127168-84-7

Basic information

• Product Name: 5-BROMOISOINDOLINE
• Synonyms: 5-BROMOISOINDOLINE;5-Bromo-2,3-dihydro-1H-isoindole;B90104;5-BroMoisoindoline HCl;1H-Isoindole, 5-bromo-2,3-dihydro-
• CAS NO: 127168-84-7
• Molecular Formula: C₈H₈BrN
• Molecular Weight: 198.06
• Mol File: 127168-84-7.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 253.389 °C at 760 mmHg
• Flash Point: 107.046 °C
• Appearance: /
• Density: 1.515 g/cm³
• Vapor Pressure: 0.018mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.60±0.20(Predicted)
• CAS DataBase Reference: 5-BROMOISOINDOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOISOINDOLINE(127168-84-7)
• EPA Substance Registry System: 5-BROMOISOINDOLINE(127168-84-7)

Safety Data

• Hazardous Substances Data: 127168-84-7(Hazardous Substances Data)

Usage

Uses

5-Bromoisoindoline is an intermediate used in the synthesis of 2,3-dihydro-1H-isoindoles with high affinity and selectivity for dopamine D3 receptor.

InChI:InChI=1/C8H8BrN/c9-8-2-1-6-4-10-5-7(6)3-8/h1-3,10H,4-5H2

Upstream product

• 127168-85-8 2-(p-toluenesulfonyl)-5-bromoisoindoline 
• 6941-75-9 5-Bromoisoindoline-1,3-dione 
• 1423-27-4 2-(trifluoromethyl)phenylboronic acid 
• 86-90-8 4-bromophthalic anhydride 
• 583-71-1 4-bromo-o-xylene 
• 69189-19-1 4-bromo-1,2-bis-bromomethyl-benzene 
• 85-44-9 phthalic anhydride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 64990-51-8 hydrochloric acid 1,4-dioxane 

Downstream Products

• 437651-72-4 {4-[2-(5-bromo-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester 
• 905273-91-8 tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate 
• 1208147-37-8 C₂₆H₁₇BrCl₂N₄O 
• 1613147-74-2 (R)-tert-butyl 5-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)isoindoline-2-carboxylate 
• 1618083-56-9 benzyl 5-allylisoindoline-2-carboxylate 
• 1618083-57-0 benzyl 5-(2,3-dihydroxypropyl)isoindoline-2-carboxylate 
• 1618083-58-1 benzyl 5-(2-oxoethyl)isoindoline-2-carboxylate 
• 1618083-59-2 2-(2-benzyloxycarbonylisoindolin-5-yl)acetic acid 
• 1618083-60-5 tert-butyl 3-((2R)-2-((2-benzyloxycarbonylisoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate 
• 1618083-61-6 tert-butyl 3-((2R)-2-((isoindolin-5-yl)acetamido)-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate 
• 1618090-65-5 tert-butyl 3-((2R)-[[2-[2-[(Z)-N,N'-bis(tert-butoxycarbonyl)carbamimidoyl]isoindolin-5-yl]acetyl]amino]-2-(2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]dec-4-yl)ethyl)-2-methoxybenzoate 
• 178445-27-7 benzyl 5-bromoisoindoline-2-carboxylate 

Relevant articles and documents

2-Amino-2,3-dihydro-1 H-indene-5-carboxamide-Based Discoidin Domain Receptor 1 (DDR1) Inhibitors: Design, Synthesis, and in Vivo Antipancreatic Cancer Efficacy

A series of 2-amino-2,3-dihydro-1H-indene-5-carboxamides were designed and synthesized as new selective discoidin domain receptor 1 (DDR1) inhibitors. One of the representative compounds, 7f, bound with DDR1 with a Kd value of 5.9 nM and suppre

The design, synthesis and structure-activity relationships of novel isoindoline-based histone deacetylase inhibitors

The design, synthesis and biological evaluation of a novel series of isoindoline-based hydroxamates is described. Several analogs were shown to inhibit HDAC1 with IC50 values in the low nanomolar range and inhibit cellular proliferation of HCT116 human colon cancer cells in the sub-micromolar range. The cellular potency of compound 17e was found to have greater in vitro anti-proliferative activity than several compounds in late stage clinical trials for the treatment of cancer. The in vitro safety profiles of selected compounds were assessed and shown to be suitable for further lead optimization.

Isoindoline scaffold-based dual inhibitors of HDAC6 and HSP90 suppressing the growth of lung cancer in vitro and in vivo

This study reports the synthesis of a series of 2-aroylisoindoline hydroxamic acids employing N-benzyl, long alkyl chain and acrylamide units as diverse linkers. In-vitro studies led to the identification of N-benzyl linker-bearing compound (10) and long

Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination

A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramolecular single electron transfer (SET) is key stage in the catalytic cycle.