Methyl 4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoate

Base Information

• Chemical Name: Methyl 4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoate
• CAS No.: 343308-49-6
• Molecular Formula: C12H14BrNO6
• Molecular Weight: 348.15
• DSSTox Substance ID: DTXSID50471206
• Nikkaji Number: J1.769.023J
• Wikidata: Q82299658
• Mol file: 343308-49-6.mol

Synonyms:343308-49-6;METHYL 4-(3-BROMOPROPOXY)-5-METHOXY-2-NITROBENZOATE;methyl 5-methoxy-4-(3-bromopropoxy)-2-nitrobenzoate;SCHEMBL4373781;DTXSID50471206;ZPGOTMLRZAILCS-UHFFFAOYSA-N;F70250

Chemical Property of Methyl 4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoate

Chemical Property:

• PSA: 90.58000
• LogP: 3.07700
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 347.00045
• Heavy Atom Count: 20
• Complexity: 334

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)C(=O)OC)[N+](=O)[O-])OCCCBr

Technology Process of Methyl 4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoate

There total 4 articles about Methyl 4-(3-bromopropoxy)-5-methoxy-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: 92.0%

methyl 4-(3-bromopropoxy)-3-methoxybenzoate (343308-46-3) → methyl 4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoate (343308-49-6)

Guidance literature:

With nitric acid; sodium nitrite; In water; acetic acid; at 40 - 50 ℃; for 5h;

Reference yield:

4-hydroxy-3-methoxybenzoic acid methyl ester (3943-74-6) → methyl 4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoate (343308-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / potassium carbonate / acetone / 48 h / Heating

2: 90 percent / stannic chloride; fuming nitric acid / CH₂Cl₂ / 0.08 h / -25 °C

With nitric acid; tin(IV) chloride; potassium carbonate; In dichloromethane; acetone;

DOI:10.1016/j.bmc.2005.08.020

Reference yield:

4-hydroxy-5-methoxy-2-nitrobenzoic acid methyl ester (27883-60-9) + 1,3-dibromo-propane (109-64-8) → methyl 4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoate (343308-49-6)

Guidance literature:

With caesium carbonate; In acetonitrile; at 15 - 50 ℃; for 16h;

DOI:10.1021/acs.jmedchem.7b01926

upstream raw materials:

methyl 4-(3-bromopropoxy)-3-methoxybenzoate

4-hydroxy-3-methoxybenzoic acid methyl ester

methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate

4-hydroxy-5-methoxy-2-nitrobenzoic acid methyl ester

Downstream raw materials:

4-(3-bromopropoxy)-5-methoxy-2-nitrobenzoic acid

methyl 5-methoxy-2-nitro-4-[3-(pyrrolidin-1-yl)propoxy]benzoate

2,4-dichloro-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline

6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)-1H-quinazoline-2,4-dione