4-Nitrobenzyl hydrogen malonate
- Product Name
- 4-Nitrobenzyl hydrogen malonate
- CAS No.
- 77359-11-6
- Chemical Name
- 4-Nitrobenzyl hydrogen malonate
- Synonyms
- 4-NITROBENZYLMALONATE;P-NITROBENZYLMALONATE;Mononitrobenzyl malonate;2-(4-Nitrobenzyl)malonate;MONO-4-NITROBENZYL MALONATE;MONO P-NITRO BENZYL MALONATE;4-Nitrobenzyl hydrogen malote;Mono-4-nitrobenzylMalonate>Mono-4-nitrobenzylmalonicacides;4-nitrobenzyl hydrogen malonate
- CBNumber
- CB1714632
- Molecular Formula
- C10H9NO6
- Formula Weight
- 239.18
- MOL File
- 77359-11-6.mol
4-Nitrobenzyl hydrogen malonate Property
- Melting point:
- 109 °C
- Boiling point:
- 455.8±30.0 °C(Predicted)
- Density
- 1.447±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- soluble in Methanol
- form
- powder to crystal
- pka
- 2.49±0.32(Predicted)
- color
- White to Almost white
- InChI
- InChI=1S/C10H9NO6/c12-9(13)5-10(14)17-6-7-1-3-8(4-2-7)11(15)16/h1-4H,5-6H2,(H,12,13)
- InChIKey
- RIGFMUNSTCPGNP-UHFFFAOYSA-N
- SMILES
- C(OCC1=CC=C([N+]([O-])=O)C=C1)(=O)CC(O)=O
- CAS DataBase Reference
- 77359-11-6(CAS DataBase Reference)
Safety
- HS Code
- 2917399590
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H341Suspected of causing genetic defects
- Precautionary statements
-
P201Obtain special instructions before use.
P202Do not handle until all safety precautions have been read and understood.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313IF exposed or concerned: Get medical advice/attention.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- M1177
- Product name
- Mono-4-nitrobenzyl Malonate
- Purity
- >98.0%(T)
- Packaging
- 5g
- Price
- $97
- Updated
- 2025/07/31
- Product number
- M1177
- Product name
- Mono-4-nitrobenzyl Malonate
- Purity
- >98.0%(T)
- Packaging
- 25g
- Price
- $248
- Updated
- 2025/07/31
- Product number
- N495570
- Product name
- 3-[(4-Nitrobenzyl)oxy]-3-oxopropanoicAcid
- Packaging
- 1g
- Price
- $45
- Updated
- 2021/12/16
- Product number
- 075703
- Product name
- 3-((4-Nitrobenzyl)oxy)-3-oxopropanoic acid
- Purity
- 95+%
- Packaging
- 100g
- Price
- $75
- Updated
- 2021/12/16
- Product number
- 075703
- Product name
- 3-((4-Nitrobenzyl)oxy)-3-oxopropanoic acid
- Purity
- 95+%
- Packaging
- 5g
- Price
- $13
- Updated
- 2021/12/16
4-Nitrobenzyl hydrogen malonate Chemical Properties,Usage,Production
Uses
4-Nitrobenzyl hydrogen malonate is a reagent used in the synthesis of (±)-thienamycin, a β-Lactam antibiotics. Also, it is useful for chiral key intermediate of carbapenem syntheses.
Preparation
Preparation of mono-4-nitrobenzyl malonate:
In a flame-dried 150 mL pressure tube under argon, add 5.00 g (34.7 mmol) of Meldrum's acid and 40 mL of anhydrous MeCN.
Add 5.58 g (36.4 mmol) of p-nitrobenzyl alcohol to the resulting solution.
Cap the tube tightly and reflux the reaction overnight.
Concentrate the reaction mixture under reduced pressure.
Purify the residue using column chromatography with a 55/45 hexane/EtOAc mixture.
The resulting product is mono-4-nitrobenzyl malonate with a yield of 87%.
Synthesis
2033-24-1
619-73-8
77359-11-6
Meldrum acid (5.00 g, 34.7 mmol) and anhydrous acetonitrile (40 mL) were added to a flame-dried 150 mL pressure tube under argon protection. To this solution was added p-nitrobenzyl alcohol (5.58 g, 36.4 mmol), the pressure tube was sealed and the reaction was carried out overnight under reflux conditions. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure and the crude product was purified using column chromatography (eluent ratio 55:45 hexane/ethyl acetate) to afford mono-p-nitrobenzyl malonate (16a, 6.86 g, 27.1 mmol) as an off-white solid in 83% yield. A small amount of the product (1.00 g) was recrystallized by tert-butanol/hexane mixed solvent to give purified mono-p-nitrobenzyl malonate (16a, 225 mg, 0.889 mmol) as a white solid.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 21, p. 4933 - 4936
[2] Tetrahedron, 2001, vol. 57, # 9, p. 1837 - 1847
[3] Tetrahedron Letters, 2003, vol. 44, # 40, p. 7499 - 7502
4-Nitrobenzyl hydrogen malonate Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 4-Nitrobenzyl hydrogen malonate manufacturers
- Product
- 4-Nitrobenzyl hydrogen malonate 77359-11-6
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 5tons
- Release date
- 2024-10-24
- Product
- Malonicacidmononitrobenzylester 77359-11-6
- Price
- US $150.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 500kg
- Release date
- 2024-11-21
- Product
- 4-Nitrobenzyl hydrogen malonate 77359-11-6
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 99.00%
- Supply Ability
- 20tons
- Release date
- 2023-09-15