DiMethyl bicyclo[2.2.1]heptane-1,4-carboxylate
- Product Name
- DiMethyl bicyclo[2.2.1]heptane-1,4-carboxylate
- CAS No.
- 15448-76-7
- Chemical Name
- DiMethyl bicyclo[2.2.1]heptane-1,4-carboxylate
- Synonyms
- dimethyl norbornane-1,4-dicarboxylate;bicyclo[2.2.1]heptane-1,4-dicarboxylate;DiMethyl bicyclo[2.2.1]heptane-1,4-carboxylate;1,4-dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate;Dimethyl (1r,4r)-bicyclo[2.2.1]heptane-1,4-dicarboxylate;Bicyclo[2.2.1]heptane-1,4-dicarboxylic acid, 1,4-dimethyl ester
- CBNumber
- CB02704647
- Molecular Formula
- C11H16O4
- Formula Weight
- 212.24
- MOL File
- 15448-76-7.mol
DiMethyl bicyclo[2.2.1]heptane-1,4-carboxylate Property
- Boiling point:
- 264.9±13.0 °C(Predicted)
- Density
- 1.248±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Appearance
- White to light yellow Solid
- InChI
- InChI=1S/C11H16O4/c1-14-8(12)10-3-5-11(7-10,6-4-10)9(13)15-2/h3-7H2,1-2H3
- InChIKey
- UBGSPDWVUMFEAZ-UHFFFAOYSA-N
- SMILES
- C12(C(OC)=O)CC(C(OC)=O)(CC1)CC2
Safety
- HS Code
- 2917200090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
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
- D368115
- Product name
- Dimethylbicyclo[2.2.1]heptane-1,4-dicarboxylate
- Packaging
- 10mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- 2223-1-85
- Product name
- Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate
- Packaging
- 250mg
- Price
- $396
- Updated
- 2021/12/16
- Product number
- CHM0392107
- Product name
- DIMETHYL BICYCLO[2.2.1]HEPTANE-1,4-DICARBOXYLATE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $505.73
- Updated
- 2021/12/16
- Product number
- 7755AA
- Product name
- Dimethylbicyclo[2.2.1]heptane-1,4-dicarboxylate
- Packaging
- 100mg
- Price
- $192
- Updated
- 2021/12/16
- Product number
- 2223-1-85
- Product name
- Dimethyl bicyclo[2.2.1]heptane-1,4-dicarboxylate
- Packaging
- 1g
- Price
- $840
- Updated
- 2021/12/16
DiMethyl bicyclo[2.2.1]heptane-1,4-carboxylate Chemical Properties,Usage,Production
Synthesis
2435-36-1
107-04-0
15448-76-7
The general procedure for the synthesis of methyl bicyclo[2.2.1]heptane-1,4-dicarboxylate from methyl cyclopentane-1,3-dicarboxylate and 1-bromo-2-chloroethane was as follows: n-butyllithium (2.5 M hexane solution, 419.0 mL, 1048 mmol) was slowly added dropwise to a solution containing diisopropylamine (152 mL, 1090 mmol) at -78 °C (dry ice/acetone bath). 1090 mmol) in a solution of anhydrous THF (1000 mL), and the reaction system was maintained in an N2 atmosphere. Subsequently, the reaction mixture was stirred at 0 °C for 0.5 h and then cooled to -78 °C again. DMPU (404 mL, 3350 mmol) was added through the addition funnel. Next, a solution of anhydrous THF (300 mL) of methyl cyclopentane-1,3-dicarboxylate (78.0 g, 419 mmol) was slowly added through the addition funnel. The reaction mixture was slowly warmed to 0 °C and stirred for 30 min, after which it was cooled again to -78 °C and a solution of anhydrous THF (200 mL) of 1-bromo-2-chloroethane (59.0 mL, 712 mmol) was added. The reaction mixture was allowed to warm slowly to room temperature and stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (400 mL). The reaction mixture was diluted with ethyl acetate (500 mL), the organic layer was separated and the aqueous layer was further extracted with ethyl acetate (2 x 500 mL). The organic extracts were combined, washed with brine (2 × 300 mL), dried over anhydrous MgSO4, filtered and concentrated to dryness. The residue was filtered through a silica gel pad and washed with ethyl acetate (2000 mL). The filtrate was concentrated to dryness and the residue was purified by fast column chromatography (petroleum ether/ethyl acetate, 30:1 to 20:1, gradient elution) to afford methyl bicyclo[2.2.1]heptane-1,4-dicarboxylate (48.5 g, 54% yield) as a white solid.1H NMR (400 MHz, CDCl3): δ 3.69 (s, 6H), 2.08- 1.99 (m, 4H), 1.91 (s, 2H), 1.73-1.63 (m, 4H).
References
[1] Patent: US2018/170931, 2018, A1. Location in patent: Paragraph 0189
[2] Patent: WO2018/112382, 2018, A1. Location in patent: Page/Page column 1714; 175
[3] Patent: US2010/267738, 2010, A1. Location in patent: Page/Page column 32
[4] Patent: WO2012/145569, 2012, A1. Location in patent: Page/Page column 180; 181
[5] Patent: WO2016/106623, 2016, A1. Location in patent: Page/Page column 80
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