89-51-0

Usage

Chemical Properties

off-white to light yellow or pale green powder

Uses

Different sources of media describe the Uses of 89-51-0 differently. You can refer to the following data:
1. antidepressant
2. A remainder phthalic acid.

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 4745, 1993 DOI: 10.1021/jo00069a047

Purification Methods

Crystallise the acid from boiling H2O (25mL/g; 63mL/g at 20o), aqueous AcOH (m 180o) Dry it at 100o. The S-benzylisothiuronium salt has m 155-156o (from EtOH). [Price Org Synth 22 611942, Grummitt et al. Org Synth Coll Vol III 449 1955, Beilstein 9 H 857, 9 II 617, 9 III 4266, 9 IV 3343.] The anhydride [703-59-3] M 162.1 has m 141-142o. [Beilstein 17/11 V 270.]

InChI:InChI=1/C9H8O4/c10-8(11)5-6-3-1-2-4-7(6)9(12)13/h1-4H,5H2,(H,10,11)(H,12,13)

Upstream product

• 87-41-2 2-benzofuran-1(3H)-one 
• 64391-30-6 3-(1-hydroxy-1-methylethyl)indene 
• 528-46-1 phthalonic acid 
• 101268-34-2 1,4-diethoxy-4,5-dihydrobenzodioxepin 
• 15028-10-1 indan-1,2-dione-2-oxime 
• 6627-91-4 2-cyanomethylbenzoic acid 
• 90224-61-6 2-bromo-3-chloro-indene 
• 64-19-7 acetic acid 
• 83-33-0 inden-1-one 
• 95-13-6 1-indene 
• 615-13-4 2-indanone 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 74897-57-7 trispiro<1,2,4,5,7,8-hexoxonan-3,2':6,2'':9,2'''-tris-indan> 
• 716-43-8 dimethyl homophthalate 

Downstream Products

• 716-43-8 dimethyl homophthalate 
• 14736-49-3 2-(2-(methoxycarbonyl)phenyl)acetic acid 
• 14736-50-6 o-(methoxycarbonylmethyl)benzoic acid 
• 894-22-4 spiro (3,4-dihydroisocoumarin-3,3'-phthalide) 
• 120613-48-1 dibenzo[c,h]indeno[1,2-f]chromene-5,11-dione 
• 39662-65-2 2-(2-indol-3-yl-ethyl)-4H-isoquinoline-1,3-dione 
• 14961-34-3 diethyl homophthalate 
• 22479-46-5 2-(ethoxycarbonylmethyl)benzoic acid 
• 611187-05-4 2-benzyloxyisoquinoline-1,3(2H,4H)-dione 
• 86-94-2 isoquinoline-1,3-diol 
• 3898-66-6 2-(carboxymethyl)-5-nitrobenzoic acid 
• 2975-71-5 2-[(3-oxo-1,3-dihydro-2-benzofuran-1-yl)methyl]benzoic acid 
• 703-59-3 homophthalic anhydride 
• 73109-31-6 2-(4-methylphenyl)-1,3(2H,4H)-dioxoisoquinoline 

Relevant academic research and scientific papers

A decatungstate-based ionic liquid exhibiting a very low dielectric constant suitable for acting as a solvent and a catalyst for the oxidation of organic substrates

In this contribution, a new POM-based ionic liquid, namely (P6,6,6,14)4[W10O32], was fully characterized. Its viscosity and its very low dielectric constant make this hybrid ionic liquid suitable to be used as a solvent for organic transformations. As a proof of concept, this unique ionic liquid having both solvent and catalyst properties was tested for the catalytic oxidation of various alcohols and alkenes in the presence of H2O2.

Expanding the repertoire of nitrilases with broad substrate specificity and high substrate tolerance for biocatalytic applications

Enzymatic conversion of nitriles to carboxylic acids by nitrilases has gained significance in the green synthesis of several pharmaceutical precursors and fine chemicals. Although nitrilases from several sources have been characterized, there exists a scope for identifying broad spectrum nitrilases exhibiting higher substrate tolerance and better thermostability to develop industrially relevant biocatalytic processes. Through genome mining, we have identified nine novel nitrilase sequences from bacteria and evaluated their activity on a broad spectrum of 23 industrially relevant nitrile substrates. Nitrilases from Zobellia galactanivorans, Achromobacter insolitus and Cupriavidus necator were highly active on varying classes of nitriles and applied as whole cell biocatalysts in lab scale processes. Z. galactanivorans nitrilase could convert 4-cyanopyridine to achieve yields of 1.79 M isonicotinic acid within 3 h via fed-batch substrate addition. The nitrilase from A. insolitus could hydrolyze 630 mM iminodiacetonitrile at a fast rate, effecting 86 % conversion to iminodiacetic acid within 1 h. The arylaliphatic nitrilase from C. necator catalysed enantioselective hydrolysis of 740 mM mandelonitrile to (R)-mandelic acid in 4 h. Significantly high product yields suggest that these enzymes would be promising additions to the suite of nitrilases for upscale biocatalytic application.

Highly efficient oxidative cleavage of alkenes and cyanosilylation of aldehydes catalysed by magnetically recoverable MIL-101

The catalytic activity of magnetically recoverable MIL-101 was investigated in the oxidation of alkenes to carboxylic acids and cyanosilylation of aldehydes. MIL-101 was treated with Fe3O4 and the prepared catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, N2 adsorption measurements, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy and inductively coupled plasma analysis. The catalytic active sites in this heterogeneous catalyst are Cr3+ nodes of the MIL-101 framework. This heterogeneous catalyst has the advantages of excellent yields, short reaction times and reusability several times without significant decrease in its initial activity and stability in both oxidation and cyanosilylation reactions. Its magnetic property allows its easy separation using an external magnetic field.

Nanocoating of Hydrophobic Mesoporous Silica around MIL-101Cr for Enhanced Catalytic Activity and Stability

The metal-organic framework (MOF) MIL-101Cr was readily encapsulated by a very thin shell (around 30 nm) of hydrophobic mesoporous silica, which replicates the irregular shape of the MOF nanocrystals. Such a silica shell facilitates the diffusion of hydrophobic reactants with enhancement of the catalytic activity of the MOF and significantly improved catalytic stability of the MOF in the oxidation of indene.

Cobalt/N-Hydroxyphthalimide(NHPI)-Catalyzed Aerobic Oxidation of Hydrocarbons with Ionic Liquid Additive

A highly efficient and solvent-free system of cobalt/NHPI-catalyzed aerobic oxidation of hydrocarbons was developed using imidazolium-based ionic liquid (IL) as an additive. These amphipathic ILs were found self-assemble at the interface between the organic hydrocarbons and the aqueous phase of catalyst combination (Co/NHPI), with forming a solution of reversed multilamellar vesicles for catalysis. The initial reaction rate was influenced by both the composition of microdomains and the structure of IL launched. Consequently, a proper water content (χH2O) of wet IL was requisite to reach the optimum reactivity. Besides, the interfacial boundary between aqueous and organic phase composed by C2-alkylated imidazolium ILs, such as [bdmim]SbF6 and [C12dmim]SbF6, not only has ternary aggregates (hydrocarbons/IL/H2O) of higher stability but renders O2 a faster diffusion rate and higher concentration, thereby offering a high reactivity of the protocol towards hydrocarbon oxidation.

Cyclic Hydroxamic Acid Analogues of Bacterial Siderophores as Iron-Complexing Agents prepared through the Castagnoli–Cushman Reaction of Unprotected Oximes

The first application of multicomponent chemistry (the Castagnoli–Cushman reaction) toward the convenient one-step preparation of cyclic hydroxamic acids is described. Cyclic hydroxamic acids are close analogues of bacterial siderophores (iron-binding com

BIOREVERSABLE PROMOIETIES FOR NITROGEN-CONTAINING AND HYDROXYL-CONTAINING DRUGS

Disclosed are promoieties of the following formula which can be used to form prodrugs of nitrogen-containing or hydroxyl-containing drug or a pharmaceutically active agent: (I) and pharmaceutical compositions comprising the prodrugs.

Synthesis and antitumor activity evaluation of 2-arylisoquinoline-1,3(2H, 4H)-diones in vitro and in vivo

Six 2-(2-acylaminobenzothiazol-6-yl)isoquinoline-1,3(2H,4H)-diones (1a-1f) and five 2-arylisoquinoline-1,3(2H,4H)-diones (1g-1k) were synthesized by refluxing homophthalic anhydrides with 2-acylaminobenzothiazolyl-6-amine or substituted aniline in glacial acetic acid. The cytotoxic activities of 1a-1k were evaluated via MTT method against A431, A549, and PC3. Compound 1b relatively displayed a higher cytotoxic activity than the others. The antitumor effect of 1b were evaluated in established nude mice PANC-1 xenograft model. The results suggest that compound 1b could potentially inhibit tumor growth.

HCV PROTEASE INHIBITORS

The present invention discloses a compound of general formula (I); A is O, S, CH, NH or NR', when O links with Z3, Z1 is N or CRZ1, Z2 is CRZ2, when Z1 links with O, Z2 is CH, Z3 is C-Ar; Ra, Rb, Rc and Rd independently is H, OH, halogen or -Y1-Rm; A1 is NH or CH2; R1' is alkyl, aryl, cycloalkyl, heterocycloalkyl or heteroaryl; A2 is N, O or linking bond; R1 is hydrogen, or, R1 linking covalently with R3 forms C5-C9 saturated or unsaturated hydrocarbon chain substituted by O or N; R3 is alkyl, cycloalkyl, heterocycloalkyl, alkyl substituted by cycloalky etc; R4 is alkoxy-CO, alkyl-NHCO, (alkyl)2NCO, or formyl substituted by aryl, cycloalkyl, heterocycloalkyl.

HCV Protease Inhibitors

A compound of general formula (I); A is O, S, CH, NH or NR′, when O links with Z3, Z1 is N or CRZ1, Z2 is CRZ2, when Z1 links with O, Z2 is CH, Z3 is C—Ar; Ra, Rb, Rc and Rd independently is H, OH, halogen or —Y1—Rm; A1 is NH or CH2; R1′ is alkyl, aryl, cycloalkyl, heterocycloalkyl or heteroaryl; A2 is N, O or linking bond; R1 is hydrogen, or, R1 linking covalently with R3 forms C5-C9 saturated or unsaturated hydrocarbon chain substituted by O or N; R3 is alkyl, cycloalkyl, heterocycloalkyl, alkyl substituted by cycloalkyl etc; R4 is alkoxy-CO, alkyl-NHCO, (alkyl)2NCO, or formyl substituted by aryl, cycloalkyl, heterocycloalkyl.