625-35-4

Basic information

• Product Name: (E)-2-Butenoyl chloride
• Synonyms: TRANS-CROTONYL CHLORIDE;E-Crotonoylchloride;Crotonoyl chloride technical grade, 90%;TRANS-2-BUTENOYL CHLORIDE;CROTONYL CHLORIDE;CROTONIC ACID CHLORIDE;E-CROTONYL CHLORIDE;(e)-2-butenoylchlorid
• CAS NO: 625-35-4
• Molecular Formula: C₄H₅ClO
• Molecular Weight: 104.53
• EINECS: 234-010-3
• Product Categories: Acid Halides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 625-35-4.mol

Chemical Properties

• Melting Point: 72-74 °C
• Boiling Point: 120-123 °C(lit.)
• Flash Point: 95 °F
• Appearance: Clear colorless to brown/Liquid
• Density: 1.091 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.459(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 506118
• CAS DataBase Reference: (E)-2-Butenoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-Butenoyl chloride(625-35-4)
• EPA Substance Registry System: (E)-2-Butenoyl chloride(625-35-4)

Safety Data

• Hazard Codes: C
• Statements: 10-34-36/37-37
• Safety Statements: 16-26-27-36/37/39-45-28A-24/25
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• F: 13-19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 625-35-4(Hazardous Substances Data)

Usage

Uses

Used in Agrochemical Industry:
(E)-2-Butenoyl chloride is used as an intermediate in the synthesis of agrochemicals for its ability to form various derivatives with biological activity. It is particularly useful in the production of pesticides and herbicides, where its reactivity allows for the formation of stable and effective compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (E)-2-Butenoyl chloride is used as a key building block in the synthesis of various drugs and drug candidates. Its reactivity enables the formation of diverse chemical structures, which can be further modified to develop new therapeutic agents with improved pharmacological properties.
Used in Dyestuff Industry:
(E)-2-Butenoyl chloride is used as a starting material in the synthesis of dyes and pigments, where its ability to form conjugated systems and reactive intermediates is exploited to create a wide range of colorants with different properties.
Used in Synthesis of α,β-Unsaturated Esters:
(E)-2-Butenoyl chloride is used as a precursor in the synthesis of α,β-unsaturated esters, which are important intermediates in organic chemistry. These esters are used in the production of various chemicals, including fragrances, flavors, and pharmaceuticals, as well as in the synthesis of other complex organic compounds.

Purification Methods

If the IR of a film has no OH bands, then fractionally distil it, taking the middle fraction and redistilling it. If OH bands are present, then add excess of oxalyl chloride, reflux for 3hours, then distil off the reagent and fractionally distil the crotonoyl chloride as before. Stabilise the distillate with 160ppm of hydroquinone. The amide forms needles m 158o from aqueous ammonia, and the anilide also forms needles but with m 115-118o from H2O. [Beilstein 2 H 411, 2 I 188, 2 II 392, 2 III 1265, 2 IV 1506.]

InChI:InChI=1/C4H5ClO/c1-2-3-4(5)6/h2-3H,1H3/b3-2+

Upstream product

• 190734-66-8 (E)-1-(but-2-enoyl)pyrrolidin-2-one 
• 625-68-3 3-chlorobutyric acid 
• 107-93-7 (E)-but-2-enoic acid 
• 3724-65-0 2-butenoic acid 
• 98-88-4 benzoyl chloride 
• 50966-31-9 1,1-dichloroethyl ethyl ether 

Downstream Products

• 97060-28-1 (E)-1-(4-bromophenyl)-3-hydroxybutan-1-one 
• 80445-62-1 1-(3,4-dimethyl-phenyl)-buten-(2t)-one-⁽¹⁾ 
• 109340-65-0 (E)-5-isopropyl-2-methylphenyl but-2-enoate 
• 35322-84-0 3,4,7-Trimethyl-1-indanone 
• 74118-09-5 CH₃CHCHCOO-menthyl 
• 101276-69-1 1-(2,4-diisopropyl-phenyl)-but-2t-en-1-one 
• 109340-66-1 (E)-2-isopropyl-5-methylphenyl but-2-enoate 
• 99059-11-7 1-(2,4,5-trihydroxy-phenyl)-but-2t-en-1-one 
• 102177-67-3 N-benzyl-N-(2-phenoxy-ethyl)-trans-crotonamide 
• 93646-32-3 N-methyl-o-chloro-crotonanilide 
• 100372-04-1 trans-crotonic acid-(4-propionyl-anilide) 
• 60034-28-8 2-Butenoyl isothiocyanate 
• 18631-68-0 3-methyl-2,3,4,5,6,7-hexahydro-inden-1-one 

Relevant articles and documents

Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum

Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.

Synthesis and Biological Evaluation of Celastrol Derivatives with Improved Cytotoxic Selectivity and Antitumor Activities

Cdc37 associates kinase clients to Hsp90 and promotes the development of cancers. Celastrol, a natural friedelane triterpenoid, can disrupt the Hsp90-Cdc37 interaction to provide antitumor effects. In this study, 31 new celastrol derivatives, 2a - 2d , 3a - 3g , and 4a - 4t , were designed and synthesized, and their Hsp90-Cdc37 disruption activities and antiproliferative activities against cancer cells were evaluated. Among these compounds, 4f , with the highest tumor cell selectivity (15.4-fold), potent Hsp90-Cdc37 disruption activity (IC50= 1.9 μM), and antiproliferative activity against MDA-MB-231 cells (IC50= 0.2 μM), was selected as the lead compound. Further studies demonstrated 4f has strong antitumor activities both in vitro and in vivo through disrupting the Hsp90-Cdc37 interaction and inhibiting angiogenesis. In addition, 4f exhibited less toxicity than celastrol and showed a good pharmacokinetics profile in vivo. These findings suggest that 4f may be a promising candidate for development of new cancer therapies.

Bromo Radical-Mediated Photoredox Aldehyde Decarbonylation towards Transition-Metal-Free Hydroalkylation of Acrylamides at Room Temperature

Herein, we report a visible-light-mediated hydroalkylation reaction of alkenes using easily available aldehydes as alkyl sources via bromo radical-promoted photoredox decarbonylation. This protocol provides an alternative entry to C(sp3)?C(sp3) bond formation and features considerable advantages including mild and clean reaction conditions, obviation for transition-metal catalyst, and good functional group compatibility.

Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes

Cross-electrophile coupling reactions of two Csp3-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center.

PROCESS FOR THE PREPARATION OF PIPERINE

The present application relates to a process for the preparation of piperine of high purity having low concentrations of isomeric impurities.

Visible light photocatalytic asymmetric synthesis of pyrrolo[1,2-: A] indoles via intermolecular [3+2] cycloaddition

The intermolecular diastereoselective and enantioselective synthesis of pyrrolo[1,2-a]indoles is developed through a [3+2] cycloaddition between silyl-indole derivatives and α,β-unsaturated N-acyl oxazolidinones by merging photocatalysis and Lewis acid catalysis.

SPIRO-LACTAM NMDA MODULATORS AND METHODS OF USING SAME

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders. Orally delivered formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

Formal Lossen Rearrangement/[3+2] Annulation Cascade Catalyzed by a Modified Cyclopentadienyl RhIII Complex

It has been established that a cyclopentadienyl RhIII complex with two phenyl groups and a pendant amide moiety catalyzes the formal Lossen rearrangement/[3+2] annulation cascade of N-pivaloyl benzamides and acrylamides with alkynes leading to substituted indoles and pyrroles. Mechanistic studies revealed that this cascade reaction proceeds via not the Lossen rearrangement to form anilides or enamides but C?H bond cleavage, alkyne insertion, and the formal Lossen rearrangement.

Design, synthesis, antiproliferative activity and docking studies of quinazoline derivatives bearing 2,3-dihydro-indole or 1,2,3,4-tetrahydroquinoline as potential EGFR inhibitors

Eight series of quinazoline derivatives bearing 2,3-dihydro-indole or 1,2,3,4-tetrahydroquinoline were designed, synthesized and evaluated for the IC50 values against three cancer cell lines (A549, MCF-7 and PC-3). Most of the forty nine target compounds showed excellent antiproliferative activity against one or several cancer cell lines. The compound 13a showed the best activity against A549, MCF-7 and PC-3 cancer cell lines, with the IC50 values of 1.09 ± 0.04 μM, 1.34 ± 0.13 μM and 1.23 ± 0.09 μM, respectively. Eight selected compounds were further selected to evaluated for the inhibitory activity against EGFR kinase. Three of them showed equal activity against EGFR kinase to positive control afatinib. AnnexinV-FITC, propidium iodide (PI) double staining and acridine orange single staining results indicated that the compound 13a could induce apoptosis of human lung cancer A549 cells.

Preliminary investigations into the synthesis and antimicrobial activities of boron-containing capsaicinoids

This preliminary study reports on the synthesis of two new boron-capsaicin derivatives containing either a short or long chain aliphatic tail group using an iridium catalyzed hydroboration reaction with pinacolborane. The boronate ester groups reside on the terminal position of the tail group and are necessary for the bioactivity of these compounds. Indeed, both compounds showed considerable activity against two Gram-positive bacteria, including Vancomycin-resistant Enterococcus. Vancomycin is considered the last resort medication for the treatment of septicemia, and new antibacterial agents that can treat sepsis are of paramount importance. The more lipophilic boron compound with the longer aliphatic chain also showed antifungal activity against Saccharomyces cerevisiae.