4-(Trifluoromethoxy)benzyl bromide

Base Information

• Chemical Name: 4-(Trifluoromethoxy)benzyl bromide
• CAS No.: 50824-05-0
• Molecular Formula: C8H6OBrF3
• Molecular Weight: 255.034
• Hs Code.: 29093090
• European Community (EC) Number: 628-274-2
• DSSTox Substance ID: DTXSID00198855
• Nikkaji Number: J2.620.201I
• Wikidata: Q72511356
• Mol file: 50824-05-0.mol

Synonyms:4-Trifluoromethoxybenzyl bromide;p-Trifluoromethoxybenzyl bromide;4-(Trifluoromethoxy)benzylbromide;1-(Bromomethyl)-4-(trifluoromethoxy)benzene;Benzene, 1-(bromomethyl)-4-(trifluoromethoxy)-;4-(Bromomethyl)phenyl trifluoromethyl ether;

Chemical Property of 4-(Trifluoromethoxy)benzyl bromide

Chemical Property:

• Appearance/Colour: yellow or slight yellow liquid
• Vapor Pressure: 3.44mmHg at 25°C
• Melting Point: 22-24 °C
• Refractive Index: n20/D 1.48(lit.)
• Boiling Point: 203.2 °C at 760 mmHg
• Flash Point: 94.4 °C
• PSA: 9.23000
• Density: 1.6 g/cm³
• LogP: 3.48010
• Storage Temp.: Refrigerated.
• Sensitive.: Lachrymatory
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 253.95541
• Heavy Atom Count: 13
• Complexity: 152

Purity/Quality:

99% ^*data from raw suppliers

4-(Trifluoromethoxy)benzyl Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1CBr)OC(F)(F)F
• Uses: 4-Trifluoromethoxybenzyl Bromide is a useful synthetic intermediate. It is used to prepare (nitro)[(trifluoromethoxy)benzyloxy]dihydroimidazo[2,1-b][1,3]oxazines with antitubercular activities. It is also used to synthesize tetrahydronaphthalenols with anti-allergic activities. 4-(Trifluoromethoxy)benzyl bromide may be used in the synthesis of bioreductive drug, (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).

Technology Process of 4-(Trifluoromethoxy)benzyl bromide

There total 5 articles about 4-(Trifluoromethoxy)benzyl bromide 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: 66.0%

4-trifluoromethoxybenzyl alcohol (1736-74-9) → 4-trifluoromethoxybenzyl bromide (50824-05-0)

Guidance literature:

With phosphorus tribromide; In dichloromethane; at 0 - 20 ℃; for 3.5h;

Reference yield: 60.0%

1-trifluoromethoxybenzene (456-55-3) → 4-trifluoromethoxybenzyl bromide (50824-05-0)

Guidance literature:

With sodium bromide; sulfuric acid; paraformaldehyde; In tert-butyl methyl ether; water; acetic acid;

Reference yield:

p-trifluoromethoxybenzaldehyde (659-28-9) → 4-trifluoromethoxybenzyl bromide (50824-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol / 20 °C

2: PBr₃ / diethyl ether / -40 °C

With sodium tetrahydroborate; phosphorus tribromide; In methanol; diethyl ether;

DOI:10.1021/jm0310737

upstream raw materials:

4-trifluoromethoxybenzyl alcohol

p-trifluoromethoxybenzaldehyde

4-trifluoromethoxy-benzoic acid ethyl ester

1-trifluoromethoxybenzene

Downstream raw materials:

C₁₅H₁₄F₃N₃O₅

C₁₅H₁₄F₃N₃O₅

2S-hydroxy-3R-(4-trifluoromethoxy-benzyl)-succinic acid dimethyl ester

C₂₅H₁₇F₆NO₂

Refernces

• 1、 Bedford, Robin B.,Brenner, Peter B.,Carter, Emma,Gallagher, Timothy,Murphy, Damien M.,Pye, Dominic R.. "Iron-catalyzed borylation of alkyl, allyl, and aryl halides: Isolation of an iron(I) boryl complex". supporting information. p. 5940 - 5943. Retrieved 2015/01/08.
• 2、 Maya, Ana B. S.,Pérez-Melero, Concepción,Mateo, Carmen,Alonso, Dulce,Fernández, José Luis,Gajate, Consuelo,Mollinedo, Faustino,Peláez, Rafael,Caballero, Esther,Medarde, Manuel. "Further naphthylcombretastatins. An investigation on the role of the naphthalene moiety". . p. 556 - 568. Retrieved 2007/10/03.