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Methyl 4-hydroxyphenylacetate
[CAS# 14199-15-6]

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Complete supplier list of Methyl 4-hydroxyphenylacetate
Identification
Classification Chemical reagent >> Organic reagent >> Ester >> Methyl ester compound
Name Methyl 4-hydroxyphenylacetate
Synonyms 4-Hydroxyphenylacetic acid methyl ester
Molecular Structure CAS # 14199-15-6, Methyl 4-hydroxyphenylacetate, 4-Hydroxyphenylacetic acid methyl ester
Molecular Formula C9H10O3
Molecular Weight 166.18
CAS Registry Number 14199-15-6
EC Number 238-050-2
SMILES COC(=O)CC1=CC=C(C=C1)O
Properties
Density 1.2±0.1 g/cm3, Calc.*
Melting point 55-58 ºC (Expl.)
Index of Refraction 1.539, Calc.*
Boiling Point 318.8±0.0 ºC (760 mmHg), Calc.*, 162-163 ºC (5 mmHg) (Expl.)
Flash Point 118.1±13.2 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H315-H319-H335    Details
Precautionary Statements P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - single exposureSTOT SE3H335
Eye irritationEye Irrit.2H319
Eye irritationEye Irrit.2AH319
SDS Available
up Discovory and Applicatios
Methyl 4-hydroxyphenylacetate is an organic compound with significant importance in pharmaceutical and industrial chemistry. Structurally, it features a phenolic hydroxyl group and an ester group derived from phenylacetic acid. These functional groups impart versatility, making it a valuable intermediate in synthesizing various biologically active compounds and specialty chemicals.

The discovery of methyl 4-hydroxyphenylacetate is rooted in the exploration of phenolic esters, known for their natural occurrence and synthetic utility. It is commonly synthesized via esterification of 4-hydroxyphenylacetic acid using methanol and acidic or enzymatic catalysts. Alternative methods include transesterification reactions, offering routes with enhanced selectivity and eco-friendliness.

Methyl 4-hydroxyphenylacetate is widely used in the pharmaceutical industry as a building block for drugs. Its phenolic hydroxyl group allows for chemical modifications, such as etherification and acylation, facilitating the synthesis of analgesics, anti-inflammatory agents, and central nervous system drugs. Researchers have explored its role in creating derivatives with improved pharmacokinetics and targeted biological activity.

In the cosmetics and personal care industry, methyl 4-hydroxyphenylacetate serves as a precursor for fragrances and flavoring agents. Its ester functionality contributes to its pleasant scent profile, often resembling floral or fruity notes. This property makes it desirable for formulating perfumes, lotions, and other aromatic products.

The compound also finds applications in materials science. It is used in polymer chemistry to produce phenolic resins and functionalized polymers, enhancing mechanical properties and thermal stability. Furthermore, its reactivity enables its inclusion in organic electronics and coatings, contributing to advancements in sustainable materials.

Ongoing research on methyl 4-hydroxyphenylacetate focuses on developing green synthesis routes and expanding its applications. Enzyme-catalyzed processes have gained attention due to their environmental benefits and high selectivity. Additionally, its derivatives are being explored for potential use in drug discovery and renewable materials.
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