Tolylene-2,4-diisocyanate

Base Information

• Chemical Name: Tolylene-2,4-diisocyanate
• CAS No.: 584-84-9
• Deprecated CAS: 59539-76-3,86-91-9,856307-56-7,1358624-38-0,1260158-01-7,1260158-01-7,1358624-38-0,856307-56-7,86-91-9
• Molecular Formula: C9H6N2O2
• Molecular Weight: 174.159
• Hs Code.: 29291010
• European Community (EC) Number: 209-544-5,607-844-4,617-935-0
• ICSC Number: 0339
• NSC Number: 56759,4791
• UN Number: 2078
• UNII: 17X7AFZ1GH
• DSSTox Substance ID: DTXSID7026156
• Nikkaji Number: J3.302B
• Wikipedia: Toluene_diisocyanate
• Wikidata: Q415183
• NCI Thesaurus Code: C44457
• Pharos Ligand ID: 5D17JUJMW2B7
• Metabolomics Workbench ID: 58653
• ChEMBL ID: CHEMBL1086446
• Mol file: 584-84-9.mol

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;

Chemical Property of Tolylene-2,4-diisocyanate

Chemical Property:

• Appearance/Colour: colourless to light yellow liquid
• Vapor Pressure: 0.03 mm Hg ( 25 °C)
• Melting Point: 20-22 °C(lit.)
• Refractive Index: n20/D 1.568(lit.)
• Boiling Point: 251 °C at 760 mmHg
• Flash Point: 110.5 °C
• PSA: 58.86000
• Density: 1.14 g/cm³
• LogP: 1.92960
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with ether, acetone, benzene, carbontetrachloride and c
• Water Solubility.: reacts
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 174.042927438
• Heavy Atom Count: 13
• Complexity: 265
• Transport DOT Label: Poison

Purity/Quality:

Tolylene 2,4-diisocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26-36/37/38-40-42/43-52/53
• Safety Statements: 23-36/37-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Diisocyanates
• Canonical SMILES: CC1=C(C=C(C=C1)N=C=O)N=C=O
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance, the vapour of this substance and the aerosol are irritating to the eyes, skin and respiratory tract. Inhalation of the vapour may cause asthma-like reactions. Inhalation of the vapour may cause chemical bronchitis, pneumonitis and lung oedema. Exposure far above the OEL could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma. This substance is possibly carcinogenic to humans.
• General Description: Tolylene-2,4-diisocyanate (2,4-TDI) is a key reactant in the selective synthesis of non-symmetrical bis-ureas, where it reacts with aromatic amines to form mono-isocyanate/mono-urea intermediates. These intermediates are further functionalized with aliphatic amines to produce bis-ureas with enhanced solubility and strong self-assembly properties. The resulting compounds exhibit improved rheological behavior when grafted onto polymers like PDMS, forming physically cross-linked networks with potential applications in material science.

Technology Process of Tolylene-2,4-diisocyanate

There total 52 articles about Tolylene-2,4-diisocyanate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

phosgene (75-44-5) + 4-methylbenzene-1,3-diamine (95-80-7,71111-07-4) → 2,4-Toluene diisocyanate (584-84-9,6144-18-9,26006-20-2)

Guidance literature:

under 1050.11 Torr; Product distribution / selectivity; Gas phase; Industry scale;

Reference yield: 93.0%

1-methyl-2,4-bis-(butoxycarbonylamino)-benzene (7469-49-0) → 2,4-Toluene diisocyanate (584-84-9,6144-18-9,26006-20-2)

Guidance literature:

at 220 ℃; under 7.50075 Torr;

Reference yield: 93.0%

toluene-2,4-dicarbamayl fluoride → 2,4-Toluene diisocyanate (584-84-9,6144-18-9,26006-20-2)

Guidance literature:

at 160 ℃; for 0.5h; Glovebox;

DOI:10.1016/j.jfluchem.2015.05.007

upstream raw materials:

phosgene

4-methylbenzene-1,3-diamine

2,4-bis-(ethoxycarbonylamino)toluene

carbon monoxide

Downstream raw materials:

3,3'-(4-methyl-m-phenylene)-bis-oxazolidin-2-one

N,N'-bis-(aziridine-1-carbonyl)-4-methyl-m-phenylenediamine

N,N'-(4-methyl-m-phenylene)-bis-carbamic acid bis-(2-piperidino-ethyl ester)

N,N'-(4-methyl-m-phenylene)-bis-carbamic acid bis-(2-morpholino-ethyl ester)

Refernces

Selective synthesis of non-symmetrical bis-ureas and their self-assembly

10.1039/b316913h

The research aims to selectively synthesize non-symmetrical bis-ureas and investigate their self-assembly properties. The study focuses on creating bis-ureas with one aromatic and one aliphatic group, which combine the solubility of aliphatic bis-ureas and the strong association of aromatic ones. The key chemicals used include various aromatic amines (such as 4-n-butylaniline and 2,6-diethylaniline), and aliphatic amines (like 2-ethylhexylamine). 2,4-toluene diisocyanate (2,4-TDI) plays a pivotal role as the core reactant for synthesizing mono-isocyanate/mono-ureas and subsequently non-symmetrical bis-ureas. The selective synthesis involves reacting an aromatic amine with an excess of 2,4-TDI to obtain mono-isocyanate/mono-ureas, which are then reacted with chosen amines to form the desired non-symmetrical bis-ureas. The synthesized compounds were characterized using techniques like 1H NMR, FTIR spectroscopy, and viscosimetry. The results show that non-symmetrical bis-ureas exhibit stronger self-assembly and better solubility compared to symmetrical bis-ureas. Additionally, bis-ureas grafted onto polydimethylsiloxanes (PDMS) form physical cross-links, leading to rubbery solids with promising rheological properties. The study concludes that the selective synthesis of non-symmetrical bis-ureas opens up new possibilities for creating materials with unique self-assembly and mechanical properties.