37526-88-8

Basic information

• Product Name: BENZYL TIGLATE
• Synonyms: 2-Butenoic acid, 2-methyl-, phenylmethyl ester, (E)-;2-Butenoicacid,2-methyl-,phenylmethylester,(E)-;2-methyl-,phenylmethylester,(e)-2-butenoicaci;2-methyl-,phenylmethylester,(E)-2-Butenoicacid;Benzyl (2E)-2-methyl-2-butenoate;trans-2-Butenoic acid, 2-methyl-, phenylmethyl ester;trans-2-Butenoicacid,2-methyl-,phenylmethylester;TIGLIC ACID BENZYL ESTER
• CAS NO: 37526-88-8
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.24
• EINECS: 253-544-8
• Product Categories: Aromatic Esters
• Mol File: 37526-88-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 139 °C9 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.031 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00802mmHg at 25°C
• Refractive Index: n20/D 1.522(lit.)
• BRN: 2556119
• CAS DataBase Reference: BENZYL TIGLATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL TIGLATE(37526-88-8)
• EPA Substance Registry System: BENZYL TIGLATE(37526-88-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• TSCA: Yes
• Hazardous Substances Data: 37526-88-8(Hazardous Substances Data)

Usage

Chemical Properties

Benzyl tiglate has an odor reminiscent of mushroom, with a rosy undertone.

Occurrence

Reported found in clove bud and rose apple (Syz. jambos Alston).

Uses

Tiglic Acid Benzyl Ester is found as one of the Geranium essential oils, and essential oil and solvent extracts of Iris planifolia (Mill) from Algeria, possessing antibacterial activity. It is also the starting material in the synthesis of (S)-α-Acetolactic Acid (A163805).

Preparation

By direct esterification of tiglic acid with benzyl alcohol under azeotropic conditions.

Taste threshold values

Taste characteristics at 100 ppm: sweet, balsamic, spice-like with a nutty almond note.

InChI:InChI=1/C12H14O2/c1-3-10(2)12(13)14-9-11-7-5-4-6-8-11/h3-8H,9H2,1-2H3/b10-3+

Upstream product

• 100-02-7 4-nitro-phenol 
• 587832-08-4 benzyl (S)-(+)-2-hydroxy-2-methylbutanoate 
• 106-44-5 p-cresol 
• 767-00-0 4-cyanophenol 
• 1730-91-2 (S)-2-Methylbutyric acid 
• 100-51-6 benzyl alcohol 
• 80-59-1 Tiglic acid 
• 100-39-0 benzyl bromide 
• 108-95-2 phenol 
• 90-05-1 2-methoxy-phenol 
• 95-48-7 ortho-cresol 
• 103-16-2 4-Benzyloxyphenol 
• 91-10-1 1,3-dimethoxy-2-hydroxy-benzene 
• 100-44-7 benzyl chloride 

Downstream Products

• 616-16-0 (R)-2-Methyl-1-butanol 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 1420904-78-4 C₂₀H₂₁NO₅ 
• 137-32-6 (+/-)-2-methyl-1-butanol 
• 211805-90-2 (2S,3R)-2,3-Dimethyl-aziridine-1,2-dicarboxylic acid dibenzyl ester 
• 211805-80-0 (4R,5S)-4,5-Dimethyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester 
• 211805-81-1 (2S,3S)-2-Azido-3-hydroxy-2-methyl-butyric acid benzyl ester 
• 211805-84-4 (2S,3S)-2-Bromo-3-hydroxy-2-methyl-butyric acid benzyl ester 
• 211805-89-9 (2S,3R)-2,3-dimethylaziridine-2-carboxylic acid benzyl ester 

Relevant articles and documents

Dienolates of Cycloalkenones and α,β-Unsaturated Esters Form Diels–Alder Adducts by a Michael/Michael-Tandem Reaction Rather Than in One Step

α,β-Unsaturated esters and lithium 1,3-dien-2-olates are known to furnish bicyclic lithium enolates by anionic Diels–Alder reactions. However, in principle, the respective products might form not only in a single step but also in two consecutive – or “tandem” – Michael additions, the first of which occurs intermolecularly, the second intramolecularly. Three cyclic lithium dienolates and four esters with a stereogenic Cα=Cβ bond reacted to give Diels–Alder adducts (10 times) or failed to react (2 times). Seven of the reactive combinations furnished adducts wherein the configuration of the former ester moiety had in part inverted. This precludes concerted pathways as their origins. This was a surprise since donors at C-2 of the 1,3-diene accelerate normal electron-demand Diels–Alder reactions in the order alkyl ⊕O? being a far better donor still, it is not obvious why the mechanism is non-concerted rather than concerted (and still more asynchronous).

Chiral bis(N-arylamino)phosphine-oxazolines: Synthesis and application in asymmetric catalysis

N-Arylation or N-alkylation of chiral 1,2-diamines followed by ring closure with phosphorus trichloride (PCl3) and subsequent coupling with an oxazoline alcohol resulted in a new class of N,P ligands. The corresponding iridium tetrakis[3,5-bis(trifluormethyl)phenyl]borate (BArF) complexes were found to be efficient catalysts for the enantioselective hydrogenation of unfunctionalized olefins and α,β-unsaturated carboxylic esters.

Stereospecific synthesis of chiral tertiary alkyl-aryl ethers via Mitsunobu reaction with complete inversion of configuration

Mitsunobu reaction of chiral tertiary alcohol (S)-2 with phenol 3 provides the desired ether (R)-1 in moderate yields at elevated temperatures (80-100°C). The SN2 displacement pathway is evident by complete inversion of the (S)-alcohol to (R)-e