337536-15-9

Basic information

• Product Name: 4-bromoisoindolin-1-one
• Synonyms: 4-bromoisoindolin-1-one;4-BroMoisoindoline-1-one;1H-Isoindol-1-one,4-broMo-2 3-dihydro-;4-broMo-2,3-dihydro-1H-isoindol-1-one
• CAS NO: 337536-15-9
• Molecular Formula: C₈H₆BrNO
• Molecular Weight: 212.04
• Mol File: 337536-15-9.mol

Chemical Properties

• Boiling Point: 448.937 °C at 760 mmHg
• Flash Point: 225.309 °C
• Appearance: /
• Density: 1.666
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.69±0.20(Predicted)
• CAS DataBase Reference: 4-bromoisoindolin-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromoisoindolin-1-one(337536-15-9)
• EPA Substance Registry System: 4-bromoisoindolin-1-one(337536-15-9)

Safety Data

• Hazardous Substances Data: 337536-15-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-bromoisoindolin-1-one is used as an organic synthesis intermediate for the preparation of a wide range of chemical compounds. Its unique structure allows for various functional group transformations and reactions, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
4-bromoisoindolin-1-one is used as a pharmaceutical intermediate in the development of new drugs and therapeutic agents. Its reactivity and structural diversity make it a promising candidate for the design and synthesis of novel pharmaceutical compounds with potential applications in various therapeutic areas.
Used in Laboratory Research and Development:
4-bromoisoindolin-1-one is utilized in laboratory research and development processes, where it serves as a key component in the synthesis and evaluation of new chemical entities. Its unique properties and reactivity enable researchers to explore new reaction pathways and develop innovative synthetic strategies.
Used in Chemical Production Process:
4-bromoisoindolin-1-one is also employed in the chemical production process, where it is used to manufacture various specialty chemicals and materials. Its versatility and reactivity make it an essential component in the production of a wide range of chemical products, contributing to the advancement of the chemical industry.

Synthesis

To a solution of the 3-bromo-2-bromomethyl-benzoic acid methyl ester (2.74 g, 8.88 [MMOL)] in tetrahydrofuran (70 [ML)] at [0°C] was added 30 percent aq. ammonia (10 ml) and the mixture stirred at room temperature under nitrogen for 18 hours. The solvent was removed by evaporation under reduced pressure. The white residue was partitioned between ethyl acetate (50 mi) and 2M citric acid (50 [ML).] The ethyl acetate was dried magnesium sulfate, filtered and solvent removed by evaporation under reduced pressure. The orange oil was dissolved in minimum [DICHLOROMETHANE] and purified by flash chromatography on silica gel eluting with a solvent gradient of [DICHOROMETHANE/METHANOL] (9: 1) to give the title compound (1.5 g, 80 percent) as a white solid.

InChI:InChI=1/C8H6BrNO/c9-7-3-1-2-5-6(7)4-10-8(5)11/h1-3H,4H2,(H,10,11)

Upstream product

• 99548-54-6 methyl 3-bromo-2-methylbenzoate 

Downstream Products

• 923590-95-8 4-bromo-2,3-dihydro-1H-isoindole hydrochloride 
• 1021874-48-5 4-acetylisoindolin-1-one 
• 765949-01-7 N-[4-(7-amino-1-oxo-2,3-dihydro-1H-isoindol-4-yl)phenyl]-N'-(3-methylphenyl)urea 

Relevant articles and documents

Novel HCV virus NS3/4A inhibitor synthesizing intermediate and synthesis method

The invention relates to a synthesis method of a medicinal intermediate, and belongs to the field of synthesis of medicines. According to the synthesis method, 4-bromoisoindoline (hydrochloride) is synthesized from 3-bromo-2-methyl-benzoic acid as a raw material. Not only is the raw material cost low, but also a preparation technology is simple, the synthesis yield is high, and industrial application and popularization values are achieved; meanwhile, the stability of the raw material of the intermediate can be improved through one-step t-butyloxycarbonylation, so that the addition amount of the raw material in the synthesis process is reduced, the cost is further reduced, and the synthesis yield is improved.

COMPOUNDS AS TNIK, IKKEPSILON AND TBK1 INHIBITORS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME

Provided is a compound of formula (I) as a TNIK (Traf2- and NCK-interacting kinase), IKKε (I-kappa-B kinase epsilon) and TBK1 (TANK-binding kinase 1) inhibitor; the compound according to the present invention effectively inhibits TNIK, IKKε and TBK1, and thus is useful not only as an anticancer agent for the treatment of various cancers including colorectal cancer, breast cancer, CNS cancer, colon cancer, non-small cell lung cancer, kidney cancer, prostate cancer, ovarian cancer, uterus cancer, stomach cancer, liver cancer, skin cancer, lung cancer, brain cancer, bladder cancer, esophageal cancer, pancreatic cancer, thyroid cancer, head and neck cancer, squamous cell carcinoma, osteosarcoma, B-cell or T-cell lymphoma, acute or chronic leukemia and multiple myeloma, but as a therapeutic agent for chronic inflammation.

Isoindolinone ureas: A novel class of KDR kinase inhibitors

A series of substituted isoindolinone ureas was prepared and evaluated for enzymatic and cellular inhibition of KDR kinase activity. Several of these analogs, such as 14c, are potent inhibitors of KDR both enzymatically (50nM) and cellularly (≤100nM). A 3D KDR/CDK2/MAP kinase overlay model with several structurally related tyrosine kinase inhibitors was used to predict the binding interactions of the isoindolinone ureas with the KDR active site.

ISOINDOLIN-1-ONE COMPOUNDS AS KINASE INHIBITORS

Compounds having the formula, (I) are useful for inhibiting protein tyrosine kinases. The present invention also discloses methods of making the compounds and compositions containing the compounds.