5-(Bromomethyl)-3-methylisoxazole

Base Information

• Chemical Name: 5-(Bromomethyl)-3-methylisoxazole
• CAS No.: 36958-61-9
• Molecular Formula: C5H6BrNO
• Molecular Weight: 176.013
• Hs Code.: 2934999090
• European Community (EC) Number: 687-945-8
• DSSTox Substance ID: DTXSID20442367
• Wikidata: Q82259605
• Mol file: 36958-61-9.mol

Synonyms:5-(Bromomethyl)-3-methylisoxazole;36958-61-9;5-(bromomethyl)-3-methyl-1,2-oxazole;MFCD09879901;Isoxazole, 5-(bromomethyl)-3-methyl-;5-bromomethyl-3-methylisoxazole;SCHEMBL933778;3-methyl-5-bromomethylisoxazole;5-Bromomethyl-3-methyl-isoxazole;DTXSID20442367;DMUJLHLWCUMHRT-UHFFFAOYSA-N;AMY23827;AKOS012021117;PS-10050;SY036655;FT-0698326;5-(Bromomethyl)-3-methylisoxazole, AldrichCPR;EN300-153614;A874239;J-516303;F2147-0855

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

Chemical Property:

• Vapor Pressure: 0.13mmHg at 25°C
• Boiling Point: 225.37oC at 760 mmHg
• PKA: -2.18±0.10(Predicted)
• Flash Point: 90.101oC
• PSA: 26.03000
• Density: 1.583g/cm3
• LogP: 1.87790
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°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

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

Safty Information:

• Hazard Codes: C,Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NOC(=C1)CBr

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

There total 9 articles about 5-(Bromomethyl)-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: 86.0%

3-methyl-5-isoxazolemethanol (14716-89-3) → 5-(bromomethyl)-3-methyl-1,2-oxazole (36958-61-9)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at -17 - 23 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201712065

Reference yield: 85.0%

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

Guidance literature:

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

DOI:10.1007/s11178-005-0314-8

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:

3,5-dimethyl-1,2-oxazole

3-methyl-5-isoxazolemethanol

Acetaldehyde oxime

propargyl bromide

Downstream raw materials:

(3-methyl-isoxazol-5-ylmethyl)-triphenyl-phosphonium; bromide

2-(3-methyl-isoxazol-5-yl)-2-methylsulfanyl-1-phenyl-ethanol

4-bromo-5-bromomethyl-3-methyl-isoxazole

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、 Aliev. "Synthesis of 5-bromomethylisoxazoles and their reactions with secondary amines". . p. 1192 - 1195. Retrieved 2007/10/03.