59259-90-4

Basic information

• Product Name: 5-DIMETHOXYMETHYL-BENZO[1,3]DIOXOLE
• Synonyms: 5-DIMETHOXYMETHYL-BENZO[1,3]DIOXOLE;Piperonal dimethyl acetal;1,3-Benzodioxole, 5-(dimethoxymethyl)-;1,3-Benzodioxole-5-carbaldehyde dimethyl acetal;3,4-Methylenedioxybenzaldehyde dimethyl acetal;5-(Dimethoxymethyl)-1,3-benzodioxole;Heliotropine dimethyl acetal;Einecs 261-679-9
• CAS NO: 59259-90-4
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.19988
• EINECS: 261-679-9
• Mol File: 59259-90-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 240.4°C at 760 mmHg
• Flash Point: 96.9°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 0.0588mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 5-DIMETHOXYMETHYL-BENZO[1,3]DIOXOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-DIMETHOXYMETHYL-BENZO[1,3]DIOXOLE(59259-90-4)
• EPA Substance Registry System: 5-DIMETHOXYMETHYL-BENZO[1,3]DIOXOLE(59259-90-4)

Safety Data

• Hazardous Substances Data: 59259-90-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H12O4/c1-11-10(12-2)7-3-4-8-9(5-7)14-6-13-8/h3-5,10H,6H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 120-57-0 piperonal 
• 149-73-5 trimethyl orthoformate 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 86633-34-3 Lithium; 6-(2,2-dimethoxy-ethyl)-2,3-dimethoxy-benzoate 
• 120-57-0 piperonal 
• 6301-72-0 1,3-benzodioxol-5-ylmethylene diacetate 
• 1296671-55-0 (2R,3R,4S)-4-(benzo[d][1,3]dioxol-5-yl)-3-(3,4,5-trimethoxybenzyl)-2-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-3,4-dihydro-2H-pyran-6-carboxylic acid methyl ester 
• 108261-07-0 5,6,7,8-Tetrahydro-4-methoxy-6-methyl-1,3-dioxolo<4,5-g>isoquinolin-8-ol 
• 550-10-7 hydrocotarnine 
• 30936-27-7 4-methoxy-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium iodide 
• 128-62-1 (±)-α-noscapine 
• 5779-99-7 4-methoxybenzo[d][1,3]dioxole-5-carbaldehyde 
• 171596-29-5 (6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione 
• 406938-39-4 (1R,3R)-1-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid 

Relevant articles and documents

Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions

We report a one-step catalytic, enantioselective method for the preparation of homoallylic N-Boc amines directly from acetals. Reactive iminium ion intermediates are generated in situ through the combination of an acetal, a chiral thiourea catalyst, trialkylsilyl triflate, and N-Boc carbamate and are subsequently trapped by a variety of allylsilane nucleophiles. No homoallylic ether byproducts are detected, consistent with allylation of the iminium intermediate being highly favored over allylation of the intermediate oxocarbenium ion. Acetals derived from aromatic aldehydes possessing a variety of functional groups and substitution patterns yield homoallylic amines with excellent levels of enantiomeric enrichment. Experimental and computational data are consistent with an anchoring hydrogen-bond interaction between the protioiminium ion and the amide of the catalyst in the enantiodetermining transition state, and with stereodifferentiation achieved through specific noncovalent interactions (NCIs) with the catalyst pyrenyl moiety. Evidence is provided that the key NCI in the major pathway is a π-stacking interaction, contrasting with the cation-πinteractions invoked in previously studied reactions promoted by the same family of aryl-pyrrolidino-H-bond-donor catalysts.

A new total synthesis of (±)-α-noscapine

A new, convergent total synthesis of (±)-α-noscapine was developed on a grams scale through the condensation of 3-trimethylsilyl-meconin derivative 9 and the iodized salt cotarnine derivative 20 as the key step. Staring from simple 2,3-dimethoxybenzoic acid, piperonal and 2,2-dimethoxyethanamine, through the traditional chemical processes to give the final product in 11.6% yield over 14 steps.

Dichotomous reactivity in the reaction of triethyl- and triphenylphosphane HBr salts with dimethyl acetals: A novel entry to α-alkoxy-functionalized ylides and general synthesis of vinyl ethers and alkoxy dienes

The discovery of dichotomous reactivity in the reaction of trialkyl- vs. triphenylphosphane HBr salts with acetals allows entry to functionalized α-methoxy phosphonium salts and a novel process for tertiary phosphane methylation. The new protocol opens a general entry to the synthesis of vinyl ethers and differentially substituted 1,3-dienes via Wittig reactions of the functionalized ylides derived from the α-methoxy phosphonium salts.