19477-73-7

Usage

Chemical Properties

Light red crystal

InChI:InChI=1/C8H5BrO2/c9-6-2-1-5-4-11-8(10)7(5)3-6/h1-3H,4H2

Upstream product

• 57319-65-0 6-aminophthalide 
• 86-90-8 4-bromophthalic anhydride 
• 79669-49-1 5-bromo-2-methylbenzoic acid 
• 87-41-2 2-benzofuran-1(3H)-one 
• 585-76-2 m-bromobenzoic acid 
• 74-95-3 1,1-dibromomethane 
• 50-00-0 formaldehyd 
• 153435-81-5 (3-bromophenyl)(morpholino)methanone 
• 220513-49-5 5-bromo-1,3-dihydroisobenzofuran 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 171011-37-3 4-bromo-2-(hydroxymethyl)benzyl alcohol 
• 610-93-5 6-nitrophthalide 

Downstream Products

• 627909-55-1 5-bromo-2-hydroxymethyl-benzoic acid 
• 90667-31-5 5-bromo-2-(phenylthiomethyl)benzoic acid 
• 138639-75-5 5-Bromo-2-(4-methoxycarbonyl-phenoxymethyl)-benzoic acid 
• 1000692-94-3 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(3-oxo-1,3-dihydroisobenzofuran-5-yl)phenyl)cyclopropanecarboxamide 
• 1000692-95-4 5'-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-4-(hydroxymethyl)-2'-methylbiphenyl-3-carboxylic acid 
• 871502-88-4 5-bromo-2-bis(5-methyl-2-furyl)methylbenzoic acid 
• 908858-91-3 5-bromo-2-bis[5-(tert-butyl)-2-furyl]methylbenzoic acid 
• 4785-52-8 5-bromo-ortho-formylbenzoic acid 
• 72985-23-0 6-methylisobenzofuran-1(3H)-one 
• 874569-19-4 6-[4-({[(2-methoxyphenyl)sulfonyl]amino}methyl)phenyl]-3-hydroisobenzofuran-1-one 
• 1240500-28-0 5-bromo-2-[(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]benzoic acid 
• 1240500-32-6 N-(4-methylphenyl)-7-bromo-1-oxo-1H-isothiochromene-3-carboxamide 
• 55104-32-0 6-hydroxy isobenzofuran-1(3H)-one 

Relevant academic research and scientific papers

Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

Squaramide-catalyzed asymmetric intramolecular oxa-michael reaction of α,β-unsaturated carbonyls containing benzyl alcohol: Construction of chiral 1-substituted phthalans

Organocatalytic enantioselective intramolecular oxa-Michael reactions of benzyl alcohol bearing α,β-unsaturated carbonyls as Michael acceptors are presented herein. Using cinchona squaramide-based organocatalyst, enones as well as α,βunsaturated esters containing benzyl alcohol provided their corresponding 1,3-dihydroisobenzofuranyl-1-methylene ketones and 1,3-dihydroisobenzofuranyl-1-methylene esters in excellent yields with high enantioselectivities. In addition, enantioenriched 1,3-dihydroisobenzofuranyl-1-methylene ketone could be obtained from the Wittig/oxa-Michael reaction cascade of 1,3-dihydro-2-benzofuran-1-ol.

Organocatalytic enantioselective synthesis of phthalans via Wittig/oxa-Michael cascade reaction

An enantioselective synthetic method for 1-substituted phthalans has been developed. The organocatalytic reaction between 1,3-dihydro-2-benzofuran-1-ols and Wittig reagents using cinchona squaramide-based organocatalyst proceeded with sequential Wittig reaction followed by an enantioselective intramolecular oxa-Michael reaction, yielding enantioenriched phthalans with moderate to good enantioselectivities.

Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters

Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure analysis of the key transition states shows that the CH-π interactions and not the previously considered cation/π-π interactions between the catalyst and substrate is the dominant factor giving rise to the observed stereocontrol.

Synthesis of 3-Unsubstituted Phthalides from Aryl Amides and Paraformaldehyde via Ruthenium(II)-Catalyzed C–H Activation

A straightforward and convenient route has been developed for the synthesis of 3-unsubstituted phthalide derivatives from aryl amides and paraformaldehyde by ruthenium(II)-catalyzed C–H activation. The reaction proceeds through tandem ortho-hydroxymethylation of aryl amide and subsequent intramolecular lactonization.

IDO/TDO Inhibitor

A compound of formula (I) given below or a pharmaceutically acceptable salt of the compound is useful as an IDO/TDO inhibitor. Thus, the compound of formula (I) or the pharmaceutically acceptable salt of the compound can be used as, for example, a therapeutic agent for a disease or a disorder selected from tumor, infectious disease, neurodegenerative disorder, cataract, organ transplant rejection, autoimmune disease, postoperative cognitive impairment, and disease related to women's reproductive health [in the following formula (I), ring A represents an aromatic ring, an aliphatic ring, a heterocyclic ring, or a condensed ring of two or more rings selected from an aromatic ring, an aliphatic ring and a heterocyclic ring; X, R1 and R2 represent a substituent on a ring atom constituting ring A; m represents an integer of 0 to 6; X represents, for example, a halogen atom; and R1 and R2 are the same or different and are selected from, for example, the group consisting of groups of formula (a) or formula (b); and in the following formula (a) and formula (b), Y is selected from the group consisting of O, S, and Se, Z is selected from the group consisting of O, S, and Se, n represents an integer of 1 to 8, r represents an integer of 1 to 8, s represents an integer of 1 to 8, R4 represents, for example, —C(═NH)—HN2, and R6 represents, for example, a substituted or unsubstituted aryl group].

A g-C3N4-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C-H oxygenations

A metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C-H oxygenations using oxygen as an oxidant. This visible light mediated oxidation reaction utilizes graphitic carbon nitride (g-C3N4) as a recyclable, nontoxic and low cost photocatalyst. Mild reaction conditions allow for the generation of synthetically and biologically valued isochromannones, phthalides, isoquinolinones, isoindolinones and xanthones from readily accessible alkyl aromatic precursors in good yields. The heterogeneous nature of the g-C3N4 catalytic system enables easy recovery and recycling as well as the use in multiple runs without loss of activity. The synthetic utility of this "green" methodology was further demonstrated by applying in bioactive and drug valued target syntheses.

Platinum-on-Carbon-Catalyzed Aqueous Oxidative Lactonization of Diols by Using Molecular Oxygen

A lactonization of various diols catalyzed by platinum on carbon (Pt/C) in water under an atmosphere of molecular oxygen was developed. Derivatives of 1,4- 1,5- and 1,6-diols were transformed into the corresponding five-, six-, and seven-membered lactones by the present oxidative lactonization method.

6 - [...] indoline - 1 - one synthetic method

The invention provides a synthesis method of 6-bromoisoindolinyl-1-one, which comprises the following steps: (a) carrying out substitution reaction on a compound (I) and a bromination reagent in an organic solvent to obtain a compound (IIa)-compound (IIb) mixture; (b) carrying out hydrolysis reaction on the compound (IIa)-compound (IIb) mixture under alkaline conditions, and separating a compound (IIIa) out of the obtained product; (c) carrying out cyclization reaction on the compound (IIIa) in an acidic solution to obtain the compound (IIa); (d) reacting the compound (IIa) and thionyl chloride in an organic solvent under the action of a catalyst to obtain a compound (IV); and (e) carrying out reflux reaction on the compound (IV) in ethanol, and adding ammonia water to react, thereby obtaining the compound (V) 6-bromoisoindolinyl-1-one. The method has the advantages of simple route, controllable conditions and high yield, and can easily implement industrial production. The reaction route of the method is disclosed in the specification.

Isomerically Pure Tetramethylrhodamine Voltage Reporters

We present the design, synthesis, and application of a new family of fluorescent voltage indicators based on isomerically pure tetramethylrhodamines. These new Rhodamine Voltage Reporters, or RhoVRs, use photoinduced electron transfer (PeT) as a trigger for voltage sensing, display excitation and emission profiles in the green to orange region of the visible spectrum, demonstrate high sensitivity to membrane potential changes (up to 47% ΔF/F per 100 mV), and employ a tertiary amide derived from sarcosine, which aids in membrane localization and simultaneously simplifies the synthetic route to the voltage sensors. The most sensitive of the RhoVR dyes, RhoVR 1, features a methoxy-substituted diethylaniline donor and phenylenevinylene molecular wire at the 5′-position of the rhodamine aryl ring, exhibits the highest voltage sensitivity to date for red-shifted PeT-based voltage sensors, and is compatible with simultaneous imaging alongside green fluorescent protein-based indicators. The discoveries that sarcosine-based tertiary amides in the context of molecular-wire voltage indicators prevent dye internalization and 5′-substituted voltage indicators exhibit improved voltage sensitivity should be broadly applicable to other types of PeT-based voltage-sensitive fluorophores.