3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid
- CAS No.
- 162401-62-9
- Chemical Name:
- 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid
- Synonyms
- RofluM;Roflumilast Impurity J;Roflumilast Acid Impurity;Roflumilast intermediate B;RofluMilast InterMediate II;Acid Impurity of Roflumilast;Roflumilast USP Related Compound D;Roflumilast Carboxylic Acid Impurity;CYCLOPROPYL DIFLUOROMETHOXYBENOZOIC ACID;3-CyclopropylMethoxy-4-isopropoxy-benzoic acid
- CBNumber:
- CB02487690
- Molecular Formula:
- C12H12F2O4
- Molecular Weight:
- 258.22
- MOL File:
- 162401-62-9.mol
- MSDS File:
- SDS
- Modify Date:
- 2023/11/8 17:00:29
Melting point | 118-120℃ |
---|---|
Boiling point | 356.4±37.0 °C(Predicted) |
Density | 1.355±0.06 g/cm3(Predicted) |
storage temp. | Sealed in dry,Room Temperature |
solubility | DMSO (Slightly), Methanol (Slightly) |
form | Solid |
pka | 3.87±0.10(Predicted) |
color | White to Off-White |
InChI | InChI=1S/C12H12F2O4/c13-12(14)18-9-4-3-8(11(15)16)5-10(9)17-6-7-1-2-7/h3-5,7,12H,1-2,6H2,(H,15,16) |
InChIKey | IGFDIFLMMLWKKY-UHFFFAOYSA-N |
SMILES | C(O)(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1 |
CAS DataBase Reference | 162401-62-9 |
3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid price More Price(4)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich(India) | MNO000161 | 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid | 162401-62-9 | 1G | ₹9017.23 | 2022-06-14 | Buy |
ALFA India | ALF-H64098-MD | 3-Cyclopropylmethoxy-4-difluoromethoxybenzoic acid, 98% | 162401-62-9 | 250mg | ₹1264 | 2022-05-26 | Buy |
ALFA India | ALF-H64098-06 | 3-Cyclopropylmethoxy-4-difluoromethoxybenzoic acid, 98% | 162401-62-9 | 5g | ₹20016 | 2022-05-26 | Buy |
ALFA India | ALF-H64098-03 | 3-Cyclopropylmethoxy-4-difluoromethoxybenzoic acid, 98% | 162401-62-9 | 1g | ₹4720 | 2022-05-26 | Buy |
3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid Chemical Properties,Uses,Production
Description
3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid (DGM) is a pharmaceutical intermediate ingredient used in the preparation of Roflumilast, a selective phosphodiesterase-4 (PDE4) inhibitor approved for the treatment of chronic bronchitis and to reduce the risk of exacerbations in patients with severe chronic obstructive pulmonary disease (COPD).
Uses
An impurity and intermediate in the preparation of selective phosphodiesterase 4 (PDE4) inhibitor, Roflumilast (R639700).
Biological Activity
It was shown that 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid (DGM) attenuated transforming growth factor-β1 (TGF-β1)-induced EMT in A549 cells and bleomycin-induced pulmonary fibrosis in rats. DGM treatment suppressed the expression of proteins such as α-SMA, waveform protein and collagen I and other proteins and increased the expression of E-cadherin. Correspondingly, the phosphorylation level of Smad2/3 was significantly reduced after DGM treatment[1].
Synthesis
3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid is synthesised using 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde as raw material by chemical reaction. The specific synthesis steps are as follows:
3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde (12 g, 50 mmol) and sulfamic acid (7.3 g, 75 mmol) were dissolved in glacial acetic acid (50 ml) and the solution added with a solution of sodium chlorite (8.2 g, 75 mmol) in water (15 ml).
The reaction mixture was stirred at room temperature for 1 hr then water (300 ml) was added so obtaining the precipitation of a solid that was filtered and dried at 40° C. under vacuum (12 g, 48 mmol, 97percent yield).
References
[1] TIANXIAO SUN. Inhibitory Effects of 3-Cyclopropylmethoxy-4-(difluoromethoxy) Benzoic Acid on TGF-β1-Induced Epithelial-Mesenchymal Transformation of In Vitro and Bleomycin-Induced Pulmonary Fibrosis In Vivo.[J]. International Journal of Molecular Sciences, 2023. DOI:10.3390/ijms24076172.
3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid Preparation Products And Raw materials
Raw materials
Preparation Products
Supplier | Tel | Country | ProdList | Advantage | Inquiry |
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VGS SYNTHESIS PRIVATE LIMITED | +91-9866975588 +91-9866975588 | Hyderabad, India | 1818 | 58 | Inquiry |
Molsyns Research | +91-9586858886 +91-9586858886 | Gujarat, India | 418 | 58 | Inquiry |
A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
SynZeal Research Pvt Ltd | +1 226-802-2078 | Gujarat, India | 6522 | 58 | Inquiry |
Nsr Laboratories Private Limited | 08048250267Ext 920 | Hyderabad, India | 25 | 58 | Inquiry |
Hefei TianRui Pharmaceutical Chemical Co., Ltd. | +86-0551-68665055 +86-+86-18616906106 | China | 129 | 58 | Inquiry |
Shanghai Famo Biotech Co Ltd | +86-36680037 +86-18550473860 | China | 528 | 58 | Inquiry |
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