dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate
- Product Name
- dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate
- CAS No.
- 1459-96-7
- Chemical Name
- dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate
- Synonyms
- o[2.2.2]octane-1,4-dicarboxyL;iMethyl bicyclo[2.2.2]octane-1,4-dicarboxylate;Dimethyl bicyclo[2.2.2]octane-l,4-dicarboxylate;DiMethyl -bicyclo[2.2.2]octan-1,4-dicarboxylate;Dimethyl bioyclo[2.2.2]octane-1,4-dicarboxylate;dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate;2,2-diMethylbicyclo[2.2.2]octane-1,4-dicarboxylate;1,4-dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate;Bicyclo[2.2.2]octane-1,4-dicarboxylic acid dimethyl ester;Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate - [D13683]
- CBNumber
- CB61512357
- Molecular Formula
- C12H18O4
- Formula Weight
- 226.27
- MOL File
- 1459-96-7.mol
dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate Property
- Boiling point:
- 273.6±20.0 °C(Predicted)
- Density
- 1.205±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Appearance
- White to off-white Solid
- InChI
- InChI=1S/C12H18O4/c1-15-9(13)11-3-6-12(7-4-11,8-5-11)10(14)16-2/h3-8H2,1-2H3
- InChIKey
- HDOVTVDGSLEUSK-UHFFFAOYSA-N
- SMILES
- C12(C(OC)=O)CCC(C(OC)=O)(CC1)CC2
Safety
- HS Code
- 2918999090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- D472968
- Product name
- Dimethylbicyclo[2.2.2]octane-1,4-dicarboxylate
- Packaging
- 10g
- Price
- $75
- Updated
- 2021/12/16
- Product number
- D13683
- Product name
- Dimethylbicyclo[2.2.2]octane-1,4-dicarboxylate
- Purity
- 95+%
- Packaging
- 5g
- Price
- $70
- Updated
- 2021/12/16
- Product number
- OR307146
- Product name
- Dimethylbicyclo[2.2.2]octane-1,4-dicarboxylate
- Packaging
- 1g
- Price
- $85
- Updated
- 2021/12/16
- Product number
- 2223-1-62
- Product name
- Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate
- Packaging
- 1g
- Price
- $93
- Updated
- 2021/12/16
- Product number
- AS59332
- Product name
- 1,4-Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate
- Purity
- 95+%
- Packaging
- 1g
- Price
- $125
- Updated
- 2021/12/16
dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate Chemical Properties,Usage,Production
Uses
Dimethyl Bicyclo[2.2.2]octane-1,4-dicarboxylate is used in preparation of cycloalkanecarboxamides and related compounds as modulators of the integrated stress pathway.
Synthesis
106004-06-2
1459-96-7
General procedure for the synthesis of dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate from dimethyl 1-(2-chloroethyl)cyclohexane-1,4-dicarboxylate: 2.5 M hexane solution of n-butyllithium (53.6 mL) was added slowly and dropwise to a solution of diisopropylamine (18.7 mL) in tetrahydrofuran (180 mL) cooled to -30 °C. The reaction mixture was stirred between -20°C and -30°C for 20 minutes and subsequently cooled to -78°C. The solution was slowly added to a tetrahydrofuran (440 mL) mixture of dimethyl dicyclo[2.2.2]octane-1,4-dicarboxylate (32 g) and hexamethylphosphorotriamine (90 mL), the product of Step A, that was cooled to -78°C over a period of 30 minutes, ensuring that the temperature of the mixture did not exceed -70°C. Stirring was continued at -78 °C for 25 minutes, followed by slow warming of the reaction mixture to room temperature over 110 hours. After being kept at room temperature for 11 h, the reaction was quenched with saturated aqueous ammonium chloride solution. Volatiles were removed by evaporation and the reaction mixture was diluted with cyclohexane and water. The aqueous phase was separated and extracted three times with cyclohexane. The combined organic phases were washed sequentially with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was recrystallized by cyclohexane to give dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate (13.8 g, 50% yield). Mass spectral analysis showed [MH]+ = 227.
References
[1] Australian Journal of Chemistry, 1985, vol. 38, # 11, p. 1705 - 1718
[2] Patent: WO2006/128184, 2006, A2. Location in patent: Page/Page column 164-165
[3] Patent: WO2008/63671, 2008, A2. Location in patent: Page/Page column 177
[4] Synthetic Communications, 2007, vol. 37, # 8, p. 1267 - 1272
[5] Patent: US6649600, 2003, B1. Location in patent: Page/Page column 51-52
dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate Preparation Products And Raw materials
Raw materials
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View Lastest Price from dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate manufacturers
- Product
- Dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate 1459-96-7
- Price
- US $2.00-5.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2025-06-19
- Product
- dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate 1459-96-7
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1000kg
- Release date
- 2025-06-11
- Product
- dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate 1459-96-7
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 99%
- Supply Ability
- 10000KGS
- Release date
- 2020-01-09