Methyl 5-bromo-2-nitrobenzoate

Base Information

• Chemical Name: Methyl 5-bromo-2-nitrobenzoate
• CAS No.: 883554-93-6
• Molecular Formula: C₈H₆BrNO₄
• Molecular Weight: 260.044
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID90590460
• Wikidata: Q72448542
• Mol file: 883554-93-6.mol

Synonyms:Methyl 5-bromo-2-nitrobenzoate;883554-93-6;5-Bromo-2-nitro-benzoic acid methyl ester;MFCD00092886;5-Bromo-2-nitrobenzoic acid methyl ester;SCHEMBL1667720;DTXSID90590460;CL8577;AKOS015852132;AM84019;SB73981;DS-12971;SY064186;DB-006978;DB-011609;CS-0150869;J-522454

Chemical Property of Methyl 5-bromo-2-nitrobenzoate

Chemical Property:

• Vapor Pressure: 0.000481mmHg at 25°C
• Melting Point: 70-71°C
• Refractive Index: 1.587
• Boiling Point: 314 °C at 760 mmHg
• Flash Point: 143.7 °C
• PSA: 72.12000
• Density: 1.673 g/cm³
• LogP: 2.66710
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 258.94802
• Heavy Atom Count: 14
• Complexity: 240

Purity/Quality:

98%min ^*data from raw suppliers

Methyl5-bromo-2-nitrobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(C=CC(=C1)Br)[N+](=O)[O-]

Technology Process of Methyl 5-bromo-2-nitrobenzoate

There total 11 articles about Methyl 5-bromo-2-nitrobenzoate 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:

methanol (67-56-1) + m-bromobenzoic acid (585-76-2) → methyl 5-bromo-2-nitro-3-methoxybenzoate (883554-93-6) + methyl 3-bromo-2-nitrobenzoate (104670-71-5)

Guidance literature:

m-bromobenzoic acid; With sulfuric acid; nitric acid; at 0 ℃;

With thionyl chloride; In pyridine; at 0 ℃;

methanol; In pyridine; at 0 ℃;

DOI:10.1039/c001122c

Reference yield:

m-bromobenzoic acid (585-76-2) + methyl iodide (74-88-4) → methyl 5-bromo-2-nitro-3-methoxybenzoate (883554-93-6)

Guidance literature:

m-bromobenzoic acid; With sulfuric acid; nitric acid; at 0 ℃; for 6h; Inert atmosphere;

methyl iodide; With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 40 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201804828

Reference yield:

3-methoxy-5-nitrobenzoic acid (78238-12-7) → methyl 5-bromo-2-nitro-3-methoxybenzoate (883554-93-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) 20percent aq. NaOH, 98percent hydrazine hydrate, Raney nickel / 1) water, 70 to 75 deg. C; 2) 70 to 80 deg. C, 30 min

2: 71 percent / H₂SO₄ (d 1.83), HNO₃ (d1.51) / -30 °C

3: 96 percent / Ba(OH)2 * 8H₂O / H₂O / 2 h / Heating

4: 99 percent / ethanol; diethyl ether / 0 - 5 °C

5: 1) H₂SO₄, NaNO₂; 2) NaBr, Cu₂Br₂ / 1) 0 deg. C, 1 h; 2) water, 3 h

With copper(I) bromide; barium dihydroxide; sodium hydroxide; sulfuric acid; nitric acid; nickel; hydrazine hydrate; sodium bromide; sodium nitrite; In diethyl ether; ethanol; water;

upstream raw materials:

methyl ester of 2-nitro-3-methoxy-5-aminobenzoic acid

3-methoxy-5-nitrobenzoic acid

3-methoxy-5-acetylaminobenzoic acid

2-nitro-3-methoxy-5-aminobenzoic acid

Downstream raw materials:

5-bromo-2-nitrobenzylic alcohol

Refernces

• 1、 Dai, Ziwen,Tam, Dick Yan,Xu, Hailiang,Chan, Miu Shan,Liu, Ling Sum,Bolze, Frédéric,Sun, Xiao Hua,Lo, Pik Kwan. "Conformational Change of Self-Assembled DNA Nanotubes Induced by Two-Photon Excitation". . p. 4090 - 4096. Retrieved 2015/09/15.
• 2、 Jacquart, Aurelie,Tauc, Patrick,Pansu, Robert B.,Ishow, Elena. "Tunable emissive thin films through ICT photodisruption of nitro-substituted triarylamines". experimental part. p. 4360 - 4362. Retrieved 2010/08/22.