372-39-4

Basic information

• Product Name: 3,5-Difluoroaniline
• Synonyms: 3,5-DIFLUOROBENZENAMINE;3,5-DIFLUOROANILINE;3,5-Difluoroaniline(AntibacterialAntiphlogistic,WeedKiller)(C6H5F2N);3,5-Difluoroaniline,98%;3,5-Difluoroaniline 98%;3,5-DIFLUOROBENZENEAMINE;Benzenamine, 3,5-difluoro;3,5-Difluoronitroaniline
• CAS NO: 372-39-4
• Molecular Formula: C₆H₅F₂N
• Molecular Weight: 129.11
• EINECS: 206-752-8
• Product Categories: Fluorobenzene Series;Fluorobenzene;Anilines, Aromatic Amines and Nitro Compounds;Miscellaneous;Amines;C2 to C6;Nitrogen Compounds
• Mol File: 372-39-4.mol

Chemical Properties

• Melting Point: 37-41 °C(lit.)
• Boiling Point: 80°C 20mm
• Flash Point: 167 °F
• Appearance: White to yellow/Low Melting Solid
• Density: 1,295 g/cm3
• Vapor Pressure: 0.7mmHg at 25°C
• Refractive Index: 1,512-1,514
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 2.57±0.10(Predicted)
• Water Solubility: Insoluble in water
• BRN: 2802286
• CAS DataBase Reference: 3,5-Difluoroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Difluoroaniline(372-39-4)
• EPA Substance Registry System: 3,5-Difluoroaniline(372-39-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 28-36/37/39-26-36
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• F: 8-10-23
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 372-39-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3,5-Difluoroaniline is used as a chemical intermediate for the preparation of 3,5-difluorodimethylaniline, which is an important compound in the synthesis of various pharmaceuticals and organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,5-difluoroaniline is used as a building block for the development of new drugs, particularly those targeting the kidney and renal system. Its nephrotoxic effects have been studied to better understand its potential applications and limitations in drug design.
Used in Research and Development:
3,5-Difluoroaniline is also utilized in research and development for the investigation of its chemical properties, reactivity, and potential applications in various fields, including material science and environmental chemistry.

Synthesis

Work on halogenated benzenes has also demonstrated the versatility of this technique and a variety of fluoro-chloro and -bromo benzenes may be de-brominated and de-chlorinated. Two patents describe removal of chlorine from 2,6-dichloro-3,5- difluoronitrobenzene giving 3,5-difluoroaniline.

InChI:InChI=1/C6H5F2N/c7-4-1-5(8)3-6(9)2-4/h1-3H,9H2

Upstream product

• 2265-94-3 1,3-difluoro-5-nitrobenzene 
• 372-38-3 1,3,5-trifluorobenzene 
• 7664-93-9 sulfuric acid 
• 404-12-6 1,2-bis(3,5-difluorophenyl)hydrazine 
• 364-30-7 2-amino-3,5-difluoronitrobenzene 
• 399-36-0 N-(2,4-difluoro-phenyl)-acetamide 
• 1634-04-4 tert-butyl methyl ether 
• 109-86-4 2-methoxy-ethanol 
• 7803-57-8 hydrazine hydrate 
• 13527-91-8 2,4,6-trichloro-3,5-difluoro-4-iodoaniline 
• 319-88-0 1,3,5-trichlorotrifluorobenzene 
• 461-96-1 3,5-difluorobromobenzene 
• 946839-66-3 N-benzyl-3,5-difluoroaniline 
• 129589-62-4 1-(tert-butoxycarbonylamino)-3,5-difluorobenzene 

Downstream Products

• 343-74-8 3,5-difluoro-N,N-dimethyl-4-phenylazo-aniline 
• 372-38-3 1,3,5-trifluorobenzene 
• 1435-43-4 1-chloro-3,5-difluorobenzene 
• 2713-34-0 3,5-difluorophenol 
• 3743-91-7 N,N'-(2,6-difluoro-p-phenylene)-bis-acetamide 
• 404-01-3 N-(3,5-difluorophenyl)acetamide 
• 1542-34-3 3,5-difluoro-4-iodoaniline 
• 123207-40-9 N-(3,5-difluorophenyl)-2-pyridinecarboxamide 
• 125830-37-7 4'-demethyl-4β-(3,5-difluoroanilino)-4-desoxypodophyllotoxin 
• 125830-37-7 4'-demethyl-4α-(3,5-difluoroanilino)-4-desoxypodophyllotoxin 
• 137606-11-2 3-Chloro-2-chloromethyl-N-(3,5-difluoro-phenyl)-2-methyl-propionamide 
• 129589-62-4 1-(tert-butoxycarbonylamino)-3,5-difluorobenzene 
• 99389-26-1 3,5-difluorobenzenethiol 
• 130721-84-5 3,5-Difluoro-N-pivaloylaniline 

Relevant articles and documents

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Copper and L-(?)-quebrachitol catalyzed hydroxylation and amination of aryl halides under air

L-(?)-Quebrachitol, a natural product obtained from waste water of the rubber industry, was utilized as an efficient ligand for the copper-catalyzed hydroxylation and amination of aryl halides to selectively give phenols and aryl amines in water or 95percent ethanol. In addition, the hydroxylation of 2-chloro-4-hydroxybenzoic acid was validated on a 100-g scale under air.

Deprotection of N-Boc Groups under Continuous-Flow High-Temperature Conditions

The scope of thermolytic, N-Boc deprotection was studied on 26 compounds from the Pfizer compound library, representing a diverse set of structural moieties. Among these compounds, 12 substrates resulted in clean (≥95% product) deprotection, and an additional three compounds gave ≥90% product. The thermal de-Boc conditions were found to be compatible with a large number of functional groups. A combination of computational modeling, statistical analysis, and kinetic model fitting was used to support an initial, slow, and concerted proton transfer with release of isobutylene, followed by a rapid decarboxylation. A strong correlation was found to exist between the electrophilicity of the N-Boc carbonyl group and the reaction rate.

Preparation method of polyfluoroaniline

The invention relates to a preparation method of polyfluoroaniline, according to the method, the polyfluoroaniline is prepared by a two-step common reaction from polyfluorobenzene as a raw material, the method has the characteristics of low reaction temperature, small pressure, low cost, and the like, is suitable for industrial production application, and is convenient for large-scale production;the polyfluoroaniline product obtained by the method has less impurities and high product purity.

Interaction of polyfluorinated 2-chloroquinolines with ammonia

We have studied the interaction of polyfluorinated (in the benzene moiety) 2-chloroquinolines with liquid and aqueous ammonia as an approach to the synthesis of halogen-containing aminoquinolines. 5,7-Difluoro-, 5,6,8-trifluoro-, and 5,7,8-trifluoro-2-chloroquinolines mostly form products of substitution of the Cl atom, whereas 5,7-difluoro-2,6-dichloroquinoline, 5,6,7,8-tetrafluoro-, and 6,7-difluoro-2-chloroquinolines yield products of substitution of an F atom at various positions. The replacement of liquid ammonia with aqueous causes an increase in the proportion of the products of aminodechlorination relative to the products of aminodefluorination. For 2-chloro-6,8-difluoroquinoline this replacement leads to 2-amino-6,8-difluoroquinoline as the main product instead of the 8-amino-derivative. Activation energy values estimated by DFT calculations for the reactions in question agree with the reaction regioselectivity observed experimentally.

Preparation method of 3,5-difluoroaniline

The invention discloses a preparation method of 3,5-difluoroaniline and relates to the technical field of organic synthesis. The preparation method comprises steps as follows: 2,4-difluoroaniline, tap water, hydrochloric acid, bromine, sodium nitrite, sodium monophosphate and ammonium hydroxide are taken as raw materials, cuprous oxide is taken as a catalyst, the tap water and dichloroethane are taken as solvents, and a product of 3,5-difluoroaniline is prepared through steps of bromination, diazotization, ammoniation, extraction, distillation and the like. According to the method, the industrially available raw materials can be utilized for reaction, the process is simple, post-treatment is simple and convenient, conditions are mild, environmental pollution is small, and the product of 3,5-difluoroaniline is prepared with high yield, and meanwhile, industrial production can be realized.

Synthesis of polyfluorinated 4-phenyl-3,4-dihydroquinolin-2-ones and quinolin-2-ones via superacidic activation of N-(polyfluorophenyl)cinnamamides

The cyclization reactions of a series of polyfluorocinnamanilides in triflic acid (CF3SO3H) yield 4-phenyl-3,4-dihydroquinolin-2-ones, which include a polyfluorinated benzene moiety as a part of the quinoline scaffold. These compounds undergo dehydrophenylation in the presence of AlCl3 to give the corresponding polyfluoroquinolin-2-ones which are converted into polyfluorinated 2-chloroquinolines on treatment with POCl3. A mechanism for the cyclization reaction presuming the intermediacy of a superelectrophilic O,C-diprotonated form of the starting material is suggested.

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS

The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed

Method of making 3,5-difluoroaniline from 1,3,5-trichlorobenzene

A method for manufacturing 3,5-difluoroaniline by fluorinating 1,3,5-trichlorobenzene and then aminating the intermediate fluorinated benzene with aqueous or anhydrous ammonia to achieve the product in yields of greater than 80%.

Process for producing 3,5-difluoroaniline and derivative thereof

A process for production of a 3,5-difluoroaniline compound with ease is disclosed, which comprise reacting an aminating agent with a 1,3,5-trifluorobenzene compound.