89-51-0

Basic information

• Product Name: Homophthalic acid
• Synonyms: TOLUENE-2,ALPHA-DICARBOXYLIC ACID;2-carboxy-benzeneaceticaci;alpha-carboxy-o-toluicaci;o-carboxylphenylaceticacid;toluene-alpha,2-dicarboxylicacid;α-Carboxy-o-toluicacid;HOMOPHTHALIC DIACID;HOMOPHTHALIC ACID
• CAS NO: 89-51-0
• Molecular Formula: C9H8O4
• Molecular Weight: 180.16
• EINECS: 201-913-9
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;Building Blocks;C9;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 89-51-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 178-182 °C(lit.)
• Boiling Point: 389.5 °C at 760 mmHg
• Flash Point: 203.5 °C
• Appearance: Off-white to light yellow or pale green/Powder
• Density: 1.392 g/cm³
• Vapor Pressure: 9.16E-07mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Dimethylformamide
• PKA: 3.72±0.36(Predicted)
• Water Solubility: 12 g/L (20 ºC)
• BRN: 1872069
• CAS DataBase Reference: Homophthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Homophthalic acid(89-51-0)
• EPA Substance Registry System: Homophthalic acid(89-51-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36/37/39-27
• WGK Germany: 3
• RTECS: CY1575590
• TSCA: Yes
• Hazardous Substances Data: 89-51-0(Hazardous Substances Data)

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 
• 101268-34-2 1,4-diethoxy-4,5-dihydrobenzodioxepin 
• 6627-91-4 2-cyanomethylbenzoic 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 
• 34497-18-2 diethyl nona-2,7-diynedioate 
• 100397-38-4 ethyl β-(1-oxo-2,3-dihydro-1H-inden-2-yl)-α-oxoacetate 
• 76-05-1 trifluoroacetic acid 
• 255841-48-6 3,3-dimethyl-3,4-dihydroisocoumarin-4-carboxylic acid 
• 60-29-7 diethyl ether 

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 
• 73109-31-6 2-(4-methylphenyl)-1,3(2H,4H)-dioxoisoquinoline 
• 53558-67-1 2-phenethyl-4H-isoquinoline-1,3-dione 
• 858426-32-1 6,9-dihydroxy-11H-dibenzo[a,d]cycloheptene-5,10-dione 
• 861065-28-3 [2-(2,5-dihydroxy-benzoyl)-phenyl]-acetic acid 
• 4494-53-5 2-methyl-1,3(2H,4H)-isoquinolinedione 
• 21640-31-3 2-(phenylmethyl)isoquinoline-1,3(2H,4H)-dione 

Relevant articles and documents

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.

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.

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.