4160-54-7

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dinitro-1-tert-butyl-benzene is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs and medications.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 2,4-Dinitro-1-tert-butyl-benzene is utilized as an intermediate for the synthesis of other organic compounds. Its versatility in chemical reactions makes it a valuable asset in creating a wide range of products.

InChI:InChI=1/C10H12N2O4/c1-10(2,3)8-5-4-7(11(13)14)6-9(8)12(15)16/h4-6H,1-3H3

Upstream product

• 253185-03-4 tert-butylbenzene 
• 1012-72-2 1,4-di-tert-butylbenzene 
• 59719-78-7 4-tert-butyl-3-nitrobenzoic acid 
• 3282-56-2 4-tert-butylnitrobenzene 

Downstream Products

• 478701-44-9 2-tert-butyl-5-methoxy-phenylamine 
• 70634-30-9 4-tert-Butyl-3-nitrophenol 
• 70634-26-3 1-tert-butyl-4-methoxy-2-nitro-benzene 
• 56140-47-7 2,4,6-trinitro-tert-butylbenzene 
• 873050-31-8 [5-[(4-oxo-1H-quinolin-3-yl)carbonylamino]-2-tert-butyl-phenyl]aminoformic acid methyl ester 
• 36919-89-8 di(tert-butyl)-biphenyl 
• 6310-21-0 2-(1,1-dimethylethyl)-benzenamine 
• 1886-57-3 1-tert-butyl-2-nitrobenzene 
• 62171-59-9 1-(tert-butyl)-2-iodobenzene 
• 2025-23-2 2,3-dinitro-4-t-butylaniline 
• 31951-11-8 4-acetamido-2-nitro-t-butylbenzene 
• 166263-22-5 N-cyano-N'-<5-cyano-2-(1,1-dimethylethyl)phenyl>carbamimidic acid phenyl ester 

Relevant academic research and scientific papers

Preparation method of M-tert-butylphenol

The invention discloses a preparation method of m-tert-butylphenol. The preparation method comprises the following steps: with tert-butylbenzene as a raw material, nitrifying tert-butylbenzene to obtain 2,4-dinitro-tert-butylbenzene, then conducting reduction and Baberger rearrangement to obtain 2,4-diamino-3-hydroxy tert-butylbenzene, and finally, performing diazotizing and reducing to remove amino groups so as to obtain m-tert-butylphenol. According to a process route in the invention, para-isomer generation is effectively avoided, and m-tert-butylphenol with a purity of 99% or above can beobtained through simple distillation; and the method has the advantages that raw materials are cheap and easy to obtain, the process is simple and has few side reactions, and the method is suitable for industrial production.

Discovery of N -(2,4-Di- tert -butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (VX-770, Ivacaftor), a potent and orally bioavailable CFTR potentiator

Quinolinone-3-carboxamide 1, a novel CFTR potentiator, was discovered using high-throughput screening in NIH-3T3 cells expressing the F508del-CFTR mutation. Extensive medicinal chemistry and iterative structure-activity relationship (SAR) studies to evaluate potency, selectivity, and pharmacokinetic properties resulted in the identification of N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (VX-770, 48, ivacaftor), an investigational drug candidate approved by the FDA for the treatment of CF patients 6 years of age and older carrying the G551D mutation.

Formation constants in C-H hydrogen bonding. 4. Effects of cyano, nitro, and trifluoromethyl substituents in aromatic compounds

Formation constants ( Keq) have been measured using 1H NMR for H-bond complexes with HMPA in CCl 4of 35 aromatic compounds variously substituted with cyano, nitro, and trifluoromethyl groups; several compounds contained F and Cl. The three strongly polar groups enhance H-bonding significantly, usually in the order NO2 > CN > CF3; all are superior to Cl and F. 1,3,5-Trinitrobenzene fails to H-bond at all; however, TNT, its tert-butyl analog, and trinitro-m-xylene show significant Keq values. Coplanarity of nitro groups with the ring blocks approach of HMPA, probably via intramolecular H-bonds. The buttressing effect is evident in some crowded compounds.

C-C bond formation via C-H bond activation: Catalytic arylation and alkenylation of alkane segments

A new system for catalytic arylation and alkenylation of alkane segments has been developed. The ortho-tert-butylaniline substrates and 2-pivaloylpyridine may be arylated and alkenylated at the tert-butyl group, while no functionalization occurred at more reactive C-H and other bonds. Arylation and alkenylation of these substrates are achieved in the presence of Ph2Si(OH)Me and Ph-CH=CH-Si(OH)Me2, respectively, and the catalytic amount of Pd(OAc)2 and stoichiometric oxidant (Cu(OAc)2, 2 equiv) in DMF. In contrast, the ortho-i-propylaniline substrate underwent cyclopalladation, but no arylation product was obtained. Complex compound 14 was synthesized via tandem arylation-alkenylation of tert-butylaniline 11. We hypothesize that the high selectivity of this system stems from the confluence of directing effect of the Schiff base or pyridine moiety and unique reactivity properties of a phenyl-palladium acetate species (Ph-Pd-OAc·Ln). Copyright

C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4

The core of teleocidin B4, a complex fragment of a natural product containing two quaternary stereocenters and a penta-substituted benzene ring, was synthesized in four C-C bond-forming steps starting from tert-butyl derivative 1. The first step involved

Vanadium(v) oxytrinitrate, VO(NO3)3. A powerful reagent for the nitration of aromatic compounds at room temperature under non-acidic conditions

Vanadium(v) oxytrinitrate is an easy to handle reagent which can be used to nitrate a range of substituted aromatic compounds in dichloromethane at room temperature, leading to >99% yields of nitration products in most cases.

Cardioselective antiischemic ATP-sensitive potassium channel openers. 4. Structure-activity studies on benzopyranylcyanoguanidines: Replacement of the benzopyran portion

The results of our efforts aimed at the replacement of the benzopyran ring of the lead cardiac selective antiischemic ATP-sensitive potassium channel (K(ATP)) opener (4) are described. Systematic modification of the benzopyran ring of 4 resulted in the discovery of a structurally simpler acyclic analog (8) with slightly lower antiischemic potency than the lead compound 4. Further structure-activity studies on the acyclic analog 8 provided the 2- phenoxy-3-pyridylurea analog 18 with improved antiischemic potency and selectivity compared to the benzopyran-based compound 4. These data demonstrate that the benzopyran ring of 4 and its congeners is not mandatory for antiischemic activity and cardiac selectivity. The results described in this paper also show that, as for the benzopyran class of compounds, the structure-activity relationships for the antiischemic and vasorelaxant activities of K(ATP) openers are distinct. The mechanism of action of the acyclic analogs (e.g., 18) still appears to involve K(ATP) opening as their cardioprotective effects are abolished by pretreatment with the K(ATP) blocker glyburide.

The Rearragement of Aromatic Nitro Compounds. Part 1. The Reactions of Nitroanilines in Aqueous Sulphuric Acid

A number of substituted 2-nitroanilines rearange in concentrated sulphuric acid at 110 deg C to yield products that appear to be derived from 1,3-migration of the 2-nitro-group.For 2,3-dinitroaniline, the rate of reaction is almost independent of acidity over the range 83-97percent sulphuric acid and the solvent isotope effect k(H2SO4)/k(D2SO4) is 1.3-1.9.Methyl and t-butyl groups, when present as additional substituents in 2,3-dinitroaniline, have only a small effect on the reaction rate but 3-methyl-2-nitroaniline reacts much more slowly than 2,3-dinitroaniline.These results are discussed in terms of a rate-determining migration of the 2-nitro group following protonation at the 2-position.