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4282-33-1

4282-33-1

Identification

  • Product Name:Dimethyl 3,4-furandicarboxylate

  • CAS Number: 4282-33-1

  • EINECS:

  • Molecular Weight:184.149

  • Molecular Formula: C8H8O5

  • HS Code:29321900

  • Mol File:4282-33-1.mol

Synonyms:3,4-Furandicarboxylicacid, dimethyl ester (6CI,7CI,8CI,9CI);3,4-Bis(methoxycarbonyl)furan;Dimethyl3,4-furandicarboxylate;NSC 191844;

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Relevant articles and documentsAll total 10 Articles be found

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

Benítez, Aida,Herrera, F. Ruth,Romero, Margarita,Talamás, Francisco X.,Muchowski, Joseph M.

, p. 1487 - 1489 (2007/10/03)

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

Tian, Guan Rong,Mori, Akira,Kato, Nobuo,Takeshita, Hitoshi

, p. 506 - 513 (2007/10/02)

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

Ho, Mei Sing,Wong, Henry N. C.

, p. 1238 - 1240 (2007/10/02)

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.

Novel preparation of 1- and 3-substituted bicyclo[3.2.2]nona-3,6,8-trien-2-ones from tropones and 2,3-bis(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptadiene by high-pressure cycloaddition-thermal cycloreversion procedure

Tian,Sugiyama,Mori,Takeshita

, p. 2393 - 2399 (2007/10/02)

-

MOLYBDENUM-PROMOTED REACTIONS OF 7-OXABICYCLOHEPTADIENE AND DERIVATIVES

Sun, Chia-Hsing,Chow, Tahsin J.

, p. 217 - 226 (2007/10/02)

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.

Process route upstream and downstream products

Process route

methyl 11-oxa-endo,endo-tetracyclo<6.2.1.1<sup>3,6</sup>.0<sup>2,7</sup>>dodec-9-ene-9,10-dicarboxylate
78416-72-5

methyl 11-oxa-endo,endo-tetracyclo<6.2.1.13,6.02,7>dodec-9-ene-9,10-dicarboxylate

norborn-2-ene
498-66-8

norborn-2-ene

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

C<sub>15</sub>H<sub>18</sub>O<sub>5</sub>
78416-73-6

C15H18O5

Conditions
Conditions Yield
In benzene-d6; at 120 - 160 ℃;
In benzene-d6; at 130 ℃; Rate constant; Equilibrium constant; Mechanism; further solvents (methanol-d4);
In benzene-d6; at 160 ℃; Rate constant; Thermodynamic data; Mechanism; ΔH(excit.), ΔS(excit.);
benzonitrile oxide
873-67-6

benzonitrile oxide

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
1829-60-3

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

furan
110-00-9

furan

3-phenylisoxazole
1006-65-1

3-phenylisoxazole

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

dimethyl 3-phenylisoxazole-4,5-dicarboxylate
7710-44-3

dimethyl 3-phenylisoxazole-4,5-dicarboxylate

Conditions
Conditions Yield
In benzene; Ambient temperature;
75.0 % Chromat.
25.0 % Chromat.
In benzene; Ambient temperature;
25 % Chromat.
75.0 % Chromat.
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
1829-60-3

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

furan
110-00-9

furan

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

1-(4-nitrophenyl)-1H-1,2,3-triazole
1204-91-7

1-(4-nitrophenyl)-1H-1,2,3-triazole

1-(4-nitro-phenyl)-1<i>H</i>-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
4999-94-4

1-(4-nitro-phenyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; Ambient temperature;
51.6 % Chromat.
48.4 % Chromat.
dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
1829-60-3

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

furan
110-00-9

furan

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

1-(4-methoxyphenyl)-1H-[1,2,3]triazole
68535-49-9

1-(4-methoxyphenyl)-1H-[1,2,3]triazole

dimethyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4,5-dicarboxylate
4953-05-3

dimethyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Conditions
Conditions Yield
In benzene; Ambient temperature;
90.8 % Chromat.
9.2 % Chromat.
dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
1829-60-3

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

p-nitrobenzonitrile oxide
2574-03-0

p-nitrobenzonitrile oxide

furan
110-00-9

furan

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

3-(p-nitrophenyl)isoxazole
4264-05-5

3-(p-nitrophenyl)isoxazole

3-(4-nitro-phenyl)-isoxazole-4,5-dicarboxylic acid dimethyl ester
53890-65-6

3-(4-nitro-phenyl)-isoxazole-4,5-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; Ambient temperature;
56.4 % Chromat.
43.6 % Chromat.
dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
1829-60-3

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

C,N-Diphenylnitrilimine
231289-36-4

C,N-Diphenylnitrilimine

furan
110-00-9

furan

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

1,3-diphenyl-1H-pyrazole
4492-01-7

1,3-diphenyl-1H-pyrazole

dimethyl 1,3-diphenyl-1H-pyrazole-4,5-dicarboxylate
41555-25-3

dimethyl 1,3-diphenyl-1H-pyrazole-4,5-dicarboxylate

Conditions
Conditions Yield
In benzene; Ambient temperature;
0.6 % Chromat.
99.4 % Chromat.
dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
1829-60-3

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

Phenyl azide
622-37-7

Phenyl azide

furan
110-00-9

furan

1-phenyl-1,2,3-triazole
1453-81-2

1-phenyl-1,2,3-triazole

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

1-phenyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester
17304-69-7

1-phenyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
In benzene; Ambient temperature;
82.4 % Chromat.
17.6 % Chromat.
dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
1829-60-3

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

4-methoxybenzonitrile oxide
15500-73-9

4-methoxybenzonitrile oxide

dimethyl 3-(4-methoxyphenyl)isoxazole-4,5-dicarboxylate
59291-70-2

dimethyl 3-(4-methoxyphenyl)isoxazole-4,5-dicarboxylate

furan
110-00-9

furan

3-(4-methoxyphenyl)isoxazole
61428-20-4

3-(4-methoxyphenyl)isoxazole

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

Conditions
Conditions Yield
In benzene; Product distribution; Ambient temperature; reaction of other dipolarophiles with different 1,3-dipoles, effect of solvent polarity;
87.3 % Chromat.
12.7 % Chromat.
In benzene; Ambient temperature;
12.7 % Chromat.
87.3 % Chromat.
dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
1829-60-3

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

phthalic acid dimethyl ester
131-11-3,64441-70-9

phthalic acid dimethyl ester

Conditions
Conditions Yield
With hexacarbonyl molybdenum; In cyclohexane; for 48h; Ambient temperature;
46%
10%
With hexacarbonyl molybdenum; In cyclohexane; for 48h; Heating;
10%
46%
dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
1829-60-3

dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

dimethyl 3,4-furandicarboxylate
4282-33-1

dimethyl 3,4-furandicarboxylate

phthalic acid dimethyl ester
131-11-3,64441-70-9

phthalic acid dimethyl ester

C<sub>21</sub>H<sub>20</sub>O<sub>11</sub>

C21H20O11

Conditions
Conditions Yield
With tris(acetonitrile)tricarbonylmolybdenum(0); In acetonitrile; for 5h; Ambient temperature;
10%
9%
16%

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