2-Nitro-4-bromobenzenemethanediol diacetate

Base Information

• Chemical Name: 2-Nitro-4-bromobenzenemethanediol diacetate
• CAS No.: 135308-80-4
• Molecular Formula: C11H10BrNO6
• Molecular Weight: 332.107
• DSSTox Substance ID: DTXSID101209200
• Nikkaji Number: J1.684.669D
• Mol file: 135308-80-4.mol

Synonyms:135308-80-4;SCHEMBL12619427;DTXSID101209200;2-Nitro-4-bromobenzenemethanediol diacetate;Methanediol, 1-(4-bromo-2-nitrophenyl)-, 1,1-diacetate

Chemical Property of 2-Nitro-4-bromobenzenemethanediol diacetate

Chemical Property:

• Melting Point: 133-136 °C
• Boiling Point: 416.9±40.0 °C(Predicted)
• PSA: 98.42000
• Density: 1.600±0.06 g/cm3(Predicted)
• LogP: 3.00530
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 330.96915
• Heavy Atom Count: 19
• Complexity: 353

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 2-Nitro-4-bromobenzenemethanediol diacetate

There total 2 articles about 2-Nitro-4-bromobenzenemethanediol diacetate 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: 65.0%

4-bromo-2-nitrotoluene (60956-26-5) + acetic anhydride (108-24-7) → 4-bromo-2-nitrobenzylidene diethanoate (135308-80-4)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In water; acetic acid; at 5 - 10 ℃; for 9h;

DOI:10.1081/SCC-100107023

Reference yield:

p-toluidine (106-49-0,12221-03-3) → 4-bromo-2-nitrobenzylidene diethanoate (135308-80-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 64 percent / H₂SO₄; HNO₃ / -5 °C

2.1: HBr; NaNO₂ / H₂O / 0 °C

2.2: 58 percent / CuBr; HBr / H₂O

3.1: 65 percent / H₂SO₄; CrO₃ / acetic acid; H₂O / 9 h / 5 - 10 °C

With chromium(VI) oxide; sulfuric acid; hydrogen bromide; nitric acid; sodium nitrite; In water; acetic acid;

DOI:10.1081/SCC-100107023

Reference yield: 93.0%

4-bromo-2-nitrobenzylidene diethanoate (135308-80-4) → 4-bromo-2-nitrobenzaldehyde (5551-12-2)

Guidance literature:

With sulfuric acid; In ethanol; for 1.5h; Heating;

DOI:10.1081/SCC-100107023

upstream raw materials:

4-bromo-2-nitrotoluene

acetic anhydride

p-toluidine

Downstream raw materials:

4-bromo-2-nitrobenzaldehyde

tyrian purple

(2E)-3-(2-amino-4-bromophenyl)-2-(4-bromophenyl)prop-2-enoic acid

(2E)-3-(4-bromo-2-nitrophenyl)-2-(4-bromophenyl)prop-2-enoic acid

Refernces

• 1、 Imming,Imhof,Zentgraf. "An improved synthetic procedure for 6,6′-dibromoindigo (Tyrian purple)". . p. 3721 - 3727. Retrieved 2001.
• 2、 -. "SUBSTITUTED BENZOAZEPINES AS TOLL-LIKE RECEPTOR MODULATORS". Page/Page column 50; 51. . Retrieved 2011/04/13.