Methyl 4,4-difluorocyclohexanecarboxylate

Base Information

• Chemical Name: Methyl 4,4-difluorocyclohexanecarboxylate
• CAS No.: 882855-71-2
• Molecular Formula: C₁₆H₁₉F₂NO₄
• Molecular Weight: 327.328
• European Community (EC) Number: 601-794-7
• DSSTox Substance ID: DTXSID40559426
• Wikidata: Q72490105
• Mol file: 882855-71-2.mol

Synonyms:METHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE;121629-14-9;METHYL 4,4-DIFLUOROCYCLOHEXANE-1-CARBOXYLATE;882855-71-2;Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester;MFCD11040454;Methyl4,4-difluorocyclohexanecarboxylate;SCHEMBL17584;DTXSID40559426;AMY15600;AKOS005063374;AB62807;CS-W020164;AS-50751;Cyclohexanecarboxylicacid, 3,3-difluoro-5-[[(phenylmethoxy)carbonyl]amino]-, methyl ester,(1R,5S)-rel-;SY108465;methyl 4,4-difluorocyclohexane carboxylate;P11009;A891566;J-520154;J-520157;4,4-Difluoro-cyclohexanecarboxylic acid methyl ester

Chemical Property of Methyl 4,4-difluorocyclohexanecarboxylate

Chemical Property:

• Boiling Point: 181.8 °C at 760 mmHg
• Flash Point: 62.4 °C
• PSA: 26.30000
• Density: 1.13 g/cm³
• LogP: 1.98490
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 178.08053595
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCC(CC1)(F)F

Technology Process of Methyl 4,4-difluorocyclohexanecarboxylate

There total 6 articles about Methyl 4,4-difluorocyclohexanecarboxylate 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: 71.0%

(cis)-methyl 3-(benzyloxycarbonylamino)-5-oxocyclohexanecarboxylate → (cis)-methyl 3-(benzyloxycarbonylamino)-5,5-difluorocyclohexanecarboxylate (882855-71-2)

Guidance literature:

With diethylamino-sulfur trifluoride; In benzene; for 18h; Heating;

DOI:10.1016/j.bmc.2005.11.010

Reference yield:

3-amino-5-hydroxybenzoic acid hydrochloride (14206-69-0) → (cis)-methyl 3-(benzyloxycarbonylamino)-5,5-difluorocyclohexanecarboxylate (882855-71-2)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Rh/Al₂O₃ / H₂O / 40 h / 90 °C / 76000 Torr

2: 1.10 g / Na₂CO₃ / H₂O / 4.5 h / 0 - 20 °C

3: 0.24 g / H₂SO₄ / 24 h / Heating

4: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 16 h / 20 °C

5: 71 percent / (diethylamino)sulfur trifluoride / benzene / 18 h / Heating

With diethylamino-sulfur trifluoride; sulfuric acid; hydrogen; sodium carbonate; Dess-Martin periodane; Rh/Al₂O₃; In dichloromethane; water; benzene; 4: Dess-Martin oxidation;

DOI:10.1016/j.bmc.2005.11.010

Reference yield:

3,5-Dihydroxybenzoic acid (99-10-5) → (cis)-methyl 3-(benzyloxycarbonylamino)-5,5-difluorocyclohexanecarboxylate (882855-71-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: aq. NH₃; NH₄Cl / 65 h / 180 °C

1.2: 62 percent Turnov_. / aq. HCl / 16 h / Heating

2.1: H₂ / Rh/Al₂O₃ / H₂O / 40 h / 90 °C / 76000 Torr

3.1: 1.10 g / Na₂CO₃ / H₂O / 4.5 h / 0 - 20 °C

4.1: 0.24 g / H₂SO₄ / 24 h / Heating

5.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 16 h / 20 °C

6.1: 71 percent / (diethylamino)sulfur trifluoride / benzene / 18 h / Heating

With ammonium hydroxide; diethylamino-sulfur trifluoride; sulfuric acid; hydrogen; sodium carbonate; ammonium chloride; Dess-Martin periodane; Rh/Al₂O₃; In dichloromethane; water; benzene; 5.1: Dess-Martin oxidation;

DOI:10.1016/j.bmc.2005.11.010

upstream raw materials:

(1S,3R,5S)-3-{[(benzyloxy)carbonyl]amino}-5-hydroxycyclohexane-1-carboxylic acid

3,5-Dihydroxybenzoic acid

3-amino-5-hydroxybenzoic acid hydrochloride

Refernces

• 1、 Wang, Zhiyong,Silverman, Richard B.. "Syntheses and evaluation of fluorinated conformationally restricted analogues of GABA as potential inhibitors of GABA aminotransferase". . p. 2242 - 2252. Retrieved 2007/10/03.