4-Chlorophenyl isocyanate

Base Information

• Chemical Name: 4-Chlorophenyl isocyanate
• CAS No.: 104-12-1
• Molecular Formula: C7H4ClNO
• Molecular Weight: 153.568
• Hs Code.: 29291090
• European Community (EC) Number: 203-176-9
• NSC Number: 76589
• UN Number: 2206
• UNII: W46XL60WI8
• DSSTox Substance ID: DTXSID7040732
• Nikkaji Number: J30.180I
• Wikidata: Q26840784
• ChEMBL ID: CHEMBL1865294
• Mol file: 104-12-1.mol

Synonyms:chlorophenyl isocyanate;p-chlorophenyl isocyanate

Chemical Property of 4-Chlorophenyl isocyanate

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid or crystal
• Vapor Pressure: 0.226mmHg at 25°C
• Melting Point: 26-29 °C(lit.)
• Refractive Index: n20/D 1.5618(lit.)
• Boiling Point: 204.2 °C at 760 mmHg
• Flash Point: 76 °C
• PSA: 29.43000
• Density: 1.26 g/cm³
• LogP: 2.30730
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive/Lachrymatory
• Water Solubility.: DECOMPOSES
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 152.9981414
• Heavy Atom Count: 10
• Complexity: 146
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-Chlorophenyl isocyanate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,T,C
• Hazard Codes: T+,T,C
• Statements: 25-26-37/38-41-42-52/53
• Safety Statements: 23-26-28-36/37/39-45-61-38-37/39-28A-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Monoisocyanates
• Canonical SMILES: C1=CC(=CC=C1N=C=O)Cl
• Uses: 4-Chlorophenyl isocyanate is used in the preparation of isothiocyanates. Aryl isocyanates undergo [2+2] cycloaddition reactions with dihydrofuran to give bicyclic ?-lactams in high yield. 4-Chlorophenyl isocyanate was used in the preparation of isothiocyanates.

Technology Process of 4-Chlorophenyl isocyanate

There total 58 articles about 4-Chlorophenyl isocyanate 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: 92.0%

bis(trichloromethyl) carbonate (32315-10-9) + 4-chloro-aniline (106-47-8) → p-chlorphenylisocyanate (104-12-1)

Guidance literature:

In ethyl acetate; at 0 - 5 ℃; for 3h; Solvent; Cooling with ice; Reflux;

Reference yield: 77.1%

Methyl 4-(bromomethyl)benzoate (2417-72-3) + N-(4-chlorophenyl)thiomorpholine-4-carboxamide 1,1-dioxide → p-chlorphenylisocyanate (104-12-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

Reference yield: 75.0%

4-chlorobenzoyl azide (21368-28-5) → p-chlorphenylisocyanate (104-12-1)

Guidance literature:

In toluene; for 1.5h; Heating;

DOI:10.1016/S0040-4020(01)81763-4

upstream raw materials:

phosgene

4-chloro-aniline

phenyl isocyanate

4-Ethoxyaniline

Downstream raw materials:

N,N-bis-(4-chloro-phenyl)-urea

(6-bromo-4,5-dihydro-3H-pyridin-2-ylidene)-(4-chloro-phenyl)-urea

N-(4-chloro-phenyl)-N'-[1,2,4]triazin-3-yl-urea

N-(4-chloro-phenyl)-N'-(5-chloro-[2]pyridyl)-urea

Refernces

• 1、 Park, Eun Bit,Jeong, Kyu-Sung. "Chloride transport activities of trans- and cis-amide-linked bisureas". . p. 9197 - 9200. Retrieved 2015.
• 2、 Woeber. "-". . p. 1354. Retrieved 1952.
• 3、 Petti, Alessia,Fagnan, Corentin,van Melis, Carlo G. W.,Tanbouza, Nour,Garcia, Anthony D.,Mastrodonato, Andrea,Leech, Matthew C.,Goodall, Iain C. A.,Dobbs, Adrian P.,Ollevier, Thierry,Lam, Kevin. "Supporting-Electrolyte-Free Anodic Oxidation of Oxamic Acids into Isocyanates: An Expedient Way to Access Ureas, Carbamates, and Thiocarbamates". supporting information. p. 2614 - 2621. Retrieved 2021/06/27.
• 4、 Hong, Wan Pyo,Tran, Van Hieu,Kim, Hee-Kwon. "Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions". . p. 15890 - 15895. Retrieved 2021/05/19.