3663-82-9

Basic information

• Product Name: 2-HYDROXYMETHYL-1,4-BENZODIOXANE
• Synonyms: 1,4-Benzodioxin-2-methanol, 2,3-dihydro-;2-(Hydroxymethyl)-2,3-dihydro-1,4-benzodioxin;2,3-Dihydro-1,4-benzodioxin-2-methanol;2-O,3-O-(1,2-Phenylene)glycerol;2-Hydroxymethyl-1,4-benzodioxan,98%;(1,4-Benzodioxan-2-yl)methanol;2-(HYDROXYMETHYL)-1,4-BENZODIOXANE FOR S;(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)Methanol
• CAS NO: 3663-82-9
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 222-921-9
• Product Categories: C9 to C10;Alcohols;Benzodioxanes;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks;Oxygen Compounds
• Mol File: 3663-82-9.mol
• Article Data: 20

Chemical Properties

• Melting Point: 87-90 °C(lit.)
• Boiling Point: 286 °C
• Flash Point: 124℃
• Appearance: /
• Density: 1.213
• Vapor Pressure: 0.00172mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 13.98±0.10(Predicted)
• BRN: 83736
• CAS DataBase Reference: 2-HYDROXYMETHYL-1,4-BENZODIOXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYMETHYL-1,4-BENZODIOXANE(3663-82-9)
• EPA Substance Registry System: 2-HYDROXYMETHYL-1,4-BENZODIOXANE(3663-82-9)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: DF3660000
• HazardClass: IRRITANT
• Hazardous Substances Data: 3663-82-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystalline powder

Uses

2-Hydroxymethyl-1,4-benzodioxane is a substituted benzodioxane with antihepatotoxic activity. 2-Hydroxymethyl-1,4-benzodioxane is used as an intermediate in the preparation of Guanoxan (G839500).

InChI:InChI=1/C9H10O3/c10-5-7-6-11-8-3-1-2-4-9(8)12-7/h1-4,7,10H,5-6H2/t7-/m1/s1

Upstream product

• 96-13-9 2,3-Dibromopropan-1-ol 
• 120-80-9 benzene-1,2-diol 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 17736-68-4 1-chloro-3-(2-hydroxy-phenoxy)-propan-2-ol 
• 3663-79-4 methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate 
• 95-56-7 2-hydroxybromobenzene 
• 26272-85-5 3-iodooxetane 
• 2171-74-6 1,3-benzodioxol-2-one 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 
• 93-14-1 guaifenesin 
• 96-18-4 1,2,3-trichloropropane 
• 533-58-4 2-Iodophenol 
• 7732-18-5 water 
• 106-89-8 epichlorohydrin 

Downstream Products

• 2164-34-3 2-(bromomethyl)-2,3-dihydrobenzo[1,4]dioxine 
• 148834-04-2 2-((4-formylphenoxy)methyl)-2,3-dihydrobenzo[1,4]dioxine 
• 7031-65-4 2-hydroxymethyl-2,3-dihydro-4H-1,4-benzodioxine methanesulfonate 
• 59987-31-4 (7-nitro-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol 
• 70918-74-0 N-(2,3-dihydro-1,4-benzodioxin-2-yl carbonyl)piperazine hydrochloride 
• 3663-80-7 1,4-benzodioxane-2-carboxylic acid 
• 70918-00-2 (2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(piperazin-1-yl)methanone 
• 74191-85-8 doxazosin 
• 104874-86-4 (R)-doxazosin 
• 23785-19-5 2-iodomethylbenzodioxan 
• 2164-33-2 2-chloromethyl-1,4-benzodioxane 
• 98572-00-0 (S)-2-hydroxymethyl-1,4-benzodioxane 
• 1094-91-3 2-(toluene-4-sulfonyloxymethyl)-2,3-dihydro-benzo[1,4]dioxine 
• 149110-60-1 1,4,-benzodioxan-2-ylmethyl 4-acetoxyphenylacetate 

Relevant articles and documents

Mild Intramolecular Ring Opening of Oxetanes

Oxetanes have been increasingly used as stable motifs in medicinal chemistry as well as versatile synthetic intermediates. Herein, an intramolecular ring opening of oxetane carboxamides with mild nucleophiles, such as nitrogen heterocycles, is presented. The reaction proceeds under metal-free basic conditions which is highly unusual in ring opening reactions of oxetanes. Amide formation and oxetane ring opening/cyclization in a one-pot approach affords high levels of molecular complexity in a single step from simple, readily available substrates.

One-pot preparation of chiral 2-vinyl-1,4-benzodioxane

2-Vinyl-1,4-benzodioxane was obtained with e.e. up to 45% by condensation of catechol and (Z)-2-butene-1,4-diylbis(methylcarbonate) in the presence of a catalytic amount of palladium(0) in association with chiral ligand such as BINAP.

An innovative synthesis pathway to benzodioxanes: The peculiar reactivity of glycerol carbonate and catechol

A peculiar reactivity of glycerol carbonate (GlyC) as an innovative and highly reactive alkylating agent for phenolic compounds is investigated in this article. In particular, 2-hydroxymethyl-1,4-benzodioxane (HMB), a key intermediate for the pharmaceutical industry, has been selectively synthesized by the reaction of a slight excess of GlyC with catechol in the presence of a basic catalyst (NaOCH3, Na-mordenite, MgO), without requiring a reaction solvent. Both reagents have been quantitatively converted in just one hour at 170 °C with a HMB yield, up to 88%, in the presence of a homogeneous basic catalyst (NaOCH3). Notably, the main side product, the HMB isomer, may be an interesting intermediate for the synthesis of calone analogues, which are important scaffolds used in fragrances. A detailed mechanistic study, supported by kinetics, GC-MS, and HMBC NMR characterization, is also reported. Accordingly, this paper describes a completely innovative and greener synthesis pathway to benzodioxanes.

GC–MS study of thermochemical conversion of guaifenesin in the presence of 1-butyl-3-methylimidazolium-based ionic liquids

Thermochemical conversion of guaifenesin was performed in the presence of 1-butyl-3-methylimidazolium tetrafluoroborate [BMIM][BF4] ionic liquid at 80?°C within 2?h. After evaluating the effect of different parameters, such as protic and nonpro