499-87-6

Basic information

• Product Name: 4,5-Dimethoxy-2-nitrobenzoic acid
• Synonyms: 3-Deoxy-D-ribo-hexonic acid γ-lactone
• CAS NO: 499-87-6
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.14
• Mol File: 499-87-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4,5-Dimethoxy-2-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dimethoxy-2-nitrobenzoic acid(499-87-6)
• EPA Substance Registry System: 4,5-Dimethoxy-2-nitrobenzoic acid(499-87-6)

Safety Data

• Hazardous Substances Data: 499-87-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,5-Dimethoxy-2-nitrobenzoic acid is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its structural properties make it a valuable building block in the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, 4,5-Dimethoxy-2-nitrobenzoic acid is used as a key intermediate for the synthesis of a wide range of chemical compounds, including dyes, pigments, and other specialty chemicals. Its reactivity and functional groups allow for further modification and incorporation into more complex molecules.
Used in Material Science:
4,5-Dimethoxy-2-nitrobenzoic acid can be utilized in the development of novel materials with specific properties, such as optical, electronic, or mechanical characteristics. Its incorporation into polymers or other materials can lead to new applications in areas like sensors, coatings, or advanced materials for various industries.
Used in Research and Development:
As a chemical intermediate, 4,5-Dimethoxy-2-nitrobenzoic acid is also used in research and development for exploring new reactions, understanding reaction mechanisms, and developing new synthetic routes for the production of various compounds.

Upstream product

• 498-43-1 3-deoxy-D-ribo-hexonic acid 
• 75800-78-1 3-deoxy-α-D-ribo-hexofuranose 
• 17510-99-5 4,5,6-trihydroxy-2-oxohexanoic acid 
• 61259-48-1 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone 
• 146-72-5 3-O-methyl-D-glucose 
• 4613-62-1 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 50480-80-3 3-deoxy-D-arabino-hexono-1,4-lactone 
• 32443-72-4 D-erythro-3-deoxy-[2]hexosulose-bis-phenylhydrazone 

Downstream Products

• 72599-55-4 tri-O-acetyl-3-deoxy-D-ribo-hexono-1,4-lactone 
• 63902-18-1 3-deoxi-D-glucitol 
• 2490-91-7 3-deoxy-D-glucose 

Relevant articles and documents

PROCESS FOR PRODUCING 2-DEOXYALDOSE COMPOUND

An object of the present invention is to provide a method for preparing 2-deoxyaldoses on industrial scale in which the yield or the volumetric efficiency is excellent and the operation is simple, as compared to the conventionally known preparation method.A compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by the catalytic hydrogenation method using a metal such as palladium or the like, or a compound represented by the general formula (1) such as 2-keto-3-deoxygluconic acid or the like is reduced by using a hydride reducing agent in a solvent of not more than 30 weight times the amount of the above compound, for synthesizing 2-keto-3-deoxyaldonic acid. The 2-keto-deoxyaldonic acid was decarboxylated to obtain 2-deoxyaldoses.The method of the present invention is economical and efficiently excellent.

Aluminium(III) Coordination to Hydroxy Carboxylates: the Influence of Hydroxy Substituents Enabling Tridentate Binding

Potentiometric evalution of the interaction between aluminium(III) and the hydroxy carboxylates 3-deoxy-D-ribo-hexonate (L1H) and 2,5-dihydroxypentanoate (L2H) provided evidence for the formation of 1:1 complexes only, though with the ligand being present in singly, doubly and quadruply deprotonated forms in the hexonate complexes, and in singly, doubly and triply deprotonated forms in those of the pentanoate.At 298 K in aqueous media, I = 0.1 (NaCl), equilibrium quotient values obtained through use of the programs PKAS and BEST were: -log(1)->+>/1H>) (or pKa(L1H)) = 3.58+/-0.03; log(1)2+>/3+>1)->) = 1.97+/-0.03; log(-1L1)+>+>/1)2+>) = -2.83+/-0.05; log(-3L1)->+>2/-1L1)+>) = -9.17+/-0.08; -log(2)->+>(2H>) (or pKa(L2H)) = 3.92+/-0.03; log(2)2+>/3+>2)->) = 2-04+/-0.03; log(-1L2)+>+>/2)2+>) = -3.14+/-0.06; log(-2L2>+>/-1L2)+>) = -2.25+/-0.09.The very close similarity of the results for 3-deoxy-D-ribo-hexonate (3-deoxygluconate) and those known for D(+)-gluconate has led to the suggestion that the complexes of the quadruply deprotonated ligands may involve trialkoxo coordination through the C1, C5 and C6 substituents.

Base-Catalyzed Rearrangement of 6-Bromo-3,6-dideoxyaldohexono-1,4-lactones

Upon treatment of 3-deoxy-D-arabino and 3-deoxy-D-xylo-hexono-1,4-lactone with hydrogen bromide in acetic acid (HBA), 6-bromo-3,6-dideoxy-D-arabino- and 6-bromo-3,6-dideoxy-D-xylo-hexono-1,4-lactone are produced.When reacted with anhydrous potassium carbonate in acetone the two bromodeoxylactones are converted into epoxides.Exposed to excess aqueous potassium hydroxide, the bromodeoxylactones, or the epoxides, rearrange to give 3-deoxy-L-ribo- and 3-deoxy-L-lyxo-hexono-1,4-lactone.Consequently, inversion at both C-4 and C-5 has taken place.In both cases, considerable amounts of anhydrides are formed along with the lactones.The mechanism of the base-induced rearrangements is discussed.The various 6-bromodeoxylactones undergo hydrogenolysis to give the corresponding 3,6-dideoxyhexono-1,4-lactones.On reduction, the 3,6-dideoxy-D-arabino-hexono-1,4-lactone affords 3,6-dideoxy-D-arabino-hexose (tyvelose).

FORMATION OF GLUCOMETASACCHARINOLACTONES IN THE PYROLYSIS OF CURDLAN, A (1->3)-β-D-GLUCAN

The volatile products of vacuum pyrolysis of curdlan are very much influenced by the presence of small proportions of sodium chloride in the polysaccharide during pyrolysis.In the absence of contamination by this salt, the major, volatile products are the 1,6-anhydro-D-glucoses (pyranose and furanose) in 49percent yield.Addition of increasing proportions of sodium chloride decrases the yield of these anhydro-D-glucoses, and causes formation of increasing proportions of 3-deoxy-D-ribo-hexono-1,4-lactone and its D-arabino epimer (i.e., the glucometasaccharinolactones ) in a combined yield of up to 38percent.It is concluded that the pyrolysis of (1->3)-glycans can lead to a peeling reaction of the same type as that already known for alkaline degradation.The effect of other salts was also studied.

Preparation of 3-Deoxy-aldonolactones by Hydrogenolysis of Acetylated Aldonolactones

Acetylated aldono-1,4-lactones, when treated with hydrogen in the presence of triethylamine and palladium on carbon, form acetylated 3-deoxy-aldono-1,4-lactones in high yield through elimination of the 3-acetoxy group and subsequent stereospecific hydrogenation of the unsaturated intermediate.Thus, acetylated D-galactono-1,4-lactone (1) yields tri-O-acetyl-3-deoxy-D-xylo-hexono-1,4-lactone (3a).Acetylated D-mannono- or D-glucono-1,4-lactone both give 3-deoxy-D-arabino-hexono-1,4-lactone (10a), whereas the four acetylated D-pentono-1,4-lactones (14-17) all afford di-O-acetyl-D-threo-pentono-1,4-lactone (18a).D-Gluconolactone can be converted into (R)-γ-caprolactone (27) on treatment with hydrogen bromide followed by a series of reductions.Similarly, D-lyxonolactone produces 2,3-dideoxy-D-glycero-pentono-1,4-lactone (29).