1,3-Phenylene diisocyanate

Base Information

• Chemical Name: 1,3-Phenylene diisocyanate
• CAS No.: 123-61-5
• Molecular Formula: C8H4 N2 O2
• Molecular Weight: 160.132
• Hs Code.: 29291000
• European Community (EC) Number: 204-637-7
• NSC Number: 511721
• UN Number: 2206
• UNII: B44H9MFH1S
• DSSTox Substance ID: DTXSID9044792
• Nikkaji Number: J49.698G
• Wikipedia: 1,3-Diisocyanatobenzene
• Wikidata: Q5649574
• Mol file: 123-61-5.mol

Synonyms:1,3-Phenylene diisocyanate;123-61-5;1,3-Diisocyanatobenzene;Benzene, 1,3-diisocyanato-;m-Phenylene diisocyanate;Benzene 1,3-diisocyanate;Nacconate 400;m-Phenylene isocyanate;Benzene, m-diisocyanato-;Benzene-1,3-diisocyanate;ISOCYANIC ACID, m-PHENYLENE ESTER;1,3-Phenylenediisocyanate;NSC 511721;EINECS 204-637-7;UNII-B44H9MFH1S;BRN 0776957;B44H9MFH1S;AI3-28286;NSC-511721;1,3-Phenylene diisocyanate [Diisocyanates];Benzene,3-diisocyanato-;SCHEMBL27873;DTXSID9044792;1,3-Phenylene diisocyanate, 95%;MFCD00002018;NSC511721;AKOS015889119;AS-33227;LS-84460;FT-0606672;P1092;Q5649574

Chemical Property of 1,3-Phenylene diisocyanate

Chemical Property:

• Appearance/Colour: White to off-white fused solid
• Vapor Pressure: 0.0801mmHg at 25°C
• Melting Point: 49-51 °C(lit.)
• Refractive Index: 1.4900 (estimate)
• Boiling Point: 121 °C25 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 58.86000
• Density: 1.17g/cm³
• LogP: 1.62120
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Moisture Sensitive
• Water Solubility.: Soluble in hot benzene. Hydrolyzes in water.
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 160.027277375
• Heavy Atom Count: 12
• Complexity: 215
• Transport DOT Label: Poison

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3-Phenylene Diisocyanate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-42
• Safety Statements: 22-26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Plastics & Rubber -> Diisocyanates
• Canonical SMILES: C1=CC(=CC(=C1)N=C=O)N=C=O

Technology Process of 1,3-Phenylene diisocyanate

There total 7 articles about 1,3-Phenylene 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: 65.0%

isophthaloyl diazide (3027-36-9) → 1,3-Phenylene diisocyanate (123-61-5)

Guidance literature:

at 85 ℃; Flow reactor;

Reference yield: 8.0%

meta-dinitrobenzene (99-65-0) + carbon monoxide (201230-82-2) → isocyanic acid (3-nitro-phenyl) ester (3320-87-4) + 1,3-Phenylene diisocyanate (123-61-5)

Guidance literature:

With MoO₃+Fe₂O₃ on Al₂O₃; trimethyleneglycol; In 1,2-dichloro-benzene; at 210 ℃; under 228000 Torr;

DOI:10.1007/BF00951891

Reference yield:

dimethyl N,N'-(1,3-phenylene)dicarbamate (4930-04-5) → 1,3-Phenylene diisocyanate (123-61-5)

Guidance literature:

With 2-chloro-1,3,2-benzodioxaborole; triethylamine; In toluene; 1.) reflux, 5 min, 2.) 0.5 h;

DOI:10.1021/jo00106a044

upstream raw materials:

isophthaloyl diazide

ethyl N-(3-ethoxycarbonylaminophenyl)carbamate

phosgene

m-phenylenediamine

Downstream raw materials:

[3-(1,1-Dimethyl-propoxycarbonylamino)-phenyl]-carbamic acid 1,1-dimethyl-propyl ester

tert-butyl N-(3-{[(tert-butoxy)carbonyl]amino}phenyl)carbamate

N,N'-bis-(4-nitrobenzylidene)-1,3-diaminobenzene

1,1'-(m-Phenylene)bis(3-hydroxy-3-methylurea)

Refernces

• 1、 -. "FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES". Paragraph 0175; 0185-0187; 0250; 0255-0260. . Retrieved 2021/06/22.
• 2、 Valli, V. L. K.,Alper, H.. "A Simple, Convenient, and Efficient Method for the Synthesis of Isocyanates from Urethanes". . p. 257 - 258. Retrieved 2007/10/02.