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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
MDL Number:
MFCD04621687
MOL File:
162401-62-9.mol
MSDS File:
SDS
Last updated:2023-11-08 17:00:29

3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid Properties

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

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P301+P310
Hazard Codes  T
Risk Statements  25
Safety Statements  45
RIDADR  2811
HazardClass  6.1
PackingGroup 
HS Code  2918999090
NFPA 704
0
2 0

3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid price More Price(31)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich MNO000161 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid 162401-62-9 1g $104 2024-03-01 Buy
Alfa Aesar H64098 3-Cyclopropylmethoxy-4-difluoromethoxybenzoic acid, 98% 162401-62-9 1g $62.9 2024-03-01 Buy
Alfa Aesar H64098 3-Cyclopropylmethoxy-4-difluoromethoxybenzoic acid, 98% 162401-62-9 5g $241 2024-03-01 Buy
Alfa Aesar H64098 3-Cyclopropylmethoxy-4-difluoromethoxybenzoic acid, 98% 162401-62-9 250mg $20.9 2023-06-20 Buy
TRC C988720 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid 162401-62-9 1g $70 2021-12-16 Buy
Product number Packaging Price Buy
MNO000161 1g $104 Buy
H64098 1g $62.9 Buy
H64098 5g $241 Buy
H64098 250mg $20.9 Buy
C988720 1g $70 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).
3-Cyclopropylmethoxy-4-difluoromethoxy-benzoic acid synthesis

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

Global( 277)Suppliers
Supplier Tel Email Country ProdList Advantage
Hefei TianRui Pharmaceutical Chemical Co., Ltd.
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View Lastest Price from 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid pictures 2024-08-23 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid
162401-62-9
US $100.00 / kg 1kg 99% 5000000 tons Wuhan Quanjinci New Material Co.,Ltd.
3-Cyclopropylmethoxy-4-difluoromethoxy-benzoic acid pictures 2023-04-20 3-Cyclopropylmethoxy-4-difluoromethoxy-benzoic acid
162401-62-9
US $0.00-0.00 / kg 5kg 99.99 1ton Hefei TianRui Pharmaceutical Chemical Co., Ltd.
3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid pictures 2022-02-10 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid
162401-62-9
US $0.00 / KG 1KG 99.1% 100 tons Honest Joy Holdings Limited
3-Cyclopropylmethoxy-4-difluoromethoxy-benzoic acid 3-CyclopropyMethoxy-4-difluoroMethoxy benzoic acid Benzoic acid, 3-(cyclopropylMethoxy)-4-(difluoroMethoxy)- CYCLOPROPYL DIFLUOROMETHOXYBENOZOIC ACID 3-CyclopropylMethoxy-4-isopropoxy-benzoic acid RofluMilast InterMediate II 3-Cyclopropylmethoxy-4-difluoromethoxybenzoic acid, >=98% Roflumilast intermediate B Roflumilast intermediate (3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid) Roflumilast Acid Impurity Roflumilast Impurity J RofluM Roflumilast Carboxylic Acid Impurity Roflumilast USP Related Compound D Acid Impurity of Roflumilast 162401-62-9 C12H12O4F2 Roflumilast interemdiate Intermediates