Methyl 4-nitrobutyrate

Base Information

• Chemical Name: Methyl 4-nitrobutyrate
• CAS No.: 13013-02-0
• Molecular Formula: C5H9NO4
• Molecular Weight: 147.131
• Hs Code.: 29159000
• European Community (EC) Number: 235-866-0
• NSC Number: 126459
• DSSTox Substance ID: DTXSID30156362
• Nikkaji Number: J129.135A
• Wikidata: Q83024415
• ChEMBL ID: CHEMBL3358703
• Mol file: 13013-02-0.mol

Synonyms:methyl 4-nitrobutyrate

Chemical Property of Methyl 4-nitrobutyrate

Chemical Property:

• Appearance/Colour: clear yellow to amber liquid
• Vapor Pressure: 0.0422mmHg at 25°C
• Refractive Index: n20/D 1.438(lit.)
• Boiling Point: 238.5 °C at 760 mmHg
• PKA: 8.27±0.29(Predicted)
• Flash Point: 107.3 °C
• PSA: 72.12000
• Density: 1.155 g/cm³
• LogP: 0.73950
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 147.05315777
• Heavy Atom Count: 10
• Complexity: 128

Purity/Quality:

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

4-NitrobutyricAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)CCC[N+](=O)[O-]
• Uses: Butyric acid derivative. Displays some anti-inflammatory activity.

Technology Process of Methyl 4-nitrobutyrate

There total 6 articles about Methyl 4-nitrobutyrate 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: 95.0%

nitromethane (75-52-5) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 4-nitrobutyrate (13013-02-0)

Guidance literature:

1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; at 0 ℃;

DOI:10.1016/S0040-4039(99)02340-0

Reference yield: 90.0%

2-nitrocyclopropane-1-carbaldehyde + methanol (67-56-1) → methyl 4-nitrobutyrate (13013-02-0)

Guidance literature:

With 2-mesityl-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazolium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 - 25 ℃; for 15h;

DOI:10.1002/anie.200601919

Reference yield: 69.0%

nitromethane (75-52-5) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 4-nitrobutyrate (13013-02-0) + dimethyl 4-nitro-1,7-heptanedioate (7766-83-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 70 - 75 ℃; for 0.5h; Microwave irradiation;

DOI:10.3390/molecules14041595

upstream raw materials:

nitromethane

acrylic acid methyl ester

methanol

Methyl 3-bromopropionate

Downstream raw materials:

4-oxobutanoic acid methyl ester

methyl 4-aminobutyrate

Methyl 3-(5-phenyl-4,5-dihydroisoxazol-3-yl)propionate

methyl 5-(4-methoxyphenyl)-4-nitro-4-pentenoate

Refernces

• 1、 Clark, Peter G. K.,Vieira, Lucas C. C.,Tallant, Cynthia,Fedorov, Oleg,Singleton, Dean C.,Rogers, Catherine M.,Monteiro, Octovia P.,Bennett, James M.,Baronio, Roberta,Müller, Susanne,Daniels, Danette L.,Méndez, Jacqui,Knapp, Stefan,Brennan, Paul E.,Dixon, Darren J.. "LP99: Discovery and synthesis of the first selective BRD7/9 bromodomain inhibitor". . p. 6217 - 6221. Retrieved 2015.
• 2、 Zhang, Yicheng,Chen, Chunlin,Wu, Guangjun,Guan, Naijia,Li, Landong,Zhang, Jian. "One-step hydrothermal amino-grafting of graphene oxide as an efficient solid base catalyst". . p. 4305 - 4308. Retrieved 2014.
• 3、 Bosica, Giovanna,Polidano, Kurt. "Solvent-Free Henry and Michael Reactions with Nitroalkanes Promoted by Potassium Carbonate as a Versatile Heterogeneous Catalyst". . . Retrieved 2017/07/11.
• 4、 Yin, Zhiping,Liu, Zengjin,Huang, Zhenggang,Chu, Yang,Chu, Zhiwen,Hu, Jia,Gao, Lu,Song, Zhenlei. "Synthesis of functionalized γ-lactone via Sakurai exo -cyclization/rearrangement of 3,3-bis(silyl) enol ester with a tethered acetal". supporting information. p. 1553 - 1556. Retrieved 2015/03/30.