3709-08-8

Basic information

• Product Name: ALPHA,ALPHA-DIMETHYL-GAMMA-BUTYROLACTONE
• Synonyms: DIHYDRO-3,3-DIMETHYL-2(3H)-FURANONE;GAMMA-DIMETHYL BUTYROLACTONE;ALPHA,ALPHA-DIMETHYL-GAMMA-BUTYROLACTONE;2(3H)-Furanone, dihydro-3,3-dimethyl-;3,3-Dimethyldihydro-2(3H)-furanone;3,3-Dimethyl-dihydro-furan-2-one;2,2-dimethyl-4-butyrolactone;3,3-Dimethyltetrahydrofuran-2-one
• CAS NO: 3709-08-8
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.14
• Mol File: 3709-08-8.mol

Chemical Properties

• Melting Point: 6 °C
• Boiling Point: 194 °C / 27mmHg
• Flash Point: 66.9 °C
• Appearance: /
• Density: 1.01
• Vapor Pressure: 0.513mmHg at 25°C
• Refractive Index: 1.4300-1.4340
• CAS DataBase Reference: ALPHA,ALPHA-DIMETHYL-GAMMA-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA,ALPHA-DIMETHYL-GAMMA-BUTYROLACTONE(3709-08-8)
• EPA Substance Registry System: ALPHA,ALPHA-DIMETHYL-GAMMA-BUTYROLACTONE(3709-08-8)

Safety Data

• Hazardous Substances Data: 3709-08-8(Hazardous Substances Data)

Usage

Uses

Used in Flavoring Agent Applications:
Alpha, alpha-dimethyl-gamma-butyrolactone is used as a flavoring agent in the food industry due to its characteristic fruity odor. It enhances the taste and aroma of various food products, contributing to a more appealing sensory experience for consumers.
Used in Pharmaceutical Production:
In the pharmaceutical industry, alpha, alpha-dimethyl-gamma-butyrolactone is utilized in the production of various medications. Its properties make it suitable for use in the synthesis of active pharmaceutical ingredients or as a component in drug formulations, aiding in the development of effective and safe medications.
Used as a Solvent in Chemical Processes:
Alpha, alpha-dimethyl-gamma-butyrolactone also serves as a solvent in various chemical processes. Its ability to dissolve a wide range of substances makes it a versatile component in the synthesis of different chemicals, facilitating reactions and improving the efficiency of chemical processes.
Used in Chemical Industry:
Alpha, alpha-dimethyl-gamma-butyrolactone is used in the chemical industry for various applications, including the synthesis of other organic compounds, the production of specialty chemicals, and as an intermediate in the manufacturing of various chemical products. Its versatility and relatively safe nature make it a valuable component in the development of new and innovative chemical products.

InChI:InChI=1/C6H10O2/c1-6(2)3-4-8-5(6)7/h3-4H2,1-2H3

Upstream product

• 681-57-2 2,2-dimethylglutaric acid 
• 32812-23-0 2,2-dimethylbutane-1,4-diol 
• 17347-61-4 2,2-dimethylsuccinic anhydride 

Downstream Products

• 681-57-2 2,2-dimethylglutaric acid 
• 5370-33-2 1,3,3-trimethyl-2-pyrrolidinone 
• 4807-92-5 4-bromo-2,2-dimethyl-butyric acid 
• 53840-29-2 ethyl 2,2-dimethyl-4-chlorobutanoate 
• 53840-39-4 4-chloro-2,2-dimethylbutanoyl chloride 
• 499194-48-8 4-benzylsulfanyl-2,2-dimethyl-butyric acid 
• 774234-70-7 3,3-dimethyl-2-[(R)-(p-tolylsulfinyl)methyl]tetrahydrofuran-2-ol 
• 1006044-21-8 N-(2-chlorobenzyl)-4-hydroxy-2,2-dimethylbutanamide 
• 774234-71-8 3,3-dimethyl-2-[(R)-(p-tolylsulfinyl)methyl]tetrahydrofuran 
• 774234-72-9 (E)-3,3-dimethyl-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol 
• 774234-39-8 methyl (2Z,6E)-5,5-dimethyl-7-[(R)-(p-tolylsulfinyl)]hepta-2,6-dienoate 
• 774234-40-1 methyl (2E,6E)-5,5-dimethyl-7-[(R)-(p-tolylsulfinyl)]hepta-2,6-dienoate 
• 499194-34-2 C₅₈H₆₄N₂O₁₅S₂ 
• 446251-23-6 3,3-dimethyl-5-phenyl-pentane-1,4-diol 

Relevant articles and documents

HIGHLY REGIOSELECTIVE RING-OPENING OF α-SUBSTITUTED CYCLIC ACID ANHYDRIDES CATALYZED BY LIPASE

Lipase Amano P irreversibly catalyzed a ring-opening of α-substituted cyclic acid anhydrides 1 preferentially at the less hindered carbonyl group to give monoesters with high regioselectivity.

Ruthenium Complex Catalyzed Regioselective Dehydrogenation of Unsymmetrical α,ω-Diols

Ruthenium complex catalyzed regioselective dehydrogenation of unsymmetrically substituted 1,4- and 1,5-diols in the presence of such a hydrogen acceptor as α,β-unsaturated ketone gave predominantly β-substituted γ-lactones and γ-substituted δ-lactones, respectively.Among the ruthenium complexes, RuH2(PPh3)4 was the most active and selective catalyst and showed high catalytic activity even at 20 deg C.For example, 2,2-dimethyl-1,4-butanediol was quantitatively converted to dihydro-4,4-dimethyl-2(3H)-furanone and dihydro-3,3-dimethyl-2(3H)-furanone in a ratio of 99.6/0.4 in the presence of 4-phenyl-3-buten-2-one (hydrogen acceptor) and a catalytic amount of RuH2(PPh3)4 at 20 deg C.The proposed main factor controlling the regioselectivity is the steric constraints produced by the substituent(s) of a diol at the coordination step of alkoxy group to ruthenium.

Regioselective Hydrogenation of Unsymmetrically Substituted Cyclic Anhydrides Catalyzed by Ruthenium Complexes with Phosphine Ligands

Regioselective hydrogenation of unsymmetrically substituted cyclic anhydrides catalyzed by ruthenium complexes with mono-, di-, or triphosphine ligands produced the corresponding two isomeric lactones, where the regioselectivity was influenced by the bulkiness of substituent(s) on the anhydrides and of the phosphine ligands of catalyst.

CATALYTIC REGIOSELECTIVE DEHYDROGENATION OF UNSYMMETRICAL α,ω-DIOLS USING RUTHENIUM COMPLEXES

Ruthenium complex catalyzed regioselective dehydrogenation of unsymmetrically substituted 1,4- and 1,5-diols in the presence of α,β-unsaturated ketone as a hydrogen acceptor and triethylamine gave β-substituted γ-lactones and γ-substituted δ-lactones as major products, respectively.

Regioselectivity in Nickel(II)-Mediated Oxidations of Diols

Oxidations of 2- and 4-substituted 1,4-butanediols to their corresponding γ-butyrolactones by the combination of molecular bromine and nickel(II) alkanoate occur with a high degree of regioselectivity.The influence of the alkanoate ligand, of substituents at the 2-position of 1,4-butanediols, and of solvent on oxidation regiocontrol is examined, and comparison of regioselectivity in diol oxidations is made with representative conventional oxidative methods.Regiocontrol in nickel(II)-mediated reactions is proposed to be derived from steric constraints for oxidativehydrogen transfer to the alkanoate ligand of nickel(II) in the diol-associated complex.Alternate use of cobalt(II) alkanoates provides regiocontrol in diol oxidations that is comparable or superior to that obtained with nickel(II) alkanoates in bromine oxidations.

Oxidation of Primary and Secondary Alcohols by the Catalysis of Palladium

Saturated and unsaturated alcohols are oxidized to the corresponding ketones in good or excellent yields by using an aryl halide (phenyl bromide or mesityl bromide) as an oxidant and palladium(0) or -(II) as a catalyst (0.6-3 mol percent relative to the alcohol) in the presence of a base (NaH or K2CO3).The similar oxidation of primary alcohols provides the corresponding aldehydes and/or esters.The aldehyde/ester selectivity is correlated to the steric and electronic features of substrates.The procedure is applied to the oxidation of 1-primary,ω-primary diols to lactones.

HIGHLY REGIOSELECTIVE REDUCTION OF UNSYMMETRICAL CYCLIC ANHYDRIDES TO LACTONES WITH HINDERED TRIALKYLBOROHYDRIDES

Lithium trialkylborohydrides reduce cyclic anhydrides to the corresponding lactones in good to excellent isolated yields.With unsymmetrical anhydrides, increasing the steric requirements of the trialkylborohydride dramatically enhances the regioselectivity of the reduction of the less hindered carbonyl group of the anhydride.

Reversal of Regioselectivity in the Reduction of gem-Disubstituted Cyclic Carboxylic Acid Anhydrides

The regioselective partial reduction of gem-disubstituted cyclic carboxylic acid anhydrides to the corresponding γ-lactones with LiAlH4 or NaBH4 is almost completely reversed when potassium tri-s-butylborohydride is used as the reducing agent.