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Cas Database

622-16-2

622-16-2

Identification

  • Product Name:Benzenamine,N,N'-methanetetraylbis-

  • CAS Number: 622-16-2

  • EINECS:210-721-4

  • Molecular Weight:194.236

  • Molecular Formula: C13H10N2

  • HS Code:

  • Mol File:622-16-2.mol

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

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 77 Articles be found

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.

Probing Interligand Electron Transfer in the 1MLCT S1 Excited State of trans-Mo2L2L′2 Compounds: A Comparative Study of Auxiliary Ligands and Solvents

Jiang, Changcheng,Young, Philip J.,Brown-Xu, Samantha E.,Kender, William T.,Hamilton, Ewan J. M.,Gallucci, Judith C.,Chisholm, Malcolm H.

, p. 9660 - 9668 (2017)

The interligand charge dynamics of the lowest singlet metal-to-ligand charge-transfer states (1MLCT S1 states) of a series of quadruply bonded trans-Mo2(NN)2(O2C-X)2 paddlewheel compounds are investigated, where NN is a π-accepting phenylpropiolamidinate ligand and O2C-X (X = Me, tBu, TiPB, or CF3) is an auxiliary carboxylate ligand. The compounds show strong light absorption in the visible region due to MLCT transitions from the Mo2 center to the NN ligands. The transferred electron density was followed by femtosecond time-resolved infrared (fs-TRIR) spectroscopy with vibrational reporters such as the ethynyl groups on the NN ligands. The observed fs-TRIR spectra show that these compounds have asymmetric 1MLCT S1 excited states where the transferred electron mainly resides on a single NN ligand. The presence of interligand electron transfer (ILET) is suggested to explain the shape of the ν(C=C) bands and the influence of auxiliary ligands and solvents on the interligand electronic coupling. The ILET in the 1MLCT S1 state is shown to be sensitive to the functional groups on the auxiliary ligands while being less responsive to changes in solvents.

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.

Synthesis and Properties of N,N′-Disubstituted Ureas and Their Isosteric Analogs Containing Polycyclic Fragments: XI. 1-[(Adamantan-1 yl)alkyl]-3-arylselenoureas

Kuznetsov, Ya. P.,Rasskazova,Pitushkin,Eshtukov,Vasipov,Burmistrov,Butov

, p. 1036 - 1046 (2021/09/08)

Abstract: A series of N,N′-disubstituted selenoureas containing an adamantane fragmenthave been synthesized in 23–75% yields. Procedures for the isolation andpurification of aromatic isoselenocyanates have been improved. The chemicalshift of the C=Se carbon nucleus in the 13C NMRspectra of selenoureas has been refined. The synthesized selenoureas have beenfound to be promising as inhibitors of not only epoxide hydrolase (sEH-H) butalso phosphatase domains (sEH-P) of human soluble epoxide hydrolase.

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.

Synthesis of 1,2,4-oxadiazolidines via [3+2] cycloaddition of nitrones with carbodiimides

Chen, Yuan,Fuyue, Liuting,Wang, Gangqiang,Wang, Hang,Lu, Chun,Guo, Haibing,St. Amant, Chiara,Sun, Shaofa,Xing, Yalan

supporting information, p. 4329 - 4332 (2019/03/19)

An efficient [3+2] cycloaddition of nitrones and carbodiimides has been developed. This 1,3-dipolar cycloaddition features high regioselectivity, mild and metal-free conditions, excellent functional group compatibility, and a broad substrate scope. The X-ray structures of two regio-isomers confirmed the regioselectivity of this transformation.

RE[N(SiMe3)2]3-Catalyzed Guanylation/Cyclization of Amino Acid Esters and Carbodiimides

Lu, Chengrong,Gong, Chao,Zhao, Bei,Hu, Lijuan,Yao, Yingming

, p. 1154 - 1159 (2018/02/10)

The example of rare-earth metal-catalyzed guanylation/cyclization of amino acid esters and carbodiimides is well-established, forming 4(3H)-2-alkylaminoquinazolinones in 65-96% yields. The rare-earth metal amides RE[N(TMS)2]3 (RE = Y, Yb, Nd, Sm, La; TMS = SiMe3) showed high activities, and La[N(TMS)2]3 performed best for a wide scope of the substrates.

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.

Process route upstream and downstream products

Process route

C,N-Diphenylnitrilimine
231289-36-4

C,N-Diphenylnitrilimine

1-aza-cyclohepta-1,2,4,6-tetraene
62248-95-7

1-aza-cyclohepta-1,2,4,6-tetraene

benzonitrile
100-47-0

benzonitrile

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
Conditions Yield
In diethyl ether; ethanol; methylbutane; at -188.1 ℃; Irradiation;
bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
Conditions Yield
With iodine; triethylamine; triphenylphosphine; In dichloromethane; for 0.0833333h; Sonication;
92%
With triphenylphosphine dibromide 1:1 addition complex; triethylamine; In dichloromethane; at 0 ℃; for 60h;
90%
With bromine; triethylamine; triphenylphosphine; In benzene; for 1.5h; Heating;
5.2%
With bromine; triethylamine; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.5h;
With Burgess Reagent;
With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane; at 0 ℃;
With sodium sulfate; mercury(II) oxide; In dichloromethane; at 20 ℃;
phenyl isocyanate
1197040-29-1,931-54-4

phenyl isocyanate

phenyl isoselenocyanate
4426-68-0

phenyl isoselenocyanate

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
Conditions Yield
With selenium; sodium hydroxide; In dichloromethane; water; at 20 ℃; for 2.5h;
42%
phenyl isocyanate
103-71-9

phenyl isocyanate

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
Conditions Yield
compound 8 (polystyrene-anchored triphenylarsine oxide); at 150 - 190 ℃; for 0.5h;
88%
With oxo(phthalocyaninato)titanium(IV); at 170 ℃; for 144h; Inert atmosphere; Neat (no solvent);
78%
2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide; a.) r.t. to 140 deg C, 3 h, b.) heating, 2 h;
76%
O=P(MeNCH2CH2)3N; at 180 - 210 ℃; for 5.5h;
65%
C5H5Mn(CO)3; In xylene; Heating;
43%
at 180 ℃; im geschlossenen Rohr;
With 2,5-dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide; at 50 ℃;
With 1-ethyl-2,5-dihydro-phosphole; at 160 ℃;
With 3-methyl-1-phenyl-3-phospholene; at 160 ℃;
With triphenylarsineoxide; In xylene; at 90 ℃; for 1.5h;
With 3-Methyl-1-phenyl-2-phospholene 1-oxide; Inert atmosphere;
With Ta(NtBu)(CH2CMe2Ph)3/SiO2; In n-heptane; for 24h; Inert atmosphere; Schlenk technique; Reflux;
phenyl isocyanate
103-71-9

phenyl isocyanate

Phenyl azide
622-37-7

Phenyl azide

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
Conditions Yield
With triphenylphosphine; In dichloromethane; at 20 ℃;
N,N-diphenylthiourea
102-08-9

N,N-diphenylthiourea

2-hydroxypyridin
142-08-5

2-hydroxypyridin

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
Conditions Yield
With di-2-pyridyl thionocarbonate; dmap; In acetonitrile; for 0.5h; Ambient temperature;
84%
phenyl isocyanate
103-71-9

phenyl isocyanate

acetophenone
98-86-2

acetophenone

phenyl(1-phenylethylidene)amine
1749-19-5

phenyl(1-phenylethylidene)amine

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
Conditions Yield
phenyl isocyanate; acetophenone; In toluene; at 110 ℃; for 54h; Inert atmosphere;
With water; In toluene; Inert atmosphere;
69%
31%
2,4-Diphenyl-5-[(E)-phenylimino]-[1,2,4]thiadiazolidin-3-one
77303-41-4

2,4-Diphenyl-5-[(E)-phenylimino]-[1,2,4]thiadiazolidin-3-one

phenyl isocyanate
103-71-9

phenyl isocyanate

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
Conditions Yield
With triphenylphosphine; In acetonitrile; for 24h;
77%
70%
methyl dichlorophosphite
3279-26-3

methyl dichlorophosphite

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

methoxy-4-oxo-1,3-diphenyl-1,3-diaza-2-phosphetidin-4-one

methoxy-4-oxo-1,3-diphenyl-1,3-diaza-2-phosphetidin-4-one

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
Conditions Yield
With triethylamine; In diethyl ether; at 20 - 35 ℃;
26%
25%
N-phenylbenzamidine
1527-91-9

N-phenylbenzamidine

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

N<sup>2</sup>-Phenylbenzamidin-N<sup>2</sup>-ium acetate

N2-Phenylbenzamidin-N2-ium acetate

bis(diphenyl)urea
102-07-8

bis(diphenyl)urea

Conditions
Conditions Yield
With [bis(acetoxy)iodo]benzene; In dichloromethane; at 25 ℃;
26%
39%
30%

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