4,4-Difluorocyclohexanone supplier

Name
4,4-Difluorocyclohexanone
EINECS
CAS No. 22515-18-0
Article Data13
CAS DataBase
Density 1.144 g/cm³
Solubility Insoluble in water.
Melting Point 35-36 °C
Formula C₆H₈F₂O
Boiling Point 157.441 °C at 760 mmHg
Molecular Weight 134.126
Flash Point 55.64 °C
Transport Information
Appearance
Safety 26-37
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Cyclohexanone, 4,4-difluoro-;
PSA 17.07000
LogP 1.76480

Synthetic route

: 176251-49-3
8,8-difluoro-1,4-dioxaspiro[4,5]decane

: 22515-18-0
4,4-difluorocyclohexanone

Conditions

Conditions	Yield
With hydrogenchloride; water at 100℃; for 12h;	93%
With hydrogenchloride In acetone for 1h; Inert atmosphere;	80%
With hydrogenchloride In water at 100℃; for 3h;	71%

: 22515-16-8
4,4-difluoroheptanedioic acid diethyl ester

: 22515-18-0
4,4-difluorocyclohexanone

Conditions

Conditions	Yield
(i) NaOEt, EtOH, (ii) aq. KOH; Multistep reaction;

: 6317-49-3
4-oxopimelate

: 22515-18-0
4,4-difluorocyclohexanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: SF4 / CH2Cl2; H2O 2: (i) NaOEt, EtOH, (ii) aq. KOH View Scheme

: 539-47-9
3-(fur-2-yl)crotonic acid

: 22515-18-0
4,4-difluorocyclohexanone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl / Heating 2: SF4 / CH2Cl2; H2O 3: (i) NaOEt, EtOH, (ii) aq. KOH View Scheme

: 4746-97-8
cyclohexanedione monoethylene ketal

: 22515-18-0
4,4-difluorocyclohexanone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: difluoro-4-morpholinylsulfonium tetrafluoroborate; triethylamine tris(hydrogen fluoride) / dichloromethane / 24 h / 20 °C / Inert atmosphere 2: hydrogenchloride / acetone / 1 h / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: morpholinosulfur trifluoride / dichloromethane / 72 h / 0 - 20 °C / Inert atmosphere 1.2: 24 h 2.1: hydrogenchloride / water / 3 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: (bis-(2-methoxyethyl)amino)sulfur trufluoride; ethanol / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: toluene-4-sulfonic acid / water; acetone / 24 h / Reflux View Scheme
Stage #1: cyclohexanedione monoethylene ketal With ethanol; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In water; acetone for 24h; Reflux;
Multi-step reaction with 2 steps 1.1: diethylamino-sulfur trifluoride / dichloromethane / 4 h / 0 - 35 °C 1.2: 20 °C 2.1: water; hydrogenchloride / 12 h / 100 °C View Scheme

: 7677-24-9
trimethylsilyl cyanide

: 22515-18-0
4,4-difluorocyclohexanone

: 1394347-52-4
4,4-difluoro-1-[(trimethylsilyl)oxy]cyclohexane carbonitrile

Conditions

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃;	100%
With zinc(II) iodide In dichloromethane at 0 - 20℃; for 1h;
With zinc(II) iodide In dichloromethane at 0 - 20℃; for 1h;	1.5 g

: 22515-18-0
4,4-difluorocyclohexanone

: 21204-67-1
methyl (triphenylphosphoranylidene)acetate

: 1189770-25-9
methyl 2-(4,4-difluorocyclohexylidene)acetate

Conditions

Conditions	Yield
In tetrahydrofuran at 65℃; for 20h; Schlenk technique; Inert atmosphere;	100%

: 22515-18-0
4,4-difluorocyclohexanone

: 22419-35-8
4,4-difluorocyclohexanol

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 25℃; for 2h;	99%
With methanol; sodium tetrahydroborate at 20℃; for 1h;	94%
With methanol; sodium tetrahydroborate for 1h; Inert atmosphere; Cooling with ice;	91%

: 22515-18-0
4,4-difluorocyclohexanone

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1283719-20-9
ethyl 2-(4,4-difluorocyclohexylidene)-acetate

Conditions

Conditions	Yield
In toluene at 100℃; for 16h;	99%
In tetrahydrofuran at 65℃; Inert atmosphere;	97%

: 870-46-2
t-butoxycarbonylhydrazine

: 22515-18-0
4,4-difluorocyclohexanone

: 1214910-72-1
N'-(4,4-difluorocyclohexyl)hydrazinecarboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With hydrogen; acetic acid; platinum(IV) oxide In isopropyl alcohol at 20℃; under 2585.81 Torr; for 12h;	98%
With hydrogen; acetic anhydride; platinum(IV) oxide In isopropyl alcohol at 20℃; under 2585.81 Torr; for 12h;	98%
With hydrogen; platinum(IV) oxide; acetic acid In isopropyl alcohol at 20℃; under 2585.81 Torr; for 12h;	98%

: 2759-28-6
1-phenylmethylpiperazine

: 7677-24-9
trimethylsilyl cyanide

: 22515-18-0
4,4-difluorocyclohexanone

: 1-(4-benzylpiperazin-1-yl)-4,4-difluorocyclohexanecarbonitrile

Conditions

Conditions	Yield
Stage #1: 1-phenylmethylpiperazine; 4,4-difluorocyclohexanone With zinc(II) iodide In methanol; toluene at 25℃; for 1h; Inert atmosphere; Stage #2: trimethylsilyl cyanide In methanol; toluene for 16h; Inert atmosphere; Heating;	97%

...Expand

: 5927-18-4
trimethyl phosphonoacetate

: 22515-18-0
4,4-difluorocyclohexanone

: 1189770-25-9
methyl 2-(4,4-difluorocyclohexylidene)acetate

Conditions

Conditions	Yield
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran; mineral oil at 4℃; for 1h; Stage #2: 4,4-difluorocyclohexanone In tetrahydrofuran; mineral oil at 0 - 20℃;	95%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 0 - 5℃; for 1h; Stage #2: 4,4-difluorocyclohexanone In tetrahydrofuran at 0 - 27℃; for 15h;	57%
Stage #1: trimethyl phosphonoacetate With sodium hydride In tetrahydrofuran at 5℃; for 1h; Stage #2: 4,4-difluorocyclohexanone In tetrahydrofuran at 5 - 20℃; Stage #3: With water In tetrahydrofuran

: 22515-18-0
4,4-difluorocyclohexanone

: 59-88-1
phenylhydrazine hydrochloride

: 1423039-61-5
3,3-difluoro-2,3,4,9-tetrahydro-1H-carbazole

Conditions

Conditions	Yield
With acetic acid at 140℃; Inert atmosphere;	95%
With silica gel at 20℃; for 3h; Fischer Indole Synthesis; Milling;	46%

: 22515-18-0
4,4-difluorocyclohexanone

: 1826-67-1
vinyl magnesium bromide

: 4,4-difluoro-1-vinylcyclohexan-1-ol

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h; Grignard Reaction; Inert atmosphere;	94%

: 22515-18-0
4,4-difluorocyclohexanone

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: (E)-2-((dimethylamino)methylene)-4,4-difluorocyclohexanone

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 18h;	92%

: 22515-18-0
4,4-difluorocyclohexanone

: 100945-15-1
N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

: methyl 2-(((benzyloxy)carbonyl)amino)-2-(4,4-difluorocyclohexylidene)acetate

Conditions

Conditions	Yield
Stage #1: N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 15℃; for 0.5h; Wittig-Horner Reaction; Large scale; Stage #2: 4,4-difluorocyclohexanone In 1-methyl-pyrrolidin-2-one at 10 - 20℃; for 12h; Large scale;	90%
Stage #1: N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 10 - 35℃; for 0.5h; Stage #2: 4,4-difluorocyclohexanone In acetonitrile at 10 - 35℃;	84%

: 22515-18-0
4,4-difluorocyclohexanone

: 1242990-43-7
ethyl 2-((tert-butyldimethylsilyl)oxy)-2-(diethoxyphosphoryl)acetate

: 1242990-75-5
C16H28F2O3Si

Conditions

Conditions	Yield
Stage #1: ethyl 2-((tert-butyldimethylsilyl)oxy)-2-(diethoxyphosphoryl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 4,4-difluorocyclohexanone In tetrahydrofuran at -78 - 20℃;	88%

: 773837-37-9
sodium cyanide

: 22515-18-0
4,4-difluorocyclohexanone

: 1393823-97-6
8,8-difluoro-1,3-diazaspiro[4.5]decane-2,4-dione

Conditions

Conditions	Yield
With ammonium carbonate In water at 0 - 60℃; for 26h;	88%

: 22515-18-0
4,4-difluorocyclohexanone

: 17150-62-8
N-benzyl-3-butenylamine

: 1-benzyl-8,8-difluoro-4-methyl-1-azaspiro[4.5]decane

Conditions

Conditions	Yield
With Ir(dMeppy)3; cyclohexa-1,4-diene; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; propionic acid In dichloromethane at 20℃; for 48h; Molecular sieve; Sealed tube; Inert atmosphere; Irradiation;	87%

: 22515-18-0
4,4-difluorocyclohexanone

: 535-11-5, 41978-69-2
Ethyl 2-bromopropionate

: ethyl 2-(4,4-difluoro-1-hydroxycyclohexyl)propanoate

Conditions

Conditions	Yield
With zinc In 1,4-dioxane at 100℃; for 24h;	85%

: 22515-18-0
4,4-difluorocyclohexanone

: tert-butyl (R)-3-(((4-(aminomethyl)benzyl)((S)-5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

: tert-butyl (R)-3-(((4-(((4,4-difluorocyclohexyl)amino)methyl)benzyl)((S)-5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Conditions

Conditions	Yield
Stage #1: 4,4-difluorocyclohexanone; tert-butyl (R)-3-(((4-(aminomethyl)benzyl)((S)-5,6,7,8-tetrahydroquinolin-8-yl)amino)methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate With acetic acid In dichloromethane at 20℃; for 2.5h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; Inert atmosphere;	84%

: 22515-18-0
4,4-difluorocyclohexanone

: 372-09-8
cyanoacetic acid

: C8H9F2N

Conditions

Conditions	Yield
With ammonium acetate In toluene at 160℃; for 3h;	84%

: 22515-18-0
4,4-difluorocyclohexanone

: 27784-76-5
tert-butyl diethylphosphonoacetate

: 1584139-35-4
tert-butyl 2-(4,4-difluorocyclohexylidene)acetate

Conditions

Conditions	Yield
Stage #1: tert-butyl diethylphosphonoacetate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: 4,4-difluorocyclohexanone In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	83%

: 22515-18-0
4,4-difluorocyclohexanone

: 616-38-6
carbonic acid dimethyl ester

: methyl 5,5-difluoro-2-oxocyclohexane-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 4,4-difluorocyclohexanone With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: carbonic acid dimethyl ester In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 16h;	83%

: 22515-18-0
4,4-difluorocyclohexanone

: 2622-05-1
allylmagnesium bromide

: 1-allyl-4,4-difluorocyclohexanol

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	82%
In tetrahydrofuran at -74 - -60℃; for 2.66667h;	46%

: 22515-18-0
4,4-difluorocyclohexanone

: 2181-42-2
trimethylsulphonium iodide

: 6,6-difluoro-1-oxaspiro[2.5]octane

Conditions

Conditions	Yield
Stage #1: trimethylsulphonium iodide With potassium tert-butylate In tetrahydrofuran at 15℃; for 0.5h; Inert atmosphere; Stage #2: 4,4-difluorocyclohexanone In tetrahydrofuran at 15℃; for 16h;	82%

: 22515-18-0
4,4-difluorocyclohexanone

: 1030268-21-3
trimethylsulfonium iodide

: 6,6-difluoro-1-oxaspiro[2.5]octane

Conditions

Conditions	Yield
Stage #1: trimethylsulfonium iodide With potassium tert-butylate In tetrahydrofuran at 15℃; for 0.5h; Inert atmosphere; Stage #2: 4,4-difluorocyclohexanone In tetrahydrofuran at 15℃; for 16h; Inert atmosphere;	82%

: 5815-08-7
tert-Butoxybis(dimethylamino)methane

: 22515-18-0
4,4-difluorocyclohexanone

: (E)-2-((dimethylamino)methylene)-4,4-difluorocyclohexanone

Conditions

Conditions	Yield
at 50℃; for 18h;	82%

: 22515-18-0
4,4-difluorocyclohexanone

: C28H38N4O2

: C34H46F2N4O2

Conditions

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 12h;	81%

: 22515-18-0
4,4-difluorocyclohexanone

: 5-bromo-3-chloro-6-oxo-1,6-dihydropyridine-2-carboxamide

: 6-bromo-8-chloro-4',4'-difluoro-spiro[2himidazo[1,5-a]pyridine-3,1'-cyclohexane]-1,5-dione

Conditions

Conditions	Yield
With sulfuric acid In 1,4-dioxane at 100℃; for 8h;	80%

: 2-(pyrrolidin-3-yl)-1H-benzo[d]imidazole-4-carboxamide

: 22515-18-0
4,4-difluorocyclohexanone

: 2-(1-(4,4-difluorocyclohexyl)pyrrolidin-3-yl)-1H-benzo[d]imidazole-4-carboxamide

Conditions

Conditions	Yield
With sodium cyanoborohydride In methanol at 20℃;	78.4%

: 22515-18-0
4,4-difluorocyclohexanone

: 73874-95-0
(piperidin-4-yl)carbamic acid tert-butyl ester

: 1262417-90-2
tert-butyl (1-(4,4-difluorocyclohexyl)piperidin-4-yl)carbamate

Conditions

Conditions	Yield
With acetic acid; tetramethylammonium triacetoxyborohydride In N,N-dimethyl-formamide	78%
Stage #1: 4,4-difluorocyclohexanone; (piperidin-4-yl)carbamic acid tert-butyl ester With acetic acid In tetrahydrofuran at 50℃; for 2h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 50℃; for 18h;

: 22515-18-0
4,4-difluorocyclohexanone

: 1197-55-3
4-aminophenylacetic acid

: 513-86-0, 52217-02-4
3-hydroxy-2-butanon

: 2-(4-(5,5-difluoro-2,3-dimethyl-4,5,6,7-tetrahydro-1H-indol-1-yl)phenyl)acetic acid

Conditions

Conditions	Yield
With acetic acid In ethanol at 100℃; for 4h; Inert atmosphere; Sealed tube; Microwave irradiation;	78%

...Expand

: 120-72-9
indole

: 22515-18-0
4,4-difluorocyclohexanone

: 1-(4,4-difluorocyclohexyl)indole

Conditions

Conditions	Yield
With formic acid; 10 mol% Pd(OH)2/C In water at 100℃; for 24h; Inert atmosphere;	78%
With formic acid; 10% palladium hydroxide on charcoal In water at 100℃; for 24h; Inert atmosphere;	78%

4,4-Difluorocyclohexanone Specification

The 4,4-Difluorocyclohexanone with the cas number 22515-18-0, is also called Cyclohexanone, 4,4-difluoro- .The properties of the 4,4-Difluorocyclohexanone are: (1)#H bond acceptors: 1 ; (2)#H bond donors: 0 ; (3)#Freely Rotating Bonds: 0 ; (4)Polar Surface Area: 17.07Å² ; (5)Index of Refraction: 1.396 ; (6)Molar Refractivity: 28.141 cm³ ; (7)Molar Volume: 117.211 cm³ ; (8)Polarizability: 11.156×10^-24cm³ ; (9)Surface Tension: 24.37 dyne/cm ; (10)Enthalpy of Vaporization: 39.412 kJ/mol ; (11)Vapour Pressure: 2.754 mmHg at 25°C.

This product can be supplied by the following suppliers:(1)Shanghai Sinofluoro Scientific Co., Ltd. ; (2)3B Pharmachem International (Wuhan) Co.,Ltd. ; (3)Alfa Aesar ; (4)Energy Chemical; (5)Beijing ALFCHEM Science Co.,Ltd. ; (6)Matrix Scientific; (7)ALFA AESAR, AVOCADO, LANCASTER ; (8)Manchester Organics.

You can still convert the following datas into molecular structure :
1.O=C1CCC(F)(F)CC1
2.InChI=1/C6H8F2O/c7-6(8)3-1-5(9)2-4-6/h1-4H2

Product Name

4,4-Difluorocyclohexanone

Synthetic route

4,4-Difluorocyclohexanone Specification

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