3-(3-(Bromomethyl)phenyl)-5-methyl-1,2,4-oxadiazole

Base Information

• Chemical Name: 3-(3-(Bromomethyl)phenyl)-5-methyl-1,2,4-oxadiazole
• CAS No.: 253273-90-4
• Molecular Formula: C10H9 Br N2 O
• Molecular Weight: 253.098
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30427625
• Wikidata: Q82240283
• Mol file: 253273-90-4.mol

Synonyms:253273-90-4;3-(3-(bromomethyl)phenyl)-5-methyl-1,2,4-oxadiazole;3-[3-(bromomethyl)phenyl]-5-methyl-1,2,4-oxadiazole;3-(3-bromomethylphenyl)-5-methyl-1,2,4-oxadiazole;3-(5-Methyl-1,2,4-oxadiazol-3-yl)benzyl bromide;SCHEMBL1301049;DTXSID30427625;CERZNQPNTHWEAD-UHFFFAOYSA-N;MFCD07368547;AKOS015900065;AC-26486;AS-31415;FT-0691889;A817788;W-206948

Chemical Property of 3-(3-(Bromomethyl)phenyl)-5-methyl-1,2,4-oxadiazole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 71 °C
• Refractive Index: 1.584
• Boiling Point: 369.4°Cat760mmHg
• PKA: -0.49±0.32(Predicted)
• Flash Point: 177.2°C
• PSA: 38.92000
• Density: 1.491g/cm³
• LogP: 2.93990
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 251.98983
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

98%min ^*data from raw suppliers

3-[3-(Bromomethyl)phenyl]-5-methyl-1,2,4-oxadiazole ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC(=NO1)C2=CC=CC(=C2)CBr

Technology Process of 3-(3-(Bromomethyl)phenyl)-5-methyl-1,2,4-oxadiazole

There total 6 articles about 3-(3-(Bromomethyl)phenyl)-5-methyl-1,2,4-oxadiazole 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: 52.4%

5-Methyl-3-(m-tolyl)-1,2,4-oxadiazole (87944-75-0) → 3-[3-(bromomethyl)phenyl]-5-methyl-1,2,4-oxadiazole (253273-90-4)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; for 2h; Irradiation; reflux;

DOI:10.1016/S0040-4020(99)00752-8

Reference yield:

[3-(5-methyl-1,2,4-oxadiazol-3-yl)-phenyl]methanol (852180-70-2) → 3-[3-(bromomethyl)phenyl]-5-methyl-1,2,4-oxadiazole (253273-90-4)

Guidance literature:

With phosphorus tribromide; In toluene; at 20 - 35 ℃; for 3h;

Reference yield:

3-Cyanobenzoic acid (1877-72-1) → 3-[3-(bromomethyl)phenyl]-5-methyl-1,2,4-oxadiazole (253273-90-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium carbonate; hydroxylamine hydrochloride / methanol / 15 h / 40 °C / Reflux

2.1: acetic anhydride; acetic acid / water / 14 h / 118 °C

3.1: sulfuric acid / 18 h / Reflux

4.1: lithium borohydride / tetrahydrofuran / 20 h / 0 - 20 °C

4.2: pH 7

5.1: phosphorus tribromide / toluene / 3 h / 20 - 35 °C

With lithium borohydride; sulfuric acid; hydroxylamine hydrochloride; acetic anhydride; phosphorus tribromide; potassium carbonate; acetic acid; In tetrahydrofuran; methanol; water; toluene;

upstream raw materials:

5-Methyl-3-(m-tolyl)-1,2,4-oxadiazole

3-Cyanobenzoic acid

methyl 3-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate

3-(5-methyl-[1,2,4]-oxadiazol-3-yl)benzoic acid

Downstream raw materials:

6-[3-(5-methyl-1,2,4-oxadiazol-2-yl)-benzyloxy]-1,2-dihydroquinolin-2-one

5-chloro-3-[3-(5-methyl-1,2,4-oxadiazol-3-yl)benzyl]-3H-benzothiazol-2-one

N-(4-fluorophenyl)-6-(3-(5-methyl-1,2,4-oxadiazol-3-yl)benzylthio)nicotinamide

2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)benzyl]-6-phenoxy-2H-pyridazin-3-one

Refernces

• 1、 Mederski, Werner W.K.R.,Lefort, Marina,Germann, Martina,Kux, Dieter. "N-aryl heterocycles via coupling reactions with arylboronic acids". . p. 12757 - 12770. Retrieved 2007/10/03.