Methyl 4-nitro-3-phenylbutanoate

Base Information

• Chemical Name: Methyl 4-nitro-3-phenylbutanoate
• CAS No.: 34687-03-1
• Molecular Formula: C11H13NO4
• Molecular Weight: 223.229
• European Community (EC) Number: 696-117-5
• Nikkaji Number: J1.738.622K
• Mol file: 34687-03-1.mol

Synonyms:methyl 4-nitro-3-phenylbutanoate;34687-03-1;beta-(Nitromethyl)benzenepropanoic Acid Methyl Ester;SCHEMBL698333;methyl4-nitro-3-phenylbutanoate;ZJFQGMLHRHGKEV-UHFFFAOYSA-;ZJFQGMLHRHGKEV-UHFFFAOYSA-N;AKOS033199372;3-Phenyl-4-nitrobutyric acid methyl ester;4-Nitro-3-phenylbutyric acid methyl ester;4-nitro-3-phenyl-butyric acid methyl ester;4-nitro-3-phenylbutanoic acid methyl ester;CS-0257251;EN300-66694;Z1065614094;InChI=1/C11H13NO4/c1-16-11(13)7-10(8-12(14)15)9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3

Chemical Property of Methyl 4-nitro-3-phenylbutanoate

Chemical Property:

• Melting Point: 37 °C
• Boiling Point: 346.0±35.0 °C(Predicted)
• PKA: 7.83±0.38(Predicted)
• PSA: 72.12000
• Density: 1.182±0.06 g/cm3(Predicted)
• LogP: 2.13320
• Solubility.: Chloroform, DCM, DMSO, Ethyl Acetate
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 223.08445790
• Heavy Atom Count: 16
• Complexity: 243

Purity/Quality:

99% ^*data from raw suppliers

β-(Nitromethyl)benzenepropanoicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CC(C[N+](=O)[O-])C1=CC=CC=C1
• Uses: β-(Nitromethyl)benzenepropanoic Acid Methyl Ester is an intermediate in the synthesis of Carphedone (C184315), a GABA derivative that exhibited apparent immunocorrection properties during immunosuppression induced by cyclophosphamide.

Technology Process of Methyl 4-nitro-3-phenylbutanoate

There total 10 articles about Methyl 4-nitro-3-phenylbutanoate 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%

nitromethane (75-52-5) + methyl cinnamate (103-26-4,1754-62-7) → 4-nitro-3-phenylbutanoic acid methyl ester (34687-03-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; toluene; at 50 ℃; for 1h; under 6000.6 Torr; Solvent;

DOI:10.1002/anie.201409765

Reference yield: 96.0%

nitromethane (75-52-5) + Methyl cinnamate (103-26-4,1754-62-7) → 4-nitro-3-phenylbutanoic acid methyl ester (34687-03-1)

Guidance literature:

With N,N,N',N'-tetramethylguanidine; for 3h; Heating;

DOI:10.1248/cpb.45.1932

Reference yield: 84.0%

methanol (67-56-1) + cycl-isopropylidene malonate (2033-24-1) + nitromethane (75-52-5) + benzaldehyde (100-52-7) → 4-nitro-3-phenylbutanoic acid methyl ester (34687-03-1)

Guidance literature:

With calcined hydrotalcite; for 24h; Reflux;

DOI:10.5935/0103-5053.20160175

upstream raw materials:

nitromethane

methyl cinnamate

Methyl cinnamate

methanol

Downstream raw materials:

4-phenylpyrrolidin-2-one

4-nitro-3-phenyl butanoic acid

4-amino-3-phenylbutanoic acid

(S)-3-cyano-3-(phenyl)-propanoic acid methyl ester

Refernces

• 1、 ?tv?s, Sándor B.,Kappe, C. Oliver,Llanes, Patricia,Pericàs, Miquel A.. "Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut". . p. 8122 - 8126. Retrieved 2020/11/03.
• 2、 -. "A process for preparing 3 - phenyl - 4 - aminobutyric acid hydrochloride process (by machine translation)". Paragraph 0035; 0036; 0037. . Retrieved 2018/01/02.