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1518-16-7

Basic Information
CAS No.: 1518-16-7
Name: Propanedinitrile,2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-
Molecular Structure:
Molecular Structure of 1518-16-7 (Propanedinitrile,2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-)
Formula: C12H4N4
Molecular Weight: 204.20
Synonyms: 7,7,8,8-Tetracyano-p-quinodimethane;NSC 105237;Quinodimethane, tetracyano-;TCNQ;Tetracyano-p-quinodimethane;Tetracyanoquinodimethane;7,7,8,8-Tetracyanoquinodimethane;2,5-Cyclohexadiene-D1,a:4,a'-dimalononitrile (6CI,7CI,8CI);(2,5-Cyclohexadiene-1,4-diylidene)dimalononitrile;1,4-Bis(dicyanomethylene)cyclohexadiene;2,2'-(2,5-Cyclohexadiene-1,4-diylidene)bis[propanedinitrile];7,7,8,8-Tetracyano-1,4-quinodimethan;
EINECS: 216-174-8
Density: 1.358 g/cm3
Melting Point: 287-289 °C (dec.)(lit.)
Boiling Point: 254.677 °C at 760 mmHg
Flash Point: 99.674 °C
Solubility: insoluble in water
Appearance: orange to green crystalline powder
Hazard Symbols: HarmfulXn; IrritantXi
Risk Codes: 20/21/22
Safety: 22-24/25-36/37-26
Transport Information: UN 3276
PSA: 95.16000
LogP: 0.08232
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    Product Name: 7,7,8,8-Tetracyanoquinodimethane CAS: 1518-16-7 MF: C12H4N4 MW: 204.19 EINECS: 216-174-8 Mol File: 1518-16-7.mol 7,7,8,8-Tetracyanoquinodimethane Structure 7,7,8,8-Tetracyanoquinodimethane Chemical Properties Melting

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    Name:7,7,8,8-Tetracyanoquinodimethane Synonyms:2,2'-(2,5-Cyclohexadiene-1,4-diylidene)bispropanedinitrile; (2,5-Cyclohexadiene-1,4-diylidene)-dimalononitrile; TCNQ Molecular Formula:C12H4N4 Molecular Weight:204.19 CAS No.:1518-16-7 App

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Specification

The Tetracyanoquinodimethane, with the CAS registry number 1518-16-7 and EINECS registry number 216-174-8, has the systematic name of 2,2'-cyclohexa-2,5-diene-1,4-diylidenedipropanedinitrile. And the molecular formula of this chemical is C12H4N4. It is an kind of orange to green crystalline powder, and belongs to the following product categories: Aromatic Nitriles; Acceptors (Charge Transfer Complexes); Charge Transfer Complexes for Organic Metals; Functional Materials; TCNQ Derivatives. In addition, it is an electron-acceptor that is used to prepare charge transfer salts, which are of interest in the area of molecular electronics.

The physical properties of Tetracyanoquinodimethane are as following: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 14.927; (5)ACD/KOC (pH 7.4): 14.927; (6)#H bond acceptors: 4; (7)#H bond donors: 0; (8)#Freely Rotating Bonds: 0; (9)Polar Surface Area: 95.16 Å2; (10)Index of Refraction: 1.63; (11)Molar Refractivity: 53.488 cm3; (12)Molar Volume: 150.343 cm3; (13)Polarizability: 21.204×10-24cm3; (14)Surface Tension: 83.235 dyne/cm; (15)Density: 1.358 g/cm3; (16)Flash Point: 99.674 °C; (17)Enthalpy of Vaporization: 49.212 kJ/mol; (18)Boiling Point: 254.677 °C at 760 mmHg; (19)Vapour Pressure: 0.017 mmHg at 25°C.

Preparation of Tetracyanoquinodimethane: It can be prepared by the condensation of 1,4-cyclohexanedione with malononitrile, followed by dehydrogenation of the resulting diene with bromine:
C6H8O2 + 2 CH2(CN)2 → C6H8(C(CN)2)2 + 2 H2O
C6H8(C(CN)2)2 + 2 Br2 → C6H4(C(CN)2)2 + 4 HBr

You should be cautious while dealing with this chemical. It is harmful by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Avoid contact with skin and eyes; Do not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(=C(C#N)C#N)ccc1=C(C#N)C#N
(2)InChI: InChI=1/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H
(3)InChIKey: PCCVSPMFGIFTHU-UHFFFAOYAI

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00796,