59795-89-0

Basic information

• Product Name: (2-ISOCYANOETHYL)BENZENE
• Synonyms: 2-PHENYLETHYL ISOCYANIDE;(2-ISOCYANOETHYL)BENZENE;HANSA ISN-0141;BIO-FARMA BF000689;PHENYLETHYL ISOCYANIDE;Phenylethyl isocyanide,96%;Phenylethyl isocyanide(2-Isocyanoethyl)benzene
• CAS NO: 59795-89-0
• Molecular Formula: C₉H₉N
• Molecular Weight: 131.17
• Mol File: 59795-89-0.mol

Chemical Properties

• Boiling Point: 52 °C (2.2503 mmHg)
• Appearance: clear light yellow liquid
• Density: 0.95
• Refractive Index: 1.518-1.52
• Storage Temp.: Refrigerator (+4°C)
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: (2-ISOCYANOETHYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: (2-ISOCYANOETHYL)BENZENE(59795-89-0)
• EPA Substance Registry System: (2-ISOCYANOETHYL)BENZENE(59795-89-0)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26
• Hazardous Substances Data: 59795-89-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2-Isocyanoethyl)Benzene is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its reactivity allows for the creation of a wide range of molecules with potential therapeutic applications.
Used in Chemical Synthesis:
(2-Isocyanoethyl)Benzene is used as a reagent in Ugi reactions, which are multi-component reactions that involve the condensation of an amine, an aldehyde or ketone, an isocyanide, and a carboxylic acid. This reaction is a powerful method for the synthesis of various complex organic molecules, including tetrazole and bisamide derivatives.
Used in Research and Development:
(2-Isocyanoethyl)Benzene is also utilized in research and development for the exploration of new chemical reactions and the synthesis of novel compounds with potential applications in various fields, such as materials science, agrochemistry, and pharmaceuticals.

Upstream product

• 6181-71-1 2-Phenylethylisocyaniddichlorid 
• 23069-99-0 N-(2-phenylethyl)formamide 
• 67-66-3 chloroform 
• 64-04-0 phenethylamine 
• 1895-39-2 sodium chlorodifluoroacetate 
• 64-18-6 formic acid 

Downstream Products

• 6181-71-1 2-Phenylethylisocyaniddichlorid 
• 215163-55-6 (S)-2-[2-([1-Phenethylcarbamoyl-2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl]-{3-[4-(4-phenoxy-phenoxy)-phenyl]-propionyl}-amino)-acetylamino]-pentanedioic acid dibenzyl ester 
• 215163-35-2 (S)-2-{(1-Phenethylcarbamoyl-ethyl)-[2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-phenoxymethyl-tetrahydro-pyran-2-yl)-acetyl]-amino}-pentanedioic acid dibenzyl ester 
• 215163-54-5 (S)-2-(2-{{1-Phenethylcarbamoyl-3-[4-(4-phenoxy-phenoxy)-phenyl]-propyl}-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-acetyl]-amino}-acetylamino)-pentanedioic acid dibenzyl ester 

Relevant articles and documents

Method for preparing isonitrile compound

The invention discloses a method for preparing an isonitrile compound, and belongs to the field of organic synthesis. According to the method, sodium chlorodifluoroacetate or potassium bromodifluoroacetate is used as a difluoromethyl source and is condensed with primary amine under the action of alkali to obtain an isocyanide target product, so that isocyanide is generated in situ on the primary amine. The reaction raw materials, alkali and solvent used in the method are simple and easy to obtain, wide in source and convenient to operate, do not need special storage and use conditions, the method has the advantages of safety, low cost, high yield, simple process, environmental friendliness and the like, and has important application value in the fields of medicine, protein and polypeptidepreparation, pesticides, high polymer materials, dyes and the like.

Discovery of a Potent Glutathione Peroxidase 4 Inhibitor as a Selective Ferroptosis Inducer

Potent and selective ferroptosis regulators promote an intensive understanding of the regulation and mechanisms underlying ferroptosis, which is highly associated with various diseases. In this study, through a stepwise structure optimization, a potent and selective ferroptosis inducer was developed targeting to inhibit glutathione peroxidase 4 (GPX4), and the structure-activity relationship (SAR) of these compounds was uncovered. Compound26aexhibited outstanding GPX4 inhibitory activity with a percent inhibition up to 71.7% at 1.0 μM compared to 45.9% of RSL-3. At the cellular level,26acould significantly induce lipid peroxide (LPO) increase and effectively induce ferroptosis with satisfactory selectivity (the value of 31.5). The morphological analysis confirmed the ferroptosis induced by26a. Furthermore,26asignificantly restrained tumor growth in a mouse 4T1 xenograft model without obvious toxicity.

PHYTOSPHINGOSINE DERIVATIVES AS ADJUVANTS IN IMMUNE STIMULATION

The invention relates to phytosphingosine derivatives, suitable as adjuvants in immune stimulation. The invention further relates to pharmaceutical compositions comprising such compounds and the medical use of said compounds and/or compositions in therapeutic or prophylactic methods of immune stimulation in a subject, and for use in the treatment of a disease, for which stimulation of an immune response in a subject produces a therapeutic benefit. The invention further relates to the phytosphingosine derivative as described herein for use as an adjuvant in a method of vaccinating a subject. The invention further relates to the phytosphingosine derivative as described herein for use in stimulating antibody production, stimulating an immune response against infection, stimulating an immune response against a cancer, or preventing and/or treating septic shock. The invention further relates to a method for the manufacture of said derivatives comprising an Ugi-4-component reaction (Ugi-4CR).

Continuous-flow synthesis of thioureas, enabled by aqueous polysulfide solution

We have developed the continuous-flow synthesis of thioureas in a multicomponent reaction starting from isocyanides, amidines, or amines and sulfur. The aqueous polysulfide solution enabled the application of sulfur under homogeneous and mild conditions. The crystallized products were isolated by simple filtration after the removal of the co-solvent, and the sulfur retained in the mother liquid. Presenting a wide range of thioureas synthesized by this procedure confirms the utility of the convenient continuous-flow application of sulfur.

Synthesis of isocyanides by reacting primary amines with difluorocarbene

A general, convenient, and friendly route for preparing a versatile building block of isocyanides from primary amines is developed. Difluorocarbene, generated in situ from decarboxylation of chlorodifluoroacetate, reacts efficiently with primary amines to produce isocyanides. Various primary amines are well tolerated, including aryl, heteroaryl, benzyl, and alkyl amines, as well as amine residues in amino acids and peptides. Late-stage functionalization of biologically active amines is demonstrated, showing its practical capacity in drug design and peptide modification.

Isocyanide 2.0

The isocyanide functionality due to its dichotomy between carbenoid and triple bond characters, with a nucleophilic and electrophilic terminal carbon, exhibits unusual reactivity in organic chemistry exemplified for example in the Ugi reaction. Unfortunately, the over proportional use of only a few isocyanides hampers novel discoveries about the fascinating reactivity of this functional group. The synthesis of a broad range of isocyanides with multiple functional groups is lengthy, inefficient, and exposes the chemist to hazardous fumes. Here we present an innovative isocyanide synthesis overcoming these problems by avoiding the aqueous workup which we exemplify by parallel synthesis from a 0.2 mmol scale performed in 96-well microtiter plates up to a 0.5 mol multigram scale. The advantages of our methodology include an increased synthesis speed, very mild conditions giving access to hitherto unknown or highly reactive classes of isocyanides, rapid access to large numbers of functionalized isocyanides, increased yields, high purity, proven scalability over 5 orders of magnitude, increased safety and less reaction waste resulting in a highly reduced environmental footprint. For example, the hitherto believed to be unstable 2-isocyanopyrimidine, 2-acylphenylisocyanides and even o-isocyanobenzaldehyde could be accessed on a preparative scale and their chemistry was explored. Our new isocyanide synthesis will enable easy access to uncharted isocyanide space and will result in many discoveries about the unusual reactivity of this functional group. This journal is

Metabolic Fate of the Isocyanide Moiety: Are Isocyanides Pharmacophore Groups Neglected by Medicinal Chemists?

Despite the isolation of hundreds of bioactive isocyanides from terrestrial fungi and bacteria as well as marine organisms, the isocyanide functionality has so far received little attention from a medicinal chemistry standpoint. The widespread tenet that isocyanides are chemically and metabolically unstable has restricted bioactivity studies to their antifouling properties and technical applications. In order to confirm or refute this idea, the hepatic metabolism of six model isocyanides was investigated. Aromatic and primary isocyanides turned out to be unstable and metabolically labile, but secondary and tertiary isocyanides resisted metabolization, showing, in some cases, cytochrome P450 inhibitory properties. The potential therefore exists for the secondary and tertiary isocyanides to qualify them as pharmacophore groups, in particular as war-heads for metalloenzyme inhibition because of their potent metal-coordinating properties.

The Generation of Difluoroketenimine and Its Application in the Synthesis of α,α-Difluoro-β-amino Amides

Fluorine-containing β-amino acids and their derivatives have attracted significant attention due to their importance in life sciences. Herein the previously unknown difluoroketenimine, the analogue of the elusive difluoroketene, has been generated by the

Efficient syntheses and anti-cancer activity of xenortides A-D including: Ent / epi -stereoisomers

A one-pot, two-step, total synthesis of naturally occurring xenortides A, B, C and D, (Xens A-D) isolated from the bacterium Xenorhabdus nematophila, and an entire complementary set of stereoisomers, has been achieved. Compounds were synthesized utilizing an isocyanide-based Ugi 4-CR followed by facile N-Boc deprotection. The reaction sequence took advantage of the chiral pool of N-Boc protected amino acids (l-Leu/Val and d-Leu/Val) with aryl isocyanides, phenyl acetaldehyde and methylamine giving the desired Xens A-D (A and B >98% ee) and all subsequent stereoisomers in reasonable yields upon deprotection followed by separation of diastereomers. Also, detailed mechanistic insights for diastereoselectivity of (-)-Xen A, as a model in the Ugi 4-CR, has been described. Moreover, for the first time, this focused library was screened for cytotoxicity against a panel of epithelial cancer cell lines as well as normal cell lines with an MTT proliferation assay. The structure-activity relationship (SAR) study demonstrated that tryptamides Xen B and D were more active than phenylethylamides Xen A and C. Furthermore, (-)-Xen B (IC50 = 19-25 μM) and ent-(+)-Xen D (IC50 = 21-26 μM) gave the highest cytotoxicity and they were also found to be non-toxic toward normal cells. Importantly, the SAR results indicate that the stereochemistry at C8 and C11 in (-)-Xen B and ent-(+)-Xen D play a critical role in cytotoxic activity.

Nonacidic Farnesoid X Receptor Modulators

As a cellular bile acid sensor, farnesoid X receptor (FXR) participates in regulation of bile acid, lipid and glucose homeostasis, and liver protection. Clinical results have validated FXR as therapeutic target in hepatic and metabolic diseases. To date, potent FXR agonists share a negatively ionizable function that might compromise their pharmacokinetic distribution and behavior. Here we report the development and characterization of a high-affinity FXR modulator not comprising an acidic residue.