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4-Bromo-N-methylphthalimide is a chemical compound belonging to the phthalimide family, characterized by the molecular formula C9H7BrNO2. It features a bromine atom and a methyl group attached to the nitrogen atom, which endows it with unique reactivity and structural properties. 4-Bromo-N-methylphthalimide is recognized for its versatility in organic synthesis and its potential as a precursor in the development of pharmaceuticals and agrochemicals.

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  • 90224-73-0 Structure
  • Basic information

    1. Product Name: 4-Bromo-N-methylphthalimide
    2. Synonyms: 4-Bromo-N-methylphthalimide;5-BroMo-2-Methylisoindoline-1,3-dione;5-bromo-2-methyl-1H-Isoindole-1,3(2H)-dione;4-Bromo-N-methylphthalimide
    3. CAS NO:90224-73-0
    4. Molecular Formula: C9H6BrNO2
    5. Molecular Weight: 240.05
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 90224-73-0.mol
  • Chemical Properties

    1. Melting Point: 147.0 to 151.0 °C
    2. Boiling Point: 333.5 °C at 760 mmHg
    3. Flash Point: 155.5 °C
    4. Appearance: /
    5. Density: 1.729 g/cm3
    6. Vapor Pressure: 0.000136mmHg at 25°C
    7. Refractive Index: 1.64
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. PKA: -3.05±0.20(Predicted)
    11. CAS DataBase Reference: 4-Bromo-N-methylphthalimide(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4-Bromo-N-methylphthalimide(90224-73-0)
    13. EPA Substance Registry System: 4-Bromo-N-methylphthalimide(90224-73-0)
  • 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: 90224-73-0(Hazardous Substances Data)

90224-73-0 Usage

Uses

Used in Organic Synthesis:
4-Bromo-N-methylphthalimide is utilized as a reagent in organic synthesis due to its propensity to participate in nucleophilic substitution reactions. Its distinctive functional groups make it an advantageous building block for constructing complex organic molecules, facilitating the creation of a wide range of chemical entities.
Used in Pharmaceutical Production:
As a precursor, 4-Bromo-N-methylphthalimide plays a significant role in the production of various pharmaceuticals. Its unique structure allows for the development of new drugs with specific therapeutic properties, contributing to advancements in medicinal chemistry.
Used in Agrochemical Development:
4-Bromo-N-methylphthalimide is also employed in the agrochemical industry, where it serves as a starting material for the synthesis of pesticides and other crop protection agents. Its use in this sector highlights its broad applicability in chemical research and product development.
Used in Selective Bromination of Aromatic Compounds:
4-Bromo-N-methylphthalimide is further applied as a reagent for the selective bromination of aromatic compounds. This selective bromination is crucial for the synthesis of specific organic compounds that require precise structural modification, underscoring the compound's importance in fine chemical synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 90224-73-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,0,2,2 and 4 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 90224-73:
(7*9)+(6*0)+(5*2)+(4*2)+(3*4)+(2*7)+(1*3)=110
110 % 10 = 0
So 90224-73-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H6BrNO2/c1-11-8(12)6-3-2-5(10)4-7(6)9(11)13/h2-4H,1H3

90224-73-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-bromo-2-methylisoindole-1,3-dione

1.2 Other means of identification

Product number -
Other names 5-Brom-2-methyl-isoindolin-1,3-dion

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:90224-73-0 SDS

90224-73-0Relevant articles and documents

Bright near-infrared chemiluminescent dyes: Phthalhydrazides conjugated with fluorescent BODIPYs

Hirano, Takashi,Li, Guanglei,Yamada, Koji

, (2020)

A series of phthalhydrazides conjugated with NIR fluorescent BODIPY dyes were synthesized (three steps, overall yields 68–83%) and found to show strong NIR chemiluminescence (CL) with maxima in the range of 670–736 nm. One of these showed a CL quantum yield reaching 8.4 times higher than that of luminol. Tuning of the fluorescence band of the BODIPY unit directly leads to a red-shifted CL, developing a strategy for designing NIR chemiluminogens.

Aziridinyl Fluorophores Demonstrate Bright Fluorescence and Superior Photostability by Effectively Inhibiting Twisted Intramolecular Charge Transfer

Liu, Xiaogang,Qiao, Qinglong,Tian, Wenming,Liu, Wenjuan,Chen, Jie,Lang, Matthew J.,Xu, Zhaochao

, p. 6960 - 6963 (2016)

Replacing conventional dialkylamino substituents with a three-membered aziridine ring in naphthalimide leads to significantly enhanced brightness and photostability by effectively suppressing twisted intramolecular charge transfer formation. This replacement is generalizable in other chemical families of fluorophores, such as coumarin, phthalimide, and nitrobenzoxadiazole dyes. In highly polar fluorophores, we show that aziridinyl dyes even outperform their azetidinyl analogues in aqueous solution. We also proposed one simple mechanism that can explain the vulnerability of quantum yield to hydrogen bond interactions in protonic solvents in various fluorophore families. Such knowledge is a critical step toward developing high-performance fluorophores for advanced fluorescence imaging.

High-selectivity aggregation induced chemiluminiscence probe for O2 as well as preparation method and application of chemiluminiscence probe

-

Paragraph 0008; 0030; 0035, (2018/11/22)

The invention discloses a high-selectivity aggregation induced chemiluminiscence probe for O2 as well as a preparation method and an application of the chemiluminiscence probe. The structural formula of the chemiluminiscence probe is shown in the descr

PHENANTHROLINE COMPOUND, ELECTRON TRANSPORT MATERIAL OBTAINED FROM SAID COMPOUND, AND ORGANIC THIN-FILM PHOTOVOLTAIC CELL COMPRISING SAID COMPOUND

-

Paragraph 0064; 0065, (2013/06/27)

A compound represented by the following formula (1), wherein L is a single bond or a divalent group, and is bonded at any one of the 6th, 8th and the 9th positions indicated by * of 1,10-phenanthroline; Rg is a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring; and X is an oxygen atom or N-R4.

Synthesis of biologically potent novel 5-(2-bromopyridin-3-yl-amino)-2- alkyl/aryl-isoindoline-1,3-dione analogs via buchwald-hartwig c-n coupling reaction

Gupta, Ankur,Kamble, Bhagyashree,Nanjan, Chandrasekar M.J.

, p. 139 - 146 (2013/07/26)

A novel series of N-alkyl/aryl substituted phthalimide analogs containing 2-bromopyridyl functionality were synthesized applying optimized Buchwald-Hartwig amination conditions using palladium acetate, cesium carbonate, and =BINAP in toluene at 110°C unde

Design and synthesis of a chemiluminescent solvatochromic dye

Yamagishi, Yutaka,Son, Sang-Hyun,Yuasa, Maiko,Yamada, Koji

supporting information; experimental part, p. 504 - 506 (2012/08/07)

Chemiluminescent solvatochromic dye has been synthesized by the condensation of a chemiluminescent moiety into a fluorescent solvatochromic dye via the SuzukiMiyaura crosscoupling. The chemiluminescent wavelength is shifted by solvent polarity, and ratiom

Rhodium(iii)-catalyzed oxidative carbonylation of benzamides with carbon monoxide

Du, Ya,Hyster, Todd K.,Rovis, Tomislav

, p. 12074 - 12076 (2011/12/14)

An efficient strategy for the oxidative carbonylation of aromatic amides via C-H/N-H activation to form phthalimides using an Rh(iii) catalyst has been developed. The reaction shows a preference for C-H bonds of electron-rich aromatic amides and tolerates a variety of functional groups. The Royal Society of Chemistry 2011.

THIAZOLYL-DIHYDRO-INDAZOLES

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Page/Page column 37; 38, (2009/10/22)

The present invention encompasses compounds of general formula (1) wherein R1 to R3 are defined as in claim 1, which are suitable for the treatment of diseases characterised by excessive or abnormal cell proliferation, and the use thereof for preparing a

SELECTIVE ESTROGEN RECEPTOR MODULATORS

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Page/Page column 35, (2010/02/13)

The present invention relates to a selective estrogen receptor modulators of formula I (I); or a pharmaceutical acid addition salt thereof; and of formula II (II); or a pharmaceutical salt thereof; useful, e.g., for treating endometriosis and/or uterine leiomyoma/leiomyomata.

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