127842-54-0

Basic information

• Product Name: 3,4-BIS-DIFLUOROMETHOXY-BENZALDEHYDE
• Synonyms: 3,4-BIS-DIFLUOROMETHOXY-BENZALDEHYDE;Benzaldehyde, 3,4-bis(difluoroMethoxy)-;Roflumilast Impurity K
• CAS NO: 127842-54-0
• Molecular Formula: C₉H₆F₄O₃
• Molecular Weight: 238.1357528
• EINECS: 1312995-182-4
• Product Categories: Aromatics;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 127842-54-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 265.8±35.0℃ (760 Torr)
• Flash Point: 111.1±20.8℃
• Appearance: /
• Density: 1.387±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3,4-BIS-DIFLUOROMETHOXY-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-BIS-DIFLUOROMETHOXY-BENZALDEHYDE(127842-54-0)
• EPA Substance Registry System: 3,4-BIS-DIFLUOROMETHOXY-BENZALDEHYDE(127842-54-0)

Safety Data

• Hazardous Substances Data: 127842-54-0(Hazardous Substances Data)

Usage

Description

3,4-Bis(difluoromethoxy)benzaldehyde is an organic compound characterized by its yellow oil appearance. It is known for its role as an impurity in the antiasthmatic drug Roflumilast (R639700) and is also utilized in the synthesis of diphenylethylene compounds.

Uses

Used in Pharmaceutical Industry:
3,4-Bis(difluoromethoxy)benzaldehyde is used as an intermediate compound for the development of PDE4 inhibitors, which are crucial in the treatment of various medical conditions such as cancer, CNS disorders, and inflammatory disorders. Its role in the synthesis of these compounds contributes to the advancement of therapeutic options for patients suffering from these conditions.
Used in Antiasthmatic Drug Production:
In the pharmaceutical industry, 3,4-Bis(difluoromethoxy)benzaldehyde is used as an impurity in the production of Roflumilast (R639700), an antiasthmatic drug. Its presence, despite being an impurity, is significant in the overall synthesis and effectiveness of the drug in treating asthma-related symptoms.
Used in Chemical Research:
3,4-Bis(difluoromethoxy)benzaldehyde's unique chemical properties make it a valuable compound for research purposes. It can be used in the study of various chemical reactions and mechanisms, contributing to the broader understanding of organic chemistry and its applications in the development of new drugs and materials.

Upstream product

• 1895-39-2 sodium chlorodifluoroacetate 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 1514-87-0 metyhyl chlorodifluoroacetate 
• 75-45-6 Chlorodifluoromethane 
• 151103-08-1 4-difluoromethoxy-3-hydroxybenzaldehyde 

Downstream Products

• 474499-53-1 (3,4-bis-difluoromethoxy-phenyl)-[4-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-ylmethyl)-phenyl]-methanol 
• 1055709-54-0 [3,4-bis(difluoromethoxy)phenyl]-{4-[2-((2-trimethylsilylethoxy)methoxy)propane-2yl]phenyl}methanol 
• 192767-12-7 (3,4-bis-difluoromethoxy-phenyl)-{4-[2,2,2-trifluoro-1-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-phenyl}-methanol 
• 775350-72-6 (3,4-bis-difluoromethoxy-phenyl)-(4-chloro-phenyl)-methanol 
• 303165-20-0 (+/-)-[3,4-bis(difluoromethoxy)phenyl]-(2-bromopyridin-5-yl)methanol 
• 474499-55-3 {4-[1-(3,4-bis-difluoromethoxy-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-acetic acid 3-hydroxy-2-hydroxymethyl-2-methyl-propyl ester 
• 192767-01-4 L 791943 
• 192767-15-0 4-(2-(3,4-bis-difluoromethoxy-phenyl)-2-{4-[2,2,2-trifluoro-1-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-phenyl}-ethyl)-pyridine 
• 192767-14-9 3-(3,4-bis-difluoromethoxy-phenyl)-2-pyridin-4-yl-3-{4-[2,2,2-trifluoro-1-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-phenyl}-propionic acid ethyl ester 
• 162401-60-7 3,4-Bis(difluoromethoxy) benzoic acid 

Relevant articles and documents

3′,4′-Bis-difluoromethoxycinnamoylanthranilate (FT061): An orally-active antifibrotic agent that reduces albuminuria in a rat model of progressive diabetic nephropathy

Cinnamoylanthranilates including tranilast have been identified as promising antifibrotics that can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. Structure-activity relationships aimed at improving potency and metabolic stability have led to the discovery of FT061. This compound, which bears a bis-difluoromethoxy catechol, attenuates TGF-β-stimulated production of collagen in cultured renal mesangial cells (approx 50% at 3 μM). When dosed orally at 20 mg/kg to male Sprague Dawley rats, FT061 exhibited a high bioavailability (73%), Cmax of 200 μM and Tmax of 150 min, and a half-life of 5.4 h. FT061 reduced albuminuria when orally dosed in rats at 200 mg kg/day in a late intervention study of a rat model of progressive diabetic nephropathy.

HALOGENATED ANALOGUES OF ANTI-FIBROTIC AGENTS

The present invention relates to halogenated compounds of formula (I) with the substituents as described within the specification. The compounds may be useful as anti-fibrqtic agents. The present invention also relates to methods for their preparation.

Design, synthesis, and structure - Activity relationship, molecular modeling, and NMR studies of a series of phenyl alkyl ketones as highly potent and selective phosphodiesterase-4 inhibitors

Phosphodiesterase 4 catalyzes the hydrolysis of cyclic AMP and is a target for the development of anti-inflammatory agents. We have designed and synthesized a series of phenyl alkyl ketones as PDE4 inhibitors. Among them, 13 compounds were identified as having submicromolar IC50 values. The most potent compounds have IC50 values of in the mid- to low-nanomolar range. Compound 5v also showed preference for PDE4 with selectivity of >2000-fold over PDE7, PDE9, PDE2, and PDE5. Docking of 5v, 5zf, and 5za into the binding pocket of the PDE4 catalytic domain revealed a similar binding profile to PDE4 with rolipram except that the fluorine atoms of the difluoromethyl groups of 5v, 5za, and 5zf are within a reasonable range for hydrogen bond formation with the amide hydrogen of Thr 333 and the long alkyl chain bears additional van der Waals interactions with His 160, Asp 318, and Tyr 159.