626-35-7 Usage
Description
Ethyl nitroacetate, an ester of nitrocarboxylic acid, is a clear colorless to slightly yellow liquid. It is widely recognized for its role as an intermediate in the synthesis of various organic compounds, particularly in the pharmaceutical and chemical industries.
Uses
1. Used in Pharmaceutical Industry:
Ethyl nitroacetate is used as an intermediate for the preparation of unsubstituted amino acids, which are essential building blocks for the synthesis of various pharmaceutical compounds and have significant applications in the development of new drugs.
2. Used in Organic Synthesis:
Ethyl nitroacetate is utilized in the synthesis of γ-oxoacids via Michael addition reaction with α,β-unsaturated ketones. This process is crucial for the creation of complex organic molecules with potential applications in various industries.
3. Used in Nucleoside Synthesis:
It is employed in the functionalization of C4-position on pyrimidine and C6-position on 2'-deoxyguanosine to produce novel nucleosides. These nucleosides have potential applications in the development of new antiviral and anticancer drugs.
4. Used in Synthesis of α,α-diisobutylglycine:
Ethyl nitroacetate is used in the facile synthesis of α,α-diisobutylglycine, which is an important compound in the development of pharmaceuticals and other chemical products.
5. Used in Synthesis of DL-4,4-difluoroglutamic acid:
It serves as an intermediate in the preparation of DL-4,4-difluoroglutamic acid, a compound with potential applications in the pharmaceutical industry for the development of new drugs.
Synthesis Reference(s)
The Journal of Organic Chemistry, 59, p. 1208, 1994 DOI: 10.1021/jo00084a047
Purification Methods
Purify the ester by repeated distillation. IR:max 1748 (CO2), 1570 and 1337 (NO2), and 800cm-1 [Haszeldine J Chem Soc 2525 1953]. The hydrazine salt crystallises from 95% EtOH or MeOH as yellow crystals m 104-105o [Ungnade & Kissinger J Org Chem 22 1661 1957, Emmons & Freeman J Am Chem Soc 77 4391 1955]. [Beilstein 2 IV 537.]
Check Digit Verification of cas no
The CAS Registry Mumber 626-35-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 6 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 626-35:
(5*6)+(4*2)+(3*6)+(2*3)+(1*5)=67
67 % 10 = 7
So 626-35-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H7NO4/c1-2-9-4(6)3-5(7)8/h2-3H2,1H3
626-35-7Relevant articles and documents
Umezawa,S.,Zen,S.
, p. 1143 - 1145 (1963)
Transesterification of Methyl 2-Nitroacetate to Superior Esters
Corsi, Massimo,Machetti, Fabrizio,Magnolfi, Stefano
, (2020/03/19)
Methyl 2-nitroacetate and methyl acetoacetate have in common the presence of an electron-withdrawing substituent geminal to the methyl ester function but the well-known ease of thermal transesterification of methyl acetoacetate has not been found in methyl 2-nitroacetate. The latter gives uncatalysed thermal transesterification only in low yield and at a temperature higher than that of methyl acetoacetate. Comparative experiments provided further insight into the reactions; protic and Lewis acid catalysts promoted the smooth exchange of the alkanoyl groups, observing first the transesterification of methyl 2-nitroacetate with ethanol, already proved difficult to proceed. Dibutyltin(IV)oxide (DBTO) catalyst offered the spur to set up a convenient synthetic methodology from methyl 2-nitroacetate, encompassing higher molecular weight and functionalised alcohols: aliphatic, unsaturated and oxidation sensitive species were suited to react, delivering the corresponding 2-nitroacetate esters in good yields in most cases.
Catalytic Enantioselective Desymmetrization of Norbornenoquinones via C(sp2)-H Alkylation
Sarkar, Rahul,Mukherjee, Santanu
supporting information, p. 6160 - 6163 (2016/12/09)
The enantioselective Diels-Alder (DA) reaction with monosubstituted p-benzoquinones is an unmet challenge. A new approach for the enantioselective synthesis of monosubstituted quinone-DA adducts is presented based on C(sp2)-H alkylative desymmetrization of meso-DA adducts. Catalyzed by a tertiary amino-thiourea derivative, this reaction utilizes nitroalkanes as the alkylating agents and generates densely functionalized products bearing at least four contiguous stereogenic centers remote from the reaction site with excellent enantioselectivities.