diphenylcarbodiimide

Base Information

• Chemical Name: diphenylcarbodiimide
• CAS No.: 622-16-2
• Molecular Formula: C13H10N2
• Molecular Weight: 194.236
• European Community (EC) Number: 210-721-4
• NSC Number: 159432
• DSSTox Substance ID: DTXSID3060746
• Nikkaji Number: J129.495D
• Mol file: 622-16-2.mol

Synonyms:Carbodiimide,diphenyl- (6CI,8CI);1,3-Diphenylcarbodiimide;Diphenylcarbodiimide;N,N'-Diphenylcarbodiimide;N,N'-Methanetetraylbis(benzenamine);NSC 159432;

Chemical Property of diphenylcarbodiimide

Chemical Property:

• Melting Point: 169°C
• Refractive Index: 1.5014 (estimate)
• Boiling Point: 331 °C at 760 mmHg
• Flash Point: 146.1 °C
• PSA: 24.72000
• Density: 0.99 g/cm³
• LogP: 3.82370
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 194.084398327
• Heavy Atom Count: 15
• Complexity: 201

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N=C=NC2=CC=CC=C2

Technology Process of diphenylcarbodiimide

There total 91 articles about diphenylcarbodiimide 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: 94.0%

N-(1,3-thiazol-2-yl)triphenyliminophosphorane (69982-05-4) + phenyl isocyanate (103-71-9) → 3-Phenyl-2-phenylimino-thiazolo<3,2-a>-1,3,5-triazin-4-on (88012-13-9) + 1,3-Diphenylcarbodiimide (622-16-2)

Guidance literature:

In benzene; for 5h; Ambient temperature;

Reference yield: 92.0%

bis(diphenyl)urea (102-07-8) → 1,3-Diphenylcarbodiimide (622-16-2)

Guidance literature:

With iodine; triethylamine; triphenylphosphine; In dichloromethane; for 0.0833333h; Sonication;

DOI:10.1007/s00706-016-1761-3

Reference yield: 88.0%

phenyl isocyanate (103-71-9) → 1,3-Diphenylcarbodiimide (622-16-2)

Guidance literature:

compound 8 (polystyrene-anchored triphenylarsine oxide); at 150 - 190 ℃; for 0.5h;

DOI:10.1021/jo00172a044

upstream raw materials:

1,5-diphenyltetrazole

3-phenyl-4-phenylimino-[1,3]thiazetidin-2-one

N,N',N''-triphenylguanidine

1,1-diphenylthiourea

Downstream raw materials:

phenyl-(3-phenyl-3H-[1,2,3]triazol-4-yl)-amine

6-methyl-3-phenyl-2-phenylimino-2,3-dihydro-[1,3]oxazin-4-one

N,N'-diphenyl-N''-p-tolyl-guanidine

4-(N'-phenyl-ureido)-benzoic acid anilide

Refernces

Substituent effect on the transition from ionic to covalent bonding in triphenylphosphonium ylide derivatives: Reactivity of 3-methyl-2,2,2-triphenyl-2H-cyclohepta[d][1,2λ⁵]oxaphosphole with heterocumulenes

10.1039/b109076n

The research investigates the substituent effect on the transition from ionic to covalent bonding in triphenylphosphonium ylide derivatives, focusing on the reactivity of 3-methyl-2,2,2-triphenyl-2H-cyclohepta[d][1,2λ5]oxaphosphole (1a) with heterocumulenes. The study employs X-ray crystal analysis, 31P and 13C NMR spectral studies, and chemical shift correlation with P1–O1 bond lengths to establish that compounds 1a–d exist as resonance hybrids of an oxaphosphole structure (A) and phosphonium ylide structures (B and C). The experiments involve the synthesis of 1a through the reaction of 2-chlorotropone with triphenylphosphonium ylide and subsequent reactions with phenyl isocyanate, diphenylcarbodiimide, and phenyl isothiocyanate to form heteroazulenes. The analyses include NMR, IR, and mass spectrometry, as well as elemental analysis, to characterize the products and confirm the structural hypotheses.