94-46-2

Basic information

• Product Name: Isoamyl benzoate
• Synonyms: Isopentyl alcohol, benzoate;isopentylalcohol,benzoate;so-Amyl benzoate;FEMA 2058;ISOPENTYL BENZOATE;ISOAMYL BENZOATE;BENZOIC ACID ISOAMYL ESTER;BENZOIC ACID ISOPENTYL ESTER
• CAS NO: 94-46-2
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25
• EINECS: 202-334-4
• Product Categories: Alphabetical Listings;Flavors and Fragrances;I-L
• Mol File: 94-46-2.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 261-262 °C(lit.)
• Flash Point: >230 °F
• Appearance: colorless to light yellow liquid
• Density: 0.99 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0125mmHg at 25°C
• Refractive Index: n20/D 1.494(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: Insoluble in water
• Merck: 14,5113
• CAS DataBase Reference: Isoamyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Isoamyl benzoate(94-46-2)
• EPA Substance Registry System: Isoamyl benzoate(94-46-2)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 2
• RTECS: DH3078000
• Hazardous Substances Data: 94-46-2(Hazardous Substances Data)

Usage

Description

Isoamyl benzoate has a fruity, slightly pungent odor. May be prepared by transesterification of methyl benzoate and isoamyl alcohol in the presence of potassium isoamylate; also by heating benzoyl chloride and isoamyl acetate.

Chemical Properties

Different sources of media describe the Chemical Properties of 94-46-2 differently. You can refer to the following data:
1. Isoamyl benzoate has a mild, sweet, fruit-like odor
2. Colorless liquid; fruity odor. Insoluble in water; soluble in alcohol. Combustible.

Occurrence

Reported found in vinegar, cocoa, sweet cherry, papaya, beer, quince, litchi, cherimoya, sea buckthorn (Hippophae rhamnoides L.) and jackfruit (Artocarpus heterophyllus Larn.)

Uses

In perfumery and cosmetics.

Preparation

By transesterification of methyl benzoate and isoamyl alcohol in the presence of potassium isoamylate; also by heating benzyl chloride and isoamyl acetate.

Taste threshold values

Taste characteristics at 25 ppm: sweet, fruity with a green tropical nuance.

Metabolism

Benzoic acid is metabolized in the mammalian body after conjugation with glycine to form hippuric acid and benzoylglucuronic acid, which are excreted in the urine(Williams, 1959).

InChI:InChI=1/C12H16O2/c1-10(2)8-9-14-12(13)11-6-4-3-5-7-11/h3-7,10H,8-9H2,1-2H3

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 123-51-3 i-Amyl alcohol 
• 98-08-8 α,α,α-trifluorotoluene 
• 93-89-0 benzoic acid ethyl ester 
• 643-94-7 o-phenylene dibenzoate 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 3741-66-0 Ethyl benzoyl carbonate 
• 94-01-9 resorcinol dibenzoate 
• 122842-83-5 1,4-bis-benzoyloxy-2-chloro-benzene 
• 628-04-6 1-ethoxy-3-methyl-butane 
• 618-38-2 benzoyl iodide 
• 123-92-2 3-methyl-1-butyl acetate 
• 65-85-0 benzoic acid 
• 582-25-2 Potassium benzoate 

Downstream Products

• 532-32-1 sodium benzoate 
• 563-45-1 3-Methyl-1-butene 
• 65-85-0 benzoic acid 
• 71-43-2 benzene 
• 1009091-33-1 2-azido-2-methylbutyl benzoate 
• 5205-04-9 (3-hydroxy-3-methylbutyl) benzoate 

Relevant articles and documents

LiHMDS: Facile, highly efficient and metal-free transesterification under solvent-free condition

Transesterification is one of the important organic reactions employed in numerous industrial as well as laboratory applications for the synthesis of various esters. Herein, we report a rapid, highly efficient, and transition metal-free transesterification reaction in the presence of LiHMDS under solvent-free conditions. The transesterification reaction was carried out with three different benzoate esters and a wide range of primary and secondary alcohols (from C3-C18) in good to excellent yields (45 examples). By considering the commercial role of esters, this method will be promising for the facile synthesis of esters in industry-relevant applications.

Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Herein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.

Metal catalyst-free photo-induced alkyl C-O bond borylation

Metal catalyst free, blue visible light-induced C-O bond borylation of unactivated tertiary alkyl methyl oxalates has been developed to furnish tertiary alkyl boronates. From the secondary alcohols activated with imidazolylthionyl, moderate yields of boronates were attained under standard photo-induced conditions. Preliminary mechanistic studies confirmed the involvement of a (DMF)2-B2cat2 adduct that weakly absorbs light at 437 nm so as to initiate a Bcat radical. A radical-chain process is proposed wherein the alkyl radical is engaged. This journal is