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| CAS No.: | 1835-49-0 |
|---|---|
| Name: | Tetrafluoroterephthalonitrile |
| Article Data: | 16 |
| Molecular Structure: | |
|
|
|
| Formula: | C8F4N2 |
| Molecular Weight: | 200.095 |
| Synonyms: | Terephthalonitrile,tetrafluoro- (7CI,8CI);1,2,4,5-Tetrafluoro-3,6-dicyanobenzene;1,4-Dicyano-2,3,5,6-tetrafluorobenzene;1,4-Dicyanotetrafluorobenzene;2,3,5,6-Tetrafluoro-1,4-benzenedicarbonitrile;2,3,5,6-Tetrafluoro-1,4-benzodinitrile;2,3,5,6-Tetrafluoroterephthalonitrile;Diamond 2031;NSC 97007;Tetrafluoroterephthalodinitrile; |
| EINECS: | 217-397-3 |
| Density: | 1.54 g/cm3 |
| Melting Point: | 197-199 °C |
| Boiling Point: | 243.3 °C at 760 mmHg |
| Flash Point: | 100.9 °C |
| Appearance: | white crystals |
| Hazard Symbols: |
 T, Xi
|
| Risk Codes: | 25-36/37/38-20/21-23/24/25 |
| Safety: | 26-45-37/39-22-36/37/39 |
| Transport Information: | UN 3439 6.1/PG 3 |
| PSA: | 47.58000 |
| LogP: | 1.98636 |
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| Conditions | Yield |
|---|---|
| With potassium fluoride; 18-crown-6 ether In N,N-dimethyl-formamide at 140℃; for 6h; | 92% |
| With potassium fluoride In N,N-dimethyl-formamide at 110℃; for 10h; Product distribution / selectivity; | 90% |
| With potassium fluoride; tetra-n-propylammonium bromide In N,N-dimethyl-formamide at 130℃; for 7h; Product distribution / selectivity; | 90% |
| Conditions | Yield |
|---|---|
| heating to 300°C, 5 h; | 74.4% |
| heating to 300°C, 5 h; | 74.4% |
| heating to 250°C, 5 h; | 68.7% |
- 773-82-0
Pentafluorobenzonitrile
- 773-82-0
2,3,4,5,6-Pentafluoro-benzonitrile
- 1835-49-0
tetrafluoroterephthalonitrile
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide |
| Conditions | Yield |
|---|---|
| With phosphorus pentoxide at 200 - 250℃; for 1.25h; |
- 344-03-6
1,4-dibromotetrafluorobenzene
- 544-92-3
copper(I) cyanide
- 1835-49-0
tetrafluoroterephthalonitrile
| Conditions | Yield |
|---|---|
| at 160 - 170℃; |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 91 percent / NH3 / diethyl ether / 8 h / 0 - 20 °C 2: 89 percent / POCl3 / 6 h / 135 °C 3: 92 percent / KF; 18-crown-6 / dimethylformamide / 6 h / 140 °C View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 89 percent / POCl3 / 6 h / 135 °C 2: 92 percent / KF; 18-crown-6 / dimethylformamide / 6 h / 140 °C View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 65 percent / Fe; Cl2 / 24 h / 180 °C 2: 91 percent / NH3 / diethyl ether / 8 h / 0 - 20 °C 3: 89 percent / POCl3 / 6 h / 135 °C 4: 92 percent / KF; 18-crown-6 / dimethylformamide / 6 h / 140 °C View Scheme |
| Conditions | Yield |
|---|---|
| With iron(III) chloride In N,N-dimethyl-formamide heating to 160-170°C, 2.5 h; pouring in soln. of FeCl3 in HCl, at 70-80°C, 0.5 h; | |
| With FeCl3 In N,N-dimethyl-formamide heating to 160-170°C, 2.5 h; pouring in soln. of FeCl3 in HCl, at 70-80°C, 0.5 h; |
| Conditions | Yield |
|---|---|
| heating in high vac.; | |
| heating in high vac.; |
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Chemistry
IUPAC: 2,3,5,6-Tetrafluorobenzene-1,4-dicarbonitrile
Synonyms: 1,4-Dicyano-2,3,5,6-tetrafluorobenzene ; 1,4-Dicyanotetrafluorobenzene ; 2,3,5,6-Tetrafluoro-4-benzenedicarbonitrile ; Diamond 2031 ; Tetrafluoroterephthalodinitrile ; 2,3,5,6-Tetrafluoro terephthalonitrile
Molecular Formula: C8F4N2
Molecular Weight: 200.09
EINECS: 217-397-3
Melting point: 197-199°C(lit.)
Flash Point: 100.9°C
Boiling Point: 243.3 °C at 760 mmHg
Density: 1.54 g/cm3
The molecular structure of Tetrafluoroterephthalonitrile (1835-49-0):
Uses
Tetrafluoroterephthalonitrile (1835-49-0) is used as organic intermediate.
Production
A method for the manufacture of tetrafluoroterephthalonitrile(1835-49-0), which comprises mixing tetrachloroterephthalonitrile, from 0.2 to 1.5 moles per atom of chloride of said tetrachloroterephthalonitrile of dry powdered potassium fluoride and a polar solvent selected from the group consisting of dimethylformamide, diethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, dimethylsulfoxide, hexamethylphosphoramide and tetramethylenesulfone having a water content of not more than 0.2% by weight, heating the resultant mixture at temperatures not exceeding the boiling point of said polar solvent but exceeding 130°C with simultaneous agitation and thereby causing formation of tetrafluoroterephthalonitrile in said mixture and separating from the mixture the formed tetrafluoroterephthalonitrile.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | oral | 56mg/kg (56mg/kg) | Journal of Medicinal Chemistry. Vol. 21, Pg. 906, 1978. |
RTECS: CZ1955000
Safety Profile
Hazard Codes: T 
Risk Statements: 25-36/37/38-20/21-23/24/25
R25: Toxic if swallowed
R36/37/38: Irritating to eyes, respiratory system and skin
R20/21: Harmful by inhalation and in contact with skin
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed
Safety Statements: 26-45-37/39-22-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the
label whenever possible.)
S37/39: Wear suitable gloves and eye/face protection
S22: Do not breathe dust
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 3439 6.1/PG 3
WGK Germany: 3
Hazard Note: Toxic
HazardClass: 6.1(b)
PackingGroup: III