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

Base Information

• Chemical Name: 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid
• CAS No.: 162401-62-9
• Molecular Formula: C12H12F2O4
• Molecular Weight: 258.222
• Hs Code.: 2942000000
• DSSTox Substance ID: DTXSID30368468
• Nikkaji Number: J3.139.855J
• Wikidata: Q72460942
• Mol file: 162401-62-9.mol

Synonyms:162401-62-9;3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid;3-CYCLOPROPYLMETHOXY-4-DIFLUOROMETHOXYBENZOIC ACID;3-Cyclopropylmethoxy-4-difluoromethoxy-benzoic acid;Benzoic acid, 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-;MFCD04621687;Roflumilast intermediate B;3-Cyclopropylmethoxy-4-difluoromethoxybenzoic-d4Acid;C12H12F2O4;SCHEMBL1030007;DTXSID30368468;BCP07140;BBL101833;STL555630;AKOS008901106;CS-T-51495;CS-W005379;WAY-615873;AC-23371;AS-18905;SY042625;AM20030096;C3395;FT-0660843;A24674;3-Cyclopropylmethoxy-4-difluoromethoxy-benzoicacid;AU-004/43508033;3-cyclopropylmethoxy 4-Difluoromethoxy benzoic acid;3-Cyclopropylmethoxy-4- difluoromethoxy-benzoic acid;J-512382;3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoicAcid;Z56943765;3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid

Chemical Property of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid

Chemical Property:

• Vapor Pressure: 1.07E-05mmHg at 25°C
• Melting Point: 118-120℃
• Refractive Index: 1.528
• Boiling Point: 356.4 °C at 760 mmHg
• PKA: 3.87±0.10(Predicted)
• Flash Point: 169.4 °C
• PSA: 55.76000
• Density: 1.355 g/cm³
• LogP: 2.77500
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 258.07036518
• Heavy Atom Count: 18
• Complexity: 294

Purity/Quality:

99% ^*data from raw suppliers

3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1COC2=C(C=CC(=C2)C(=O)O)OC(F)F
• Uses: An impurity and intermediate in the preparation of selective phosphodiesterase 4 (PDE4) inhibitor, Roflumilast (R639700).

Technology Process of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid

There total 18 articles about 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid methyl ester → 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid (162401-62-9)

Guidance literature:

With sodium hydroxide; In methanol; at 50 ℃; for 3h;

DOI:10.1055/s-0032-1317527

Reference yield: 97.3%

3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde (151103-09-2) → 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid (162401-62-9)

Guidance literature:

With sodium chlorite; aminosulfonic acid; In water; acetic acid; at 20 ℃; for 1h;

Reference yield: 95.0%

4-bromo-2-(cyclopropylmethoxy)-1-(difluoromethoxy)benzene (680184-55-8) + carbon dioxide (124-38-9,18923-20-1) → 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid (162401-62-9)

Guidance literature:

4-bromo-2-(cyclopropylmethoxy)-1-(difluoromethoxy)benzene; With ethylmagnesium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; for 1h; Reflux;

carbon dioxide; In tetrahydrofuran; 1,2-dimethoxyethane;

With hydrogenchloride; In tetrahydrofuran; 1,2-dimethoxyethane; water; Temperature; Solvent; Reagent/catalyst; Acidic conditions;

upstream raw materials:

3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde

3-hydroxy-4-iodobenzoic acid

methyl 3-hydroxy-4-iodobenzoate

methyl 3-(cyclopropylmethoxy)-4-iodobenzoate

Downstream raw materials:

roflumilast

(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-methanol

(S)-3,5-dichloro-4-(2-((3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzyloxy)carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)pyridine 1-oxide

1-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(3,5-dichloropyridin-4-yl)ethyl 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoate

Refernces

• 1、 -. "Synthesis method of roflumilast key intermediate". Paragraph 0038; 0049-0051. . Retrieved 2017/07/21.
• 2、 -. "Synthesis method of roflumilast". Paragraph 0032; 0033; 0034; 0035; 0036; 0037; 0038-0041. . Retrieved 2017/07/26.