Welcome to LookChem.com Sign In|Join Free

CAS

  • or
3-(2-Isocyanoethyl)-1H-indole is a chemical compound with the molecular formula C11H10N2O. It is a derivative of indole, a heterocyclic compound commonly found in naturally occurring molecules. 3-(2-Isocyanoethyl)-1H-indole is known for its potential biological activities and is of interest in medicinal chemistry.

100571-64-0 Suppliers

Post Buying Request

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier
  • 100571-64-0 Structure
  • Basic information

    1. Product Name: 3-(2-isocyanoethyl)-1H-indole
    2. Synonyms: 3-(2-isocyanoethyl)-1H-indole;1H-Indole, 3-(2-isocyanoethyl)-
    3. CAS NO:100571-64-0
    4. Molecular Formula: C11H10N2
    5. Molecular Weight: 170.214
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 100571-64-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 3-(2-isocyanoethyl)-1H-indole(CAS DataBase Reference)
    10. NIST Chemistry Reference: 3-(2-isocyanoethyl)-1H-indole(100571-64-0)
    11. EPA Substance Registry System: 3-(2-isocyanoethyl)-1H-indole(100571-64-0)
  • 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: 100571-64-0(Hazardous Substances Data)

100571-64-0 Usage

Uses

Used in Pharmaceutical Synthesis:
3-(2-Isocyanoethyl)-1H-indole is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a building block for the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 3-(2-Isocyanoethyl)-1H-indole is used as a compound of interest for its potential biological activities. Researchers explore its properties to understand how it can be utilized in the creation of novel therapeutic agents.
Used in Chemical Process Development:
3-(2-Isocyanoethyl)-1H-indole is also used in the development of new chemical processes. Its versatility as a compound makes it a valuable asset in the search for more efficient and innovative methods in chemical synthesis.
Used in Chemical Biology Research:
3-(2-Isocyanoethyl)-1H-indole has been investigated for its potential as a fluorescent probe in chemical biology research. Its properties may allow it to be used in the study of biological processes, offering insights into cellular mechanisms and interactions.

Check Digit Verification of cas no

The CAS Registry Mumber 100571-64-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,0,5,7 and 1 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 100571-64:
(8*1)+(7*0)+(6*0)+(5*5)+(4*7)+(3*1)+(2*6)+(1*4)=80
80 % 10 = 0
So 100571-64-0 is a valid CAS Registry Number.

100571-64-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-(2-isocyanoethyl)-1H-indole

1.2 Other means of identification

Product number -
Other names 3-(2-isocyano-ethyl)-1H-indole

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:100571-64-0 SDS

100571-64-0Downstream Products

100571-64-0Relevant articles and documents

Hydrogen-Bonding-Promoted Cascade Rearrangement Involving the Enlargement of Two Rings: Efficient Access to Polycyclic Quinoline Derivatives

Cao, Wen-Bin,Ji, Shun-Jun,Lan, Yu,Li, Haiyan,Li, Shijun,Xu, Meng-Meng,Xu, Xiao-Ping

, p. 21425 - 21430 (2020)

An efficient cascade reaction of tryptamine-derived isocyanides with C,N-cyclic azomethine imines is described. The polycyclic pyrrolo[2,3-c]quinoline derivatives, which benefited from rearrangement process driven by hydrogen bonding, could be directly assembled in moderate to good yields (40–87 %) under metal-free and mild conditions. This transformation involved four new heterocyclic rings formations and uniquely, ring opening of indole as well as ring expansion of C,N-cyclic azomethine imine. Both experimental and DFT studies provided guidance on the in-depth insight into the reaction pathways and hydrogen bonding was identified to lower the free energy barrier in transition states. This work constitutes a rare example of tryptamine-derived isocyanide-based cascade reactions, and potentially could be a powerful synthetic strategy for accessing polycyclic analogues involved in natural products.

Synthesis of polycyclic spiroindolines by highly diastereoselective interrupted Ugi cascade reactions of 3-(2-isocyanoethyl)indoles

Saya, Jordy M.,Oppelaar, Barry,Cioc, Rǎzvan C.,Van Der Heijden, Gydo,Vande Velde, Christophe M. L.,Orru, Romano V. A.,Ruijter, Eelco

, p. 12482 - 12485 (2016)

We report a highly diastereoselective interrupted Ugi reaction to construct a broad range of structurally congested and stereochemically complex spiroindolines from tryptamine-derived isocyanides. The reaction is facilitated by using fluorinated alcohols (TFE or HFIP) as solvents and tolerates a broad range of amines, aldehydes and 2-isocyanoethylindoles to give polycyclic products in moderate to excellent yields.

A Convergent Approach to Heterocycle Synthesis via Silver Ion Mediated α-Keto Imidoyl Halide-Arene Cyclizations. An Application to the Synthesis of the Erythrinane Skeleton

Westling, Mark,Smith, Richard,Livinghouse, Tom

, p. 1159 - 1165 (1986)

α-Keto imidoyl halides formed by the reaction of representative 2-phenylethyl and related isocyanides with acyl halides undergo facile cyclization induced by silver salts to provide the corresponding heterocycles in good to excellent yield.An efficient synthesis of the erythrinane skeletal system which relies upon the sequential utlization of this method followed by an azomethine ylide cycloaddition reaction is described.

Iodospirocyclization of Tryptamine-Derived Isocyanides: Formal Total Synthesis of Aspidofractinine

Saya, Jordy M.,Roose, Thomas R.,Peek, Jarryt J.,Weijers, Bram,de Waal, Thomas J. S.,Vande Velde, Christophe M. L.,Orru, Romano V. A.,Ruijter, Eelco

, p. 15232 - 15236 (2018)

The N-iodosuccinimide-mediated spirocyclization of tryptamine-derived isocyanides to generate spiroindolenines is reported. The products contain both an imine and an imidoyl iodide as flexible handles for follow-up chemistry. Nucleophilic addition typical

Visible-Light-Induced Trifluoromethylation of Isonitrile-Substituted Indole Derivatives: Access to 1-(Trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indole and β-Carboline Derivatives

Liu, Jiaxin,Li, Longhai,Yu, Liuzhu,Tang, Lisha,Chen, Qin,Shi, Min

, p. 2959 - 2965 (2018)

A visible-light-induced trifluoromethylation of isonitrile-substituted indole derivatives has been developed from the reaction of isonitrile-substituted indoles with Togni II reagent, affording 1-(trifluoromethyl)-4,9-dihydro-3H-pyrido[3,4-b]indoles in mo

Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water

Buyck, Thomas,Pasche, Delphine,Wang, Qian,Zhu, Jieping

, p. 2278 - 2281 (2016)

Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs2CO3 afforded oxazolidin-2-ones in good yields. This unprecedented heteroannulation process created four chemical bonds in a s

Asymmetric dearomatization of indoles through a Michael/Friedel-Crafts-Type cascade to construct polycyclic spiroindolines

Zhao, Xiaohu,Liu, Xiaohua,Mei, Hongjiang,Guo, Jing,Lin, Lili,Feng, Xiaoming

, p. 4032 - 4035 (2015)

A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N-dioxide/MgII catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction.

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

ábrányi-Balogh, Péter,Keser?, Gy?rgy M.,Mándity, István M.,Németh, András Gy.,Orsy, Gy?rgy,Szabó, Renáta

, (2021/06/25)

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.

Isocyanide 2.0

Ahmadian-Moghaddam, Maryam,D?mling, Alexander,Patil, Pravin

supporting information, p. 6902 - 6911 (2020/11/09)

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

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

Esmati,Maddirala,Hussein,Amawi,Tiwari,Andreana

, p. 5332 - 5342 (2018/08/03)

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.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 100571-64-0