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2-Bromo-1H-indole-3-carbaldehyde is a chemical compound characterized by its molecular formula C9H6BrNO. It is a yellowish solid that serves as a versatile intermediate in the synthesis of various organic compounds. 2-BroMo-1H-indole-3-carbaldehyde is distinguished by the presence of a bromine atom attached to an indole ring and a formyl group at the 3-position of the indole ring. Its potential in medical applications, particularly in the development of anti-cancer and anti-inflammatory drugs, makes it a significant compound in pharmaceutical research and medicinal chemistry.

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  • 119910-45-1 Structure
  • Basic information

    1. Product Name: 2-BroMo-1H-indole-3-carbaldehyde
    2. Synonyms: 2-BroMo-1H-indole-3-carbaldehyde;2-Bromo-1H-indole-3-carboxaldehyde;2-Bromoindole-3-carbaldehyde;3-Formyl-2-bromoindole;NSC 622163
    3. CAS NO:119910-45-1
    4. Molecular Formula: C9H6BrNO
    5. Molecular Weight: 224.05404
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 119910-45-1.mol
  • Chemical Properties

    1. Melting Point: 230℃ (ethanol water )
    2. Boiling Point: 385.2±22.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.727±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    8. Solubility: N/A
    9. PKA: 13.84±0.30(Predicted)
    10. CAS DataBase Reference: 2-BroMo-1H-indole-3-carbaldehyde(CAS DataBase Reference)
    11. NIST Chemistry Reference: 2-BroMo-1H-indole-3-carbaldehyde(119910-45-1)
    12. EPA Substance Registry System: 2-BroMo-1H-indole-3-carbaldehyde(119910-45-1)
  • 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: 119910-45-1(Hazardous Substances Data)

119910-45-1 Usage

Uses

Used in Pharmaceutical Research:
2-Bromo-1H-indole-3-carbaldehyde is utilized as a key intermediate in the synthesis of a variety of organic compounds, particularly those with potential pharmaceutical applications. Its unique structure allows for the development of new drugs with specific therapeutic properties.
Used in Drug Development:
In the field of drug development, 2-Bromo-1H-indole-3-carbaldehyde is employed as a building block for the creation of novel anti-cancer and anti-inflammatory agents. Its wide range of biological activities and the ability to be modified in organic synthesis make it a valuable compound for the design of new therapeutic agents.
Used in Medicinal Chemistry:
2-Bromo-1H-indole-3-carbaldehyde is used as a research tool in medicinal chemistry to explore its potential in the treatment of various diseases. Its diverse biological activities and structural features contribute to the understanding of its mechanism of action and its potential as a lead compound in drug discovery.

Check Digit Verification of cas no

The CAS Registry Mumber 119910-45-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,9,9,1 and 0 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 119910-45:
(8*1)+(7*1)+(6*9)+(5*9)+(4*1)+(3*0)+(2*4)+(1*5)=131
131 % 10 = 1
So 119910-45-1 is a valid CAS Registry Number.

119910-45-1Relevant articles and documents

BENZOFURAN-BASED N-ACYLHYDRAZONE DERIVATIVES AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

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Paragraph 0232-0235, (2021/02/02)

A benzofuran-based N-acylhydrazone derivative according to the present invention has an excellent anticancer effect while having low toxicity and excellent solubility, and, thus, a pharmaceutical composition comprising the derivative can be usefully used to prevent or treat a cell proliferative disorder including various cancers. To this end, the present invention provides a compound represented by chemical formula 1, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof.

One-Pot Regiodirected Annulations for the Rapid Synthesis of ?-Extended Oligomers

Bianchi, Gabriele,Botta, Chiara,Calcagno, Giuseppe,Etkind, Samuel I.,Nitti, Andrea,Osw, Peshawa,Pasini, Dario,Po, Riccardo,Swager, Timothy M.

supporting information, p. 3263 - 3267 (2020/04/21)

We demonstrate the broad applicability of the annulation protocol combining, in one pot, a direct arylation and cross aldol condensation for the straightforward synthesis at gram-scale of ?-extended thiophene-based scaffolds. The regiospecific direct arylation drives the subsequent cross-aldol condensation proceed under the same basic conditions, and the overall protocol has broad applicability in the synthesis of extended aromatics wherein the thiophene ring is annulated with furans, pyridines, indoles, benzothiophenes, and benzofurans. These scaffolds can be further elaborated into ?-extended, highly fluorescent oligomers with a central deficient benzothiadiazole unit with up to nine aromatic rings through coupling reactions.

Synthesis, Antiviral Activity, and Induction of Plant Resistance of Indole Analogues Bearing Dithioacetal Moiety

Wei, Chunle,Zhang, Jian,Shi, Jing,Gan, Xiuhai,Hu, Deyu,Song, Baoan

, p. 13882 - 13891 (2019/12/04)

A series of compounds with potential activity to induce plant resistance was synthesized from indole and thiol compounds and methodically evaluated for antiviral activity. The results indicated that some of the synthesized compounds had high antipotato virus Y (PVY), anticucumber mosaic virus, and antitobacco mosaic virus activities. Notably, compound D21 exhibited the best activity against PVY among these compounds in vivo, and the 50% effective concentrations (EC50) of protection activity is 122 μg/mL, which was distinctively better than the corresponding values for ribavirin (653 μg/mL), Ningnanmycin (464 μg/mL), and Xiangcaoliusuobingmi (279 μg/mL). Interestingly, we found that the protection activity of D21 was associated with improvement of chlorophyll content and defense-related enzyme activities. Moreover, D21 could trigger the malate dehydrogenase (MDH) signaling pathway, as further confirmed by the MDH activity evaluation. Hence, D21 can protect plants against viral activity and has potential as a novel activator for plant resistance induction.

H-bonding vs Protonation of Alkynes in Regioselective Hydroamination Reactions: A Glimpse into the Reactivity of Arylogous Ynolethers and Ynamines

Abe, Masahiro,Jean, Alexandre,Blanchet, Jér?me,Rouden, Jacques,Maddaluno, Jacques,De Paolis, Micha?l

, p. 15448 - 15475 (2019/11/29)

In this paper is described the competition and transition between hydrogen bonding and protonation of alkynes connected, on one side, to various aromatic rings and to chiral amino ester appendages on the other side. While the first mode of activation indu

Metal-Free Carbonyl-Assisted Regioselective Hydration of Alkynes: An Access to Dicarbonyls

Verma, Shalini,Kumar, Manoj,Mishra, Pawan K.,Verma, Akhilesh K.

supporting information, p. 5059 - 5063 (2019/07/03)

Metal-free regioselective hydration of o-alkynylaldehydes with the assistance of neighboring carbonyl oxygen is disclosed. The developed protocol provides a facile route to synthesize a series of multisubstituted carbonyl containing scaffolds that enable

Flexible synthesis of isomeric pyranoindolones and evaluation of cytotoxicity towards HeLa cells

Jeyaveeran,Praveen, Chandrasekar,Arun,Prince,Perumal

, p. 787 - 802 (2016/05/19)

A hybrid pharmacophore approach for the synthesis of isomeric pyranoindolones was achieved by employing gold(III) chloride-catalyzed cycloisomerization of alkyne-tethered indole carboxylic acids in good to excellent yield. All the synthesized compounds were evaluated for their tumor cell growth inhibitory activity against human cervix adenocarcinoma (HeLa) which revealed that three compounds exhibited activity comparable with the standard cis-platin (IC50 = 0.08 μM). Molecular docking of all the compounds in Vaccinia H1-Related (VHR) Phosphatase receptor also supported that compound 7d as the most active with a free energy of binding as ?8.27 kcal/mol. [Figure not available: see fulltext.]

Design, synthesis and cytotoxicity of pyrano[4,3-b]indol-1(5H)-ones: A hybrid pharmacophore approach via gold catalyzed cyclization

Praveen, Chandrasekar,Ananth, D. Babu

supporting information, p. 2507 - 2512 (2016/07/07)

Reported herein is the gold(III)-catalyzed 6-endo-dig cycloisomerization of 2-alkynyl-indole-3-carboxylic acids to form pyrano[4,3-b]indol-1(5H)-ones, which are pharmaceutically important structural motifs. The hitherto unknown substrates required for thi

One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes

Burroughs, Laurence,Eccleshare, Lee,Ritchie, John,Kulkarni, Omkar,Lygo, Barry,Woodward, Simon,Lewis, William

supporting information, p. 10648 - 10651 (2015/09/02)

An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields. A cascade process that is triggered by an intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene leads to the formation of 4-substituted cycloocta-2,5-dien-1-ones. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.

Rapid access to novel 1,2,3-triazolo-heterocyclic scaffolds via tandem knoevenagel condensation/azide-alkyne 1,3-dipolar cycloaddition reaction in one pot

Maurya, Ram Awatar,Adiyala, Praveen Reddy,Chandrasekhar,Reddy, Chada Narsimha,Kapure, Jeevak Sopanrao,Kamal, Ahmed

, p. 466 - 477 (2014/12/10)

An operationally simple, one-pot, two-step cascade method has been developed to afford biologically important fused 1,2,3-triazolo-heterocyclic scaffolds from 2-alkynyl aryl(heteroaryl) aldehydes and phenacyl azides. This unique atom economical transformation engages four reactive centers (aldehyde, alkyne, active methylene, and azide) under metal-free catalysis.

Substituent-guided switch between C-H activation and decarboxylative cross-coupling during palladium/copper-catalyzed cascade reactions of 2-aminobenzoates with 2-haloarylaldehydes

Bhowmik, Subhendu,Pandey, Garima,Batra, Sanjay

supporting information, p. 10487 - 10491 (2013/08/23)

Cascade switch: Phenanthridines, pyrazole[4,3-c]quinolines and isocryptolepine were prepared in one step from the Pd/Cu-catalyzed reaction between potassium 2-aminobenzoates and 2-haloarylaldehydes (see scheme). Although the reactions of 2-aminobenzoates proceeded via a cascade imination/C-H functionalization, the reactions of 6-nitro-2-aminobenzoates ensued via a tandem imination/decarboxylative cross-coupling. Copyright

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