5-(Chloromethyl)-3-methylisoxazole

Base Information

• Chemical Name: 5-(Chloromethyl)-3-methylisoxazole
• CAS No.: 40340-41-8
• Molecular Formula: C5H6ClNO
• Molecular Weight: 131.562
• Hs Code.: 2934999090
• European Community (EC) Number: 815-447-4
• DSSTox Substance ID: DTXSID30427923
• Wikidata: Q82240670
• Mol file: 40340-41-8.mol

Synonyms:5-(chloromethyl)-3-methylisoxazole;40340-41-8;5-(chloromethyl)-3-methyl-1,2-oxazole;ISOXAZOLE, 5-(CHLOROMETHYL)-3-METHYL-;5-Chloromethyl-3-methyl-isoxazole;Isoxazole,5-(chloromethyl)-3-methyl-;SCHEMBL1578634;3-methyl-5-chloromethylisoxazole;5-chloromethyl-3-methylisoxazole;DTXSID30427923;ZWBJJNWJUXXFNP-UHFFFAOYSA-N;5-(Chloromethyl)-3-methyl-isoxazole;MFCD07687105;STK506108;5-chloromethyl-3-methyl-1,2-oxazole;AKOS005172459;AB42093;BS-12882;BB 0259378;CS-0085295;FT-0679631;EN300-15253;E87529;J-516324;Z119990894

Chemical Property of 5-(Chloromethyl)-3-methylisoxazole

Chemical Property:

• Vapor Pressure: 0.263mmHg at 25°C
• Refractive Index: 1.482
• Boiling Point: 211.6 °C at 760 mmHg
• PKA: -2.14±0.10(Predicted)
• Flash Point: 81.8 °C
• PSA: 26.03000
• Density: 1.202 g/cm³
• LogP: 1.72180
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 131.0137915
• Heavy Atom Count: 8
• Complexity: 78.8

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-(Chloromethyl)-3-methylisoxazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NOC(=C1)CCl

Technology Process of 5-(Chloromethyl)-3-methylisoxazole

There total 10 articles about 5-(Chloromethyl)-3-methylisoxazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

3-methyl-5-isoxazolemethanol (14716-89-3) → 5-chloromethyl-3-methylisoxazole (40340-41-8)

Guidance literature:

With thionyl chloride; at 80 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1002/anie.201602908

Reference yield: 83.0%

(E)-5-Chloro-4-isothiocyanato-pent-3-en-2-one → 5-chloromethyl-3-methylisoxazole (40340-41-8)

Guidance literature:

With potassium hydroxide; hydroxylamine hydrochloride; In methanol; water; at 55 - 60 ℃; for 5h;

DOI:10.1023/A:1016398512557

Reference yield: 46.0%

Acetaldehyde oxime (107-29-9) + 2-propynyl chloride (624-65-7) → 5-chloromethyl-3-methylisoxazole (40340-41-8)

Guidance literature:

With sodium hypochlorite; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jm020471r

upstream raw materials:

3-methyl-5-isoxazolemethanol

acetohydroximoyl chloride

2-propynyl chloride

(Z)-4,5-dichloro-pent-3-en-2-one

Downstream raw materials:

3-methyl-5-(N,N-dimethylaminomethyl) isoxazole

diethyl [(3-methyl-1,2-oxazol-5-yl)methyl]phosphonate

N-{(E)-[4-(3-methyl-1,2-oxazol-5-yl)methoxy]benzylidene}biphenyl-4-amine

N-{(E)-4-[(3-methyl-1,2-oxazol-5-yl)methoxy]benzylidene}-4-phenoxyaniline

Refernces

• 1、 Sekirnik (née Measures), Angelina R.,Hewings, David S.,Theodoulou, Natalie H.,Jursins, Lukass,Lewendon, Katie R.,Jennings, Laura E.,Rooney, Timothy P. C.,Heightman, Tom D.,Conway, Stuart J.. "Isoxazole-Derived Amino Acids are Bromodomain-Binding Acetyl-Lysine Mimics: Incorporation into Histone H4 Peptides and Histone H3". supporting information. p. 8353 - 8357. Retrieved 2016/07/19.
• 2、 Gadzhily,Aliev. "Synthesis and properties of 3-alkyl(aryl)-5-chloromethylisoxazoles". . p. 415 - 418. Retrieved 2007/10/03.