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Basic Information
CAS No.: 462-06-6
Name: Fluorobenzene
Article Data: 381
Molecular Structure:
Molecular Structure of 462-06-6 (Fluorobenzene)
Formula: C6H5F
Molecular Weight: 96.1041
Synonyms: Monofluorobenzene;NSC 68416;Phenyl fluoride;Fluorbenzene;
EINECS: 207-321-7
Density: 1.026 g/cm3
Melting Point: -42 °C
Boiling Point: 84.7 °C at 760 mmHg
Flash Point: -15 °C
Solubility: insoluble in water
Appearance: Colorless liquid
Hazard Symbols: IrritantXi, FlammableF, ToxicT
Risk Codes: 36/37/38-11-39/23/24/25-23/24/25-52/53-36
Safety: 16-26-36-7-33-29-45-36/37-61-7/9
Transport Information: UN 2387 3/PG 2
PSA: 0.00000
LogP: 1.82570
Synthetic route
99506-39-5

4-fluorophenyl(m-carboran-9-yl)iodonium tetrafluoroborate

7647-14-5

sodium chloride

A

462-06-6

fluorobenzene

B

17157-02-7

9-iodo-m-carborane

C

17819-85-1

9-chloro-m-carborane

D

352-34-1

4-fluoro-1-iodobenzene

Conditions
ConditionsYield
In chloroform; water mixt. of aryl(m-carboran-9-yl)iodonium tetrafluoroborate, NaCl, water and chloroform was vigorously stirred under reflux at 56°C, 2-2.5 h; internal standard (chlorobenzene) added and org. layer was analysed by GLC;A 0%
B 0%
C 100%
D 100%
3038-48-0

2-(trifluoromethyl)phenylacetic acid

214360-58-4

2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A

462-06-6

fluorobenzene

B

C15H10F4O2

Conditions
ConditionsYield
With t-Boc-L-valine; 2,5-di-tert-butyl-p-benzoquinone; oxygen; potassium hydrogencarbonate In tert-Amyl alcohol at 90℃; under 2280.15 Torr; for 24h; Catalytic behavior;A n/a
B 99%
62-53-3

aniline

462-06-6

fluorobenzene

Conditions
ConditionsYield
Stage #1: aniline With hydrogen fluoride at -10 - 0.5℃; Flow reactor; Large scale;
Stage #2: With nitrosylsulfuric acid at 0 - 10℃; Temperature; Flow reactor; Large scale;
98.9%
With pyridine; hydrogen fluoride; sodium nitrite Product distribution; changed molar ratio HF/Pyr, changed time and temperature, only HF; multistep reaction; 1.) 20 deg C, 30 min., 2.) 55 deg C, 1 h;95%
Stage #1: aniline With hydrogenchloride; fluoroboric acid; sodium nitrite In water at 25℃; for 0.00416667h; Balz-Schiemann Reaction;
Stage #2: at 125℃; for 0.0166667h; Balz-Schiemann Reaction;
92%
446-46-8

2-fluorobenzenediazonium tetrafluoroborate

A

462-06-6

fluorobenzene

B

367-11-3

ortho-difluorobenzene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; hydrogen fluoride at 12℃; for 1h; Decomposition; Fluoro-dediazoniation; Irradiation;A 0.2%
B 98.9%
With boron trifluoride diethyl etherate at 12℃; for 3h; Decomposition; Fluoro-dediazoniation; Irradiation;A 10.7%
B 84.6%
1435-46-7

1-fluoro-3,5-dichlorobenzene

462-06-6

fluorobenzene

Conditions
ConditionsYield
With C60H48BP3Pd; potassium formate; [2.2.2]cryptande In tetrahydrofuran at 60℃; for 72h; Schlenk technique; Inert atmosphere;97%
1072-85-1

o-fluorobromobenzene

A

462-06-6

fluorobenzene

B

388-82-9

2,2'-difluorobiphenyl

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 2-pentanol at 100℃; for 18h; Inert atmosphere;A 95.5%
B 4.5%
With palladium; hydroquinone; potassium hydroxide In glycerol at 90℃; for 18h; chemoselective reaction;A n/a
B 71 %Chromat.
369-57-3

benzenediazonium tetrafluoroborate

462-06-6

fluorobenzene

Conditions
ConditionsYield
With pyridine; hydrogen fluoride at 55℃; for 1h; Product distribution; Rate constant; Thermodynamic data; changed molar ratio HF/Pyr, temp. and time; energy/enthalpy of activation;95%
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; cesium fluoride In acetone at 30℃; Irradiation;37%
With sodium difluorohydrogenate; 1,2,4-Trichlorobenzene
71-43-2

benzene

462-06-6

fluorobenzene

Conditions
ConditionsYield
With fluorine at 60℃; under 3750.38 Torr; Temperature;95%
With trifluorormethanesulfonic acid; Selectfluor In dichloromethane at 40℃; for 20h; Fluorination;83%
With Al2CuF8 at 500℃; Reagent/catalyst; Inert atmosphere;47%
352-34-1

4-fluoro-1-iodobenzene

462-06-6

fluorobenzene

Conditions
ConditionsYield
With formaldehyd; palladium diacetate; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h;94%
With sodium tetrahydroborate; di-tert-butyl peroxide In N,N-dimethyl-formamide at 70℃; for 2h; Irradiation;82 % Chromat.
With hydrogenchloride; CuI*P(Et)3; naphthalen-1-yl-lithium 1.) THF, 25 deg C, 10 min; Yield given. Multistep reaction;
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Chemistry

Product Name:Fluorobenzene(462-06-6)
CAS No:462-06-6
MF: C6H5F
MW: 96.1
mp : -42 °C
bp : 85 °C(lit.)
density : 1.024 g/mL at 25 °C(lit.)
vapor density : 3.31 (vs air)
refractive index : n20/D 1.465(lit.)
Fp : 9 °F
storage temp. : 0-6°C 
Water Solubility : Insoluble
Synonyms: benzene,benzene,fluoro-;fluoro-benzen;Fluorobenzenes;Fluorylfluoride;Monofluorobenzene;Phenyl fluoride;Phenylfluoride;FLUOROBENZENE
Molecular Structure:

General Description of Fluorobenzene(462-06-6): A clear, colorless liquid with a characteristic aromatic odor. About the same density as water. Flash point 5°F. Vapors heavier than air. May irritate the skin, eyes, and mucous membranes. Used as an insecticide, larvacide and as a reagent for plastic or resin polymers.

Production

On the laboratory scale, PhF is conveniently prepared by the thermal decomposition of the phenyldiazonium tetrafluoroborate:
PhN2BF4 → PhF + BF3 + N2
According to the procedure, solid [PhN2]BF4 is heated with a flame to initiate an exothermic reaction that affords two volatile products, PhF and BF3, which are readily separated because of their differing boiling points.PhF was first reported in 1886 by O. Wallach at the University of Bonn, who prepared the compound in two steps, starting also with a phenyldiazonium salt. The diazonium chloride was first converted to its piperidinide, which in turn was cleaved using hydrofluoric acid.
[PhN2]Cl + 2 C5H10NH → PhN=N-NC5H10 + [C5H10NH2]Cl
PhN=N-NC5H10 + 2 HF → PhF + N2 + [C5H10NH2]F
An interesting historical note: in Wallach’s era, the element fluorine was symbolized with “Fl”. Thus, his procedure is subtitled “Fluorbenzol(462-06-6), C6H5Fl”.The technical synthesis is by the reaction of cyclopentadiene with difluorocarbene. The initially formed cyclopropane undergoes a ring expansion and subsequent elimination of hydrogen fluoride.

Toxicity Data With Reference

RTECS#: CAS# 462-06-6: DA0800000
LD50/LC50: RTECS:
CAS# 462-06-6: Inhalation, mouse: LC50 = 45 gm/m3/2H;
Inhalation, mouse: LC50 = 45000 mg/m3/2H;
Inhalation, rat: LC50 = 26908 mg/m3;
Oral, rat: LD50 = 4399 mg/kg;
Carcinogenicity: Fluorobenzene - Not listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.
Other: See actual entry in RTECS for complete information.

Safety Profile

Hazard Codes : F,Xi,T
Risk Statements : 36/37/38-11-39/23/24/25-23/24/25-52/53-36
Safety Statements : 16-26-36-7-33-29-45-36/37-61
RIDADR : UN 2387 3/PG 2
WGK  Germany : 2
Hazard Note : Flammable
TSCA : T
HazardClass : 3
PackingGroup : II

Specification

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F 
Risk Phrases:
R 11 Highly flammable. 
Safety Phrases:
S 7 Keep container tightly closed. 
S 16 Keep away from sources of ignition - No smoking. 
S 29 Do not empty into drains. 
S 33 Take precautionary measures against static discharges. 
WGK (Water Danger/Protection)
CAS# 462-06-6: 2
Canada
CAS# 462-06-6 is listed on Canada's DSL List
US Federal
TSCA
CAS# 462-06-6 is listed on the TSCA Inventory.