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584-84-9

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Basic Information
CAS No.: 584-84-9
Name: Tolylene-2,4-diisocyanate
Article Data: 84
Molecular Structure:
Molecular Structure of 584-84-9 (Tolylene-2,4-diisocyanate)
Formula: C9H6N2O2
Molecular Weight: 174.159
Synonyms: Isocyanicacid, 4-methyl-m-phenylene ester (8CI);1,3-Diisocyanato-4-methylbenzene;2,4-Diisocyanato-1-methylbenzene;2,4-Diisocyanatotoluene;2,4-TDI;2,4-Toluenediisocyanate;2,4-Toluylene diisocyanate;2,4-Tolylene diisocyanate;4-Methyl-1,3-phenylene diisocyanate;4-Methyl-m-phenylene diisocyanate;4-Methyl-m-phenylene isocyanate;NSC 4791;NSC 56759;TDI 100;Toluene 2,4-diisocyanate;
EINECS: 209-544-5
Density: 1.14 g/cm3
Melting Point: 20-22 °C(lit.)
Boiling Point: 251 °C at 760 mmHg
Flash Point: 110.5 °C
Solubility: reacts with water
Appearance: colourless to light yellow liquid
Hazard Symbols: VeryT+
Risk Codes: 26-36/37/38-40-42/43-52/53
Safety: 23-36/37-45-61
Transport Information: UN 2078 6.1/PG 2
PSA: 58.86000
LogP: 1.92960
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Specification

The IUPAC name of Toluene-2,4-diisocyanate is 2,4-diisocyanato-1-methylbenzene. With the CAS registry number 584-84-9, it is also named as 2,4-Diisocyanatotoluene. The product's category is Intermediates of Dyes and Pigments. It is colourless to light yellow liquid which is miscible with ether, acetone, carbon tetrachloride, benzene, chlorobenzene and gasoline. And it is stable, but decomposes in the presence of moisture. In addition, Toluene-2,4-diisocyanate is also heat and light sensitive. It readily polymerizes in contact with base and reacts with compounds containing active hydrogen. Exposure to this chemical and its vapors should be avoided. When heated to decomposition it emits highly toxic fumes of NOx. Additioanlly, Toluene-2,4-diisocyanate should be sealed in the container and stored at low temperature.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.47; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.47; (4)ACD/LogD (pH 7.4): 3.47; (5)ACD/BCF (pH 5.5): 253.66; (6)ACD/BCF (pH 7.4): 253.66; (7)ACD/KOC (pH 5.5): 1830.51; (8)ACD/KOC (pH 7.4): 1830.51; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.559; (13)Molar Refractivity: 49.09 cm3; (14)Molar Volume: 152 cm3; (15)Polarizability: 19.46×10-24 cm3; (16)Surface Tension: 43.4 dyne/cm; (17)Enthalpy of Vaporization: 48.83 kJ/mol; (18)Vapour Pressure: 0.021 mmHg at 25 °C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 174.042927; (21)MonoIsotopic Mass: 174.042927; (22)Topological Polar Surface Area: 58.9; (23)Heavy Atom Count: 13; (24)Complexity: 265.

Preparation of Toluene-2,4-diisocyanate: Firstly, we can get the dinitrotoluene by nitration. Secondly, we get toluene diamine by reduction. At last, toluene diamine reacts with phosgene to obtain TDI.

Uses of Toluene-2,4-diisocyanate: It is mainly used in polyurethane products, including foamed plastic, polyurethane coating and polyurethane rubber. And it is also used as adhesive. In additioan, it can react with methanol to get N,N'-(4-methyl-m-phenylene)-bis-carbamic acid dimethyl ester. This reaction reacts by heating. The reaction time is 1.5 days. The yield is 98%.

When you are using this chemical, please be cautious about it as the following:
It is not only very toxic by inhalation, but also irritating to eyes, respiratory system and skin, so people should not breathe vapour. And it also has limited evidence of a carcinogenic effect. What's more, this chemical is harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure. 
1. Smiles:c1(c(ccc(c1)N=C=O)C)N=C=O
2. InChI:InChI=1/C9H6N2O2/c1-7-2-3-8(10-5-12)4-9(7)11-6-13/h2-4H,1H3

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 100mg/kg (100mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
 
guinea pig LC50 inhalation 13ppm/4H (13ppm) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: CHANGES IN PULMONARY VASCULAR RESISTANCE

LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION
American Industrial Hygiene Association Journal. Vol. 23, Pg. 447, 1962.
human TCLo inhalation 20ppb/2Y (0.02ppm) LUNGS, THORAX, OR RESPIRATION: COUGH

LUNGS, THORAX, OR RESPIRATION: SPUTUM
Proceedings of the Royal Society of Medicine. Vol. 63, Pg. 372, 1970.
 
human TCLo inhalation 80ppb (0.08ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archiv fuer Toxikologie. Vol. 19, Pg. 364, 1962.
human TCLo inhalation 500ppb (0.5ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Occupational Medicine. Vol. 1, Pg. 448, 1959.
mouse LC50 inhalation 10ppm/4H (10ppm) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: CHANGES IN PULMONARY VASCULAR RESISTANCE
American Industrial Hygiene Association Journal. Vol. 23, Pg. 447, 1962.
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07807,
rabbit LC50 inhalation 11ppm/4H (11ppm) BEHAVIORAL: EXCITEMENT

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Industrial Hygiene Association Journal. Vol. 23, Pg. 447, 1962.
rabbit LD50 skin > 16mL/kg (16mL/kg)   Union Carbide Data Sheet. Vol. 3/8/1973,
rat LC50 inhalation 14ppm/4H (14ppm) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Industrial Hygiene Association Journal. Vol. 23, Pg. 447, 1962.
rat LD50 oral 5800mg/kg (5800mg/kg) GASTROINTESTINAL: OTHER CHANGES AMA Archives of Industrial Health. Vol. 15, Pg. 324, 1957.
women TCLo inhalation 300ppt/8H/5D (0.0003ppm) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION Lancet. Vol. 1, Pg. 756, 1980.