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Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester is a chemical compound characterized by the molecular formula C9H24O2F2. It is a colorless liquid with a faint odor, known for its unique chemical properties that make it a valuable intermediate in the synthesis of pharmaceuticals and agrochemicals. This versatile compound is also utilized in research and development for the production of various organic compounds, showcasing its potential in the pharmaceutical industry for the development of new drugs and in the synthesis of agricultural and specialty chemicals.

121629-14-9

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121629-14-9 Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester is used as an intermediate in the synthesis of new drugs for various medical conditions. Its unique chemical properties contribute to the development of innovative pharmaceutical compounds, enhancing treatment options for patients.
Used in Agrochemical Synthesis:
In the agrochemical industry, Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester is utilized as a building block for the production of agricultural chemicals. Its role in the synthesis process aids in the creation of effective compounds for crop protection and other agricultural applications.
Used in Specialty Chemicals Production:
Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester is also employed in the synthesis of specialty chemicals, where its unique properties are leveraged to produce compounds with specific applications in various industries, further demonstrating its versatility in organic chemistry.
Used in Research and Development:
As a key intermediate, Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester is used in research and development to explore its potential applications and to create new organic compounds. Its presence in the lab setting facilitates advancements in the field of organic chemistry and contributes to the discovery of novel uses for Cyclohexanecarboxylic acid, 4,4-difluoro-, methyl ester.

Check Digit Verification of cas no

The CAS Registry Mumber 121629-14-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,1,6,2 and 9 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 121629-14:
(8*1)+(7*2)+(6*1)+(5*6)+(4*2)+(3*9)+(2*1)+(1*4)=99
99 % 10 = 9
So 121629-14-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H12F2O2/c1-12-7(11)6-2-4-8(9,10)5-3-6/h6H,2-5H2,1H3

121629-14-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl 4,4-difluorocyclohexanecarboxylate

1.2 Other means of identification

Product number -
Other names Benzene,(3,3-difluoropropyl)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:121629-14-9 SDS

121629-14-9Synthetic route

4,4-difluorocyclohexanecarboxylic acid
122665-97-8

4,4-difluorocyclohexanecarboxylic acid

methanol
67-56-1

methanol

methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

Conditions
ConditionsYield
With sulfuric acid at 0 - 70℃; for 16h;90.82%
sulfuric acid for 16h; Reflux;
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

dimethyl [2-(4,4-difluorocyclohexyl)-2-oxoethyl]phosphonate
1402838-40-7

dimethyl [2-(4,4-difluorocyclohexyl)-2-oxoethyl]phosphonate

Conditions
ConditionsYield
Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: methyl 4,4-difluorocyclohexane-1-carboxylate In tetrahydrofuran at -78 - 0℃; for 1.5h; Inert atmosphere;
82%
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(4,4-difluorocyclohexyl)methanol
178312-48-6

(4,4-difluorocyclohexyl)methanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;81%
Stage #1: methyl 4,4-difluorocyclohexane-1-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: With potassium hydroxide In tetrahydrofuran; diethyl ether; water at 0℃; for 1h; Inert atmosphere;
81%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 18h; Inert atmosphere;77%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;71.55%
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran; ethanol at 0 - 20℃;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

((4,4-difluorocyclohexylidene)(methoxy)methoxy)trimethylsilane

((4,4-difluorocyclohexylidene)(methoxy)methoxy)trimethylsilane

Conditions
ConditionsYield
Stage #1: methyl 4,4-difluorocyclohexane-1-carboxylate With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃; for 12h;
72%
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

methyl iodide
74-88-4

methyl iodide

methyl 4,4-difluoro-1-methylcyclohexanecarboxylate
1360568-90-6

methyl 4,4-difluoro-1-methylcyclohexanecarboxylate

Conditions
ConditionsYield
Stage #1: methyl 4,4-difluorocyclohexane-1-carboxylate With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 2h;
Stage #2: methyl iodide In tetrahydrofuran at 20℃;
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(2S,3R,4R,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-methylphenyl)6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
1360569-34-1

(2S,3R,4R,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-methylphenyl)6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: caesium carbonate / N,N-dimethyl-formamide / 12 h / 120 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
1360569-47-6

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere
5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere
5.2: 2 h / -78 °C
5.3: 12 h / 20 °C
6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere
7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(2S,3R4R5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
1360569-48-7

(2S,3R4R5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere
5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere
5.2: 2 h / -78 °C
5.3: 12 h / 20 °C
6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere
7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: ammonia / methanol / 20 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(4,4-difluoro-1-methylcyclohexyl)methanol
1360568-91-7

(4,4-difluoro-1-methylcyclohexyl)methanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(4,4-difluoro-1-methylcyclohexyl)methyl 4-methylbenzenesulfonate
1360568-92-8

(4,4-difluoro-1-methylcyclohexyl)methyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

4-bromo-1-chloro-2-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)benzene
1360569-03-4

4-bromo-1-chloro-2-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)benzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

4-bromo-2-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-1-fluorobenzene
1360569-12-5

4-bromo-2-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-1-fluorobenzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(3R,4S,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1360569-13-6

(3R,4S,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere
5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere
5.2: 2 h / -78 °C
5.3: 12 h / 20 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(3R,4R,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
1360569-14-7

(3R,4R,5S,6R)-2-(3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere
5.1: tert.-butyl lithium / tetrahydrofuran; toluene / 0.5 h / -78 - 20 °C / Inert atmosphere
5.2: 2 h / -78 °C
5.3: 12 h / 20 °C
6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
1360569-41-0

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -78 °C / Inert atmosphere
5.2: 2 h / -78 °C
5.3: 12 h / 20 °C
6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere
7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: ammonia / methanol / 20 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)tetratydro-2H-3,4,5-triyl triacetate
1360569-42-1

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)tetratydro-2H-3,4,5-triyl triacetate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -78 °C / Inert atmosphere
5.2: 2 h / -78 °C
5.3: 12 h / 20 °C
6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere
7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(3R,4S,5S,6R)-2-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
1360569-04-5

(3R,4S,5S,6R)-2-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -78 °C / Inert atmosphere
5.2: 2 h / -78 °C
5.3: 12 h / 20 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(3R,4R,5S,6R)-2-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
1360569-05-6

(3R,4R,5S,6R)-2-(4-chloro-3-(4-((4,4-difluoro-1-methylcyclohexyl)methoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / -78 °C
1.2: 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C
3.1: triethylamine / dmap / 20 °C
4.1: N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -78 °C / Inert atmosphere
5.2: 2 h / -78 °C
5.3: 12 h / 20 °C
6.1: triethylsilane; boron trifluoride diethyl etherate / diethyl ether; dichloromethane; acetonitrile / 6 h / 0 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(4,4-difluorocyclohexyl)methyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

(4,4-difluorocyclohexyl)methyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere
2: dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(4,4-difluorocyclohexyl)methyl 2-pyridyl carbonate

(4,4-difluorocyclohexyl)methyl 2-pyridyl carbonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere
2: dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(4,4-difluorocyclohexyl)methyl 2-oxopyridine-1-carboxylate

(4,4-difluorocyclohexyl)methyl 2-oxopyridine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere
2: dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

4,4-difluorocyclohexane carboxyaldehyde
265108-36-9

4,4-difluorocyclohexane carboxyaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
2.2: -78 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere
1.2: 1 h / 0 °C / Inert atmosphere
2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2: Dess-Martin periodane / dichloromethane / 2 h / 0 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

A

[(Z)-4-(4,4-difluorocyclohexyl)but-3-enoxy]methylbenzene

[(Z)-4-(4,4-difluorocyclohexyl)but-3-enoxy]methylbenzene

B

[(E)-4-(4,4-difluorocyclohexyl)but-3-enoxy]methylbenzene

[(E)-4-(4,4-difluorocyclohexyl)but-3-enoxy]methylbenzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere
2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
2.2: -78 - 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -30 °C / Inert atmosphere
3.2: 16.5 h / -30 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere
1.2: 1 h / 0 °C / Inert atmosphere
2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -30 °C / Inert atmosphere
3.2: 16 h / -30 - 20 °C / Inert atmosphere
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

methyl (R)-4,4-difluoro-1-(1-(4-methoxyphenyl)allyl)cyclohexane-1-carboxylate

methyl (R)-4,4-difluoro-1-(1-(4-methoxyphenyl)allyl)cyclohexane-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 2 h / -78 °C
1.2: 12 h / 20 °C
2.1: C55H54IrNO4P(1+)*BF4(1-); tetrabutylammonium benzoate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere; Sealed tube
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(4,4-difluorocyclohexyl)methyl methanesulfonate
194427-24-2

(4,4-difluorocyclohexyl)methyl methanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 °C / Inert atmosphere
2: triethylamine / dichloromethane / 4 h / 0 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

1-(4,4-difluorocyclohexylmethyl)-3,7-dimethyl-3,7-dihydropurine-2,6-dione

1-(4,4-difluorocyclohexylmethyl)-3,7-dimethyl-3,7-dihydropurine-2,6-dione

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 °C / Inert atmosphere
2: triethylamine / dichloromethane / 4 h / 0 °C
3: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 3 h / 120 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(3-bromo-2-thienyl)-(4,4-difluorocyclohexyl)methanol

(3-bromo-2-thienyl)-(4,4-difluorocyclohexyl)methanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C
3.1: n-butyllithium; diisopropylamine / diethyl ether / 1 h / -78 °C
3.2: 1 h / -78 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

1-[(3-bromothien-2-yl)(4,4-difluorocyclohexyl)methyl]-1H-imidazole

1-[(3-bromothien-2-yl)(4,4-difluorocyclohexyl)methyl]-1H-imidazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C
3.1: n-butyllithium; diisopropylamine / diethyl ether / 1 h / -78 °C
3.2: 1 h / -78 °C
4.1: acetonitrile / 16 h / 80 °C
View Scheme
methyl 4,4-difluorocyclohexane-1-carboxylate
121629-14-9

methyl 4,4-difluorocyclohexane-1-carboxylate

(1S)-1-(4,4-difluorocyclohexyl)but-3-en-1-ol

(1S)-1-(4,4-difluorocyclohexyl)but-3-en-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C
3.1: indium; (1S,2R)-2-Amino-1,2-diphenylethanol; pyridine / tetrahydrofuran / 3 h / 18 °C / Inert atmosphere
3.2: 2 h / -78 °C / Inert atmosphere
View Scheme

121629-14-9Downstream Products

121629-14-9Relevant academic research and scientific papers

TRICYCLIC COMPOUND SERVING AS IMMUNOMODULATOR

-

Paragraph 0298-0299, (2019/01/04)

Provided are compounds of formula I and formula II or pharmaceutically acceptable salts of the compounds and pharmaceutical compositions thereof. The compounds of formula I and formula II or the pharmaceutically acceptable salts of the compounds provide indole 2,3-dioxygenase (IDO) inhibitory activity and are capable of treating IDO-mediated immunosuppressive diseases, such as infectious diseases or cancer.

CYCLOALKYL METHOXYBENZYL PHENYL PYRAN DERIVATIVES AS SODIUM DEPENDENT GLUCOSE CO TRANSPORTER (SGLT2) INHIBITORS

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Page/Page column 44-45, (2012/03/26)

The invention relates to the cycloalkyl methoxybenzyl phenyl pyran derivatives as Sodium dependent glucose co transporter (SGLT) inhibitors, particularly SGLT2 and method of treating diseases, conditions and/or disorders inhibited by SGLT2 with them, and processes for preparing them.

Fluorinated carbocylic compounds

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, (2008/06/13)

Fluoro-substituted carbocyclic compounds are prepared by (A) reacting hydrogen fluoride with a chloro-cyclohexenyl compound of the formula STR1 where R1 and R2 are independently selected from the group consisting of --H, --CH2 OH, --COF, --COCl, --CF3, --CN, STR2 and --CH2 R, where R is --H or alkyl of 1-4 carbon atoms, to form a gem-dihalocyclohexane compound of the formula STR3 where X is chlorine and R1 and R2 are as defined above, (B) dehydrohalogenating the gem-dihalocyclohexane compound in the vapor phase to form a fluoro-cyclohexenyl compound of the formula STR4 (C) contacting the fluoro-cyclohexenyl compound, in the vapor phase, with a dehydrogenation catalyst to form a fluoro-substituted aromatic compound of the formula STR5

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