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Cas Database

1829-60-3

1829-60-3

Identification

  • Product Name:7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid, dimethyl ester

  • CAS Number: 1829-60-3

  • EINECS:

  • Molecular Weight:210.186

  • Molecular Formula: C10H10O5

  • HS Code:

  • Mol File:1829-60-3.mol

Synonyms:dimethyl oxanorbornadiene-2,3-dicarboxylate;dimethyl 7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate;2,3-bis(methoxycarbonyl)-7-oxabicyclo{2.2.1}hepta-2,5-diene;7-oxa-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester;7-Oxa-norborna-2,5-dien-2,3-dicarbonsaeure-dimethylester;dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
  • Packaging:500mg
  • Price:$ 110
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TCI Chemical
  • Product Description:Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate >95.0%(GC)
  • Packaging:1g
  • Price:$ 53
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:TCI Chemical
  • Product Description:Dimethyl 7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate >95.0%(GC)
  • Packaging:5g
  • Price:$ 180
  • Delivery:In stock
  • Buy Now
  • Manufacture/Brand:AK Scientific
  • Product Description:7-Oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylicaciddimethylester
  • Packaging:1g
  • Price:$ 124
  • Delivery:In stock
  • Buy Now

Relevant articles and documentsAll total 24 Articles be found

-

Gandhi,Chadha

, p. 552 (1968)

-

Simple and convenient preparation of some bicyclic alcohols and epoxide derivatives: Promising antibiotic activities of (rac)-dimethyl 3,8-dioxatricyclo[3.2.1.02,4]oct-6-ene-6,7-dicarboxylate

Yilmaz, ?zgür,?im?ek Ku?, Nermin,Küce, Pinar,Coral, G?khan,?elik, Ayla,Gültekin, Mehmet Serdar

, p. 2709 - 2716 (2015)

The biological activity of alcohol and epoxide groups containing bicyclic skeletal structures was investigated in terms of antibiotic and toxic effects at cellular level. The present protocol, which utilizes readily available starting materials and mild reaction conditions, provides an attractive approach to a series of functionalized bicyclic alcohol and epoxide derivatives with promising biological applications. In this protocol, while some of the bicyclic compounds were synthesized as in the literature, the other bicyclic compounds were synthesized by new synthetic methods. The antibiotic and toxic properties of the synthesized bicyclic compounds were investigated, and some of their biological activities were tested in prokaryotic and eukaryotic systems. (rac)-Dimethyl 3,8-dioxatricyclo[3.2.1.02,4]oct-6-ene-6,7-dicarboxylate, one of the synthesized molecules that showed antibiotic activity, was tested in two different living systems (prokaryotic and eukaryotic) in terms of biological and toxic effects at cellular level using a peripheral lymphocyte culture assay. Mitotic index for this compound was calculated in lymphocyte cultures.

-

Just,Grozinger

, p. 2701 (1975)

-

Palladium-Catalyzed Ortho-Silylation of Aryl Iodides with Concomitant Arylsilylation of Oxanorbornadiene: Accessing Functionalized (Z)-β-Substituted Vinylsilanes and Their Analogues

Lv, Weiwei,Wen, Si,Yu, Jia,Cheng, Guolin

, p. 4984 - 4987 (2018)

A palladium-catalyzed ortho-silylation of aryl iodides/arylsilylation of oxanorbornadiene/retro-Diels-Alder domino reaction was developed. Such a transformation provides access to various functionalized (Z)-β-substituted vinylsilanes with exclusive selectivity using hexamethyldisilane as a bis-silylation reagent and 2,3-dicarbomethoxy-7-oxanorbornadiene (ONBD) as an ortho-C-H activator and ethylene surrogate. A variety of (Z)-β-substituted vinylgermanes and (Z)-β-substituted vinylstannanes were also obtained under mild reaction conditions. This atom-economical, stereoselective, and scalable approach is compatible with a diverse range of readily available functionalized aryl iodides.

NBE-Controlled Palladium-Catalyzed Interannular Selective C-H Silylation: Access to Divergent Silicon-Containing 1,1′-Biaryl-2-Acetamides

Li, Wenguang,Chen, Wenqi,Zhou, Bang,Xu, Yankun,Deng, Guobo,Liang, Yun,Yang, Yuan

supporting information, p. 2718 - 2722 (2019/04/16)

A novel palladium-catalyzed interannular selective C-H silylation of 1,1′-biaryl-2-acetamides is described. The combination of palladium catalyst with copper oxidant enables meta- or ortho-selective C-H silylation by employing hexamethyldisilane as a trimethylsilyl source, which relies on the control of NBE derivatives as a switch, thus providing straightforward access to divergent silicon-containing 1,1′-biaryl-2-acetamides.

Regioselective arene homologation through rhenium-catalyzed deoxygenative aromatization of 7-oxabicyclo[2.2.1]hepta-2,5-dienes

Murai, Masahito,Ogita, Takuya,Takai, Kazuhiko

, p. 2332 - 2335 (2019/02/27)

Combined use of oxorhenium catalysts with triphenyl phosphite as an oxygen acceptor allowed efficient deoxygenative aromatization of oxabicyclic dienes. The reaction proceeded under neutral conditions and was compatible with various functional groups. Combining this deoxygenation with regioselective bromination and trapping of the generated aryne with furan resulted in benzannulative π-extension at the periphery of the PAHs. This enabled direct use of unfunctionalized PAHs for extension of π-conjugation. Iteration of the transformations increased the number of fused-benzene rings one at a time, which has the potential to alter the properties of PAHs by fine-tuning the degree of π-conjugation, shape, and edge topology.

METHOD TO PREPARE PHENOLICS FROM BIOMASS

-

Paragraph 29; 30, (2016/08/10)

The present invention is directed to a method for preparing a final phenolic product from biomass comprising the steps of providing a furanic compound obtainable from biomass; reacting the furanic compound with a dienophile to obtain a phenolic compound; reacting the phenolic compound further to obtain the final phenolic product.

1,3-Dipolar Cycloaddition with Diazo Groups: Noncovalent Interactions Overwhelm Strain

Gold, Brian,Aronoff, Matthew R.,Raines, Ronald T.

supporting information, p. 4466 - 4469 (2016/09/28)

Like azides, diazoacetamides undergo 1,3-dipolar cycloadditions with oxanorbornadienes (OND) in a reaction that is accelerated by the relief of strain in the transition state. The cycloaddition of a diazoacetamide with unstrained ethyl 4,4,4-trifluoro-2-butynoate is, however, 35-fold faster than with the analogous OND because of favorable interactions with the fluoro groups. Its rate constant (k = 0.53 M-1 s-1 in methanol) is comparable to those of strain-promoted azide-cyclooctyne cycloadditions.

Process route upstream and downstream products

Process route

furan
110-00-9

furan

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

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

Conditions
Conditions Yield
In dichloromethane; at -15 - 20 ℃; for 24h;
92%
Pd/borosilicate; In dimethyl sulfoxide; at 205 ℃; under 760.051 Torr; microwave irradiation;
74%
at 100 ℃; for 2h; Sealed tube;
56%
With iridium(III) chloride trihydrate; In toluene; at 70 ℃; for 48h; Air atmosphere;
92 %Spectr.
In diethyl ether; at 22 ℃;
furan
110-00-9

furan

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

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

Conditions
Conditions Yield
Heating;
85%
In diethyl ether; at 20 ℃; for 168h;
70%
In diethyl ether; for 20h; under 2250180 Torr; Ambient temperature;
66%
In toluene; at 80 ℃; for 14h; Sealed tube;
63%
In toluene; at 80 ℃; for 14h;
63%
In toluene; at 80 ℃; for 14h; Inert atmosphere;
63%
In toluene; at 80 ℃; for 14h;
63%
at 100 ℃; for 20h; in sealed tube;
47%
dimethyl acetylenedicarboxylate; With 1-butyl-3-methylimidazolium Tetrafluoroborate; zinc(II) iodide; at 20 ℃;
furan; at 20 ℃;
32%
for 20h; Heating;
27%
With benzene;
With diethyl ether;
With aluminium trichloride; nitrobenzene; In dichloromethane; at 22 ℃;
50 % Chromat.
at 80 ℃;
at 25 ℃;
In toluene; at 80 ℃; for 12h; Inert atmosphere;
furan
110-00-9

furan

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

1,4,5,8-tetrahydro-1<i>t</i>,4<i>t</i>;5<i>t</i>,8<i>t</i>-diepoxido-naphthalene-4a<i>r</i>,8a<i>c</i>-dicarboxylic acid dimethyl ester
10152-89-3,25860-27-9

1,4,5,8-tetrahydro-1t,4t;5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester

anti-methyl 11,12-dioxatetracyclo[6.2.1.1<sup>3,6</sup>.0<sup>2,7</sup>.]dodeca-4.9-diene-2,7-dicarboxylate
25860-27-9

anti-methyl 11,12-dioxatetracyclo[6.2.1.13,6.02,7.]dodeca-4.9-diene-2,7-dicarboxylate

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

Conditions
Conditions Yield
With Zn(II)-exchanged K10 montmorillonite; at 25 ℃; for 96h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
2,5-dimethylfuran
625-86-5

2,5-dimethylfuran

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

1,4,5,8-tetrahydro-1<i>t</i>,4<i>t</i>;5<i>t</i>,8<i>t</i>-diepoxido-naphthalene-4a<i>r</i>,8a<i>c</i>-dicarboxylic acid dimethyl ester
10152-89-3,25860-27-9

1,4,5,8-tetrahydro-1t,4t;5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester

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 1,4-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate
18063-93-9

dimethyl 1,4-dimethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

Conditions
Conditions Yield
With Zn(II)-exchanged K10 montmorillonite; at 25 ℃; for 20h; Yields of byproduct given. Title compound not separated from byproducts;
furan
110-00-9

furan

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

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

1,4,5,8-tetrahydro-1<i>t</i>,4<i>t</i>;5<i>t</i>,8<i>t</i>-diepoxido-naphthalene-4a<i>r</i>,8a<i>c</i>-dicarboxylic acid dimethyl ester
10152-89-3,25860-27-9

1,4,5,8-tetrahydro-1t,4t;5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester

Conditions
Conditions Yield
at 100 ℃;
1,4-Dioxocin
51153-59-4

1,4-Dioxocin

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

Tetramethyl 7-oxabicyclo<2.2.1>hepta-2,5-diene-2,3,5,6-tetracarboxylate
18064-10-3

Tetramethyl 7-oxabicyclo<2.2.1>hepta-2,5-diene-2,3,5,6-tetracarboxylate

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

Conditions
Conditions Yield
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

Conditions
Conditions Yield
furan
110-00-9

furan

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

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

Conditions
Conditions Yield
In dichloromethane; at -15 - 20 ℃; for 24h;
92%
Pd/borosilicate; In dimethyl sulfoxide; at 205 ℃; under 760.051 Torr; microwave irradiation;
74%
at 100 ℃; for 2h; Sealed tube;
56%
With iridium(III) chloride trihydrate; In toluene; at 70 ℃; for 48h; Air atmosphere;
92 %Spectr.
In diethyl ether; at 22 ℃;
furan
110-00-9

furan

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

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

Conditions
Conditions Yield
Heating;
85%
In diethyl ether; at 20 ℃; for 168h;
70%
In diethyl ether; for 20h; under 2250180 Torr; Ambient temperature;
66%
In toluene; at 80 ℃; for 14h; Sealed tube;
63%
In toluene; at 80 ℃; for 14h;
63%
In toluene; at 80 ℃; for 14h; Inert atmosphere;
63%
In toluene; at 80 ℃; for 14h;
63%
at 100 ℃; for 20h; in sealed tube;
47%
dimethyl acetylenedicarboxylate; With 1-butyl-3-methylimidazolium Tetrafluoroborate; zinc(II) iodide; at 20 ℃;
furan; at 20 ℃;
32%
for 20h; Heating;
27%
With benzene;
With diethyl ether;
With aluminium trichloride; nitrobenzene; In dichloromethane; at 22 ℃;
50 % Chromat.
at 80 ℃;
at 25 ℃;
In toluene; at 80 ℃; for 12h; Inert atmosphere;
furan
110-00-9

furan

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

1,4,5,8-tetrahydro-1<i>t</i>,4<i>t</i>;5<i>t</i>,8<i>t</i>-diepoxido-naphthalene-4a<i>r</i>,8a<i>c</i>-dicarboxylic acid dimethyl ester
10152-89-3,25860-27-9

1,4,5,8-tetrahydro-1t,4t;5t,8t-diepoxido-naphthalene-4ar,8ac-dicarboxylic acid dimethyl ester

anti-methyl 11,12-dioxatetracyclo[6.2.1.1<sup>3,6</sup>.0<sup>2,7</sup>.]dodeca-4.9-diene-2,7-dicarboxylate
25860-27-9

anti-methyl 11,12-dioxatetracyclo[6.2.1.13,6.02,7.]dodeca-4.9-diene-2,7-dicarboxylate

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

Conditions
Conditions Yield
With Zn(II)-exchanged K10 montmorillonite; at 25 ℃; for 96h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

Global suppliers and manufacturers

Global( 2) Suppliers
  • Company Name
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  • Emails
  • Main Products
  • Country
  • Synthelor SAS
  • Business Type:Lab/Research institutions
  • Contact Tel:+33 (0) 383 156 731
  • Emails:contact@synthelor.com
  • Main Products:1
  • Country:France
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