14316-68-8

Basic information

• Product Name: TIGLIC ANHYDRIDE
• Synonyms: TIGLIC ANHYDRIDE;(E)-2-METHYL-2-BUTENOIC ANHYDRIDE;2-METHYLCROTONIC ANHYDRIDE;2-Methylcrotonic anhydride (Tiglic anhydride);2-METHYLCROTONIC ANHYDRIDE TIGLIC ANHYDRIDE;(E)-2-Methyl-2-butenoic Anhydride 2-Methylcrotonic Anhydride;2-Butenoic acid, 2-Methyl-, anhydride, (2E,2'E)-
• CAS NO: 14316-68-8
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22
• Mol File: 14316-68-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.03
• Refractive Index: 1.4800 to 1.4830
• CAS DataBase Reference: TIGLIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TIGLIC ANHYDRIDE(14316-68-8)
• EPA Substance Registry System: TIGLIC ANHYDRIDE(14316-68-8)

Safety Data

• RIDADR: UN 3265 8/PG III
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 14316-68-8(Hazardous Substances Data)

Usage

General Description

Tiglic anhydride, also known as 2-methylbut-2-enoic anhydride, is a chemical compound used in organic synthesis. It is a colorless to pale yellow liquid with a pungent odor and is highly flammable. Tiglic anhydride is primarily used as an intermediate in the production of pharmaceuticals, agrochemicals, and fragrances. It is also used in the manufacturing of plasticizers and is a key building block for the synthesis of various organic compounds. Tiglic anhydride is considered to be a hazardous substance and proper safety measures should be taken when handling and storing it.

Upstream product

• 35660-94-7 (E)-2-methylbut-2-enoyl chloride 
• 80-59-1 Tiglic acid 
• 25576-97-0 2,3,6-trimethoxytoluene 
• 1192-37-6 methylenecyclohexane 
• 565-63-9 Angelic acid 
• 77573-43-4 (6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one 
• 6422-95-3 tiglic acid sodium salt 

Downstream Products

• 77448-64-7 atripliciolide tiglate 
• 36413-91-9 geiparvarin 

Relevant articles and documents

A METHOD OF PRODUCING INGENOL-3-ANGELATE

The present invention relates to methods of producing ingenol-3-angelate (I) from ingenol (II). Formula (I) and (II). Furthermore, the invention relates to intermediates useful for the synthesis of ingenol-3-angelate (I) from ingenol (II) and to methods of producing said intermediates.

Friedel-Crafts Reaction of 2-Methylfuran with Saturated and α,β-Unsaturated Acid Anhydrides

2-Methylfuran (5) reacts with the saturated acid anhydrides 16 - 26 in the presence of SnCl4 to give the 2-acyl-5-methylfurans 37 - 47 selectively.The unsaturated anhydrides 27 - 32, however, yield mixtures which only in the case of senecioic acid anhydride (29) contain the respective primary product 48.Subsequent reactions lead to the addition products 55 (from 27) and 56 (from 29), and to (E,Z)-mixtures of their enol esters 57 - 62 which could partially be separated and assigned. - The olfactory properties of 2, 37 - 48, 50, 52, and 53 were investigated.