Phenyl-d5 isocyanate

Base Information

• Chemical Name: Phenyl-d5 isocyanate
• CAS No.: 83286-56-0
• Molecular Formula: C₇H₅NO
• Molecular Weight: 124.083
• European Community (EC) Number: 693-117-7
• DSSTox Substance ID: DTXSID10584063
• Mol file: 83286-56-0.mol

Synonyms:Phenyl-d5 isocyanate;83286-56-0;1,2,3,4,5-pentadeuterio-6-isocyanatobenzene;SCHEMBL6375900;1-Isocyanato(~2~H_5_)benzene;DTXSID10584063;Phenyl-d5 isocyanate, 98 atom % D

Chemical Property of Phenyl-d5 isocyanate

Chemical Property:

• Melting Point: −30 °C(lit.)
• Refractive Index: n20/D 1.535(lit.)
• Boiling Point: 162-163 °C(lit.)
• Flash Point: 132 °F
• PSA: 29.43000
• Density: 1.142 g/mL at 25 °C
• LogP: 1.65390
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 124.068497513
• Heavy Atom Count: 9
• Complexity: 121

Purity/Quality:

99% ^*data from raw suppliers

PhenylIsocyanate-d5 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,T+
• Statements: 23/24/25-34-42/43-52-42-26-22-10
• Safety Statements: 26-27-36/37/39-45-28-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N=C=O
• Isomeric SMILES: [2H]C1=C(C(=C(C(=C1[2H])[2H])N=C=O)[2H])[2H]
• Uses: Phenyl Isocyanate-d5 is an isotope labelled compound of Phenyl Isocyanate (P335375), used in the synthesis of cyanopyridine derivatives in the search for anticancer compounds. It is also used in the synthesis of aminobenzimidazole derivatives with phenylcyclohexyl acetic groups showing antiobesity-antidiabetic activity.

Technology Process of Phenyl-d5 isocyanate

There total 7 articles about Phenyl-d5 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: 50.0%

aniline-d7 (14545-23-4) → phenyl isocyanate-D5 (83286-56-0)

Guidance literature:

Reference yield:

bis(trichloromethyl) carbonate (32315-10-9) + aniline-d5 (4165-61-1) → phenyl isocyanate-D5 (83286-56-0)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c1ob05636k

Reference yield:

benzoic acid-2,3,4,5,6-d5 (1079-02-3) → phenyl isocyanate-D5 (83286-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / dichloromethane / 8 h / Reflux; Inert atmosphere

2: sodium azide / benzene; water / 24 h

3: benzene / 6 h / Reflux; Inert atmosphere

With thionyl chloride; sodium azide; In dichloromethane; water; benzene; 3: |Curtius Rearrangement;

DOI:10.1021/jo4003008

upstream raw materials:

aniline-d₇

bis(trichloromethyl) carbonate

aniline-d5

benzoic acid-2,3,4,5,6-d5

Refernces

• 1、 Kumar, Amrendra,Tadigoppula, Narender. "Synthesis of Unprotected and Highly Substituted Indoles by the Ruthenium(II)-Catalyzed Reaction of Phenyl Isocyanates with Diaryl/Diheteroaryl Alkynes/Ethyl-3-phenyl Propiolates". supporting information. p. 8 - 12. Retrieved 2021/01/13.
• 2、 Willwacher, Jens,Rakshit, Souvik,Glorius, Frank. "Investigating N-methoxy-N′-aryl ureas in oxidative C-H olefination reactions: An unexpected oxidation behaviour". supporting information; experimental part. p. 4736 - 4740. Retrieved 2011/08/06.