122-91-8

Basic information

• Product Name: 4-METHOXYBENZYL FORMATE
• Synonyms: 4-methoxy-benzenemethanoformate;anisyl;Benzenemethanol,4-methoxy-,formate;FEMA 2101;ANISYL FORMATE;4-METHOXYBENZYL FORMATE;ANISYL FORMATE 90+% FCC;Formic acid 4-methoxybenzyl ester
• CAS NO: 122-91-8
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 204-582-9
• Mol File: 122-91-8.mol

Chemical Properties

• Boiling Point: 220 °C(lit.)
• Flash Point: 113 °C
• Appearance: /
• Density: 1.035 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.159Pa at 25℃
• Refractive Index: n20/D 1.523(lit.)
• Water Solubility: 2.679g/L at 25℃
• CAS DataBase Reference: 4-METHOXYBENZYL FORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYBENZYL FORMATE(122-91-8)
• EPA Substance Registry System: 4-METHOXYBENZYL FORMATE(122-91-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 122-91-8(Hazardous Substances Data)

Usage

Uses

Used in Perfumery:
4-METHOXYBENZYL FORMATE is used as a fragrance ingredient for its sweet, spicy, and vanilla-like odor with powdery fruity nuances, enhancing the overall scent of perfumes.
Used in Flavoring Industry:
4-METHOXYBENZYL FORMATE is used as a flavoring agent for its floral and sweet taste, adding a unique flavor to various products such as beverages, candy, and baked goods. It is particularly used in berry flavors at concentrations of 3-10 ppm.
Used in Food Industry:
4-METHOXYBENZYL FORMATE is used as a flavor enhancer in the food industry, providing a sweet, vanilla, and spice taste with fruity heliotropine-like nuances at a taste threshold value of 50 ppm.
Occurrence:
4-METHOXYBENZYL FORMATE has been reported to be found in natural sources such as Vanilla fragrans and Ribes species, which contribute to its desirable flavor and aroma characteristics.

Preparation

By direct esterification of anisic alcohol with formic acid.

Flammability and Explosibility

Notclassified

Metabolism

Esters of benzyl alcohol, such as the acetate, are rapidly hydrolysed in vivo to benzyl alcohol, which is then oxidized. The expected general reaction of primary aromatic alcohols in the animal body is oxidation to the corresponding aromatic acid, which is usually excreted as a glycine conjugate and to a lesser extent as an ester glucuronide. In rabbits, benzyl alcohol is almost entirely converted to benzoic acid, which is excreted mainly as hippuric acid . In substituted anisoles with a carboxyl group or a potential carboxyl group attached to the aromatic ring, the ether link is relatively stable(Williams, 1959).

InChI:InChI=1/C9H10O3/c1-11-9-4-2-8(3-5-9)6-12-7-10/h2-5,7H,6H2,1H3

Upstream product

• 77287-34-4 formamide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 64-18-6 formic acid 
• 195392-61-1 4-formyloxy-1-[1'-(4-methoxybenzyloxy)propan-3'-yl]azetidin-2-one 
• 109-94-4 formic acid ethyl ester 
• 18494-82-1 2-(4-methoxy-benzyloxy)-tetrahydro-pyran 
• 14629-56-2 trimethyl(4-methoxybenzyloxy)silane 
• 195392-62-2 1-[1'-(4-methoxybenzyloxy)propan-3'-yl]-4-vinyloxyazetidin-2-one 
• 50-00-0 formaldehyd 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 64-17-5 ethanol 

Downstream Products

• 133788-00-8 6-phenyl-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one 
• 67-56-1 methanol 
• 5405-95-8 4,4'-dimethoxydibenzyl ether 
• 105-13-5 4-Methoxybenzyl alcohol 

Relevant articles and documents

Method for preparing formate-type compound

The invention discloses a method for preparing a formate-type compound. The method comprises the following steps of: adopting an alcohol-type compound and 1,3-dihydroxyacetone as reaction raw materials, and under the existence of a composite catalyst and an oxidant, reacting for 2-48 hours in a reaction medium in a reactor at a reaction temperature of 25-100 DEG C so as to obtain the formate-typecompound. The method disclosed by the invention is simple, and is mild in reaction condition, and by the method, a target product can be obtained by low cost and high yield; the used catalyst has highcatalytic activity, and is easily separated from a reaction system to be repeatedly used; the whole process is environment-friendly, and the reaction raw material (1,3-dihydroxyacetone) is easily converted from a side product (glycerol) of biodiesel, so that the utilization of the glycerol is promoted.

Application of polydopamine sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (Fe3O4@PDA-SO3H) as a heterogeneous and recyclable nanocatalyst for the formylation of alcohols and amines under solvent-free conditions

Herein, formylation of structurally different amines and alcohols with ethyl formate was carried out in the presence of a catalytic proportion of sulfonic acid supported on polydopamine (PDA)-encapsulated Fe3O4 nanoparticles as a heterogeneous, recyclable, and greatly efficient catalyst; this method provided the corresponding N-formyl compounds in good to excellent yields under solvent-free conditions. The magnetically catalytic system was recovered, by-passing the time-consuming filtration operation using an external magnet device. This procedure also increases the purity of the product and promises economic and ecological advantages. Furthermore, the recovery and reuse of the catalyst was demonstrated five times without detectable loss in the activity.

Acidic ionic liquid immobilized on nanoporous Na+-montmorillonite as an efficient and reusable catalyst for the formylation of amines and alcohols

In this work, nanoporous sodium montmorillonite clay (Na+-MMT) was used as a support for the immobilization of 1-methyl-3-(trimethoxysilylpropyl)-imidazolium hydrogen sulfate. The Na+-MMT chemical modification ([Na+-MMT-[pmim]HSO4) was confirmed by a variety of techniques including Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy and potentiometric titration. The catalytic performance of this immobilized acidic ionic liquid was probed for the N-formylation of a variety of amines using formic acid under solvent-free conditions. This reagent is also useful for the formylation of benzylic alcohols. The procedure gave the products in excellent yields in very short reaction times. Also, this catalyst can be reused ten times without loss of its catalytic activity.

Br?nsted acidic ionic liquid supported on rice husk ash (RHA-[pmim]HSO4): A highly efficient and reusable catalyst for the formylation of amines and alcohols

In this work, rice husk ash (RHA), as a natural source of amorphous silica, was used as a support for the immobilization of 1-methyl-3-(trimethoxysilylpropyl)-imidazolium hydrogen sulfate. The immobilized acidic ionic liquid was characterized with a variety of techniques including infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy (SEM) and pH analysis. The catalytic performance of this heterogeneous ionic liquid was probed for the N-formylation of a variety of amines using formic acid under solvent free conditions. It is also useful for the formylation of benzylic alcohols. The procedure gave the products in excellent yields in very short reaction times. Also this catalyst can be reused ten times without loss of its catalytic activity.

(Cyclopentadienone)iron shvo complexes: Synthesis and applications to hydrogen transfer reactions

A series of (cyclopendienone)iron tricarbonyl complexes were prepared using an intramolecular cyclization strategy. These were applied to the catalysis of the oxidation of alcohols to aldehydes and ketones. When paraformaldehyde was used as the hydrogen acceptor, formate esters were obtained as coproducts and, in several cases, the major products.

Formylation of amines and alcohols using aminopropylated mesoporous SBA-15 silica (APMS) as an efficient and recyclable catalyst

Aminopropylated mesoporous SBA-15 silica (APMS) is introduced as a new, recyclable and efficient catalyst for the formylation of a variety of amines and alcohols by using readily available formic acid under solvent-free conditions.

Formylation of alcohol with formic acid under solvent-free and neutral conditions catalyzed by free I2 or I2 generated in situ from Fe(NO3)3·9H2O/NaI

Different alcohols were formylated by formic acid under solvent-free conditions in the presence of iodine as the catalyst with good-to-high yields at room temperature. I2 generated in situ from Fe(NO3) 3·9H2O/NaI also catalyzed the formylation of the alcohols under solvent-free conditions. This gives a green and efficient reaction at room temperature, in which the use of toxic and corrosive molecular I2 is avoided.

N,N′-dibromo-N,N′-1,2-ethanediylbis(benzene sulfonamide) as an efficient catalyst for acetylation and formylation of alcohols under mild conditions

An efficient method for the acylation and formylation of alcohols and phenols by using an acylating/formylating agent (acetic anhydride and formic acid) in the presence of a catalytic amount of N,N′-dibromo-N,N′-1, 2-ethanediylbis(benzene sulfonamide) under mild and solvent-free conditions at room temperature in good to excellent yields is described. The use of protic acids and metal Lewis acids is avoided.

Dual behavior of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions

The dual behavior phenomenon of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions (SFRCs) is described; the governing factor is the stability of the carbonium ion generated from the alcohol; high concentration reaction conditions (HCRCs) or dilute solutions are much less suitable. In the case of benzylic alcohols, loss of optical activity was noted, whereas alkyl alcohols furnished a product with retention of stereochemistry.