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91-15-6

Basic Information
CAS No.: 91-15-6
Name: Phthalonitrile
Article Data: 122
Molecular Structure:
Molecular Structure of 91-15-6 (Phthalonitrile)
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: ToxicT
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
Synthetic route
112069-03-1

N,N'-o-phthaloylbis(P,P,P-triphenylphospha-λ5-azene)

91-15-6

phthalonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide at 140℃; intramolecular aza-Wittig reaction;100%
626-35-7

nitroacetic acid ethyl ester

4387-36-4

2-iodobenzonitrile

91-15-6

phthalonitrile

Conditions
ConditionsYield
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%
4387-36-4

2-iodobenzonitrile

91-15-6

phthalonitrile

Conditions
ConditionsYield
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
ConditionsYield
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%
4387-36-4

2-iodobenzonitrile

potassium ferrocyanide

91-15-6

phthalonitrile

Conditions
ConditionsYield
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.

potassium hexacyanoferrate(II) trihydrate

2042-37-7

o-cyanobromobenzene

91-15-6

phthalonitrile

Conditions
ConditionsYield
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%

potassiumhexacyanoferrate(II) trihydrate

4387-36-4

2-iodobenzonitrile

91-15-6

phthalonitrile

Conditions
ConditionsYield
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
ConditionsYield
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

4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

A

6295-97-2

4-bromo-benzenesulfonic acid-(4-chloro-anilide)

B

91-15-6

phthalonitrile

Conditions
ConditionsYield
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

N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide

A

16937-03-4

4-nitro-N-(4-chlorophenyl)benzenesulfonamide

B

91-15-6

phthalonitrile

Conditions
ConditionsYield
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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    Synonyms: 1,2-Benzenedicarbonitrile 1,2-Dicyanobenzene o-Phthalodinitrile Molecular Formula: C8H4N2 Molecular Weight: 128.13 CAS Registry Number: 91-15-6 EINECS: 202-044-8 Density: 1.24

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    Product Name: Phthalonitrile MF: C8H4N2 MW: 128.13 EINECS: 202-044-8 Mol File: 91-15-6.mol Phthalonitrile Structure Phthalonitrile Chemical Properties Melting point 137-139 °C (lit.) Boiling point 227.54°C (rough est

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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/cm
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.

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: ToxicT
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.