108-58-7

Basic information

• Product Name: 1,3-Diacetoxybenzene
• Synonyms: 1,3-Benzenediol,diacetate;1,3-Dihydroxybenzene diacetate;1,3-dihydroxybenzenediacetate;3-(Acetyloxy)phenyl acetate;Dihydroxybenzene diacetate;Resorcinyl acetate;1,3-DIACETOXYBENZENE;1,3-PHENYLENE DIACETATE
• CAS NO: 108-58-7
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• EINECS: 203-596-2
• Product Categories: Aromatic Ethers
• Mol File: 108-58-7.mol
• Article Data: 67

Chemical Properties

• Melting Point: 145-146 °C
• Boiling Point: 146 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless liquid
• Density: 1.178 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00422mmHg at 25°C
• Refractive Index: n20/D 1.503(lit.)
• Water Solubility: HYDROLYSIS
• BRN: 1875007
• CAS DataBase Reference: 1,3-Diacetoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Diacetoxybenzene(108-58-7)
• EPA Substance Registry System: 1,3-Diacetoxybenzene(108-58-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• WGK Germany: 3
• RTECS: VH0580000
• TSCA: Yes
• Hazardous Substances Data: 108-58-7(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLORLESS LIQUID

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 3696, 1974 DOI: 10.1021/jo00939a018

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by intraperitoneal route. A severe eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C10H10O4/c1-7(11)13-9-4-3-5-10(6-9)14-8(2)12/h3-6H,1-2H3

Upstream product

• 64-19-7 acetic acid 
• 108-46-3 recorcinol 
• 504421-93-6 2,4-diacetoxy-1-iodobenzene 
• 673477-43-5 1-ethynyl-2-methoxy-4,5-methylenedioxybenzene 
• 72712-19-7 2,4-diacetoxy acetophenone 
• 5792-36-9 2',4'-dihydroxypropiophenone 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 201230-82-2 carbon monoxide 
• 74-88-4 methyl iodide 
• 2033-24-1 cycl-isopropylidene malonate 
• 13031-41-9 4-cyanophenyl acetate 
• 830-03-5 4-nitrophenol acetate 
• 102-29-4 Resorcinol monoacetate 

Downstream Products

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 699-83-2 2,6-dihydroxylacetophenone 
• 22665-91-4 1-(2,4-diacetoxyphenyl)-2-phenylethanone 
• 1228552-17-7 C₁₆H₂₁BO₆ 
• 1227732-23-1 (R)-1-(3,5-dimethylphenyl)ethanol acetate 
• 950759-27-0 (S)-1-(2-chlorophenyl)ethanol acetate 
• 172585-57-8 (R)-acetic acid 1-(4-fluoro-phenyl)-ethyl ester 
• 136705-69-6 (R)-1-(3-chloroethylphenyl)ethyl acetate 
• 1227732-24-2 (R)-1-(2,5-dimethylphenyl)ethanol acetate 
• 16197-92-5 (R)-1-phenethyl acetate 
• 84194-74-1 (R)-1-(p-tolyl)ethyl acetate 
• 19759-40-1 (S)-1-(4-methylphenyl)ethanol acetate 
• 102-29-4 Resorcinol monoacetate 
• 484653-22-7 2-bromo-4,6-dinitro-resorcinol 

Relevant articles and documents

Further hydroxyiodination of 1-acetoxycyclohex-2-enes: Preparation of tetraAcetyl conduritol D

1,2-iodohydroxylation of 1-acetoxycyclohex-2-enes has been extrapolated: tetraacetyl Conduritol D may be prepared by iteration of the reaction.

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An efficient method to prepare aryl acetates by the carbonylation of aryl methyl ethers or phenols

Synthesis of valuable chemicals from lignin based compounds is critical for the application of biomass. Here, we develop a method of preparing aryl acetates by the carbonylation of aryl methyl ethers or phenols under low CO pressure. Good to excellent yields of aryl acetates were obtained using different substrates, and a possible reaction mechanism was proposed by conducting a series of control experiments. This method may provide a potential way for the utilization of lignin.

Unprecedented acetylation of phenols using a catalytic amount of magnesium powder

The acetylation of phenols with acetic anhydride was achieved using a catalytic amount of magnesium metal powder under air and solvent-free conditions to afford corresponding phenyl acetates in excellent yield (up to 98%).

Acyl Donors and Additives for the Biocatalytic Friedel–Crafts Acylation

The Friedel–Crafts acylation is a broadly applied reaction that can be conducted using various types of catalyst. However, a biocatalytic alternative has only been reported recently. In this study, the scope of acetyl donors is described, showing that, in addition to vinyl acetate derivatives, phenyl esters are also suitable donors. Furthermore, it was found that various amines enhance the reaction, whereby the effect do not seem to be correlated to the pH but to the structure of the donor. For instance, 1,4-diazabicyclo[2.2.2]octane (DABCO) turned out to be a viable alternative to imidazole; however the former performed best at pH 9.85, whereas the latter performed best at pH 8.3.