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| CAS No.: | 91-15-6 |
|---|---|
| Name: | Phthalonitrile |
| Molecular Structure: | |
|
|
|
| Formula: | C8H4N2 |
| Molecular Weight: | 128.133 |
| Synonyms: | Phthalonitrile(8CI);1,2-Benzodinitrile;1,2-Bis(cyano)benzene;1,2-Dicyanobenzene;NSC17562;o-Benzenedicarbonitrile;o-Benzenedinitrile;o-Cyanobenzonitrile;o-Dicyanobenzene; |
| EINECS: | 202-044-8 |
| Density: | 1.24 g/cm3 |
| Melting Point: | 137-139 °C(lit.) |
| Boiling Point: | 304.6 °C at 760 mmHg |
| Flash Point: | 153.3 °C |
| Solubility: | 50 mg/mL, clear in benzene, 0.56 g/L (25 °C) in water |
| Appearance: | off-white to tan powder |
| Hazard Symbols: |
 T
|
| Risk Codes: | 25-23/24/25 |
| Safety: | 36/37/39-45-28A |
| Transport Information: | UN 3439 6.1/PG 2 |
| PSA: | 47.58000 |
| LogP: | 1.42996 |
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- 112069-03-1
N,N'-o-phthaloylbis(P,P,P-triphenylphospha-λ5-azene)
- 91-15-6
phthalonitrile
| Conditions | Yield |
|---|---|
| In dimethyl sulfoxide at 140℃; intramolecular aza-Wittig reaction; | 100% |
| Conditions | Yield |
|---|---|
| With potassium phenolate; palladium diacetate; potassium carbonate; dimethyl cis-but-2-ene-1,4-dioate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 24h; Schlenk technique; Inert atmosphere; | 95% |
| Conditions | Yield |
|---|---|
| With sodium carbonate; potassium ferrocyanide In N,N-dimethyl-formamide at 120℃; for 5h; | 93% |
- 17300-02-6
1,2-benzenedimethanamine
- 91-15-6
phthalonitrile
| Conditions | Yield |
|---|---|
| With aluminum oxide In N,N-dimethyl-formamide at 120℃; for 6h; Inert atmosphere; | 92% |
| With [Ru(p-cymene)(pzH-NP)(Cl)]Cl; potassium tert-butylate In toluene at 70℃; for 24h; Schlenk technique; Inert atmosphere; | 68% |
| Conditions | Yield |
|---|---|
| With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; | 91% |
| With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Schlenk technique; Green chemistry; | 90% |
| With 3% Pd/CeO2; sodium acetate In N,N-dimethyl-formamide; isopropyl alcohol at 65℃; for 10h; Irradiation; | 42% |
| With tri-tert-butyl phosphine; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 24h; Reagent/catalyst; Inert atmosphere; | 75 %Chromat. |
| Conditions | Yield |
|---|---|
| With dichloro(2,2-bis(diphenylphosphino)diphenyl ether)palladium(II); potassium acetate In 1,4-dioxane; water at 90℃; for 1.33333h; Sealed tube; | 91% |
| Conditions | Yield |
|---|---|
| With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere; | 91% |
| With sodium acetate In N,N-dimethyl-formamide; isopropyl alcohol at 55℃; Irradiation; Sealed tube; |
- 89942-45-0
2-(hydroxymethyl)benzenecorbonitrile
- 91-15-6
phthalonitrile
| Conditions | Yield |
|---|---|
| With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water for 24h; Reflux; Green chemistry; | 90% |
- 13506-83-7
[2-(dihydroxyboranyl)phenyl]boronic acid
A
- 6295-97-2
4-bromo-benzenesulfonic acid-(4-chloro-anilide)
B
- 91-15-6
phthalonitrile
| Conditions | Yield |
|---|---|
| With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 15h; Catalytic behavior; Reflux; | A n/a B 90% |
- 13506-83-7
[2-(dihydroxyboranyl)phenyl]boronic acid
A
- 16937-03-4
4-nitro-N-(4-chlorophenyl)benzenesulfonamide
B
- 91-15-6
phthalonitrile
| Conditions | Yield |
|---|---|
| With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 14h; Catalytic behavior; Reflux; | A n/a B 90% |
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Chemistry
Molecule structure of 1,2-Benzenedicarbonitrile (CAS NO.91-15-6):
IUPAC Name: Benzene-1,2-dicarbonitrile
Molecular Weight: 128.13076 g/mol
Molecular Formula: C8H4N2
Density: 1.24 g/cm3
Melting Point: 137-139 °C(lit.)
Boiling Point: 304.6 °C at 760 mmHg
Flash Point: 153.3 °C
Index of Refraction: 1.565
Molar Refractivity: 35.88 cm3
Molar Volume: 110 cm3
Polarizability: 14.22×10-24 cm3
Surface Tension: 55.6 dyne/cm
Enthalpy of Vaporization: 54.5 kJ/mol
Vapour Pressure: 0.000865 mmHg at 25 °C
Solubility Benzene: 50 mg/mL, clear
Water Solubility: 0.56 g/L (25 °C)
XLogP3: 1
H-Bond Acceptor: 2
Exact Mass: 128.037448
MonoIsotopic Mass: 128.037448
Topological Polar Surface Area: 47.6
Heavy Atom Count: 10
Complexity: 178
Canonical SMILES: C1=CC=C(C(=C1)C#N)C#N
InChI: InChI=1S/C8H4N2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H
InChIKey: XQZYPMVTSDWCCE-UHFFFAOYSA-N
EINECS: 202-044-8
Product Categories: Industrial/Fine Chemicals; Organics; Functional Materials; Phthalonitriles & Naphthalonitriles; Phthalonitriles (Building Blocks for Phthalocyanines); C8 to C9; Cyanides/Nitriles; Nitrogen Compounds
History
In 1896, the first formation of 1,2-Benzenedicarbonitrile was reported by Johannes Pinnow. It was noted to be a byproduct of the reaction between orthamidobenzonitrile hydrochloride, sodium nitrite, and hydrochloric acid to synthesize orthodicyanodiazoamidobenzene. In 1907, the first intentional method derived for the synthesis of 1,2-Benzenedicarbonitrile appeared, when 1,2-Benzenedicarbonitrile was boiled with acetic anhydride. While initial yields were small, it was a precursor that eventually to the contemporary large-scale synthesis seen today.
Uses
1,2-Benzenedicarbonitrile (CAS NO.91-15-6) is widely used for the sythesis of phthalein sulfonamide durgs, phthalocyanine pigments and dyes, high-resistance polyamide fiber, xylyl, di-isocyanate plastic and desulfuration catalyst. It is also used for dyes, pigments and other organic synthesis.
Production
1,2-Benzenedicarbonitrile is made by the ammoxidation of o-xylene in the presence of a vanadium oxide-antimony-oxide catalyst over heat (480 °C). This process passes a gaseous mixture of ammonia, oxygen, ando-xylene through a distributor plate into a fluidized bed reactor, containing the catalyst.
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Toxicity Data With Reference
| 1. | orl-rat TDLo:7425 mg/kg/66W-I:ETA | VOONAW Voprosy Onkologii. Problems of Onkology. 18 (1)(1972),81. | ||
| 2. | ipr-rat LD50:62 mg/kg | KJMDA6 Kobe Journal of the Medical Sciences. 11 (1965),63. | ||
| 3. | orl-mus LD50:65 mg/kg | INHEAO Industrial Health. 4 (1966),11. | ||
| 4. | ipr-mus LD50:25 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 . | ||
| 5. | scu-mus LD50:46 mg/kg | INHEAO Industrial Health. 4 (1966),11. |
Consensus Reports
Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.
Safety Profile
Hazard Codes: 
T
Risk Statements: 25-23/24/25
R25 :Toxic if swallowed.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 36/37/39-45-28A
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 3439 6.1/PG 2
WGK Germany: 1
RTECS: TI8575000
HazardClass: 6.1
PackingGroup: II
HS Code: 29269095
Hazardous Substances Data: 91-15-6(Hazardous Substances Data)
Poison by ingestion, subcutaneous, and intraperitoneal routes. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of CN− and NOx.
Specification
1,2-Benzenedicarbonitrile (CAS NO.91-15-6) is also named as 1,2-Benzodinitrile ; 1,2-Dicyanobenzene ; AI3-00049 ; CCRIS 8898 ; Ftalodinitril ; Ftalodinitril [Czech] ; Ftalonitril ; Ftalonitril [Czech] ; HSDB 5273 ; NSC 17562 ; Phthalic acid dinitrile ; Phthalodinitrile ; Phthalonitrile ; USAF ND-09 ; o-Benzenedicarbonitrile ; o-Benzenedinitrile ; o-Cyanobenzonitrile ; o-Dicyanobenzene ; o-Pdn ; o-Phthalodinitrile ; ortho-Dicyanobenzene . 1,2-Benzenedicarbonitrile (CAS NO.91-15-6) is off-white to tan powder. It is soluble in alcohol, ether, chloroform and benzene, insoluble in oil. It can be volatile with steam. 1,2-Benzenedicarbonitrile is stable and incompatible with strong bases, strong acids, strong oxidizing agents, strong reducing agents.