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
- Molecular Weight:
- 239.18
- MDL Number:
- MFCD00191556
- MOL File:
- 77359-11-6.mol
| 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
Risk and Safety Statements
| Symbol(GHS) |  GHS08 |
|---|---|
| Signal word | Warning |
| Hazard statements | H341 |
| Precautionary statements | P201-P202-P280-P308+P313-P405-P501 |
| HS Code | 2917399590 |
4-Nitrobenzyl hydrogen malonate price More Price(14)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| TCI Chemical | M1177 | Mono-4-nitrobenzyl Malonate >98.0%(T) | 77359-11-6 | 5g | $97 | 2025-07-31 | Buy |
| TCI Chemical | M1177 | Mono-4-nitrobenzyl Malonate >98.0%(T) | 77359-11-6 | 25g | $248 | 2025-07-31 | Buy |
| TRC | N495570 | 3-[(4-Nitrobenzyl)oxy]-3-oxopropanoicAcid | 77359-11-6 | 1g | $45 | 2021-12-16 | Buy |
| Matrix Scientific | 075703 | 3-((4-Nitrobenzyl)oxy)-3-oxopropanoic acid 95+% | 77359-11-6 | 100g | $75 | 2021-12-16 | Buy |
| Matrix Scientific | 075703 | 3-((4-Nitrobenzyl)oxy)-3-oxopropanoic acid 95+% | 77359-11-6 | 5g | $13 | 2021-12-16 | Buy |
4-Nitrobenzyl hydrogen malonate Chemical Properties,Uses,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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hebei Chuanghai Biotechnology Co., Ltd | +8617732866630 | abby@chuanghaibio.com | China | 8773 | 58 |
| Hebei Chuanghai Biotechnology Co,.LTD | +86-13131129325 | sales1@chuanghaibio.com | China | 5251 | 58 |
| Capot Chemical Co.,Ltd. | +86-（0）57185586718; +8613336195806 | sales@capot.com | China | 29734 | 60 |
| career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29852 | 58 |
| Xiamen AmoyChem Co., Ltd | +86-86-5926051114 +8615060885618 | sales@amoychem.com | China | 6369 | 58 |
| Huaian yishu technology co.,ltd | 86-0517-85883738 13852390259 | sales@yishuchem.com | CHINA | 53 | 58 |
| Hubei xin bonus chemical co. LTD | 86-13657291602 | linda@hubeijusheng.com | CHINA | 22963 | 58 |
| Alchem Pharmtech,Inc. | 8485655694 | sales@alchempharmtech.com | United States | 63687 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49975 | 58 |
| Neostar United (Changzhou) Industrial Co., Ltd. | +86-0519-85551759 +8613506123987 | marketing1@neostarunited.com | China | 8826 | 58 |
View Lastest Price from 4-Nitrobenzyl hydrogen malonate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2025-06-24 | 4-Nitrobenzyl hydrogen malonate
77359-11-6
|
US $10.00 / KG | 1KG | 99% | 5tons | Hebei Chuanghai Biotechnology Co., Ltd | |
 |
2025-06-20 | 4-Nitrobenzyl hydrogen malonate
77359-11-6
|
US $0.00 / kg | 1kg | 99.00% | 20tons | Hebei Yanxi Chemical Co., Ltd. | |
 |
2025-05-26 | Mono-4-Nitrobenzyl Malonate
77359-11-6
|
US $5.00-2.00 / KG | 1KG | 99% | 10000kg | Hebei Chuanghai Biotechnology Co,.LTD |
-
- 4-Nitrobenzyl hydrogen malonate
77359-11-6
- US $10.00 / KG
- 99%
- Hebei Chuanghai Biotechnology Co., Ltd
-
- 4-Nitrobenzyl hydrogen malonate
77359-11-6
- US $0.00 / kg
- 99.00%
- Hebei Yanxi Chemical Co., Ltd.
-
- Mono-4-Nitrobenzyl Malonate
77359-11-6
- US $5.00-2.00 / KG
- 99%
- Hebei Chuanghai Biotechnology Co,.LTD
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