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

Description

4,5-Dimethoxy-2-nitrobenzoic acid is an organic compound characterized by the presence of two methoxy groups at the 4th and 5th positions and a nitro group at the 2nd position on a benzoic acid backbone. It is a versatile chemical intermediate with potential applications in various industries due to its unique structural features.

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

Downstream Products

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

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.

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).

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).