151414-46-9

Basic information

• Product Name: 3,5-Difluoro-2-nitrophenol
• Synonyms: 3,5-DIFLUORO-2-NITROPHENOL;2,4-Difluoro-6-hydroxynitrobenzene
• CAS NO: 151414-46-9
• Molecular Formula: C₆H₃F₂NO₃
• Molecular Weight: 175.09
• Mol File: 151414-46-9.mol

Chemical Properties

• Melting Point: 46.1-46.5
• Boiling Point: 241.6 °C at 760 mmHg
• Flash Point: 99.9 °C
• Appearance: /
• Density: 1.619 g/cm³
• Vapor Pressure: 0.0229mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 2.60±0.20(Predicted)
• CAS DataBase Reference: 3,5-Difluoro-2-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Difluoro-2-nitrophenol(151414-46-9)
• EPA Substance Registry System: 3,5-Difluoro-2-nitrophenol(151414-46-9)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 151414-46-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3,5-Difluoro-2-nitrophenol is utilized as a building block in the organic synthesis industry for the preparation of various pharmaceuticals and agrochemicals. Its unique chemical structure makes it a valuable intermediate in the creation of a range of compounds with potential therapeutic and agricultural applications.
Used in Dyes and Pigments Production:
In the dye and pigment industry, 3,5-Difluoro-2-nitrophenol serves as a reagent in the production process. Its chemical properties contribute to the development of dyes and pigments with specific characteristics, such as color intensity and stability, which are essential for various applications in textiles, plastics, and other industries.

InChI:InChI=1/C6H3F2NO3/c7-3-1-4(8)6(9(11)12)5(10)2-3/h1-2,10H

Upstream product

• 315-14-0 1,3,5-trifluoro-2-nitrobenzene 
• 124-41-4 sodium methylate 
• 372-38-3 1,3,5-trifluorobenzene 
• 771-69-7 2,3,4-trifluoronitrobenzene 
• 62018-65-9 chloroform ethyl acetate 
• 2713-34-0 3,5-difluorophenol 

Downstream Products

• 66684-61-5 1,5-difluoro-3-methoxy-2-nitrobenzene 
• 356558-24-2 2-[(3,5-difluoro-2-nitrophenoxy)methyl]oxirane 
• 256523-59-8 1-(benzyloxy)-3,5-difluoro-2-nitrobenzene 

Relevant articles and documents

Novel triazines as potent and selective phosphodiesterase 10A inhibitors

The identification of highly potent and orally active triazines for the inhibition of PDE10A is reported. The new analogs exhibit low-nanomolar potency for PDE10A, demonstrate high selectivity against all other members of the PDE family, and show desired drug-like properties. Employing structure-based drug design approaches, we investigated the selectivity of PDE10A inhibitors against other known PDE isoforms, by methodically exploring the various sub-regions of the PDE10A ligand binding pocket. A systematic assessment of the ADME and pharmacokinetic properties of the newly synthesized compounds has led to the design of drug-like candidates with good brain permeability and desirable drug kinetics (t1/2, bioavailability, clearance). Compound 66 was highly potent for PDE10A (IC50 = 1.4 nM), demonstrated high selectivity (>200×) for the other PDEs, and was efficacious in animal models of psychoses; reversal of MK-801 induced hyperactivity (MED = 0.1 mg/kg) and conditioned avoidance responding (CAR; ID50 = 0.2 mg/kg).

Highly potent, selective, and orally active phosphodiesterase 10A inhibitors

The identification of highly potent and orally active phenylpyrazines for the inhibition of PDE10A is reported. The new analogues exhibit subnanomolar potency for PDE10A, demonstrate high selectivity against all other members of the PDE family, and show desired druglike properties. Employing structure-based drug design approaches, we methodically explored two key regions of the binding pocket of the PDE10A enzyme to alter the planarity of the parent compound 1 and optimize its affinity for PDE10A. Bulky substituents at the C9 position led to elimination of the mutagenicity of 1, while a crucial hydrogen bond interaction with Glu716 markedly enhanced its potency and selectivity. A systematic assessment of the ADME and PK properties of the new analogues led to druglike development candidates. One of the more potent compounds, 96, displayed an IC50 for PDE10A of 0.7 nM and was active in predictive antipsychotic animal models.

NOVEL MEK INHIBITORS, USEFUL IN THE TREATMENT OF DISEASES

The invention pertains to compound of Formula (I) wherein X, Y, Z, R1, R2, R3, R4, A and A' are as described hereinabove. Formula (I) and (II) compounds can be used in pharmaceutical compositions, useful for the treatment of diseases

IMIDAZO[5,1-C][1,2,4]BENZOTRIAZINE DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASES

The invention relates to imidazo[5,1-c][1,2,4]benzotriazine derivatives of formula I: which are inhibitors of phosphodiesterase 2 or 10 useful in treating central nervous system diseases such as psychosis and also in treating, for example, obesity, type 2 diabetes, metabolic syndrome, glucose intolerance, and pain.

1-ORTHOFLUOROPHENYL SUBSTITUTED 1, 2 , 5-THIAZOLIDINEDIONE DERIVATIVES AS PTP-AS INHIBITORS

Compounds of the formula (I) are inhibitors of protein tyrosine phosphatases (PTPases) and, thus, may be employed for the treatment of conditions mediated by PTPase activity. The compounds of the present invention may also be employed as inhibitors of other enzymes characterized with a phosphotyrosine binding region such as the SH2 domain. Accordingly, the compounds of formula (I) may be employed for prevention and/or treatment of insulin resistance associated with obesity, glucose intolerance, diabetes mellitus, hypertension and ischemic diseases of the large and small blood vessels, conditions that accompany type-2 diabetes, including hyperlipidemia, hypertriglyceridemia, atherosclerosis, vascular restenosis, irritable bowel syndrome, pancreatitis, adipose cell tumors and carcinomas such as liposarcoma, dyslipidemia, and other disorders where insulin resistance is indicated. In addition, the compounds of the present invention may be employed to treat and/or prevent cancer, osteoporosis, neurodegenerative and infectious diseases, and diseases involving inflammation and the immune system.

VANILLOID RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS

Pyrimidine ethers and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritus, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

VLA-4 INHIBITORS

The present invention relates to a compound represented by the following formula (I): (wherein, W represents WA-A1 -WB - (in which, WA is substituted or unsubstituted aryl, etc., A1 is -NR1-, single bond, -C(O)-, etc., and WB is substituted or unsubstituted arylene, etc.), R is single bond, -NH-, -OCH2-, alkenylene, etc., X is -C(O) -CH2-, etc., and M is, for example, the following formula: (in which, R11, R12 and R13 each independently represents hydrogen, hydroxyl, amino, halogen, etc., R14 is hydrogen or lower alkyl, Y represents -CH2-O-, etc., Z is substituted or unsubstituted arylene, etc., A2 is single bond, etc, and R10 is hydroxyl or lower alkoxy)), or salt thereof; and a medicament containing the same. This compound or salt thereof selectively inhibits binding of cell adhesion molecules to VAL-4 and exhibits high bioavailability so that it is useful as a preventive and/or remedy for inflammatory diseases, autoimmune diseases, metastasis, bronchial asthma, rhinostenosis, diabetes, and the like.

Novel compounds

The invention provides compounds of general formula (I) wherein Q, R, R2, R4, R5, R6, R7 and R8 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

Chemical compounds

Compound of formula (I) wherein: A is a bicyclic heteroaryl, optionally substituted with one or more substituents; B is linker group connecting group A to group D and comprising a 3 or 4 atom linker where each atom is independently selected from carbon, oxygen, nitrogen and sulphur and is optionally subsituted with one or more C1-6alkyl groups or two of such adjacent alkyl substituents may form a ring; C is aryl or a mono or bicyclic heteroaryl, each of which can be optionally substituted; D is an aryl or heteroaryl, both of which are optionally substituted R1is hydrogen, C1-5alkyl, C1-3alkanoyl or C1-3alkoxycarbonyl; R2to R5are each independently selected from hydrogen, C1-6alkyl, aryl and heteroaryl containing up to 2 heteroatoms chosen from oxygen, sulphur and nitrogen, the aryl and heteroaryl optionally substituted with C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-4alkoxy, C1-4alkanoyl, C1-6alkylamino, C1-4alkylC1-6alkyoxyl, C1-6alkylaminoC1-6alkyl, nitro, cyano, halogeno, trifluoromethyl, hydroxy, (CH2)pOH where p is 1 or 2, —CO2Ra, and —CONRaRb, where Raand Rbare independently selected from hydrogen and C1-6alkyl or two of R2to R5can be taken together to form a 3 to 7 membered ring; R6is an acidic functional group; r and s are each independently 0 or 1 with the proviso that r and s cannot both be 0; or a pharmaceutically acceptable salt or in vivo hydrolysable derivative thereof.

Synthesis and characterization of two improved NMR indicators for cytosolic Ca2+: 3FBAPTA and 35FBAPTA

Fluorinated derivatives of the calcium-selective chelator BAPTA [1,2-bis(2-aminophenoxy)ethane-N,N,N′,N′-tetraacetic acid] are popular NMR probes for cytosolic calcium ion concentration. Two such derivatives were synthesized and evaluated, 3FBAPTA [1,2-bis(2-amino-3-fluorophenoxy)ethane-N,N,N′,N′-tetraacetic acid] and 35FBAPTA [1,2-bis(2-amino-3,5-difluorophenoxy)ethane-N,N,N′,N′-tetraacetic acid]. The dissociation constant ratios obtained at 37°C were K3FD/K5FD = 0.60 and K35FD/K5FD = 0.88; similar values were obtained at 25°C. Hence 3FBAPTA binds calcium ions more tightly than 5FBAPTA [1,2-bis(2-amino-5-fluorophenoxy)ethane-N,N,N′,N′-tetraacetic acid, the currently most frequently utilized indicator], while the doubly substituted derivative exhibits intermediate affinity. The dissociation rate constants for the calcium complexes measured at 37°C exhibit a similar trend, with k5-1 > k35-1 > k3-1. Both of the additional derivatives exhibit slow exchange kinetics, and should be superior fluorine NMR probes owing to the decreased T1 values and, in the case of 35FBAPTA, the presence of two calcium-sensitive fluorine nuclei which are measured simultaneously.