 2-[(Z)-3-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1-thiophen-2-yl-allylidene]-malononitrile 
• 77198-56-2 3-amino-5-(thiophen-2-yl)-[1,1'-biphenyl]-2,4-dicarbonitrile 
• 112906-24-8 2-[(Z)-3-(4-Dimethylamino-phenyl)-1-thiophen-2-yl-allylidene]-malononitrile 
• 6017-21-6 benzeneazomalononitrile 
• 112906-22-6 2-[(Z)-3-(4-Chloro-phenyl)-1-thiophen-2-yl-allylidene]-malononitrile 
• 120131-39-7 6-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-2-imino-4-thiophen-2-yl-cyclohex-3-ene-1,1,3-tricarbonitrile 
• 112906-25-9 2-[(E)-3-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-1-thiophen-2-yl-allylidene]-malononitrile 
• 112906-21-5 2-((Z)-3-Phenyl-1-thiophen-2-yl-allylidene)-malononitrile 
• 133379-60-9 5-(2-thienyl)-2,7-dithioxo-3,8-N-phenyl-1,2,3,7,8-pentahydropyrido<2,3-d>pyrimidine-4-imine 
• 102354-26-7 2-[(E)-3-(Ethyl-phenyl-amino)-1-thiophen-2-yl-allylidene]-malononitrile 
• 102354-27-8 2-[(E)-3-(Butyl-phenyl-amino)-1-thiophen-2-yl-allylidene]-malononitrile 

Relevant articles and documents

Synthesis of Substituted 4-(Thiophen-2-yl)nicotinonitriles

Abstract: A series of 4-(thiophen-2-yl)-substituted nicotinonitriles were prepared by a three step procedure including condensation and cyclization of 2-acetylthiophene. A more efficient synthesis of the target products is proposed and the transformation

Asymmetric organocatalytic vinylogous Michael addition triggered triple-cascade reactions of 2-hydroxycinnamaldehydes and vinylogous nucleophiles: construction of benzofused oxabicyclo[3.3.1]nonane scaffolds

An organocatalytic vinylogous Michael addition triggered triple-cascade reaction has been developed. 2-Hydroxycinnamaldehydes worked under iminium activation with either acyclic or cyclic ketone-derived α,α-dicyanoalkenes, yielding the benzofused oxabicyclo[3.3.1]nonanes bearing one quaternary stereocenter with excellent stereoselectivities.

A [5 + 1] annulation strategy for the synthesis of multifunctional biaryls and: P -teraryls from 1,6-Michael acceptor ketene dithioacetals

A new type of ketene dithioacetal, 2-(3,3-bis-methylsulfanyl-1-arylallylidene)malononitriles containing 1,4 and 1,6-Michael acceptors, were synthesized to study their reactivity for the synthesis of a new molecular entity. We report a [5 + 1] annulation s

Transition metal free synthesis of multifunctional thiomethylated-benzenes from aryl/heteroaryl/cyclopropyl methyl ketones

A base-promoted strategic synthesis of various functionalized thiomethylated-benzenes has been established from aryl/heteroaryl/cyclopropyl methyl ketone. We can directly access the thiomethylated-benzene nucleus embedded with diverse functional group by

"on Water" Direct Catalytic Vinylogous Aldol Reaction of Silyl Glyoxylates

The unique reactivity of water in the direct catalytic vinylogous aldol reaction of silyl glyoxylates is reported. With the hydrogen-bonding networks from water, the unfavorable homogeneous reactions in organic solvents were severely suppressed, and the "

Chemoselective synthesis of m-teraryls through ring transformation of 2 H-pyran-2-ones by 2-(1-arylethylidene)-malononitriles

We have developed a simple, efficient and chemoselective approach for the synthesis of m-teraryls by the reaction of 6-aryl-2-oxo-4-(sec.amino)-2H-pyran-3-carbonitriles and 2-(1-arylethylidene)malononitriles under basic conditions. We used 6-aryl-2-oxo-4-

Synthesis and antimicrobial activity of some novel 2-thienyl substituted heterocycles

A series of 2-thienyl substituted derivatives of thiazoles, oxazoles and spiro(indole-azole) were synthesized. The structures of the synthesized compounds were confirmed by IR, NMR and mass spectral data.

Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors

Inactivation of the NF-κB signaling pathway by inhibition of IKKβ is a well-known approach to treat inflammatory diseases such as rheumatoid arthritis and cancer. Thienopyrimidine-based analogues were designed through modification of the known IKKβ inhibitor, SPC-839, and then biologically evaluated. The resulting analogues had good inhibitory activity against both nitric oxide and TNF-α, which are well-known inflammatory responses generated by activated NF-κB. However, no inhibitory activity against IKKβ was observed with these compounds. The thienopyrimidine-based analogues were subsequently screened for a target kinase, and FLT3, which is a potential target for acute myeloid leukemia (AML), was identified. Thienopyrimidine-based FLT3 inhibitors showed good inhibition profiles against FLT3 under 1 μM. Overall, these compounds represent a promising family of inhibitors for future development of a treatment for AML.

Discovery of thienopyrimidine-based FLT3 inhibitors from the structural modification of known IKKβ inhibitors

Inactivation of the NF-κB signaling pathway by inhibition of IKKβ is a well-known approach to treat inflammatory diseases such as rheumatoid arthritis and cancer. Thienopyrimidine-based analogues were designed through modification of the known IKKβ inhibitor, SPC-839, and then biologically evaluated. The resulting analogues had good inhibitory activity against both nitric oxide and TNF-α, which are well-known inflammatory responses generated by activated NF-κB. However, no inhibitory activity against IKKβ was observed with these compounds. The thienopyrimidine-based analogues were subsequently screened for a target kinase, and FLT3, which is a potential target for acute myeloid leukemia (AML), was identified. Thienopyrimidine-based FLT3 inhibitors showed good inhibition profiles against FLT3 under 1 μM. Overall, these compounds represent a promising family of inhibitors for future development of a treatment for AML.

Improved synthesis of mono- and disubstituted 2-halonicotinonitriles from alkylidene malononitriles

Pyridines with 2,3,4 and/or 5 substitution remain challenging to prepare. Existing strategies to form multisubstituted 2-halonicotinonitriles via enamines suffer from dimerization of the starting alkylidene malononitriles resulting in low yields. Through alteration of reaction conditions, a new high yielding method into enamines was realized by condensing DMF-DMA and alkylidene malononitriles in the presence of substoichiometric acetic anhydride. Cyclization of the resulting enamines under Pinner conditions provided 2-halonicotinonitriles in high overall yields.