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103-28-6

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103-28-6 Usage

Chemical Properties

Benzyl isobutyrate has a fresh, floral, somewhat jasmine-like, fruity odor and sweet, strawberry-like taste.

Occurrence

Reported found in mint, spearmint, beer, cherimoya (Annona cherimolia Mill.) and Passiflora edulis hybrid juice.

Preparation

May be prepared from benzyl alcohol and isobutyric acid, by the action of aluminum ethylate on a mixture of benzyl and butyric aldehydes.

Taste threshold values

Taste characteristics at 10 ppm: fruity and sweet with ripe berry nuances.

Synthesis Reference(s)

Synthesis, p. 1017, 1986 DOI: 10.1055/s-1986-31855

Flammability and Explosibility

Nonflammable

Check Digit Verification of cas no

The CAS Registry Mumber 103-28-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 3 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 103-28:
(5*1)+(4*0)+(3*3)+(2*2)+(1*8)=26
26 % 10 = 6
So 103-28-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H14O2/c1-9(2)11(12)13-8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3

103-28-6 Well-known Company Product Price

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  • Alfa Aesar

  • (L05930)  Benzyl isobutyrate, 98+%   

  • 103-28-6

  • 50g

  • 356.0CNY

  • Detail
  • Alfa Aesar

  • (L05930)  Benzyl isobutyrate, 98+%   

  • 103-28-6

  • 250g

  • 1387.0CNY

  • Detail

103-28-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzyl Isobutyrate

1.2 Other means of identification

Product number -
Other names Isobutyric Acid Benzyl Ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:103-28-6 SDS

103-28-6Relevant articles and documents

Hafnium inspired activation of highly hindered anhydrides in the acylation of alcohols and polyols

Mensah, Enoch,Day, Aaron,Thomas, Raven

, p. 1094 - 1098 (2018)

A novel and highly efficient method for activating highly hindered acid anhydrides towards the acylation of alcohols and carbohydrate-derived polyols has been developed. This new method relies on the capacity of the hafnium triflate catalyst Hf(OTf)2 to activate highly hindered acid anhydrides, and to direct the acylation reaction. This new acylation protocol is mild and proceed at room temperature with low catalyst loading. The method is versatile and has been extended to different alcohol substrates with different steric encumbrance as well as carbohydrate-derived polyols to afford the corresponding ester products in good to excellent yields.

Thorium complexes possessing expanded ring N-heterocyclic iminato ligands: Synthesis and applications

Ghatak, Tapas,Drucker, Shani,Fridman, Natalia,Eisen, Moris S.

, p. 12005 - 12009 (2017)

Six and seven membered N-heterocyclic iminato ligands (L) are introduced allowing access a new class of Th(iv) complexes of the type Cp?2Th(L)(CH3). These complexes were studied in the Tishchenko reaction. Stoichiometric reactions together with kinetic and thermodynamic studies permit us to propose a plausible mechanism.

Development of a practical and scalable preparation using sonication of Pd/fibroin catalyst for chemoselective hydrogenation

Kitamura, Yoshiaki,Tanaka, Asami,Sato, Mutsumi,Oono, Keiji,Ikawa, Takashi,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao

, p. 4381 - 4388 (2007)

A practical and efficient preparation method of palladium-fibroin (Pd/Fib), silk-fibroin-supported Pd(0) by means of sonication, has been developed. The Pd/Fib catalyst could be prepared within 12 h at room temperature starting from commercial silk-fibroin and Pd(OAc)2 in MeOH, whereas our previous preparation method required at least 4 days. The present improved process is applicable to a large-scale preparation of Pd/Fib. The Pd/Fib prepared by the present method also catalyzed chemoselective hydrogenation of acetylenes, olefins, and azides in the presence of aromatic ketones, aldehydes, and halides; N-Cbz protective groups; and benzyl esters, which are readily hydrogenated under the Pd/C- or Pd/C(en)-catalyzed hydrogenation conditions. Copyright Taylor & Francis Group, LLC.

Steric effects in the uncatalyzed and DMAP-catalyzed acylation of alcohols - Quantifying the window of opportunity in kinetic resolution experiments

Fischer, Christian B.,Xu, Shangjie,Zipse, Hendrik

, p. 5779 - 5784 (2006)

The kinetics of the reaction of several alcohols (benzyl alcohol, ethanol, 1-phenylethanol, cyclohexanol, and 1-methyl-1-phenylethanol) with a selection of anhydrides (acetic anyhydride, propionic anhydride, isobutyric anhydride, isovaleric anhydride, and pivalic anhydride) as catalyzed by 4-(N,N-dimethylamino)pyridine (DMAP)/triethyl amine have been studied in CH 2Cl2 at 20°C. In all cases the reaction kinetics can be described by rate laws containing a DMAP-catalyzed term and an uncatalyzed (back-ground) term. The rate constants for the background reaction respond sensi tively to changes in the steric demand of the alcohol and the anhydride substrates, making the reaction of cyclohexanol with acetic anhydride 526 times faster than the reaction with pivalic anhydride. Steric effects are even larger for the catalyzed reaction and the reactivity difference between acetic and pivalic anhydride exceeds a factor of 8000 for the reaction of cyclohexa nol. There is, however, no linear correlation between the steric effects on the catalyzed and the uncatalyzed part. As a consequence there are substrate combinations with dominating catalytic terms (such as the reaction of benzyl alcohol with isobutyric anhydride), while other substrate combinations (such as the reaction of cyclohexanol with pivalic anhydride) are characterized through a dominating background process. The implications of these findings for the kinetic resolution of alcohols are discussed.

Reductive esterification of aromatic aldehydes using Zn/Ac 2O/imidazole or Zn/Yb(OTf)3/(RCO)2O system

Hirao, Toshikazu,Santhitikul, Sirida,Takeuchi, Hiroki,Ogawa, Akiya,Sakurai, Hidehiro

, p. 10147 - 10152 (2003)

Benzaldehydes are reduced by metallic zinc in the presence of Ac 2O and imidazole, giving the corresponding benzyl acetates in good yields. Reductive esterification of aromatic aldehydes is also carried out via gem-diacetoxy compounds. Carbonyl compounds are readily converted to the gem-diacyloxy compounds in excellent yields on treatment with 2molar amounts of acid anhydride and 10mol% of Yb(OTf)3 in MeCN at room temperature. Thus-formed diacyloxy compounds derived from aromatic aldehydes are reduced in situ by metallic zinc to afford the corresponding esters.

Reusable and efficient polyvinylpolypyrrolidone-supported triflic acid catalyst for acylation of alcohols, phenols, amines, and thiols under solvent-free conditions

Tajbakhsh, Mahgol,Tajbakhsh, Mahmoud,Khaksar, Samad,Gazvini, Helia Janatian,Heidary, Marzieh

, p. 1117 - 1122 (2017)

Abstract: A triflic acid-functionalized polyvinylpolypyrrolidone was prepared and fully characterized by FT-IR, TGA, and SEM. This super acidic solid catalyst shows high catalytic activity for selective acylation of alcohols, phenols, amines, and thiols with anhydrides under solvent-free conditions at room temperature. In addition, this method features an easy to handle solid super acid catalyst and an operationally simple procedure, affording the desired acylated products in excellent yields. Graphical abstract: [Figure not available: see fulltext.].

Markedly chemoselective hydrogenation with retention of benzyl ester and N-Cbz functions using a heterogeneous Pd-fibroin catalyst

Sajiki, Hironao,Ikawa, Takashi,Hirota, Kosaku

, p. 8437 - 8439 (2003)

The chemoselective catalytic hydrogenation of acetylene, olefin and azido derivatives bearing benzyl ester and N-Cbz functionalities using a Pd-fibroin (Pd/Fib) catalyst was investigated. Perfect selectivity was accomplished, and the benzyl ester and N-Cbz functionalities are tolerated under the reaction conditions.

N-Heterocyclic Carbene/Carboxylic Acid Co-Catalysis Enables Oxidative Esterification of Demanding Aldehydes/Enals, at Low Catalyst Loading

Berkessel, Albrecht,Biswas, Animesh,Harnying, Wacharee,Sudkaow, Panyapon

supporting information, p. 19631 - 19636 (2021/08/09)

We report the discovery that simple carboxylic acids, such as benzoic acid, boost the activity of N-heterocyclic carbene (NHC) catalysts in the oxidative esterification of aldehydes. A simple and efficient protocol for the transformation of a wide range of sterically hindered α- and β-substituted aliphatic aldehydes/enals, catalyzed by a novel and readily accessible N-Mes-/N-2,4,6-trichlorophenyl 1,2,4-triazolium salt, and benzoic acid as co-catalyst, was developed. A whole series of α/β-substituted aliphatic aldehydes/enals hitherto not amenable to NHC-catalyzed esterification could be reacted at typical catalyst loadings of 0.02–1.0 mol %. For benzaldehyde, even 0.005 mol % of NHC catalyst proved sufficient: the lowest value ever achieved in NHC catalysis. Preliminary studies point to carboxylic acid-induced acceleration of acyl transfer from azolium enolate intermediates as the mechanistic basis of the observed effect.

Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor

Zhang, Deliang,Iwai, Tomohiro,Sawamura, Masaya

supporting information, p. 5867 - 5872 (2019/08/26)

The iridium-catalyzed transfer hydrogenation of alkenes using 1,4-dioxane as a hydrogen donor is described. The use of 1,2-bis(dicyclohexylphosphino)ethane (DCyPE), featuring bulky and highly electron-donating properties, led to high catalytic activity. A polystyrene-cross-linking bisphosphine PS-DPPBz produced a reusable heterogeneous catalyst. These homogeneous and heterogeneous protocols achieved chemoselective transfer hydrogenation of alkenes over other potentially reducible functional groups such as carbonyl, nitro, cyano, and imino groups in the same molecule.

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