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622-16-2

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622-16-2 Usage

Preparation

Triphenylphosphine (2.62 g, 0.01 mol) in THF (10 mL) was added dropwise to N,N'-diphenylthiourea (2.28 g, 0.01 mol) and diethyl azodicarboxylate (1.74 g, 0.01 mol) in THF (20 mL) at room temperature. After standing overnight, the solvent was removed under reduced pressure and the residue was extracted with light petroleum (bp 30–60 C°) to separate soluble material from the remainder. The light petroleum extract was concentrated and distilled to give diphenylcarbodiimide; bp 85–90 C°/ 0.2 mmHg, 1.27 g, 65%. A further development of the method by immobilization of DEAD effects an easily separable (insoluble) and non-explosive reagent in Mitsunobu reactions. The methyl azodicarboxylate reagent immobilized on polystyrene 1742 functions well in Mitsunobu reactions and gives yields comparable to those obtained with soluble DEAD. Diphenylcarbodiimide was obtained in 41% yield.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 2613, 1986 DOI: 10.1021/jo00363a046Synthetic Communications, 7, p. 387, 1977 DOI: 10.1080/00397917708050769

Check Digit Verification of cas no

The CAS Registry Mumber 622-16-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 2 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 622-16:
(5*6)+(4*2)+(3*2)+(2*1)+(1*6)=52
52 % 10 = 2
So 622-16-2 is a valid CAS Registry Number.
InChI:InChI=1/C13H10N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h1-10H

622-16-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N'-diphenylmethanediimine

1.2 Other means of identification

Product number -
Other names Ph-N=C=N-Ph

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:622-16-2 SDS

622-16-2Relevant articles and documents

Synthesis, Structure, and Photophysical Properties of Mo2(NN)4 and Mo2(NN)2(TiPB)2, Where NN = N,N′-Diphenylphenylpropiolamidinate and TiPB = 2,4,6-Triisopropylbenzoate

Jiang, Changcheng,Young, Philip J.,Durr, Christopher B.,Spilker, Thomas F.,Chisholm, Malcolm H.

, p. 5836 - 5844 (2016)

Two dimolybdenum compounds featuring amidinate ligands with a bond, Mo2(NN)4 (I), where NN = N,N′-diphenylphenylpropiolamidinate, and trans-Mo2(NN)2(TiPB)2 (II), where TiPB = 2,4,6-triisopropylbenzoate, have been prepared and structurally characterized by single-crystal X-ray crystallography. Together with Mo2(DAniF)4 (III), where DAniF = N,N′-bis(p-anisyl)formamidinate, all three compounds have been studied with steady-state UV-vis, IR, and time-resolved spectroscopy methods. I and II display intense metal to ligand charge transfer (MLCT). Singlet state (S1) lifetimes of I-III are determined to be 0.7, 19.1, and 2.0 ps, respectively. All three compounds have long-lived triplet state (T1) lifetimes around 100 μs. In femtosecond time-resolved infrared (fs-TRIR) experiments, one band is observed at the S1 state for I but two for II, which indicate different patterns of charge distribution. The electron would have to be localized on one NN ligand in I and partially delocalized over two NN ligands in II to account for the observations. The result is a standard showcase of excited-state mixed valence in coordination compounds.

Synthesis of 1,4-diphenyl-3-phenylimino-1,2-dihydro-1,2,4-triazolium hydroxide (nitron)

Kriven'ko,Morozova

, p. 506 - 507 (2006)

1,4-Diphenyl-3-phenylimino-1,2-dihydro-1,2,4-triazolium hydroxide (Nitron) is prepared by the reaction of Pb3O4 with diphenylthiourea, followed by the reaction of the obtained diphenylcarbodiimide with phenylhydrazine to form triphenylaminoguanidine, whose heterocyclization yields 1,4-diphenyl-3-phenyl-imino-1,2-dihydro-1,2,4-triazole, which is subsequently oxidized. Pleiades Publishing, Inc., 2006.

A Mild Photocatalytic Synthesis of Guanidine from Thiourea under Visible Light

Saetan, Trin,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit

supporting information, p. 7864 - 7869 (2020/11/02)

In this work, we developed the catalytic guanylation of thiourea using Ru(bpy)3Cl2 as a photocatalyst under irradiation by visible light. The conversion of various thioureas to the corresponding guanidines was achieved using 1-5 mol % of photocatalyst in a mixture of water and ethanol at room temperature. Key benefits of this reaction include the use of photoredox catalyst, low-toxicity solvents/base, ambient temperature, and an open-flask environment.

A facile method for the preparation of carbodiimides from thioureas and (Boc)2O

Wu, He,Sun, Yan-Fang,Zhang, Chen,Miao, Chun-Bao,Yang, Hai-Tao

supporting information, p. 739 - 742 (2018/01/27)

A concise method for the preparation of carbodiimides from thioureas using di-tert-butyl dicarbonate [(Boc)2O] as the dehydrosulfurizative reagent has been developed. Using DMAP as the catalyst, a variety of symmetric and asymmetric 1,3-diaryl thioureas were converted into the corresponding carbodiimides efficiently in a short time.

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