3-Phenoxybenzyl chloride

Base Information

• Chemical Name: 3-Phenoxybenzyl chloride
• CAS No.: 53874-66-1
• Molecular Formula: C13H11 Cl O
• Molecular Weight: 218.683
• Hs Code.: 2909309090
• European Community (EC) Number: 258-831-1
• UNII: Q8R767G4B4
• DSSTox Substance ID: DTXSID00202128
• Nikkaji Number: J31.983J
• Wikidata: Q72500982
• Mol file: 53874-66-1.mol

Synonyms:3-phenoxybenzyl chloride

Chemical Property of 3-Phenoxybenzyl chloride

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 0.000603mmHg at 25°C
• Refractive Index: n20/D 1.5900(lit.)
• Boiling Point: 320.2 °C at 760 mmHg
• Flash Point: 148.6 °C
• PSA: 9.23000
• Density: 1.189 g/mL at 25 °C(lit.)
• LogP: 4.21770
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Lachrymatory
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 218.0498427
• Heavy Atom Count: 15
• Complexity: 177

Purity/Quality:

97% ^*data from raw suppliers

3-Phenoxybenzyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): CXn
• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-27-28-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2=CC=CC(=C2)CCl
• General Description: 3-Phenoxybenzyl chloride exhibits reduced reactivity compared to unsubstituted benzyl chloride, particularly in reactions with sodium thiobarbiturate, leading to lower conversion rates (50%) and the formation of 2-[(3-phenoxybenzyl)thio]pyrimidin-4,6(1H,5H)dione. The presence of the meta-phenoxy substituent decreases reactivity by 5.8 times, as demonstrated in the study, with steric factors influencing the reaction pathway and yielding 54% for the S-benzylation product.

Technology Process of 3-Phenoxybenzyl chloride

There total 13 articles about 3-Phenoxybenzyl chloride 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: 98.0%

3-Phenoxybenzyl alcohol (13826-35-2) → 3-phenoxybenzyl chloride (53874-66-1)

Guidance literature:

With thionyl chloride; In chloroform; Heating / reflux;

Reference yield: 59.8%

3-phenoxytoluene (3586-14-9) → α,α-dichloro-3-phenoxytoluene (53874-68-3) + 3-phenoxybenzyl chloride (53874-66-1)

Guidance literature:

Reference yield: 0.9%

3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (61949-76-6,93388-66-0) → 3-phenoxybenzyl chloride (53874-66-1) + cis-permethrinic acid (59042-49-8) + 3-Phenoxybenzyl alcohol (13826-35-2) + 3-phenoxybenzyl (1RS)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (93388-66-0)

Guidance literature:

With potassium chlorate; at 210 ℃; for 0.25h; Further Variations:; Reagents; Solvents; reaction time; Product distribution;

DOI:10.1002/ps.438

upstream raw materials:

3-Phenoxybenzyl alcohol

3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

3-Phenoxybenzaldehyde

3-phenoxytoluene

Downstream raw materials:

3-phenoxyphenylacetonitrile

N-(3-phenoxy-benzyl)-N-(2-chromanyl-methyl)-amine, maleate

triethyl-3-phenoxybenzyl ammonium chloride

ethyl 3-(4-fluorophenyl)-3-oxo-2-((3-(phenyloxy)phenyl)methyl)propionate

Refernces

Specific features of the reaction of m-phenoxybenzyl chloride with sodium thiobarbiturate

10.1134/S1070363209020339

The research discusses the specific features of the reaction between m-phenoxybenzyl chloride and sodium thiobarbiturate. The purpose of the study was to investigate how the introduction of a phenoxy substituent to the meta position of benzyl chloride affects its reactivity. The researchers found that this substitution decreased the reactivity with the sodium salt of 6-methyl-2-thiouracyl by 5.8 times. The reaction of m-phenoxybenzyl chloride with sodium thiobarbiturate resulted in a lower conversion (50%) compared to benzyl chloride, leading to the formation of 2-[(3-phenoxybenzyl)thio]pyrimidin-4,6(1H,5H)dione. The chemicals used in the process included thiobarbituric acid, sodium hydroxide, dioxane, water, and m-phenoxybenzyl chloride. The study concluded with a yield of 54% for the S-benzylation product of compound III and 70% for compound V, with quantum chemical analysis supporting the reaction's direction being influenced by the steric availability of the reaction center.