40340-41-8

Basic information

• Product Name: 5-(CHLOROMETHYL)-3-METHYLISOXAZOLE
• Synonyms: isoxazole, 5-(chloromethyl)-3-methyl-;5-(chloromethyl)-3-methylisoxazole(SALTDATA: FREE);5-(chloromethyl)-3-methyl-1,2-oxazole
• CAS NO: 40340-41-8
• Molecular Formula: C₅H₆ClNO
• Molecular Weight: 131.56
• Mol File: 40340-41-8.mol

Chemical Properties

• Boiling Point: 211.6 °C at 760 mmHg
• Flash Point: 81.8 °C
• Appearance: /
• Density: 1.202 g/cm³
• Vapor Pressure: 0.263mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: 2-8°C
• PKA: -2.14±0.10(Predicted)
• CAS DataBase Reference: 5-(CHLOROMETHYL)-3-METHYLISOXAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(CHLOROMETHYL)-3-METHYLISOXAZOLE(40340-41-8)
• EPA Substance Registry System: 5-(CHLOROMETHYL)-3-METHYLISOXAZOLE(40340-41-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 40340-41-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
5-(Chloromethyl)-3-methylisoxazole is used as a key intermediate in the synthesis of pharmaceuticals for its ability to form new compounds through chemical reactions. Its reactivity contributes to the development of diverse medicinal agents.
Used in Agrochemical Synthesis:
In the agrochemical industry, 5-(Chloromethyl)-3-methylisoxazole serves as a precursor in the creation of various agrochemicals, leveraging its reactive nature to produce compounds that can be used in crop protection and other agricultural applications.
Used in Organic Chemistry:
5-(Chloromethyl)-3-methylisoxazole is utilized as a building block in the synthesis of a wide range of other organic compounds, highlighting its importance in the field of organic chemistry due to its versatility and reactivity.

InChI:InChI=1/C5H6ClNO/c1-4-2-5(3-6)8-7-4/h2H,3H2,1H3

Upstream product

• 14716-89-3 3-methyl-5-isoxazolemethanol 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 683-58-9 acetohydroximoyl chloride 
• 615-79-2 ethyl 2,4-diketopentanoate 
• 63366-79-0 3-methylisoxazole-5-carboxylic acid ethyl ester 
• 5780-37-0 (E)-acetaldoxime 
• 624-65-7 2-propynyl chloride 
• 107-29-9 Acetaldehyde oxime 
• 54813-96-6 (Z)-4,5-dichloro-pent-3-en-2-one 

Downstream Products

• 30856-31-6 diethyl [(3-methyl-1,2-oxazol-5-yl)methyl]phosphonate 
• 105829-37-6 N-(3-methyl-5-isoxazolyl)methylethylenediamine 
• 171826-63-4 1,2-bis(2-(3-methyl-5-isoxazolyl)methoxyethoxy)benzene 
• 173850-54-9 3-methyl-5-(N,N-dimethylaminomethyl) isoxazole 
• 528593-71-7 5-(1H-1-indolylmethyl)-3-methylisoxazole 
• 1027392-37-5 [1-(3-methyl-isoxazol-5-ylmethyl)-1H-indol-3-yl]-oxo-acetyl chloride 
• 171826-64-5 1,2-bis(8-amino-1,4-dioxa-6-oxo-7-nonenyl)benzene 
• 220060-32-2 1,2-bis(1,4-dioxa-6,9-dioxononyl)benzene 
• 72398-78-8 3-methyl-5-<2-(2-hydroxyphenyl)ethenyl>isoxazole 
• 127450-32-2 5-[4-(sec-Butoxy)-phenoxymethyl]-3-methylisoxazole 
• 1192477-78-3 C₁₂H₂₀N₂O 
• 1220115-04-7 C₁₇H₂₅N₃O₂ 
• 13999-31-0 5-methoxymethyl-3-methylisoxazole 
• 43214-88-6 (3-methylisoxazol-5-yl)methyl acetate 

Relevant articles and documents

Simple one-pot synthesis of 5-(chloromethyl)isoxazoles from aldoximes and 2,3-dichloro-1-propene

[Figure not available: see fulltext.] A one-pot synthesis of 3-substituted 5-chloromethylisoxazoles from available starting aldoximes and 2,3-dichloro-1-propene, serving both as a solvent and reagent, is proposed. Excess 2,3-dichloro-1-propene is recovered after the reaction. The synthesis is effective for oximes of both aromatic and aliphatic aldehydes.

Isoxazole-Derived Amino Acids are Bromodomain-Binding Acetyl-Lysine Mimics: Incorporation into Histone H4 Peptides and Histone H3

A range of isoxazole-containing amino acids was synthesized that displaced acetyl-lysine-containing peptides from the BAZ2A, BRD4(1), and BRD9 bromodomains. Three of these amino acids were incorporated into a histone H4-mimicking peptide and their affinity for BRD4(1) was assessed. Affinities of the isoxazole-containing peptides are comparable to those of a hyperacetylated histone H4-mimicking cognate peptide, and demonstrated a dependence on the position at which the unnatural residue was incorporated. An isoxazole-based alkylating agent was developed to selectively alkylate cysteine residues in situ. Selective monoalkylation of a histone H4-mimicking peptide, containing a lysine to cysteine residue substitution (K12C), resulted in acetyl-lysine mimic incorporation, with high affinity for the BRD4 bromodomain. The same technology was used to alkylate a K18C mutant of histone H3.

Synthesis and biological evaluation of N-heterocyclic indolyl glyoxylamides as orally active anticancer agents

A series of N-heterocyclic indolyl glyoxylamides were synthesized and evaluated for in vitro and in vivo anticancer activities. They exhibited a broad spectrum of anticancer activity not only in murine leukemic cancer cells but also in human gastric, breast, and uterus cancer cells as well as their multidrug resistant sublines with a wide range of IC50 values. They also induced apoptosis and caused DNA fragmentation in human gastric cancer cells. Among the compounds studied, 7 showed the most potent activity of growth inhibition (IC50 17-1711 nM) in several human cancer cells. Given orally, compounds 7 and 13 dose-dependently prolonged the survival of animals inoculated with P388 leukemic cancer cells. N-Heterocyclic indolyl glyoxylamides may be useful as orally active chemotherapeutic agents against cancer and refractory cancerous diseases of multidrug resistance phenotype.

Synthesis and properties of 3-alkyl(aryl)-5-chloromethylisoxazoles

3-Chloro-2-isothiocyanato-1-propenyl alkyl(aryl) ketones react with hydroxylamine hydrochloride to give 3-alkyl(aryl)-5-chloromethylisoxazole. Treatment of the latter with dimethylamine and ammonium thiocyanate leads to formation of previously unknown 3-alkyl(aryl)-5-dimethylamino(or isothiocyanato)-methylisoxazoles.

Extractant for selectively extracting strontium from aqueous solution containing the same

An extractant for selectively extracting strontium from an aqueous solution containing the same, which comprises a 1,2-benzenebis(1,4-dioxanonyl-6,8-dionato)metal complex of the following structural formula: STR1 wherein M represents a metal ion of Cu (II), Zn (II) or Ni (II).