3-(Bromomethyl)-5-methylisoxazole

Base Information

• Chemical Name: 3-(Bromomethyl)-5-methylisoxazole
• CAS No.: 130628-75-0
• Molecular Formula: C5H6BrNO
• Molecular Weight: 176.013
• Hs Code.: 2934999090
• European Community (EC) Number: 691-819-8
• DSSTox Substance ID: DTXSID70379972
• Wikidata: Q72447373
• Mol file: 130628-75-0.mol

Synonyms:3-(Bromomethyl)-5-methylisoxazole;130628-75-0;3-(bromomethyl)-5-methyl-1,2-oxazole;3-Bromomethyl-5-methyl-isoxazole;MFCD02677720;3-(bromomethyl)-5-methyl-isoxazole;3-bromomethyl-5-methylisoxazole;Isoxazole, 3-(bromomethyl)-5-methyl-;Ketone, 2-fluorenyl methyl;SCHEMBL125303;DTXSID70379972;3-(bromomethyl)-5-methylisoxazol;ASGJFGPILHALRC-UHFFFAOYSA-N;3-(bromomethyl)-5-methylisooxazole;AKOS006230462;CS-10406;CS-0085258;FT-0613724;3-(bromomethyl)-5-methylisoxazole, AldrichCPR;EN300-216088;F30090;A1-00825;W-205329

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

Chemical Property:

• Vapor Pressure: 0.109mmHg at 25°C
• Refractive Index: 1.525
• Boiling Point: 228.8 °C at 760 mmHg
• PKA: -3.41±0.12(Predicted)
• Flash Point: 92.2 °C
• PSA: 26.03000
• Density: 1.582g/cm³
• LogP: 1.87790
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 174.96328
• Heavy Atom Count: 8
• Complexity: 78.8

Purity/Quality:

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

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

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,Xn
• Statements: 34-36-22
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NO1)CBr

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

There total 5 articles about 3-(Bromomethyl)-5-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: 65.0%

(5-methyl-isoxazol-3-yl)-methanol (35166-33-7) → 3-(bromomethyl)-5-methylisoxazole (130628-75-0)

Guidance literature:

With triphenylphosphine dibromide 1:1 addition complex; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(00)60386-6

Reference yield: 39.0%

→ 3-(bromomethyl)-5-methylisoxazole (130628-75-0)

Guidance literature:

Reference yield:

(Z)-5-Bromo-4-chloro-pent-3-en-2-one → 3-(bromomethyl)-5-methylisoxazole (130628-75-0) + 5-(bromomethyl)-3-methyl-1,2-oxazole (36958-61-9)

Guidance literature:

With hydroxylamine hydrochloride; In methanol; at 65 - 70 ℃; for 6h;

DOI:10.1007/s11178-005-0314-8

upstream raw materials:

(5-methyl-isoxazol-3-yl)-methanol

ethyl 5-methylisoxazole-3-carboxylate

ethyl 2,4-diketopentanoate

Downstream raw materials:

3-(azidomethyl)-5-methylisoxazole

benzyl (2S,3R,5R)-2,3-dimethoxy-2,3,5-trimethyl-5-(5-methylisoxazol-3-ylmethyl)-6-oxomorpholine-4-carboxylate

benzyl (2S,3R,5R)-5-benzyl-2,3-dimethoxy-2,3-dimethyl-5-(5-methylisoxazol-3-ylmethyl)-6-oxomorpholine-4-carboxylate

(5-methyl-3-isoxazolyl)methylamine

Refernces

• 1、 Aliev. "Synthesis of 5-bromomethylisoxazoles and their reactions with secondary amines". . p. 1192 - 1195. Retrieved 2007/10/03.
• 2、 Pei,Wickhan. "Regioselective syntheses of 3-aminomethyl-5-substituted isoxazoles: A facile and chemoselective reduction of azide to amino by sodium borohydride using 1,3-propanedithiol as a catalyst". . p. 7509 - 7512. Retrieved 2007/10/02.