176690-89-4

Basic information

• Product Name: (2E)-3-(4-tert-butylphenyl)acryloyl chloride
• Synonyms: (2E)-3-(4-tert-butylphenyl)acryloyl chloride;2-propenoyl chloride, 3-[4-(1,1-dimethylethyl)phenyl]-, (2;3-(4-tert-Butyl-phenyl)-acryloyl chloride
• CAS NO: 176690-89-4
• Molecular Formula: C13H15ClO
• Molecular Weight: 223
• Mol File: 176690-89-4.mol

Chemical Properties

• Boiling Point: 302.5±11.0 °C(Predicted)
• Appearance: /
• Density: 1.083±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (2E)-3-(4-tert-butylphenyl)acryloyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-(4-tert-butylphenyl)acryloyl chloride(176690-89-4)
• EPA Substance Registry System: (2E)-3-(4-tert-butylphenyl)acryloyl chloride(176690-89-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 176690-89-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2E)-3-(4-tert-butylphenyl)acryloyl chloride is used as a reagent for introducing acryloyl functional groups into a variety of organic compounds. Its presence in cross-coupling reactions and other synthetic processes facilitates the creation of a wide range of organic compounds with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (2E)-3-(4-tert-butylphenyl)acryloyl chloride is used as an intermediate in the synthesis of pharmaceutical compounds. Its ability to form various derivatives and functionalized products makes it a valuable component in the development of new drugs and medicinal agents.
Used in Chemical Research:
(2E)-3-(4-tert-butylphenyl)acryloyl chloride is utilized as a research compound in chemical laboratories. Its reactivity with nucleophiles and its role in cross-coupling reactions make it an important tool for studying reaction mechanisms and developing new synthetic methodologies.
Used in Material Science:
In material science, (2E)-3-(4-tert-butylphenyl)acryloyl chloride is used as a precursor in the development of new materials with specific properties. Its ability to form functionalized products can contribute to the creation of advanced materials for various applications, such as coatings, adhesives, and polymers.

Upstream product

• 1208-65-7 4-tert-butyl-trans-cinnamic acid 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 105393-26-8 ethyl 3-(4-t-butylphenyl) propenoate 
• 1208-65-7 3-(4-(tert-butyl)phenyl)acrylic acid 

Downstream Products

• 956282-58-9 (E)-5-bromo-2-[2-(4-tert-butylphenyl)vinyl]-1H-benzoimidazole 

Relevant articles and documents

Design, synthesis and evaluation against Chikungunya virus of novel small-molecule antiviral agents

Chikungunya virus is a re-emerging arbovirus transmitted to humans by mosquitoes, responsible for an acute flu-like illness associated with debilitating arthralgia, which can persist for several months or become chronic. In recent years, this viral infection has spread worldwide with a previously unknown virulence. To date, no specific antivirals treatments nor vaccines are available against this important pathogen. Starting from the structures of two antiviral hits previously identified in our research group with in silico techniques, this work describes the design and preparation of 31 novel structural analogues, with which different pharmacophoric features of the two hits have been explored and correlated with the inhibition of Chikungunya virus replication in cells. Structure-activity relationships were elucidated for the original scaffolds, and different novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these promising novel structures as antiviral agents against Chikungunya virus.

Rational modifications on a benzylidene-acrylohydrazide antiviral scaffold, synthesis and evaluation of bioactivity against Chikungunya virus

Chikungunya virus is a re-emerging arbovirus transmitted to humans by Aedes mosquitoes, responsible for an acute febrile illness associated with painful and debilitating arthralgia, which can persist for several months or become chronic. Over the past few years, infection with this virus has spread worldwide with a previously unknown virulence. No specific antiviral treatments nor vaccines are currently available against this important pathogen. Starting from the structure of a class of selective anti-CHIKV agents previously identified in our research group, different modifications to this scaffold were rationally designed, and 69 novel small-molecule derivatives were synthesised and evaluated for their inhibition of Chikungunya virus replication in Vero cells. Further structure-activity relationships associated with this class of antiviral agents were elucidated for the original scaffolds, and novel antiviral compounds with EC50 values in the low micromolar range were identified. This work provides the foundation for further investigation of these new structures as antivirals against Chikungunya virus.

Identification and Structure-Activity Relationships of Novel Compounds that Potentiate the Activities of Antibiotics in Escherichia coli

In Gram-negative bacteria, efflux pumps are able to prevent effective cellular concentrations from being achieved for a number of antibiotics. Small molecule adjuvants that act as efflux pump inhibitors (EPIs) have the potential to reinvigorate existing antibiotics that are currently ineffective due to efflux mechanisms. Through a combination of rigorous experimental screening and in silico virtual screening, we recently identified novel classes of EPIs that interact with the membrane fusion protein AcrA, a critical component of the AcrAB-TolC efflux pump in Escherichia coli. Herein, we present initial optimization efforts and structure-activity relationships around one of those previously described hits, NSC 60339 (1). From these efforts we identified two compounds, SLUPP-225 (17h) and SLUPP-417 (17o), which demonstrate favorable properties as potential EPIs in E. coli cells including the ability to penetrate the outer membrane, improved inhibition of efflux relative to 1, and potentiation of the activity of novobiocin and erythromycin.

Discovery and Characterization of ACT-451840: an Antimalarial Drug with a Novel Mechanism of Action

More than 40 % of the world's population is at risk of being infected with malaria. Most malaria cases occur in the countries of sub-Saharan Africa, Central and South America, and Asia. Resistance to standard therapy, including artemisinin combinations, is increasing. There is an urgent need for novel antimalarials with new mechanisms of action. In a phenotypic screen, we identified a series of phenylalanine-based compounds that exhibit antimalarial activity via a new and yet unknown mechanism of action. Our optimization efforts culminated in the selection of ACT-451840 [(S,E)-N-(4-(4-acetylpiperazin-1-yl)benzyl)-3-(4-(tert-butyl)phenyl)-N-(1-(4-(4-cyanobenzyl)piperazin-1-yl)-1-oxo-3-phenylpropan-2-yl)acrylamide] for clinical development. Herein we describe our optimization efforts from the screening hit to the potential drug candidate with respect to antiparasitic activity, drug metabolism and pharmacokinetics (DMPK) properties, and in vivo pharmacological efficacy.

Benzo[d]imidazole transient receptor potential vanilloid 1 antagonists for the treatment of pain: Discovery of trans-2-(2-{2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-1H-benzimidazol-5-yl}-phenyl)-propan-2-ol (Mavatrep)

Reported herein is the design, synthesis, and pharmacologic characterization of a class of TRPV1 antagonists constructed on a benzo[d]imidazole platform that evolved from a biaryl amide lead. This design composes three sections: a 2-substituted 5-phenyl headgroup attached to the benzo[d]imidazole platform, which is tethered at the two position to a phenyl tail group. Optimization of this design led to the identification of 4 (mavatrep), comprising a trifluoromethyl-phenyl-vinyl tail. In a TRPV1 functional assay, using cells expressing recombinant human TRPV1 channels, 4 antagonized capsaicin-induced Ca2+ influx, with an IC50 value of 4.6 nM. In the complete Freund's adjuvant- and carrageenan-induced thermal hypersensitivity models, 4 exhibited full efficacy, with ED80 values of 7.8 and 0.5 mg/kg, respectively, corresponding to plasma levels of 270.8 and 9.2 ng/mL, respectively. On the basis of its superior pharmacologic and safety profile, 4 (mavatrep) was selected for clinical development for the treatment of pain.

Palladium-catalyzed alkoxycarbonylation of terminal alkenes to produce α,β-unsaturated esters: The key role of acetonitrile as a ligand

A mild protocol has been developed for the PdII-catalyzed alkoxycarbonylation of terminal olefins to produce α,β-unsaturated esters with a wide range of substrates. Key features are the use of MeCN as solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O2, which facilitates the CuII-mediated reoxidation of the Pd0 complex to Pd II and prevents double carbonylation. Acetonitrile is the key! A mild protocol has been developed for the PdII-catalyzed alkoxycarbonylation of terminal olefins to produce α,β-unsaturated esters with a wide range of substrates (see scheme). Key features are the use of MeCN as a solvent (and/or ligand) to control the reactivity of the intermediate Pd complexes and the combination of CO with O2, which facilitates the CuII-mediated reoxidation of Pd0 to PdII and prevents double carbonylation.

The design, synthesis and in vitro immunosuppressive evaluation of novel isobenzofuran derivatives

The synthesis and biological evaluation of a series of novel isobenzofuran-based compounds are described. The compounds were evaluated for their immunosuppressive effects of T-cell proliferation and IMPDH type II inhibitor activity in vitro, as well as their structure-activity relationships were assessed. Several compounds demonstrated highly efficacious immunosuppressive properties, especially compounds 2d, 2e, 2h and 2j, which were superior to MPA, while compounds 2k, 2m, 2n, 4c and 5d exhibited an equipotent inhibitory activity compared to MPA. Generally, it was obviously demonstrated that α,β-unsaturated amides proved more potent than the diamide and urea series. The present study provides a guide for further research on development of safe and effective immunosuppressive agents.

Discovery of potent, orally available vanilloid receptor-1 antagonists. Structure-activity relationship of N-aryl cinnamides

The vanilloid receptor-1 (TRPV1 or VR1) is a member of the transient receptor potential (TRP) family of ion channels and plays a role in regulating the function of sensory nerves. A growing body of evidence demonstrates the therapeutic potential of TRPV1 modulators, particularly in the management of pain. As a result of our screening efforts, we identified (E)-3-(4-tert- butylphenyl)-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylamide (1), an antagonist that blocks the capsaicin-induced and pH-induced uptake of 45Ca2+ in TRPV1-expressing Chinese hamster ovary cells with IC50 values of 17 ± 5 and 150 ± 80 nM, respectively. In this report, we describe the synthesis and structure-activity relationship of a series of N-aryl cinnamides, the most potent of which (49a and 49b) exhibit good oral bioavailability in rats (Foral = 39% and 17%, respectively).

Non-thiol farnesyltransferase inhibitors: Utilization of the far aryl binding site by 5-cinnamoylaminobenzophenones

We recently described two novel aryl binding sites of farnesyltransferase. In this study, the cinnamoyl residue was designed as an appropriate substituent for our benzophenone-based AAX-peptidomimetic compound capable of occupying the far aryl binding site.