4-Difluoromethoxy-3-hydroxybenzaldehyde

Base Information

• Chemical Name: 4-Difluoromethoxy-3-hydroxybenzaldehyde
• CAS No.: 151103-08-1
• Molecular Formula: C8H6 F2 O3
• Molecular Weight: 188.131
• Hs Code.: 2913000090
• European Community (EC) Number: 687-745-0
• DSSTox Substance ID: DTXSID70374265
• Nikkaji Number: J3.209.872J
• Wikidata: Q72463298
• ChEMBL ID: CHEMBL1673314
• Mol file: 151103-08-1.mol

Synonyms:4-Difluoromethoxy-3-hydroxybenzaldehyde;151103-08-1;4-(difluoromethoxy)-3-hydroxybenzaldehyde;Benzaldehyde, 4-(difluoromethoxy)-3-hydroxy-;MFCD04406687;CHEMBL1673314;4-Difluoromethoxy-3-hydroxy-benzaldehyde;3-HYDROXY-4-(DIFLUOROMETHOXY)BENZALDEHYDE;SCHEMBL142767;DTXSID70374265;BCP05191;BBL102434;BDBM50336529;CL8349;GEO-02629;STL556236;AKOS005063854;3-hydroxy-4-difluoromethoxybenzaldehyde;CS-W016828;GS-3641;3-hydroxy-4-difluoromethoxy benzaldehyde;4-Difluoromethoxy 3-hydroxy benzaldehyde;4-difluoromethoxy-3-hydroxy benzaldehyde;AC-29998;SY028766;3-hydroxy-4-(difluoromethoxy)-benzaldehyde;4-(difluoromethoxy)-3-hydroxy benzaldehyde;AM20030028;D4505;FT-0643464;A20888;4-(Difluoromethoxy)-3-hydroxybenzaldehyde, 95%;EN300-2056860;W-200127;F0293-0136;Z1255395774

Chemical Property of 4-Difluoromethoxy-3-hydroxybenzaldehyde

Chemical Property:

• Vapor Pressure: 0.0022mmHg at 25°C
• Melting Point: 85-90°C
• Boiling Point: °Cat760mmHg
• PKA: 7.85±0.35(Predicted)
• Flash Point: °C
• PSA: 46.53000
• Density: 1.883g/cm³
• LogP: 1.80610
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 188.02850037
• Heavy Atom Count: 13
• Complexity: 175

Purity/Quality:

99% ^*data from raw suppliers

4-(Difluoromethoxy)-3-hydroxybenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-51-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=O)O)OC(F)F
• Uses: 4-Difluoromethoxy-3-hydroxybenzaldehyde is a phenyl alkyl ketone derivative used in the preparation of phosphodiesterase-4 (PDE4) inhibitors.

Technology Process of 4-Difluoromethoxy-3-hydroxybenzaldehyde

There total 20 articles about 4-Difluoromethoxy-3-hydroxybenzaldehyde 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: 90.3%

methyl bromodifluoroacetate (683-98-7) + 3,4-dihydroxybenzaldehyde (139-85-5) → 4-difluoromethoxy-3-hydroxybenzaldehyde (151103-08-1)

Guidance literature:

With hydroxylamine; In water; acetonitrile; at 45 ℃; Concentration; Reagent/catalyst;

Reference yield: 88.3%

4-(difluoromethoxy)-3-methoxybenzaldehyde (162401-70-9) → 4-difluoromethoxy-3-hydroxybenzaldehyde (151103-08-1)

Guidance literature:

With potassium carbonate; In 1-methyl-pyrrolidin-2-one;

DOI:10.1016/j.cclet.2013.05.009

Reference yield: 83.0%

C11H12F2O4 (773093-32-6) → 4-difluoromethoxy-3-hydroxybenzaldehyde (151103-08-1)

Guidance literature:

C₁₁H₁₂F₂O₄; With lithium diphenylphosphide; In tetrahydrofuran; for 3 - 4h;

With hydrogenchloride; water; pH=3 - 4;

upstream raw materials:

metyhyl chlorodifluoroacetate

3,4-dihydroxybenzaldehyde

sodium chlorodifluoroacetate

Chlorodifluoromethane

Downstream raw materials:

3,4-bis-(difluoromethoxy)-benzaldehyde

3-cyclobutoxy-4-difluoromethoxy-benzaldehyde

3-[(3-bromo-pyridin-N-oxide-4-yl)oxyl]-4-(difluoromethoxy)benzaldehyde

4-(difluoromethoxy)-3-(trityloxy)benzaldehyde

Refernces

• 1、 Dorokhov, Valentin S.,Golovanov, Ivan S.,Tartakovsky, Vladimir A.,Sukhorukov, Alexey Yu.,Ioffe, Sema L.. "Diastereoselective synthesis and profiling of bicyclic imidazolidinone derivatives bearing a difluoromethylated catechol unit as potent phosphodiesterase 4 inhibitors". . p. 6900 - 6908. Retrieved 2018.
• 2、 Lee, Johnny W.,Lim, Sanghyun,Maienshein, Daniel N.,Liu, Peng,Ngai, Ming-Yu. "Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C?H Di- and Trifluoromethoxylation". supporting information. p. 21475 - 21480. Retrieved 2020/10/02.
• 3、 -. "DIFLUOROMETHOXYLATION AND TRIFLUOROMETHOXYLATION COMPOSITIONS AND METHODS FOR SYNTHESIZING SAME". Page/Page column 75; 79; 89; 98-99. . Retrieved 2019/09/18.