(p-fluorophenyl)trimethylsilane
A
trimethylsilyl fluoride
B
para-difluorobenzene
Conditions | Yield |
---|---|
With xenon fluoride In dichloromethane Inert atmosphere; | A n/a B 100% |
C6H4FN2(1+)*C6BF8(1-)
A
sodium tetrafluoroborate
B
para-difluorobenzene
Conditions | Yield |
---|---|
at 160 - 170℃; Glovebox; | A 5% B 95% C 83% D 10% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.166667h; Inert atmosphere; Microwave irradiation; | 93% |
Conditions | Yield |
---|---|
at 90 - 95℃; | A 90% B 4% C 3% D 5% |
Conditions | Yield |
---|---|
at 158 - 160℃; | 86% |
Conditions | Yield |
---|---|
Stage #1: 4-fluoroboronic acid With sodium hydroxide In methanol at 23℃; for 0.25h; Inert atmosphere; Stage #2: With silver trifluoromethanesulfonate In methanol at 0℃; for 0.5h; Inert atmosphere; Stage #3: With Selectfluor In acetone at 23℃; for 1h; Inert atmosphere; Molecular sieve; regiospecific reaction; | 85% |
Multi-step reaction with 2 steps 1: diethyl ether / 20 °C / Inert atmosphere; Molecular sieve 2: silver fluoride; (tBuCN)2Cu*OTf; 1-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate / tetrahydrofuran / 18 h / 50 °C / Inert atmosphere View Scheme | |
With potassium fluoride; copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 60℃; for 20h; Sealed tube; | |
Multi-step reaction with 2 steps 1: potassium fluoride / acetonitrile / 16 h / 90 °C 2: 2,6-dichloro-1-fluoropyridin-1-ium tetrafluoroborate / chloroform / 6 h / 110 °C View Scheme |
C6H4FN2(1+)*C6BF16(1-)
A
perfluorohexyldifluoroborane
B
para-difluorobenzene
Conditions | Yield |
---|---|
at 110 - 115℃; | A 85% B 67% |
Conditions | Yield |
---|---|
at 140 - 145℃; | A 79% B 85% |
Conditions | Yield |
---|---|
With hydrogenchloride; tetrafluoroboric acid; sodium nitrite In water at 50℃; for 0.0166667h; Temperature; Large scale; | 83% |
With pyridine hydrogenfluoride; sodium nitrite 1.) O deg C, 20 min, 2.) 120 deg C, 1 h; | 65% |
With pyridine; hydrogen fluoride; sodium nitrite 1.) room temperature, 2.) 0 deg C, 3.) 120 deg C; Yield given. Multistep reaction; |
C6H4FN2(1+)*C12BF28(1-)
A
sodium tetrafluoroborate
B
para-difluorobenzene
C
C12BF28(1-)*Na(1+)
D
C12BF28(1-)*Na(1+)
Conditions | Yield |
---|---|
at 25 - 200℃; for 0.133333h; Glovebox; | A 17% B 81% C 39% D 33% |
A
para-difluorobenzene
B
perfluoro-trans-hex-1-enyldifluoroborane
Conditions | Yield |
---|---|
at 80 - 90℃; | A 80% B 49% |
C6H4FN2(1+)*C6BF8(1-)
A
sodium tetrafluoroborate
B
para-difluorobenzene
C
C6BF8(1-)*Na(1+)
Conditions | Yield |
---|---|
at 160 - 170℃; Glovebox; | A 11% B 79% C 71% |
Conditions | Yield |
---|---|
With 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; cesium fluoride; diphenylzinc In toluene at 110℃; for 20h; Product distribution / selectivity; Sealed vial; | 78% |
With 1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1h-imidazole; cesium fluoride In toluene at 23 - 110℃; for 20.5h; Inert atmosphere; | 74 %Spectr. |
Conditions | Yield |
---|---|
at 160 - 170℃; Glovebox; | A 17% B 77% C 3% D 65% E 12% |
C6H4FN2(1+)*C3BF6(1-)
A
sodium tetrafluoroborate
B
para-difluorobenzene
C
C3BF6(1-)*Na(1+)
Conditions | Yield |
---|---|
at 160 - 170℃; Glovebox; | A 76% B 51% C 9% D 76% |
Conditions | Yield |
---|---|
With xenon difluoride In dichloromethane at 20℃; for 1h; Pyrex vessel; | 73% |
With lead(IV) acetate; boron trifluoride diethyl etherate Ambient temperature; | 43 % Chromat. |
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate; silver trifluoromethanesulfonate; Selectfluor In ethyl acetate at 55℃; Sealed tube; | A n/a B 65% |
Conditions | Yield |
---|---|
With sodium nitrite In Et3N-3HF | 63.1% |
With HF; sodium nitrite In tetrahydrofuran; ice-salt water | 40% |
Pentafluorobenzene
A
para-difluorobenzene
B
1,2,4,5-Tetrafluorobenzene
C
1,2,4-trifluorobenzene
Conditions | Yield |
---|---|
With C32H46N2Ru; sodium carbonate; isopropyl alcohol at 70℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; | A 7% B 60% C 21% |
C6H4FN2(1+)*C6BF8(1-)
A
para-difluorobenzene
B
Pentafluorobenzene
C
decafluorobiphenyl
Conditions | Yield |
---|---|
at 95 - 100℃; | A 54% B 24% C 16% |
trifluoroborane diethyl ether
A
fluorobenzene
C
para-difluorobenzene
D
lead acetate
Conditions | Yield |
---|---|
Stirring of Pb-compd. in excess of BF3*Et2O overnight at room temp.; GC anal.; | A 7% B n/a C 49% D n/a |
4-fluorophenyl trifluoromethanesulfonate
para-difluorobenzene
Conditions | Yield |
---|---|
With 18-crown-6 ether; tetramethlyammonium chloride; cesium fluoride In acetonitrile at 60℃; for 16h; Glovebox; | 49% |
benzene
A
fluorobenzene
B
para-difluorobenzene
C
ortho-difluorobenzene
D
3,3,6-trifluoro-1,4-cyclohexadiene
E
cis-3,6-difluorocyclohexadiene
F
trans,cis,trans-3,4,5,6-tetrafluorocyclohexene
Conditions | Yield |
---|---|
With silver(II) fluoride In hexane at 40℃; for 0.2h; Product distribution; Mechanism; other solvents, times, temperatures, ratios; | A 47% B 2.3% C 1.9% D 6.3% E 4.1% F 7.4% |
1,2,4,5-Tetrafluorobenzene
A
para-difluorobenzene
B
1,2,4-trifluorobenzene
Conditions | Yield |
---|---|
Stage #1: 1,2,4,5-Tetrafluorobenzene With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [(HC[(CMe)N(2,4,6-Me3C6H2)]2)Al(H)2] In benzene-d6; benzene at 100℃; for 8h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: With methanol In benzene-d6; benzene at 100℃; for 2h; Catalytic behavior; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction; | A 19.5% B 47% |
(p-fluorophenyl)trimethylsilane
lead(IV) tetraacetate
trifluoroborane diethyl ether
A
fluorobenzene
B
para-difluorobenzene
Conditions | Yield |
---|---|
Stirring of silane with a slurry of Pb(OAc)4 in excess of BF3*Et2O overnight at room temp.; GC anal.; | A 0% B 43% |
Conditions | Yield |
---|---|
With Al2CuF8 at 500℃; Gas phase; Inert atmosphere; | A 42% B 11% |
Conditions | Yield |
---|---|
With Al2CuF8 at 500℃; Inert atmosphere; | A 11% B 42% |
1-chloro-2-fluorobenzene
A
fluorobenzene
B
1,3-Difluorobenzene
C
para-difluorobenzene
D
ortho-difluorobenzene
Conditions | Yield |
---|---|
With Al2CuF8 at 500℃; Gas phase; Inert atmosphere; | A 39% B 21% C 7% D 16% |
With Al2CuF8 at 500℃; Inert atmosphere; | A 39% B 21% C 7% D 16% |
1,2,3,5-tetrafluorobenzene
A
1,2,3-trifluorobenzene
B
1,3-Difluorobenzene
C
para-difluorobenzene
D
ortho-difluorobenzene
E
1,2,4-trifluorobenzene
Conditions | Yield |
---|---|
Stage #1: 1,2,3,5-tetrafluorobenzene With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; [(HC[(CMe)N(2,4,6-Me3C6H2)]2)Al(H)2] In benzene-d6; benzene at 100℃; for 8h; Inert atmosphere; Glovebox; Sealed tube; Stage #2: With methanol In benzene-d6; benzene at 100℃; for 2h; Catalytic behavior; Inert atmosphere; Glovebox; Sealed tube; Overall yield = 69.5 %; regioselective reaction; | A 8.5% B 9.5% C 7% D 5.5% E 39% |
para-difluorobenzene
5-methyl-dihydro-furan-2-one
5,8-difluoro-4-methyl-3,4-dihydronaphthalen-1(2H)-one
Conditions | Yield |
---|---|
Stage #1: para-difluorobenzene; 5-methyl-dihydro-furan-2-one With aluminum (III) chloride Heating / reflux; Stage #2: With hydrogenchloride In water at 0℃; | 100% |
With aluminum (III) chloride for 16h; Heating / reflux; | 81% |
With aluminium trichloride for 16h; Heating; | 55% |
para-difluorobenzene
1,1,4,4-tetrakis(trimethylsilyl)butane-1,4-diylsilylene
Conditions | Yield |
---|---|
Irradiation; | 100% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 30 - 70℃; for 0.0333333h; Large scale; | 98% |
With 2C2H3F3O*BF3; potassium nitrate at 20℃; for 6h; | 84% |
With sulfuric acid; potassium nitrate at 5℃; Large scale; | 83% |
Conditions | Yield |
---|---|
With rubidium carbonate; 2,2-dimetyl-3-(adamantan-1-yl)propanoic acid; palladium dichloride In N,N-dimethyl acetamide at 60℃; for 40h; Inert atmosphere; Schlenk technique; | 98% |
para-difluorobenzene
para-methylphenylmagnesium bromide
1,4-bis(p-tolyl)benzene
Conditions | Yield |
---|---|
With C35H31BrN4NiP In tetrahydrofuran at 25℃; for 13h; Schlenk technique; Inert atmosphere; | 97% |
With C26H24ClN2NiP*0.1C7H8 In toluene at 25℃; for 24h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere; | 74% |
para-difluorobenzene
4-methoxyphenyl magnesium bromide
4,4-dimethoxy-1,1':4',1-terphenyl
Conditions | Yield |
---|---|
With C35H31BrN4NiP In tetrahydrofuran at 25℃; for 12h; Schlenk technique; Inert atmosphere; | 97% |
para-difluorobenzene
4-dimethylaminophenylmagnesium bromide
4-[4-(4-dimethylaminophenyl)phenyl]-N,N-dimethylaniline
Conditions | Yield |
---|---|
With C35H31BrN4NiP In tetrahydrofuran at 25℃; for 12h; Schlenk technique; Inert atmosphere; | 97% |
ortho-tolylmagnesium bromide
para-difluorobenzene
2,2”-dimethyl-1,1‘:4’,1“-terphenyl
Conditions | Yield |
---|---|
With C35H31BrN4NiP In tetrahydrofuran at 70℃; for 22h; Schlenk technique; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
Stage #1: para-difluorobenzene With sec.-butyllithium; copper(l) cyanide In hexane; cyclohexane at -78℃; for 3h; Schlenk technique; Inert atmosphere; Stage #2: carbon disulfide In hexane; cyclohexane at -50 - 20℃; for 1h; Schlenk technique; Inert atmosphere; Stage #3: benzyl bromide In hexane; cyclohexane at 20℃; for 4h; Schlenk technique; Inert atmosphere; | 97% |
para-difluorobenzene
4-<(2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl>morpholine
(2S)-1-(2,5-difluoro-phenyl)-2-(tetrahydro-pyran-2-yloxy)-propan-1-one
Conditions | Yield |
---|---|
Stage #1: para-difluorobenzene; 4-<(2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl>morpholine With lithium diisopropyl amide In tetrahydrofuran; n-heptane at 0℃; for 2.333h; Stage #2: With ammonium chloride In tetrahydrofuran; n-heptane; water | 96.2% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; boron trifluoride at 20℃; for 6h; | 96% |
With N-Bromosuccinimide; sulfuric acid at 30 - 40℃; for 1h; Large scale; | 92.7% |
Conditions | Yield |
---|---|
With sodium acetylacetonate; C107H126N2NiO2; sodium hydride In neat (no solvent) at 120℃; for 24h; Reagent/catalyst; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
With rubidium carbonate; 2,2-dimetyl-3-(adamantan-1-yl)propanoic acid; palladium dichloride In N,N-dimethyl acetamide at 60℃; for 40h; Inert atmosphere; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
With trimethoxybenzene In benzene-d6 at 60℃; for 2h; | 95% |
Conditions | Yield |
---|---|
With silver(I) acetate; palladium diacetate In dimethyl sulfoxide at 130℃; for 4h; Sealed tube; regioselective reaction; | 95% |
Conditions | Yield |
---|---|
With rubidium carbonate; 2,2-dimetyl-3-(adamantan-1-yl)propanoic acid; palladium dichloride In N,N-dimethyl acetamide at 60℃; for 40h; Inert atmosphere; Schlenk technique; | 95% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 60℃; for 0.416667h; | A 6% B 94% |
para-difluorobenzene
benzaldehyde
4-fluorobenzhydrol
Conditions | Yield |
---|---|
With calcium In tetrahydrofuran at -78℃; for 0.5h; | 93% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid Ambient temperature; | 92% |
Conditions | Yield |
---|---|
Stage #1: para-difluorobenzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -71 - -68℃; for 1.5h; Stage #2: benzaldehyde In tetrahydrofuran; hexane at -71 - -68℃; for 1h; | 92% |
Conditions | Yield |
---|---|
With 1-[2-(diphenylphosphino)phenyl]ethanol; bis(acetylacetonate)nickel(II) In diethyl ether at 20℃; for 1h; | 92% |
Conditions | Yield |
---|---|
Stage #1: para-difluorobenzene; phenylmagnesium bromide; 1-[2-(diphenylphosphino)phenyl]ethanol; bis(acetylacetonate)nickel(II) In diethyl ether for 1h; Stage #2: With methanol In diethyl ether Product distribution / selectivity; | 92% |
With nickel(II) chloride hexahydrate; C32H39N2OP In tetrahydrofuran at 25℃; for 20h; Kumada coupling reaction; Inert atmosphere; | 92% |
Stage #1: para-difluorobenzene; phenylmagnesium bromide; bis(acetylacetonate)nickel(II); ((2-hydroxymethyl)phenyl)diphenylphosphine In diethyl ether for 2h; Stage #2: With methanol In diethyl ether Product distribution / selectivity; | 92 %Chromat. |
para-difluorobenzene
N-Methyl-N-methoxy-4-chlorobutanamide
4‐chloro‐1‐(2,5-difluorophenyl)butan-1-one
Conditions | Yield |
---|---|
Stage #1: para-difluorobenzene With n-butyllithium In tetrahydrofuran at -70 - -60℃; for 3h; Stage #2: N-Methyl-N-methoxy-4-chlorobutanamide In tetrahydrofuran at -70 - 20℃; for 2h; | 91.33% |
para-difluorobenzene
A
[(tris(3,5-dimethylpyrazolyl)borate)RhH(κ2-C6H4-2-PMe2)]
B
[Rh(tris(3,5-dimethylpyrazolyl)borate)H(2,5-C6F2H3)(PMe2Ph)]
Conditions | Yield |
---|---|
In neat (no solvent) Irradiation (UV/VIS); (N2, Schlenk) a soln. of complex in fluorobenzene-compound in NMR tube was irradiated for 5 h, heated at 120°C for 1 h; flash chromy. (silica gel, 5:1 hexane-THF), washed with a min amount of ice-cold hexane; elem. anal.; | A n/a B 91% |
Conditions | Yield |
---|---|
Stage #1: para-difluorobenzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -70℃; Stage #2: 3-pyridinecarboxaldehyde In tetrahydrofuran at -70℃; for 1h; | 90% |
Conditions | Yield |
---|---|
Stage #1: para-difluorobenzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -70℃; Stage #2: cyclohexanedione monoethylene ketal In tetrahydrofuran at -70℃; for 1h; | 90% |
IUPAC Name: 1,4-Difluorobenzene
Synonyms of 1,4-Difluorobenzene (CAS NO.540-36-3): p-Difluorobenzene ; para-Difluorobenzene ; Benzene, 1,4-difluoro- ; Benzene, 1,4-difluoro- (9CI) ; Benzene, p-difluoro-
CAS NO: 540-36-3
Molecular Formula: C6H4F2
Molecular Weight : 114.0928
Molecular Structure:
EINECS: 208-742-9
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: Å2
Index of Refraction: 1.448
Molar Refractivity: 26.24 cm3
Molar Volume: 97.8 cm3
Melting Point: -13 °C
Surface Tension: 26.2 dyne/cm
Density: 1.165 g/cm3
Flash Point: 2.1 °C
Enthalpy of Vaporization: 31.77 kJ/mol
Boiling Point: 90.4 °C at 760 mmHg
Vapour Pressure: 63.6 mmHg at 25°C
Storage temp: Flammables area
Appearance: 1,4-Difluorobenzene (CAS NO.540-36-3) is clear colorless to light yellow liquid .
Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Fluorobenzene;Aryl;C6;Halogenated Hydrocarbons;Method 8020;600 Series Wastewater Methods;8000 Series Solidwaste Methods;FluoroEPA;Method 624EPA;Alpha Sort;D;DAlphabetic;DID - DINChemical Class;Fluoro;Halogenated;Volatiles/ Semivolatiles
1,4-Difluorobenzene (CAS NO.540-36-3) is used as intermediates of medicine, pesticide and liquid crystal .
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 55gm/m3/2H (55000mg/m3) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS | Izvestiya Sibirskogo Otdeleniya Akademii Nauk SSSR, Seriya Biologomeditsinskikh Nauk. Vol. 3, Pg. 91, 1965. |
Hazard Codes:F,Xn,T
Risk Statements: 11-20-39/23/24/25
R11: Highly flammable.
R20: Harmful by inhalation.
R39/23/24/25: Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed
Safety Statements: 16-29-33-45-36/37-7/9
S7/9: Keep container tightly closed and in a well-ventilated place
S16: Keep away from sources of ignition.
S33:Take precautionary measures against static discharges.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37: Wear suitable protective clothing and gloves.
RIDADR: UN 1993 3/PG 2
WGK Germany: 3
RTECS: CZ5658000
Hazard Note: Highly Flammable
HazardClass: 3
PackingGroup: II
HS Code: 29036990
Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Will burn if involved in a fire. Flammable liquid and vapor.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage: Keep away from sources of ignition. Store in a cool, dry place. Keep container closed when not in use. Flammables-area.
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