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6-Bromo-1,3-dihydro-2H-indol-2-one, also known as 6-Bromo-2-Oxindole, is an indolinone derivative characterized by its light yellow crystalline appearance. It is a chemical compound that holds significant value in the pharmaceutical industry due to its potential applications in the development of anti-inflammatory agents.

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  • 99365-40-9 Structure
  • Basic information

    1. Product Name: 6-Bromo-1,3-dihydro-2H-indol-2-one
    2. Synonyms: 6-BROMO-1,3-DIHYDRO-INDOL-2-ONE;6-BROMO-2-OXYINDOLE;6-BROMO-2-OXINDOLE;6-BROMOOXINDOLE;2H-INDOL-2-ONE, 6-BROMO-1,3-DIHYDRO-;BROMOOXINDOLE (6-);6-Bromo-1,3-dihydro-2H-indol-2-one;6-Bromooxoindole
    3. CAS NO:99365-40-9
    4. Molecular Formula: C8H6BrNO
    5. Molecular Weight: 212.04
    6. EINECS: 1312995-182-4
    7. Product Categories: blocks;Bromides;IndolesOxindoles;Indoline & Oxindole;Halogenated Heterocycles;Heterocyclic Building Blocks;Indoles;IndolesBuilding Blocks;Aromatics;Heterocycles;Indole Derivatives;Intermediates;Heterocycle-Indole series
    8. Mol File: 99365-40-9.mol
  • Chemical Properties

    1. Melting Point: 217-221 °C(lit.)
    2. Boiling Point: 343.6 °C at 760 mmHg
    3. Flash Point: 161.6 °C
    4. Appearance: light yelllow crystal
    5. Density: 1.666 g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.698
    8. Storage Temp.: 2-8°C
    9. Solubility: DMSo
    10. PKA: 13.39±0.20(Predicted)
    11. Water Solubility: Slightly soluble in water.
    12. CAS DataBase Reference: 6-Bromo-1,3-dihydro-2H-indol-2-one(CAS DataBase Reference)
    13. NIST Chemistry Reference: 6-Bromo-1,3-dihydro-2H-indol-2-one(99365-40-9)
    14. EPA Substance Registry System: 6-Bromo-1,3-dihydro-2H-indol-2-one(99365-40-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36/37/39-24/25
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 99365-40-9(Hazardous Substances Data)

99365-40-9 Usage

Uses

Used in Pharmaceutical Industry:
6-Bromo-1,3-dihydro-2H-indol-2-one serves as an intermediate in the preparation of p38α inhibitors, which are considered potential anti-inflammatory agents. Its role in the synthesis of these inhibitors is crucial for developing new treatments aimed at managing inflammation-related conditions.
As an intermediate in pharmaceuticals, 6-Bromo-1,3-dihydro-2H-indol-2-one is used for the development of p38alpha inhibitors, which are being explored for their potential as anti-inflammatory medications. This application underscores its importance in the advancement of modern healthcare and therapeutics.

Check Digit Verification of cas no

The CAS Registry Mumber 99365-40-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,9,3,6 and 5 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 99365-40:
(7*9)+(6*9)+(5*3)+(4*6)+(3*5)+(2*4)+(1*0)=179
179 % 10 = 9
So 99365-40-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H4BrNO/c9-6-2-1-5-3-8(11)10-7(5)4-6/h1-4H

99365-40-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Alfa Aesar

  • (H56012)  6-Bromooxindole, 97%   

  • 99365-40-9

  • 1g

  • 1155.0CNY

  • Detail
  • Alfa Aesar

  • (H56012)  6-Bromooxindole, 97%   

  • 99365-40-9

  • 5g

  • 3465.0CNY

  • Detail
  • Alfa Aesar

  • (H56012)  6-Bromooxindole, 97%   

  • 99365-40-9

  • 100g

  • 10395.0CNY

  • Detail
  • Alfa Aesar

  • (H56012)  6-Bromooxindole, 97%   

  • 99365-40-9

  • 500g

  • 15593.0CNY

  • Detail
  • Aldrich

  • (586595)  6-Bromo-2-oxindole  97%

  • 99365-40-9

  • 586595-500MG

  • 1,787.76CNY

  • Detail

99365-40-9SDS

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 6-Bromooxindole

1.2 Other means of identification

Product number -
Other names 6-Bromo-1,3-dihydro-2H-indol-2-one

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:99365-40-9 SDS

99365-40-9Relevant articles and documents

Synthesis and photophysical characterization of isoindigo building blocks as molecular acceptors for organic photovoltaics

Din?alp, Haluk,Saltan, G?zde Murat,Zafer, Ceylan,Mutlu, Adem

, p. 196 - 206 (2018)

Five isoindigo-based donor-acceptor-donor (D-A-D) type small molecules have been synthesized in order to investigate their intramolecular charge transfer characteristics. UV–vis absorption of these dyes exhibits a wide absorption band ranging from 300 to 650 nm with two distinct bands, giving the narrow bandgaps between 1.72 and 1.85 eV. Taking into account their HOMO-LUMO energy levels and bandgaps, isoindigo dyes have been used in the active layer of organic solar cell (OSC) devices. When these small molecule semiconductors were used as acceptors with the donor poly(3-hexylthiophene-2,5-diyl (P3HT) polymer in the inverted OSC devices, the highest power conversion efficiency (PCE) was obtained as 0.10% for pyrene-substituted isoindigo derivative.

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

Liu, Li,Li, Yue,Huang, Tiao,Kong, Dulin,Wu, Mingshu

, p. 2321 - 2328 (2021/09/22)

A novel method for the synthesis of 3-monohalooxindoles by acidolysis of isatin-derived 3-phosphate-substituted oxindoles with haloid acids was developed. This synthetic strategy involved the preparation of 3-phosphate-substituted oxindole intermediates and SN1 reactions with haloid acids. This new procedure features mild reaction conditions, simple operation, good yield, readily available and inexpensive starting materials, and gram-scalability.

Novel calamitic liquid crystalline organic semiconductors based on electron-deficient dibenzo[: C, h] [2,6]naphthyridine: Synthesis, mesophase, and charge transport properties by the time-of-flight technique

Yang, Ming-Cong,Hanna, Jun-Ichi,Iino, Hiroaki

, p. 13192 - 13202 (2019/11/13)

Calamitic liquid crystalline organic semiconductors based on an electron-deficient dibenzo[c,h][2,6]naphthyridine (DBN) core were designed for electron transport materials and synthesized from 6-bromoisatin to form a key intermediate without tedious purification by means of a one-pot reaction including 4 steps, and then the target products were obtained in an additional 3 steps in a total yield of 13%. Two dialkylated DBN derivatives, 2,8-didecyl DBN (C10-DBN-C10) and 2,8-didodecyl DBN (C12-DBN-C12), exhibited a low ordered mesophase of smectic C (SmC) only. Their phase transitions, photophysical properties, and charge carrier transport properties were investigated and compared with their carbon analogs, i.e., chrysene and the DBN isomers of isoquino[8,7-h]isoquinoline derivatives. In the SmC phase, transient photocurrents had well-defined transits, which allowed us to evaluate their exact mobilities. The mobility for negative and positive carriers in the SmC phase depended on both electric field and temperature, which suggested that the conduction mechanism is via electronic hopping transport for both holes and electrons. It was unexpectedly found that C10-DBN-C10 in the SmC phase exhibited quite low mobility on the order of 10-5 cm2 V-1 s-1, which is two orders of magnitude smaller than that for dialkylated chrysenes, and is comparable to the typical mobility in liquid crystalline semiconductors with large dipole moments, even though the DBN core has no dipole moment; this is also true for holes. This new phenomenon has not been reported before, and may provide new insight into how mobility in liquid-crystal phases is determined.

Synthesis of novel 3-(benzothiazol-2-ylmethylene)indolin-2-ones

Zhang, Chao,Xu, Juan,Zhao, Xinyu,Kang, Congmin

, p. 537 - 540 (2017/10/03)

A mild method for the synthesis of 3-(benzothiazol-2-ylmethylene)indolin-2-ones via the aldol condensation of substituted indolin-2-ones and benzothiazole-2-carbaldehyde is described. This new procedure has significant advantages, such as mild conditions, high yields and simple work-up.

A trifluro yl-carbonyl heteroploid indigo derivative and its synthetic method

-

, (2017/02/09)

The invention relates to a trifluoromethyl carbonyl isoindigo derivative and a synthesis method for the same. The LUMO (lowest unoccupied molecular orbital) energy level of the compound is greatly lowered by introducing trifluoromethyl and carbonyl which

Polymer based on benzothiadiazole-bridged bis-isoindigo for organic field-effect transistor applications

Deng, Ping,Li, Shugang,Wu, Jian,Zhang, Qing,Lei, Yanlian,Zhu, Furong,Zheng, Xuelin,Ong, Beng S.

, p. 407 - 413 (2015/12/30)

Two isoindigos were symmetrically connected by 2,1,3-benzothiadiazole core to form an acceptor2-acceptor1-acceptor2 monomer. The new monomer was used as electron acceptor unit in construction of a unique donor/acceptor polymer with donor-acceptor2-accepto

A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: Construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters

Gui, Yong-Yuan,Yang, Jian,Qi, Liang-Wen,Wang, Xiao,Tian, Fang,Li, Xiao-Nian,Peng, Lin,Wang, Li-Xin

supporting information, p. 6371 - 6379 (2015/06/08)

A cinchona alkaloid catalyzed diastereoselective and enantioselective sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and isoindigos has been successfully developed to afford the highly congested bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters in high yields (up to 91%), excellent diastereoselectivities (up to >20 : 1 dr), and good enantioselectivities (up to 98% ee). Some synthetic transformations of the reaction products were also studied.

COMPOSITIONS FOR THE TREATMENT OF HYPERTENSION AND/OR FIBROSIS

-

, (2015/04/15)

The present invention relates to novel compounds and their use in the prophylactic and/or therapeutic treatment of hypertension and/or fibrosis.

Molybdenum hexacarbonyl mediated synthesis of indolin-2-one & azaindolin-2-one under catalyst free conditions

Patil, Vikas S.,Pal, Shyam S.,Pathare, Ramdas S.,Reddy,Pathak, Arunendra

supporting information, p. 6370 - 6372 (2015/11/16)

Syntheses of indolin-2-ones and azaindolin-2-ones have been realized. The strategy involves the formation of tosylhydrazone from tosylhydrazine and 2-amino aryl or pyridyl aldehydes/ketones which then undergo intramolecular aminocarbonylation to afford indolin-2-ones and azaindolin-2-ones. The generality of the method was demonstrated by synthesizing C3 substituted and unsubstituted indolin-2-one and azaindolin-2-one derivatives.

Selective reduction of carbonyl groups in the presence of low-valent titanium reagents

Lin, Wei,Hu, Ming-Hua,Feng, Xian,Fu, Lei,Cao, Cheng-Pao,Huang, Zhi-Bin,Shi, Da-Qing

, p. 2238 - 2242 (2014/04/17)

The chemoselective reduction of several structurally diverse compounds containing carbonyl groups was achieved in the presence of low-valent titanium reagents. This novel synthetic method provides easy access to highly selective reduction of carbonyl groups, and possesses several advantages including one-step procedure, convenient manipulation, good to excellent yields, and short reaction times.

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