4282-33-1

Basic information

• Product Name: DIMETHYL 3,4-FURANDICARBOXYLATE
• Synonyms: DIMETHYL FURAN-3,4-DICARBOXYLATE;DIMETHYL 3,4-FURANDICARBOXYLATE;LABOTEST-BB LT00159967;3,4-Furandicarboxylic acid dimethyl ester;Dimethyl 3,4-furandicarboxylate,97%;DiMethyl 3,4-furandicarboxylate 98%;Dimethyl 3,4-furandicarboxylate purum, >=96.0% (GC)
• CAS NO: 4282-33-1
• Molecular Formula: C₈H₈O₅
• Molecular Weight: 184.15
• Product Categories: API intermediates;DID - DINBuilding Blocks;Alphabetic;D;Building Blocks;Furans;Heterocyclic Building Blocks
• Mol File: 4282-33-1.mol

Chemical Properties

• Melting Point: 46-49 °C(lit.)
• Boiling Point: 91-93 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: white to light yellow-beige crystalline powder
• Density: 1.3840 (rough estimate)
• Vapor Pressure: 0.00659mmHg at 25°C
• Refractive Index: 1.5690 (estimate)
• Storage Temp.: 2-8°C
• BRN: 152468
• CAS DataBase Reference: DIMETHYL 3,4-FURANDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 3,4-FURANDICARBOXYLATE(4282-33-1)
• EPA Substance Registry System: DIMETHYL 3,4-FURANDICARBOXYLATE(4282-33-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4282-33-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H8O5/c1-11-7(9)5-3-13-4-6(5)8(10)12-2/h3-4H,1-2H3

Upstream product

• 873-67-6 benzonitrile oxide 
• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 1516-60-5 4-nitrophenyl azide 
• 539-80-0 Tropone 
• 533-75-5 2-hydroxy-2,4,6-cycloheptatrien-1-one 
• 2101-87-3 p-methoxy-phenylazide 
• 3839-48-3 2-chlorotropone 
• 2574-03-0 p-nitrobenzonitrile oxide 
• 231289-36-4 C,N-Diphenylnitrilimine 
• 622-37-7 Phenyl azide 
• 15500-73-9 4-methoxybenzonitrile oxide 
• 1829-60-3 dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 126386-46-7 3,4-Bis(trimethylsilyl)furan 
• 762-42-5 dimethyl acetylenedicarboxylate 

Downstream Products

• 14496-24-3 3,4-bis(hydroxymethyl)furan 
• 18800-15-2 4-(Hydroxymethyl)furan-3-carboxaldehyde 
• 350792-31-3 tert-butyl{[4,5-di[(benzyloxy)methyl]-10-({[1-(tert-butyl)-1,1-dimethylsilyl]oxy}methyl)-11-oxatricyclo[6.2.1.0-2,7-]undeca-2,4,6,9-tetraen-9-yl]methoxy}dimethylsilane 
• 96194-82-0 3,4-bis(benzyloxymethyl)furan 
• 364069-24-9 3,4-bis-(3,5-bis-benzyloxy-benzyloxymethyl)-furan 
• 301851-35-4 (2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(1,2-dihydroxyethyl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime] 
• 301851-34-3 (2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime] 
• 301851-36-5 (2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-4-[1'-hydroxy-2'-(2-trimethylsilylethoxymethoxy)ethyl]-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime] 
• 301851-37-6 (4R,5R,8R,9S)-8-(tert-butyldiphenylsilyloxymethyl)-9-hydroxy-2,2-dimethyl-6-oxo-4-(2-trimethylsilylethoxymethoxymethyl)-1,3,7-trioxa-spiro[4.4]nonane-9-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime] 
• 104919-85-9 2-Hydroxy-5-oxo-2,5-dihydro-furan-3,4-dicarboxylic acid dimethyl ester 
• 30614-73-4 3,4-furan-dimethanol diacetate 
• 3387-26-6 furan-3,4-dicarboxylic acid 
• 52762-41-1 furan-3,4-dicarbonyl dichloride 
• 1595194-80-1 methyl 4-(3,5-dimethoxybenzoyl)-3-furoate 

Relevant articles and documents

Site selectivity of the diels-alder reactions of 3-[1-(tert-butyldimethylsilyloxy)vin-1-yl]furan and 3-(propen-2-yl)furan. Synthesis of 4-substituted benzofurans

The Diels-Alder reaction of 3-vinylfurans 5 and 27 with DMAD, N-phenylmaleimide, and dimethyl maleate afforded products derived both from addition to the furan ring diene system (intraannular addition) and to the furan 2,3-double bond 3-vinyl group diene system (extraannular addition). For example, compounds 6 and 7 were obtained from 5 and DMAD. In contrast, dienophiles containing a phenylsulfinyl group, such as 19-21, gave products derived exclusively from the extraannular reaction mode. These products are useful precursors of 4-substituted benzofurans, especially 4-hydroxybenzofurans.

Synthetic Photochemistry. XLVI. Cycloaddition of exo, endo-2,7-Bis(methoxycarbonyl)-11,12-dioxatetracyclo3,6.O2,7>dodeca-4,9-diene and Conjugated Enones and p-Quinones

Photocycloaddition of exo,endo-2,7-bis(methoxycarbonyl)-11,12-dioxatetracyclo3,6.O2.7>dodeca-4,9-diene with conjugated and p-quinones occurred exclusively at the exo-addition moiety to give -cycloadducts.From cyclohexeno

Synthesis and Reactions of 3,4-Bis(trimethylsilyl)furan and 2-Methyl-3,4-bis(trimethylsilyl)furan

3,4-Bis(trimethylsilyl)furan (2) and 2-methyl-3,4-bis(trimethylsilyl)furan (3) have been synthesised and found to undergo a Diels-Alder reaction as well as a regiospecific Friedel-Crafts acylation (regioselective desilylation), regiospecific deuteriodesilylation.

MOLYBDENUM-PROMOTED REACTIONS OF 7-OXABICYCLOHEPTADIENE AND DERIVATIVES

The reactions of 2,3-bis(methoxycarbonyl)-7-oxabicycloheptadiene (1a) and related compounds 1b, 1c, and 2 with molybdenum carbonyl complexes are examined at two different temperatures.In refluxed cyclohexane, reactions of 1a-c with hexacarbonylmolybdenum produce mainly the corresponding derivatives of dimethyl phthalate (3a-c) and 3,4-bis(methoxycarbonyl)furan (4a-c), while the reaction of 2 produces naphthalene and 1-naphthol.At room temperature, reactions of 1a,b with tris(acetonitrile)tricarbonylmolybdenum yield the dimer ketones 5a,b in addition to 3a,b and 4a,b, while the reaction of 2 produces naphthalene as the only prod uct.The mechanism for the generation 3, 4, and 5 is rationalized as going through complex intermediate with structure of a molybdenum chelated by 1.

Novel Two-Step Synthesis of Homobarrelenones, Bicyclonona-3,6,8-trien-2-ones, from Tropones and 2,3-Bis(methoxycarbonyl)-7-oxabicyclohepta-diene by High-Pressure Cycloaddition-Thermal Cyclorevision Procedure

The Diels-Alder adduct of tropone with 2,3-bis(methoxycarbonyl)-7-oxabicyclohepta-2,5-diene formed homobarrelenone by heating at ca. 130 deg C.Similarly prepared were 1-hydroxy-, 3-methoxy-, 1-chloro-, and 3-chlorohomobarrelenones.High-pressure cycloaddition improved the yields of the Diels-Alder adducts.

Reactions of 2,3-dicarbomethoxy-7-oxabicycloheptadiene with molybdenum carbonyls

Thermolysis with either Mo(CO)6 or Mo(CH3CN)3(CO)3 of 2,3-dicarbomethoxy-7-oxabicycloheptadiene (I) gave three major products, i.e. dimethyl phthalate (V), 3,4-dicarbomethoxyfuran (VI), and a dimeric ketone (IX) linked in an exo-trans-exo orientation.The formation of V and IX indicates two reaction pathways which start from a common organometallic intermediate.Compound VI is the major product in the thermal decomposition of IX.

SITE-SELECTIVITY OF 1,3-DIPOLAR CYCLOADDITIONS TO 2,3-DIMETHOXYCARBONYL-7-OXABICYCLO-HEPTADIENE

Site-selectivity of dipolar cycloaddition to the title compound was studied.Azomethine X afforded a 1:1 cycloadduct XI at the deactivated double bond at room temperature;upon thermolysis at 110 degC it afforded the acetylated enamine XIII, wich was formed wia a direct cycloaddition at the mentioned temperature.The cycloaddition course was investigated in various solvents;the enamine XIV formed by solvolysis of XIII was the final products in methanol.Cycloaddition of title compound to azides, benzoylnitrile N-oxide and C-acetyl-N-phenylnitrilimine furnished the product of cycloreversion instead of the not isolable 1:1 cycloadducts.5-Azido-2-furancarbaldehyde and 4-nitrophenylazide yielded cycloaddition products to both multiple bonds in an approximately 1:1 ratio: HN3, tosylazide,benzoylnitrile N-oxide and C-acetyl-N-phenylnitrilimine gave the addition products to the deactivated double bond.The solvent-effect of site-selectivity of 1,3-dipolarcycloaddition was inwestigated and the title compound was found to be an exellent synthetic equivalent for acetylene and dimethyl butinedioate.

SITE SELECTIVITY IN THE REACTIONS OF 1,3-DIPOLES WITH NORBORNADIENE DERIVATIVES

The cycloadditions of arylazides, benzonitrile oxides and diphenylnitrile imine to norbornadiene derivatives 1a-c showed varying degree of site- and stereo-selectivity.With dipolarophile 1a arylazides and benzonitrile oxides attack, preferentially, the electron-poor tetrasubstituted double bond, while in the case of 1b and 1c is the substituted double bond which enters the cycloaddition.By contrast, 2-diazopropane and C-phenyl-N-methylnitrone react with the sole tetrasubstituted double bond of 1a-c in stereo- and site-specific cycloadditions.The quantitative evaluation of the two possible reaction paths was performed by glc analysis.The compounds detected were those arising from Diels-Alder cycloreversions of the thermally labile intermediate adducts 2 and 3 (Scheme 1).The results were rationalized on the basis of a qualitative perturbation treatment which considers frontier orbital interactions only.