3-Bromo-5-nitrobenzotrifluoride

Base Information

• Chemical Name: 3-Bromo-5-nitrobenzotrifluoride
• CAS No.: 630125-49-4
• Molecular Formula: C7H3BrF3NO2
• Molecular Weight: 270.006
• Hs Code.: 29049090
• European Community (EC) Number: 642-502-8
• UNII: U6FE5HAA43
• DSSTox Substance ID: DTXSID50426736
• Wikidata: Q72448560
• Mol file: 630125-49-4.mol

Synonyms:3-bromo-5-nitrobenzotrifluoride;630125-49-4;1-bromo-3-nitro-5-(trifluoromethyl)benzene;1-Bromo-3-nitro-5-trifluoromethylbenzene;Benzene, 1-bromo-3-nitro-5-(trifluoromethyl)-;MFCD03788719;3-bromo-5-trifluoromethylnitrobenzene;3-Bromo-5-(trifluoromethyl)nitrobenzene;1-Bromo-3-nitro-5-trifluoromethyl-benzene;U6FE5HAA43;SCHEMBL788056;DTXSID50426736;BCP11280;BBL101513;STL555309;AKOS005259227;CS-W003108;GS-6875;PB48658;AC-19352;SY014293;A8702;AM20040906;B5333;FT-0600888;EN300-1939105

Chemical Property of 3-Bromo-5-nitrobenzotrifluoride

Chemical Property:

• Refractive Index: 1.515
• Boiling Point: 223.7 °C at 760 mmHg
• Flash Point: 89.1 °C
• PSA: 45.82000
• Density: 1.788 g/cm³
• LogP: 3.89930
• Storage Temp.: Room temperature.
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 268.92993
• Heavy Atom Count: 14
• Complexity: 228

Purity/Quality:

98% ^*data from raw suppliers

3-Bromo-5-nitrobenzotrifluoride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38-36/38
• Safety Statements: 26-36/37/39-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C=C1[N+](=O)[O-])Br)C(F)(F)F
• Uses: 3-Bromo-5-nitrobenzotrifluoride is an efficient D-glucosamine-based copper catalyst for C-X couplings and its application in synthesis of nilotinib intermediate. 3-Bromo-5-nitrobenzotrifluoride is also an intermediate for Nilotinib (N465300).

Technology Process of 3-Bromo-5-nitrobenzotrifluoride

There total 5 articles about 3-Bromo-5-nitrobenzotrifluoride 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: 89.6%

3-trifluoromethylnitrobenzene (98-46-4) → 1-bromo-3-nitro-5-(trifluoromethyl)benzene (630125-49-4)

Guidance literature:

3-trifluoromethylnitrobenzene; With sulfuric acid; In dichloromethane; water; at 35 ℃; for 0.166667h;

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In dichloromethane; water; at 35 ℃; for 24h;

With sodium hydroxide; In dichloromethane; water; at 0 - 35 ℃; for 0.333333h;

Reference yield: 38.0%

2-nitro-4-trifluoromethylbenzoic acid (320-94-5) → 1-bromo-3-nitro-5-(trifluoromethyl)benzene (630125-49-4)

Guidance literature:

With copper(I) oxide; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bismuth (III) nitrate pentahydrate; oxygen; sodium bromide; In dimethyl sulfoxide; at 170 ℃; for 10h; regioselective reaction; Schlenk technique; Green chemistry;

DOI:10.1021/acs.orglett.9b00460

Reference yield:

2-(3-bromo-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (479411-92-2) → 1-bromo-3-nitro-5-(trifluoromethyl)benzene (630125-49-4)

Guidance literature:

With copper diacetate; triethylamine; sodium nitrite; In acetonitrile; at 80 ℃; for 12h;

DOI:10.1002/chem.201901633

upstream raw materials:

3-trifluoromethylnitrobenzene

α,α,α-trifluorotoluene

2-nitro-4-trifluoromethylbenzoic acid

3-bromo-1-trifluoromethylbenzene

Downstream raw materials:

[3-bromo-5-(trifluoromethyl)phenyl]amine

3-methyl-5-(trifluoromethyl)aniline

1-Methyl-3-nitro-5-trifluoromethyl-benzene

Refernces

• 1、 Li, Xuejing,Deng, Xingwang,Coyne, Anthony G.,Srinivasan, Rajavel. "meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation". . p. 8018 - 8023. Retrieved 2019/05/29.
• 2、 Wen, Ming,Shen, Chao,Wang, Linfang,Zhang, Pengfei,Jin, Jianzhong. "An efficient d-glucosamine-based copper catalyst for C-X couplings and its application in the synthesis of nilotinib intermediate". . p. 1522 - 1528. Retrieved 2015/02/18.