3209-70-9

Basic information

• Product Name: ETHYL ISOXAZOLE-3-CARBOXYLATE
• Synonyms: AKOS PAO-1389;ETHYL ISOXAZOLE-3-CARBOXYLATE;4-CHLOROISOINDOLINE HCL;isoxazole-3-carboxylic acid ethyl ester;3-Isoxazolecarboxylic acid ethyl ester;Methyl isoxazole-3-carboxylate;3-Ethoxycarbonylisoxazole;Ethyl 3-isoxazolecarboxylate
• CAS NO: 3209-70-9
• Molecular Formula: C6H7NO3
• Molecular Weight: 141.12
• Mol File: 3209-70-9.mol

Chemical Properties

• Boiling Point: 219℃
• Flash Point: 87℃
• Appearance: /
• Density: 1.177
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: -5.43±0.50(Predicted)
• CAS DataBase Reference: ETHYL ISOXAZOLE-3-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL ISOXAZOLE-3-CARBOXYLATE(3209-70-9)
• EPA Substance Registry System: ETHYL ISOXAZOLE-3-CARBOXYLATE(3209-70-9)

Safety Data

• Hazardous Substances Data: 3209-70-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL ISOXAZOLE-3-CARBOXYLATE is used as a reactant for the preparation of demethyl 2-amino-3-(3-carboxy-5-methyl-4-isoxazolyl)propionic acid (ACPA). ACPA demonstrates activity at metabotropic receptors and serves as a weak antagonist at the mGlu2 receptor subtype, which has potential applications in the treatment of neurological disorders and conditions related to glutamate signaling.

Synthesis Reference(s)

Canadian Journal of Chemistry, 48, p. 467, 1970 DOI: 10.1139/v70-075

Upstream product

• 2960-66-9 ethyl 4-oxo-2-butenoate 
• 626-35-7 nitroacetic acid ethyl ester 
• 74-86-2 acetylene 
• 60212-44-4 ethyl trans-2-ethoxycyclopropanecarboxylate 
• 71666-09-6 ethyl cis-2-ethoxycyclopropanecarboxylate 
• 14337-43-0 ethyl 2-chloro-2-(hydroxyimino)acetate 
• 1112-00-1 trimethylstannylacetylene 
• 1066-26-8 sodium acetylide 
• 71-43-2 benzene 
• 51026-98-3 ethyl 2-nitro-3-oxobutyrate 

Downstream Products

• 89102-73-8 3-hydroxymethyl isoxazole 
• 89180-61-0 isoxazole-3-carboxaldehyde 
• 33036-67-8 ethyl oxazole-2-carboxylate 

Relevant articles and documents

Ethyl 2-nitroacetate as a new synthetic equivalent of ethoxycarbonylnitrile oxide

It was shown that ethyl 2-nitroacetoacetate is a synthetic precursor of ethoxycarbonylnitrile oxide as well as of isoxazole- and isoxazoline-3-carboxylic acids and their esters.The elimination of acetic acid from ethyl 2-nitroacetoacetate occurs in a mixture of acetic acid and acetic anhydride in the presence of strong mineral acids, e.g., H2SO4, at room temperature and gives isoxazolines in yields of up to 85 - 91percent. - Key words: ethoxycarbonylnitrile oxide, isoxazoles, isoxazolines.

Efficient and regioselective one-pot synthesis of 3-substituted and 3,5-disubstituted isoxazoles

(Figure Presented) A series of 3-substituted and 3,5-disubstituted isoxazoles have been efficiently synthesized in moderate to excellent yields by the reaction of N-hydroxyl-4-toluenesulfonamide with α,β-unsaturated aldehydes/ketones. This novel strategy is associated with readily available starting materials, mild conditions, high regioselectivity, and wide scope.

Ring-opening reactions of cyclopropanes. Part 8.1 Nitrosation of donor-acceptor cyclopropanes

The reaction of 2,2-dialkoxycyclopropane-1-carboxylates 1a-d and monoalkoxycyclopropane 1e with NOCl gives isoxazoline- and/or isoxazole-3-carboxylates by regioselective ring-opening at C1-C2 bond. A mechanistic interpretation suggests the intermediacy of well-stabilised dipolar species.

4-[(4-(CARBOXYETHYL) PIPERIDINYL) METHYL] PYRROLIDINES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

3-Substituted pyrrolidines having a 4-carboxypiperidinylmethyl substituent on the 4-position of the ring are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-3 and/or CCR-5.

4(SPIROPIPERIDINYL)METHYL SUBSTITUTED PYRROLIDINES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY

3-Substituted pyrrolidines having a spiropiperidinylmethyl substituent on the 4-position of the ring are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-3 and/or CCR-5.

Composition and antiviral activity of substituted indoleoxoacetic piperazine derivatives

The invention comprises substituted indoleoxoacetic piperazine derivatives of general Formula I, compositions thereof and their use as antiviral agents, and particularly for treating HIV infection.

Substituted 1,2,4-triazolo[3,4-a]phthalazine derivatives as GABA alpha 5 ligands

Substituted 1,2,4-Triazolo[3,4-A]phthalazine derivatives are GABA Alpha 5 ligands and are represented by the formula

1,3-Dipolar cycloaddition reaction of substituted trimethylstannylacetylenes with nitrile oxides

1,3-Dipolar cycloaddition reaction of trimethylstannylacetylene with nitrile oxides yielded 3-substituted 5-(trimethylstannyl)isoxazoles. On the other hand, the same reaction of (trimethylstannyl)phenylacetylene, -1-hexyne, and -(trimethylsilyl)acetylene