19444-84-9

Basic information

• Product Name: ALPHA-HYDROXY-GAMMA-BUTYROLACTONE
• Synonyms: DIHYDRO-3-HYDROXY-2(3H)-FURANONE;2-HYDROXY-GAMMA-BUTYROLACTONE;3-HYDROXYTETRAHYDROFURAN-2-ONE;AKOS 224;ALPHA-HYDROXY-GAMMA-BUTYROLACTONE;4,5-Dihydro-3-hydroxy-2(3H)-furanone;α-Hydroxy-γ-butyrolactone;4,5-Dihydroxy-3-hydroxy-2(3H)-furanone
• CAS NO: 19444-84-9
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.09
• Mol File: 19444-84-9.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 133 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Viscous Liquid
• Density: 1.309 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00371mmHg at 25°C
• Refractive Index: n20/D 1.468(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 13.07±0.20(Predicted)
• BRN: 80587
• CAS DataBase Reference: ALPHA-HYDROXY-GAMMA-BUTYROLACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-HYDROXY-GAMMA-BUTYROLACTONE(19444-84-9)
• EPA Substance Registry System: ALPHA-HYDROXY-GAMMA-BUTYROLACTONE(19444-84-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 19444-84-9(Hazardous Substances Data)

Usage

Description

ALPHA-HYDROXY-GAMMA-BUTYROLACTONE, also known as α-Hydroxy-γ-butyrolactone, is a 5-membered cyclic ester derived from biomass through the tin-conversion of 1,3-dihydroxyacetone (DHA) and formaldehyde. It is a clear colorless to yellow viscous liquid with unique chemical properties that make it a versatile compound in various applications.

Uses

Used in Pharmaceutical Industry:
ALPHA-HYDROXY-GAMMA-BUTYROLACTONE is used as a starting reagent for the synthesis of a series of seco-pseudonucleoside synthons via aminolysis. This application is due to its ability to serve as a key building block in the development of novel pharmaceutical compounds.
Used in Organic Chemistry:
ALPHA-HYDROXY-GAMMA-BUTYROLACTONE is used as a starting reagent in the synthesis of enantiomerically pure orthogonally protected δ-azaproline, via Mitsunobu reaction. This application highlights its utility in creating complex organic molecules with potential applications in various fields, including pharmaceuticals and materials science.

Purification Methods

It has been purified by repeated fractionation and forms a colourless liquid. It has to be distilled at high vacuum; otherwise it will dehydrate. The acetox

InChI:InChI=1/C4H6O3/c5-3-1-2-7-4(3)6/h3,5H,1-2H2/t3-/m1/s1

Upstream product

• 5061-21-2 α-bromo-γ-butyrolactone 
• 1404079-44-2 2-(2,2,6,6-tetramethylpiperidin-1-yloxy)butyrolactone 
• 50-00-0 formaldehyd 
• 40031-31-0 erythrulose 
• 96-26-4 dihydroxyacetone 
• 107-21-1 ethylene glycol 
• 56-81-5 glycerol 
• 117-34-0 2,2-diphenylacetic acid 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 76-86-8 Triphenylsilyl chloride 
• 617-48-1 malic acid 
• 62386-30-5 2-hydroxy-4-oxo-butyric acid 
• 96-48-0 4-butanolide 
• 73991-95-4 2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid 

Downstream Products

• 118535-02-7 6,6a-dihydrofuro<3,2-b>furan-2(5H)-one 
• 40732-91-0 γ-phthalimidoimino-α-hydroxybutyric acid 
• 31701-91-4 (R)-2-hydroxy-4-phthalimidobutyric acid 
• 152978-82-0 (+/-)-3-(2-oxotetrahydrofuranyl) (E)-4-phenyl-3-butenoate 
• 118534-92-2 bromoacetic acid 2-oxotetrahydrofuran-3-yl ester 
• 99253-66-4 1-(Perimidin-2-yl)propan-1,3-diol 
• 99253-67-5 8-Hydroxy-8H-9,10-dihydropyrrolo<1,2-a>perimidin 
• 120964-19-4 (R)-4-Oxo-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester 
• 86677-82-9 2,3-dideoxy-2-fluoro-L-glycero-tetronolactone 
• 189046-93-3 dihydro-3-(2-propenyloxy)furan-2(2H)-one 
• 189046-99-9 dihydro-3-(2-propynyloxy)furan-2(2H)-one 
• 189046-54-6 3-(2-Bromo-allyloxy)-dihydro-furan-2-one 
• 121925-65-3 α-Benzyloxy-γ-butyrolactone 
• 264260-33-5 N-{[(3,5-bis-trifluoromethyl-benzyl)-methyl-carbamoyl]-methyl}-2,4-dihydroxy-butyramide 

Relevant articles and documents

Synthesis of α-hydroxy-γ-butyrolactones from acrylates and 1,3-dioxolanes using N-hydroxyphthalimide (NHPI) as a key catalyst

A new route to α-hydroxy-γ-butyrolactones through three-component radical coupling of 1,3-dioxoranes, acrylates, and molecular oxygen using N-hydroxyphthalimide (NHPI) as a key catalyst has been developed. For example, the addition of 1,3-dioxarane to methyl acrylate under dioxygen by NHPI followed by catalytic hydrogenation of the resulting adduct on Pd/C afforded α-hydroxy-γ-butyrolactone in good yield. This method provides a facile approach to α-hydroxy-γ-butyrolactones, which are difficult to synthesize by conventional methods.

Preparation method of alpha-hydroxyl-gamma-butyrolactone

The invention belongs to the field of preparation of organic compounds, and provides a preparation method of alpha-hydroxyl-gamma-butyrolactone. The method is characterized in that malic acid is used as a raw material, and alpha-hydroxyl-gamma-butyrolactone is synthesized with high yield through four steps of reactions, namely, carboxyl and alpha-hydroxyl protection, beta-carboxyl reduction, protecting group removal and internal esterification. The method has the advantages of easily available raw materials, mild reaction conditions and low cost, and is suitable for large-scale preparation of alpha-hydroxy-gamma-butyrolactone.

Preparation method of DL-hydroxy selenomethionine

The invention belongs to the field of preparation of organic compounds. The invention provides a preparation method of DL-hydroxy selenomethionine. The method is characterized in that gamma-butyrolactone is used as a raw material, alpha-hydroxyl-gamma-butyrolactone is synthesized through alpha-bromination and hydroxylation, and then the alpha-hydroxyl-gamma-butyrolactone reacts with sodium methyl selenol to obtain the DL-hydroxyl selenomethionine. The method has the advantages of easily available raw materials, mild reaction conditions and low cost, and is suitable for large-scale preparation of DL-hydroxyselenomethionine.