Methyl nitroacetate

Base Information

• Chemical Name: Methyl nitroacetate
• CAS No.: 2483-57-0
• Molecular Formula: C3H5NO4
• Molecular Weight: 119.077
• Hs Code.: 29161995
• European Community (EC) Number: 219-622-0
• NSC Number: 16153
• DSSTox Substance ID: DTXSID10179539
• Nikkaji Number: J129.146G
• Wikidata: Q72493361
• Mol file: 2483-57-0.mol

Synonyms:Aceticacid, nitro-, methyl ester (6CI,7CI,8CI,9CI);Methyl 2-nitroacetate;Methylnitroacetate;Methyl a-nitroacetate;NSC 16153;Nitroacetic acid methyl ester;Methyl Nitroacetate;

Chemical Property of Methyl nitroacetate

Chemical Property:

• Appearance/Colour: clear yellow liquid
• Vapor Pressure: 0.397mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• Boiling Point: 196.5 °C at 760 mmHg
• PKA: 5.73±0.29(Predicted)
• Flash Point: 105 °C
• PSA: 72.12000
• Density: 1.262 g/cm³
• LogP: -0.04070
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Solubility.: Miscible with ethanol, ether and most organic solvents.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 119.02185764
• Heavy Atom Count: 8
• Complexity: 104

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl nitroacetate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C[N+](=O)[O-]
• Uses: Methyl nitroacetate is used in the synthesis of aromatic and heteroaromatic linear (E)-alfa-nitro-arylpentenoates. It is also used to prepare phenyliodonium ylide. Further, it is utilized in the highly enantioselective and diastereoselective copper(I)-catalyzed cyclopropanation of alkenes. In addition to this, it is employed in the production of methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate through reaction with 4-nitrobenzylideneaniline.

Technology Process of Methyl nitroacetate

There total 20 articles about Methyl nitroacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

methyl 2-nitro-acetoacetate (29291-62-1) → methyl 2-nitroacetate (2483-57-0)

Guidance literature:

With sulfuric acid; In methanol; for 1h;

DOI:10.1007/BF00699138

Reference yield: 80.0%

methanol (67-56-1) + nitroacetic acid (625-75-2) → methyl 2-nitroacetate (2483-57-0)

Guidance literature:

With hydrogenchloride; for 3h; Ambient temperature;

Reference yield: 73.0%

→ methyl 2-nitroacetate (2483-57-0)

Guidance literature:

upstream raw materials:

methanol

nitroacetic acid

acetoacetic acid methyl ester

nitromethane

Downstream raw materials:

2,4-dinitro-3-phenyl-pentanedioic acid dimethyl ester

3-Anilino-2-nitro-propensaeure-methylester

2-Nitro-4-benzoyl-buttersaeure-methylester

methyl 5-phenyl-4,5-dihydroisoxazole-3-carboxylate

Refernces

• 1、 Weisblat,Lyttle. "-". . p. 3079. Retrieved 1949.
• 2、 Johnson, Eric C.,Guzmán, Pablo E.,Wingard, Leah A.,Sabatini, Jesse J.,Pesce-Rodriguez, Rose A.. "A Convenient and greener Synthesis of Methyl Nitroacetate". . p. 1088 - 1090. Retrieved 2017.
• 3、 Chen, Xin-fei,Ren, Chao,Xu, Xiao-yong,Shao, Xu-sheng,Li, Zhong. "Direct one-pot synthesis of 3-nitroquinolin-2(1H)-one via H2O/AcOH system: An improvement to classical Friedlander reaction". . p. 1433 - 1436. Retrieved 2017/03/23.
• 4、 Kislyi, V. P.,Laikhter, A. L.,Ugrak, B. I.,Semenov, V. V.. "Synthesis of α-functional nitro compounds by the nitration of activated carbonyl compounds in a two-phase system". . p. 70 - 74. Retrieved 2007/10/02.