547-65-9

Basic information

• Product Name: Tulipalin A
• Synonyms: ALPHA-METHYLENE-GAMMA-BUTYROLACTONE, STA B.;Stabilizedwith2,6-Ditert-butyl-p-cresol;alpha-Methylene-gamma-butyrolactone, stabilized, 95%;α-methylene-γ-butyrolactone;2-METHYLENE-4-BUTYROLACTONE;3-methylideneoxolan-2-one;alpha-Methylene-gamma-butyrolactone (stabilized with 2,6-Di-tert-butyl-p-cresol);3-Methylenedihydro-2(3H)-furanone, Tulipane
• CAS NO: 547-65-9
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.1
• EINECS: 208-931-6
• Product Categories: Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactones;Organic Building Blocks
• Mol File: 547-65-9.mol
• Article Data: 61

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 86-88 °C12 mm Hg(lit.)
• Flash Point: 99 °F
• Appearance: Clear colorless to light yellow or slightly pink/Liquid
• Density: 1.119 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.264mmHg at 25°C
• Refractive Index: n20/D 1.472(lit.)
• Storage Temp.: 2-8°C
• Solubility: water: soluble(lit.)
• Merck: 14,6062
• BRN: 107939
• CAS DataBase Reference: Tulipalin A(CAS DataBase Reference)
• NIST Chemistry Reference: Tulipalin A(547-65-9)
• EPA Substance Registry System: Tulipalin A(547-65-9)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43-52/53-10
• Safety Statements: 23-36/37-61-45
• RIDADR: 1993
• WGK Germany: 3
• RTECS: LU3580400
• F: 1-8-10
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 547-65-9(Hazardous Substances Data)

Usage

Description

Tulipalin A is an unsubstituted -methylene-butyrolaetone eontained in the sap of tulips, Alstroemeria spp. (Peruvian lily) and Erythronium (dog tooth violet, fawn-lily). Tulipalin B seems to have a weak capacities to sensitize.

Chemical Properties

clear colourless to light yellow or slightly pink

Uses

Different sources of media describe the Uses of 547-65-9 differently. You can refer to the following data:
1. Very reactive Michael-acceptor; the α-methylene-γ-butyrolactone ring system exists in many natural products of biological interest
2. Allergen in the Liliaeeae family of plants to whieh speeies such as Tulip, Alstromeria, Erythronium dens canis and americanum belong.
3. α-Methylene-γ-butyrolactone (Tulipane) was used to develop optically active spiro-[butyrolactone-pyrrolidine] via Cu(I)-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides.

Definition

ChEBI: A butan-4-olide having a methylene group at the 3-position.

InChI:InChI=1/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2

Upstream product

• 96-48-0 4-butanolide 
• 50-00-0 formaldehyd 
• 109-94-4 formic acid ethyl ester 
• 5061-21-2 α-bromo-γ-butyrolactone 
• 33797-51-2 eschenmoser's salt 
• 34932-07-5 3-(triphenylphosphoranyliden)dihydro-2(3H)-furanone 
• 72277-33-9 methyl 1-(diisopropylaminomethyl)cyclopropanecarboxylate 
• 201230-82-2 carbon monoxide 
• 927-74-2 3-Butyn-1-ol 
• 17435-72-2 ethyl 2-bromomethyl-2-propenoate 
• 76334-36-6 3-bromobut-3-en-1-ol 
• 72707-66-5 2-(bromomethyl)acrylic acid 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 
• 61541-20-6 methyl 4-hydroxy-2-methylenebutanoate 

Downstream Products

• 119102-90-8 7-benzyl-7-aza-2-oxaspiro<4.4>nonan-1-one 
• 54353-61-6 3-phenylsulfanylmethyl-dihydro-furan-2-one 
• 126812-00-8 2-(1-Benzyl-4,5-dihydro-1H-imidazol-2-yl)-3-(2-oxo-tetrahydro-furan-3-yl)-propionic acid ethyl ester 
• 141526-86-5 C₁₇H₁₆O₄S 
• 76299-53-1 3-(toluene-4-sulfonyloxymethylene)-dihydro-furan-2-one 
• 22122-36-7 3-methyl-5H-furan-2-one 
• 98011-07-5 1,5-Dioxa-spiro[2.4]heptan-4-one 
• 51348-66-4 (+/-)-Tulipalin B 
• 178613-68-8 (3S,1'R)-3-[(2-oxo-1-methylcyclohexyl)methyl]-2(5H)-3,4-dihydrofuranone 
• 68975-07-5 3-benzyltetrahydrofuran-2-one 
• 5837-78-5 Ethyl tiglate 

Relevant articles and documents

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Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

Novel multi-dentate phosphines for Pd-catalyzed alkoxycarbonylation of alkynes promoted by H2O additive

A series of novel multi (bi-/tri-/tetra-)-dentate phosphines with good robustness against water and oxygen were synthesized and fully characterized. It was found that the developed ionic tri-dentate phosphine (L2′) enabled Pd-catalyzed alkoxycarbonylation of alkynes most efficiently while H2O was used as an additive instead of acid. As for L2′, its unique steric configuration with two types of potential P-P chelation modes (P?P distance of 4.31 ? and 4.36 ? respectively) to Pd-centre rendered the corresponding Pd-catalyst high activity and good stability for alkoxycarbonylation of alkynes. The in situ FT-IR analysis also verified that the formation and stability of Pd–H active species were greatly facilitated with the presence of L2′ as well as H2O additive. In addition, as an ionic phosphine, L2′ based PdCl2(MeCN)2 system immobilized in RTIL of [Bmim]NTf2 could be recycled for 7 runs without obvious activity loss or metal leaching.

Synthesis of methylene butyrolactone polymers from itaconic acid

Herein, we report the transformation of β-monomethyl itaconate, an inexpensive and biorenewable alternative to petroleum feedstocks, to the high-value monomer α-methylene-γ,γ-dimethyl-γ-butyrolactone (Me2MBL) through a selective addition strategy. This strategy is also applied to the synthesis of α-methylene-γ-butyrolactone (MBL, tulipalin A), a monomer that can be polymerized to give materials with desirable properties (high decomposition temperature, glass transition temperature, and refractive index). Subsequent polymerization of both Me2MBL and MBL through reversible addition-fragmentation chain-transfer polymerization generates well-defined poly(Me2MBL) and poly(MBL) (PMBL). Physical characterization of poly(Me2MBL) shows good physical properties comparable with known PMBL materials.