About This Product:
CAS Number : 824-94-2
Molecular Weight : 156.61
Molecular Formula : C8H9ClO
Synonym(s) : PMBCl;4-METHOXYBENZYL CHLORIDE;
: P-METHOXYBENZYL CHLORIDE;PBMCl;
: 4-(Chloromethyl)-1-methoxybenzene;
: 4-Methoxybenzylchloride stabilized,;
: 4-Methoxybenzylchloride stabilized,;
Physical Properties:
Appearance : Clear to slight yellow Coloured Liquid
Purity : >95.00% (GC)
Melting Point : NA
Boiling Point : 117°C to 118°C at 14 mmHg
Storage Temperature : 2-8°C inert atmosphere
LOD : NA
Solubility : Mixable in Methanol and Ethyl acetate
Density : 1.155 g/mL at 25°C
Moisture content : 0.50 %
Description : 4-Methoxy Benzyl Chloride (CAS 824-94-2 (PMBCl), also known as p-anisyl chloride or 4-(chloromethyl) anisole, is a colorless liquid used as a versatile research chemical and protecting group reagent in peptide synthesis. It acts as a reagent in various reactions, such as the synthesis of diarylmethanes via Suzuki coupling and the mono-alkylation of diamines, and can be cleaved with mild oxidizing agents like ceric ammonium nitrate
Scientific Research Applications
Pharmaceutical Applications
Anticancer Agents
PMB-Cl is instrumental in synthesizing stilbene and dihydrostilbene derivatives, which have shown potential as anticancer agents. Research indicates that these derivatives exhibit significant cytotoxic activity against cancer cell lines, making PMB-Cl a valuable precursor in cancer drug development .
Protecting Group in Organic Synthesis
In organic chemistry, PMB-Cl serves as a protecting group for carboxylic acids and alcohols. The 4-methoxybenzyl (PMB) group can be easily introduced and removed under mild conditions, making it a “workhorse” protecting group in multi-step syntheses. This property is particularly useful in peptide synthesis and the preparation of complex natural products .
Industrial Applications
Synthesis of Fine Chemicals
PMB-Cl is utilized in the synthesis of various fine chemicals, including agrochemicals and specialty chemicals. Its reactivity allows for the formation of esters and amides through acylation reactions with alcohols and amines, facilitating the production of diverse chemical compounds .
Carbohydrate Chemistry
The PMB group is extensively used in carbohydrate chemistry due to its stability and ease of removal under oxidative conditions. This application is crucial for synthesizing glycosides and other carbohydrate derivatives, enabling researchers to explore complex glycosylation reactions
Case Study 1: Anticancer Derivatives
A study published in Organic Chemistry demonstrated the synthesis of PMB-protected stilbene derivatives that exhibited potent anticancer activity against various tumor cell lines. The research highlighted the efficacy of these compounds in inhibiting cell proliferation and inducing apoptosis, showcasing PMB-Cl’s role as a key intermediate in drug discovery .
Case Study 2: Peptide Synthesis
In another significant study, researchers utilized PMB-Cl to protect amino acids during peptide synthesis. The PMB group allowed for selective deprotection under mild conditions, resulting in high yields of desired peptide products. This methodology emphasizes the importance of PMB-Cl in developing peptide-based therapeutics .
Data Tables
| Application Area | Specific Uses |
| Pharmaceuticals | Anticancer agents |
| Organic Synthesis | Protecting group for carboxylic acids |
| Fine Chemicals | Synthesis of esters and amides |
| Carbohydrate Chemistry | Glycoside synthesis |
Mechanism of Action
The mechanism of action of 4-methoxybenzyl chloride involves its reactivity as an electrophile. The chlorine atom in the molecule is highly reactive and can be easily displaced by nucleophiles. This reactivity makes it a valuable intermediate in organic synthesis, where it can be used to introduce the 4-methoxybenzyl group into various molecules
Key applications
- Protecting group:It is used to protect hydroxyl groups in alcohols and amines during multi-step syntheses. This is particularly common in peptide synthesis, where it is used to protect amino acids.
- Suzuki cross-coupling:It serves as a reagent in Suzuki cross-coupling reactions to form diarylmethanes and other complex molecules.
- Heterocyclic compound synthesis:It is a precursor for synthesizing various heterocyclic compounds, such as pyrazoles and N-heterocycles, through reactions like carboamination and other one-pot syntheses.
- Specialty chemical synthesis:
- It is used in the synthesis of acylphosphine ligands for catalytic applications.
- It has been used to modify indium tin oxide (ITO) cathodes for the fabrication of organic light-emitting diodes (OLEDs).
- It is a building block for the total synthesis of bioactive compounds like salinosporamide A.
