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Cas Database

103-71-9

103-71-9

Identification

  • Product Name:Phenyl isocyanate

  • CAS Number: 103-71-9

  • EINECS:203-137-6

  • Molecular Weight:119.123

  • Molecular Formula: C7H5NO

  • HS Code:29291000

  • Mol File:103-71-9.mol

Synonyms:Benzene, isocyanato-;Carbanil;Isocyanatobenzene;Mondur P;Phenyl carbonimide;Fenylisokyanat;Isocyanic acid, phenyl ester;Karbanil;

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Safety information and MSDS view more

  • Pictogram(s):VeryT+

  • Hazard Codes:T+,T,C

  • Signal Word:Danger

  • Hazard Statement:H226 Flammable liquid and vapourH302 Harmful if swallowed H314 Causes severe skin burns and eye damage H317 May cause an allergic skin reaction H330 Fatal if inhaled H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled H335 May cause respiratory irritation H400 Very toxic to aquatic life H411 Toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention . Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Isocyanates, aliphatic thiocyanates, and related compounds/

  • Fire-fighting measures: Suitable extinguishing media If material on fire or involved in fire: Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. (ERG, 2016) 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. Personal protection: chemical protection suit including self-contained breathing apparatus. Ventilation. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Decontamination of spilled isocyanates and disposal of isocyanate waste are best conducted by using aqueous ammonia (3-8% concentrated ammonia solution in 90-95% water with 0.2-5% liquid detergent) or aqueous sodium carbonate (5-10% sodium carbonate in 90-95% water and 0.2-5% liquid detergent). An alcoholic solution (50% ethanol, isopropyl alcohol, or butanol; 45% water; and 5% concentrated ammonia) may be preferred because of the low miscibility of isocyanates with water. /Isocyanates/

  • 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. Fireproof. Keep in a well-ventilated room. Dry.Isocyanates are transported in railroad tank cars, tank trucks, tanks in ships, containers, and drums. They are stored in steel tanks and processed in steel equipment. For long-term storage stainless steel is recommended. To avoid contamination by atmospheric moisture, a dry air or inert gas blanket is essential. /Isocyanates/

  • 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 273 Articles be found

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Hoshino et al.

, p. 3097 (1952)

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Barrett,Porter

, p. 3434 (1941)

CARBONYLATION OF NITROBENZENE WITH RUTHENIUM CLUSTERS

Basu, Amitabha,Bhaduri, Sumit,Khwaja, Hanif

, p. C28 - C30 (1987)

Evidence is presented for the participation of cluster intermediates in the carbonylation of nitrobenzene.

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King et al.

, p. 351 (1978)

-

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Kurita,K. et al.

, p. 2070 - 2071 (1976)

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Carbamoyl complexes as a source of isocyanates or carbamyl chlorides

Giannoccaro, Potenzo,Tommasi, Immacolata,Aresta, Michele

, p. 13 - 18 (1994)

Isocyanates or carbamyl chlorides have been prepared by reaction of carbamoyl complexes of nickel and palladium with CuCl2.Isocyanates are selectively produced from the carbamoyl complexes of primary amines, , (L=2,6-bis(diphenylphosphinomethyl) pyridine; R=C6H5, p-CH3C6H4, or p-ClC6H4)) and , whereas carbamoyl complexes of secondary amines, such as , afford carbamyl chloride.As expected, the reaction of the resulting isocyanates or carbamyl chlorides in situ with alcohols or amines produces carbamates or N,N'-substituted ureas, respectively.Key words: Carbamyl chloride; Carbamate; Carboxamide; Chloroformamide; Complex; Isocyanates; Palladium; Phosphine; Synthesis

Preferred Binding of Carboxylates by Chiral Urea Derivatives Containing α-Phenylethyl Group

Cortés-Hernández, Mayra,Rojas-Lima, Susana,Hernández-Rodríguez, Marcos,Cruz-Borbolla, Julián,López-Ruiz, Heraclio

, p. 416 - 424 (2016)

An efficient, simple protocol for the synthesis of a new family of chiral ureas 1 – 4 is described. The binding properties of 1 – 4 toward different anion (acetate, benzoate, fluoride, and chloride) have been studied by1H-NMR titration and have been observed in the case of 4 is a selective receptor for acetate. The theoretical calculation M06/6-311+G(d,p) helped us explain the binding properties observed. The most interesting observation is that this calculated structure is consistent with expected, based on the concept of allylic 1,3-strain (A1,3strain). When chiral caboxylates were studied, urea 1 was the best in discriminating between enantiomers.

Design, Synthesis and Biological Evaluation of a New Series of 1-Aryl-3-{4-[(pyridin-2-ylmethyl)thio]phenyl}urea Derivatives as Antiproliferative Agents

Zhang, Chuanming,Tan, Xiaoyu,Feng, Jian,Ding, Ning,Li, Yongpeng,Jin, Zhe,Meng, Qingguo,Liu, Xiaoping,Hu, Chun

, (2019)

To discover new antiproliferative agents with high efficacy and selectivity, a new series of 1-aryl-3-{4-[(pyridin-2-ylmethyl)thio]phenyl}urea derivatives (7a–7t) were designed, synthesized and evaluated for their antiproliferative activity against A549, HCT-116 and PC-3 cancer cell lines in vitro. Most of the target compounds demonstrated significant antiproliferative effects on all the selective cancer cell lines. Among them, the target compound, 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-{4-{{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}thio}phenyl}urea (7i) was identified to be the most active one against three cell lines, which was more potent than the positive control with an IC50 value of 1.53 ± 0.46, 1.11 ± 0.34 and 1.98 ± 1.27 μM, respectively. Further cellular mechanism studies confirmed that compound 7i could induce the apoptosis of A549 cells in a concentration-dependent manner and elucidated compound 7i arrests cell cycle at G1 phase by flow cytometry analysis. Herein, the studies suggested that the 1-aryl-3-{4-[(pyridin-2-ylmethyl)thio]phenyl}urea skeleton might be regarded as new chemotypes for designing effective antiproliferative agents.

SYNTHESIS OF ISOCYANATES BY THE CARBONYLATION OF AROMATIC NITRO COMPOUNDS, AZOBENZENE, AND AZOXYBENZENE ON PALLADIUM CATALYSTS CONTAINING MOLYBDENUM AND VANADIUM

Lapidus, A. L.,Manov-Yuvenskii, V. I.,Petrovskii, K. B.

, p. 2282 - 2284 (1981)

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Multijet oscillating disc millireactor: A novel approach for continuous flow organic synthesis

Liguori, Lucia,Bjorsvik, Hans-Rene

, p. 997 - 1009 (2011)

This report discloses proof of concept and experimental results from a project involving design, development, and investigation of a novel approach for flow chemistry and the realization of equipment operating according to this new approach. This device is named multijet oscillating disk (MJOD) reactor and is dedicated to continuous flow organic synthesis in milliscale. Characteristics such as the importance of the multijet disk unit, with or without oscillating, and possible limitations, such as back-mixing, have been explored, and the flow system is benchmarked with other technologies. Several well-known reactions and syntheses usefully both in the chemical industry as well as in the research laboratory have been conducted using the new system, which have been benchmarked with batch- and microreactor protocols. In particular the Haloform reaction, the Nef reaction, nucleophilic aromatic substitution, the Paal-Knorr pyrrole synthesis, sodium borohydride reduction, O-allylation, the Suzuki cross-coupling reaction, the Hofmann rearrangement and N-acylation were performed during the study of the MJOD reactor performance. Our investigations revealed that the MJOD millireactor system can produce various organic compounds at a high rate concomitant with an excellent selectivity. A Hofmann rearrangement was conducted, a reaction that involves handling of a slurry of the substrate. This reaction was successfully conducted, achieving a quantitative conversion into the target molecule.

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Manov-Yuvenskii,Nefedov

, (1979)

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CO2 conversion to phenyl isocyanates by uranium(vi) bis(imido) complexes

Maria, Leonor,Bandeira, Nuno A. G.,Mar?alo, Joaquim,Santos, Isabel C.,Gibson, John K.

, p. 431 - 434 (2020)

Uranium(vi) trans-bis(imido) complexes [U(κ4-{(tBu2ArO)2Me2-cyclam})(NPh)(NPhR)] react with CO2 to eliminate phenyl isocyanates and afford uranium(vi) trans-[OUNR]2+ complexes, including [U(κ4-{(tBu2ArO)2Me2-cyclam})(NPh)(O)] that was crystallographically characterized. DFT studies indicate that the reaction proceeds by endergonic formation of a cycloaddition intermediate; the secondary reaction to form a dioxo uranyl complex is both thermodynamically and kinetically hindered.

The curtius rearrangement of acyl azides revisited - Formation of cyanate (R-O-CN)

Wentrup, Curt,Bornemann, Holger

, p. 4521 - 4524 (2005)

The Curtius rearrangement is a synthesis of isocyanates (R-N=C=O) by thermal or photochemical rearrangement of acyl acides and/or acylnitrenes. The photochemical rearrangement of benzoyl azide is now shown for the first time to produce a small amount of phenyl cyanate (Ph-O-CN) together with phenyl isocyanate. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

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Hanssen

, p. 5 (1850)

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CATALYTIC CARBONYLATION OF NITRO COMPOUNDS IN THE PRESENCE OF CARBONYL IONIC COMPLEXES OF Rh(I), Ir(I), Pd(I), AND Pd(II)

Abakumov, G. A.,Knyazeva, I. L.,Vavilina, N. N.,Gorbunova, L. V.,Zhivtsova, S. V.

, p. 1242 - 1245 (1984)

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Palladium-catalyzed reductive carbonylation of nitrobenzene for producing phenyl isocyanate

Nguyen, Thanh Tung,Tran, Anh Vy,Lee, Hye Jin,Baek, Jayeon,Kim, Yong Jin

, (2019)

Direct reductive carbonylation of nitrobenzene to phenyl isocyanate with carbon monoxide was performed using various types of palladium catalysts together with many types of N-donor ligands. The effect of reaction time, pressure, temperature, ligand amount, and molar ratio to establish the optimized conditions was also investigated. With this, we were able to achieve up to 100% conversion and 63.5% yield with PdCl2 and alkylimidazole system (1:3) within 2 h at 220 °C and 1400 psi of CO in toluene.

EFFECT OF CATALYST COMPOSITION AND REACTION CONDITIONS ON SYNTHESIS OF PHENYL ISOCYANATE BY CARBONYLATION OF NITROBENZENE

Manov-Yuvenskii, V. I.,Nefedov, B. K.,Smetanin, A. V.

, p. 1817 - 1819 (1980)

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Development of tyrosinase labile protecting groups for amines

Osborn, Helen M. I.,Williams, Nana Aba O.

, p. 3111 - 3113 (2004)

(Chemical Equation Presented) The development of two novel protecting groups for amines is described. Thus, a range of amines have been converted to ureas, and the deprotection of these upon exposure to mushroom tyrosinase (E.C. 1.14.18.1) has been demonstrated.

Reactivity of Carbamoyl Radicals: the First General and Convenient Free-radical Synthesis of Isocyanates

Minisci, Francesco,Coppa, Fausta,Fontana, Francesca

, p. 679 - 680 (1994)

The first free-radical synthesis of isocyanates was performed by oxidation of oxalic acid monoamides by S2O82-, catalysed by silver(I) and copper(II) salts, in a two-phase system.

A new and efficient palladium-catalyzed synthesis of a 2,3,4,5- tetrahydro-1H-2,4-benzodiazepine-1,3-dione derivative

Bocelli, Gabriele,Catellani, Marta,Cugini, Federica,Ferraccioli, Raffaella

, p. 2623 - 2624 (1999)

The palladium-catalyzed intramolecular cyclization of 1-butyl-1(o- iodobenzyl)-3-phenylurea 1 at 80°C in the presence of carbon monoxide at atmospheric pressure gives the corresponding 2,3,4,5-tetrahydro-1H-2,4- benzodiazepine-1,3-dione derivative 2 in 91% yield. Yield and selectivity are strongly affected by the solvent.

Synthesis and biological evaluation of novel 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives as potential antitumor agents

Hu, Min,Meng, Nana,Xia, Yong,Xu, Youzhi,Yu, Luoting,Zeng, Xiuxiu,Zhou, Shuyan

, (2021)

A novel series of 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives were synthesized and evaluated against different tumor cell lines. Experiments in vitro showed that these derivatives could inhibit the proliferation of two kinds of human cancer cell lines (HepG2, HCT116) at low micromolar concentrations and the most potent analog 5q possessed broad-spectrum antiproliferative activity. Experiments in vivo demonstrated that 5q could effectively prolong the longevity of colon carcinoma-burdened mice and slow down the progression of cancer cells by suppression of angiogenesis and the induction of apoptosis and necrosis.

Continuous Flow Synthesis of Urea-Containing Compound Libraries Based on the Piperidin-4-one Scaffold

Riesco-Domínguez, Alejandra,Blanco-Ania, Daniel,Rutjes, Floris P. J. T.

, p. 1312 - 1320 (2018)

The advantages of performing reactions in continuous flow vs. the classic batch processes render flow chemistry a suitable technique for library synthesis. Inspired by our recent work to create fluorine-containing nitrogen heterocycles and by the potentia

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Hofmann,A. W.

, p. 655 (1870)

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One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines

Kim, Hee-Kwon,Lee, Anna

, p. 4890 - 4892 (2016)

A highly efficient one-pot procedure for the synthesis of carbamates and thiocarbamates has been described. In the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, the isocyanate intermediates were generated in situ for further reactions with alcohols and thiols to afford the desired carbamates and thiocarbamates in high yields.

Synthesis of new coumarin compounds and its hypoglycemic activity and structure-activity relationship

Qi, Gang,Zhang, Wenguo

, p. 9835 - 9839 (2013)

Novel coumarin compounds were designed and synthesized by combining the active moieties of hypoglycemic drugs. The coumarin compounds were made by sulfanilamide with isocynate, the intermediate sulfanilamide was formed from coumarin by chlorosulfonated and aminated. These targeted compounds were characterized by FT-IR, 1H NMR and MS spectra and their hypoglycemic activities were evaluated in mice. The preliminary results showed that some compounds exhibited evident hypoglycemic effect (P > 0.01, CMC-Na as negative control). The relationship between these compounds structure with their hypoglycemic activities were studied in order to design new antidiabetic agents.

Matrix isolation, time-resolved IR, and computational study of the photochemistry of benzoyl azide

Pritchina, Elena A.,Gritsan, Nina P.,Maltsev, Alexander,Bally, Thomas,Autrey, Tom,Liu, Yonglin,Wang, Yuhong,Toscano, John P.

, p. 1010 - 1018 (2003)

It was shown recently on the basis of DFT calculations (N. P. Gritsan and E. A. Pritchina, Mendeleev Commun., 2001, 11, 94) that the singlet states of aroylnitrenes undergo tremendous stabilization due to an extra N-O bonding interaction. To test experimentally the multiplicity and the structure of the lowest state of benzoylnitrenes we performed a study of their photochemistry in Ar matrices at 12 K. Formation of two species was observed on irradiation of benzoyl azide (1b) and its 4-acetyl derivative (1c). One of these species has an IR spectrum, which is consistent with that of isocyanate (2b,c). The IR and UV spectra of the second intermediate are in very good agreement with the calculated spectra of the singlet species (3b,c), whose structure is intermediate between that of a carbonylnitrene and an oxazirene. We further examined the photochemistry of benzoyl azide in solution at ambient temperatures by nanosecond time-resolved IR methods and obtained additional evidence for the singlet ground state of benzoylnitrene as well as insight into its reactivity in acetonitrile, cyclohexane, and dichloromethane. The above experiments were accompanied by quantum chemical calculations which included also a thorough investigation of the parent species, formylnitrene, at different levels of theory.

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Magee,Daniels

, p. 829 (1957)

-

-

Johnson,Daughhetee

, p. 246 (1964)

-

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Mukaiyama,T. et al.

, p. 4381 - 4384 (1961)

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Synthesis of furan derivatives. LXXXVII. Kinetic studies of the thermal Curtius rearrangement of 2-benzofuroyl azide and related compounds

Saikachi,Kitagawa,Nasu,Sasaki

, p. 237 - 244 (1981)

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Preparation and photocatalytic property of hexagonal cylinder-like bipods ZnO microcrystal photocatalyst

Liu, Yumin,Hua, Lv,Li, Shuangqing,Xing, Xinyan,Xi, Guoxi

, p. 443 - 449 (2012)

Single crystalline ZnO with hexagonal cylinder-like bipods morphologies were successfully synthesized via a cationic surfactant-assisted hydrothermal microemulsion route. The structure, morphologies and properties of the as-prepared samples were determined using X-ray diffraction, scanning electron microscopy, photoluminescence spectrum and Ultraviolet and Visible absorption spectroscopy. The photocatalytic activities of the obtained products were evaluated by the degradation of Reactive Brilliant Red K-2BP in aqueous solution under a variety of conditions. Under the optimum condition, approximately 99.5% decolorization efficiency within 45 min and 65.3% TOC removal efficiency within 3 h were achieved, which were higher than that by the commercial ZnO. Moreover, the degradation products were analyzed by a gas chromatography coupled with mass spectrometry system and the probable pathways for the formation of the intermediates were proposed. The photocatalytic results indicated that the as-prepared ZnO showed good photocatalytic activity and it could be considered as a promising photocatalyst for dyes wastewater treatment.

Kinetics of the homogeneous, unimolecular elimination reactions of ethyl oxamate, ethyl N,N-dimethyloxamate and ethyl oxanilate in the gas phase

Chacin, Esker V.,Tosta, Maria,Herize, Armando,Dominguez, Rosa M.,Alvarado, Ysaias,Chuchani, Gabriel

, p. 539 - 545 (2005)

The gas-phase elimination kinetics of the title compounds were determined over the temperature range 350-430°C and pressure range 35-240 Torr (1 Torr = 133.3 Pa). The reactions, which were carried out in a static reactor system, seasoned with allyl bromide and in the presence of a free radical inhibitor, are homogeneous, unimolecular and obey a first-order rate law. The temperature dependences of the overall rate coefficients are given by the following Arrhenius equations: for ethyl oxamate, log [k1 (s-1)] = (13.28±0.20)-(203.7±2.5)kJ mol-1 (2.303RT) -1, for ethyl N,N-dimethyloxamate, log [k1(s -1)] = (13.06±0.34)-(206.8±4.4)kJ mol -1(2.303RT)-1, and for ethyl oxanilate, log [k1 (s-1)] = (13.86±0.12)-(207.4±1.5)kJ mol -1(2.303RT)-1. The overall rates, the partial rates and the kinetic and thermodynamic parameters of these eliminations are presented and discussed. These reactions appear to proceed through moderately polar cyclic transition states. Copyright

EFFECT OF SOLVENT AND TRANSITION-METAL OXIDE AND CHLORIDE ON CATALYST ACTIVITY IN PHENYL ISOCYANATE SYNTHESIS BY NITROBENZENE CARBOXYLATION

Manov-Yuvenskii, V. I.,Nefedov, B. K.

, p. 816 - 819 (1981)

-

Porter,Young

, p. 1497 (1938)

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Bamberger,Destraz

, p. 1885 (1902)

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CATALYTIC SYNTHESIS OF ISOCYANATES BY CARBONYLATION OF NITRO COMPOUNDS IN THE PRESENCE OF 2 PROMOTED BY PYRIDINE AND PYRIDINE HYDROCHLORIDE

Manov-Yuvenskii, V. I.,Smetanin, A. V.,Nefedov, B. K.

, p. 1813 - 1817 (1980)

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Thermal Decomposition of Benzoyl Azide and Diazoacetone in the Gas Phase

Prokudin, V. G.,Sipyagin, A. M.,Kartsev, V. G.,Vozchikova, S. A.

, p. 1541 - 1544 (1988)

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Photoinduced Cascade Reaction of Tertiary Amines with Sulfonyl Azides: Synthesis of Amidine Derivatives

Ding, Rui,Chen, Hui,Xu, Yan-Li,Tang, Hai-Tao,Chen, Yan-Yan,Pan, Ying-Ming

, p. 3656 - 3660 (2019)

A metal-free cascade reaction of tertiary amines with sulfonyl azides promoted by acridinium salts under blue light irradiation was developed and provided amidine derivatives in moderate to good yields. Enamine was generated from tertiary amine via single-electron transfer promoted by acridinium salts, and the following [3+2] cyclization with sulfonyl azide and CH2N2 release afforded the desired products. (Figure presented.).

Coleman et al.

, p. 4534,4535 (1954)

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Reisch,Niemeyer

, p. 3247 (1968)

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Design, synthesis and structure-activity relationships of novel diaryl urea derivatives as potential EGFR inhibitors

Jiang, Nan,Bu, Yanxin,Wang, Yu,Nie, Minhua,Zhang, Dajun,Zhai, Xin

, (2016)

Two novel series of diaryl urea derivatives 5a-i and 13a-l were synthesized and evaluated for their cytotoxicity against H-460, HT-29, A549, and MDA-MB-231 cancer cell lines in vitro. Therein, 4-aminoquinazolinyl-diaryl urea derivatives 5a-i demonstrated significant activity, and seven of them are more active than sorafenib, with IC50 values ranging from 0.089 to 5.46 μM. Especially, compound 5a exhibited the most active potency both in cellular (IC50 = 0.15, 0.089, 0.36, and 0.75 μM, respectively) and enzymatic assay (IC50 = 56 nM against EGFR), representing a promising lead for further optimization.

CATALYTIC CARBONYLATION OF NITRO COMPOUNDS WITH CARBON MONOXIDE IN PRESENCE OF RHODIUM-CARBONYL HYDRIDE COMPLEX

Gorbunova, L. V.,Knyazeva, I. L.,Davydova, E. A.,Abakumov, G. A.

, p. 761 - 764 (1980)

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Synthesis and Crystal Structure of , a Ruthenium Cluster with a Phenyl Isocyanate Ligand

Bhaduri, Sumit,Khwaja, Hanif,Jones, Peter G.

, p. 194 - 195 (1988)

The ruthenium cluster = (Ph3P)2N> has been synthesised by intramolecular nucleophilic attack on CO and characterised by X-ray structure determination.

Palladium nitrosoarene complexes in reductive carbonylation of nitroarenes

Stromnova,Orlova

, p. 2286 - 2289 (2002)

The reactions of carbon monoxide with the palladium nitrosoarene complexes Pd2(μ-OCOR)2(-CH2C6H 4NO)2 (1, R = Me, CF3, But, or Ph) and Pd2(μ-OCOR)2(PhNC6H4NO) 2 (2, R = Me, CF3, But, or Ph) were studied. Complexes 1 contain the o-nitrosotoluene molecule metallated at the methyl group. In complexes 2, the phenyl-o-nitrosophenylamide ligand coordinated via two nitrogen atoms can be considered as a nitrosobenzene derivative bearing the NPh group in the ortho position of the Ph ring. It all cases, carbonylation of the complexes afforded the corresponding aryl isocyanates Ar-N=C=O or the products of their further transformations. The mechanism of reductive carbonylation of nitroarenes catalyzed by palladium compounds and the role of palladium nitrosoarene complexes as possible intermediates in this process are discussed.

Aminolysis of phenyl N-phenylcarbamate via an isocyanate intermediate: Theory and experiment

Ilieva, Sonia,Nalbantova, Didi,Hadjieva, Boriana,Galabov, Boris

, p. 6440 - 6449 (2013)

A comprehensive examination of the mechanism of the uncatalyzed and base-catalyzed aminolysis of phenyl N-phenylcarbamate by theoretical quantum mechanical methods at M06-2X/6-311+G(2d,2p) and B3LYP-D3/6-31G(d,p) levels, combined with an IR spectroscopic study of the reaction, was carried out. Three alternative reaction channels were theoretically characterized: concerted, stepwise via a tetrahedral intermediate, and stepwise involving an isocyanate intermediate. In contrast to dominating views, the theoretical results revealed that the reaction pathway through the isocyanate intermediate (E1cB) is energetically favored. These conclusions were supported by an IR spectroscopic investigation of the interactions of phenyl N-phenylcarbamate with several amines possessing varying basicities and nucleophilicities: n-butylamine, diethylamine, triethylamine, N-methylpyrrolidine, and trimethylamine. The reactivity of substituted phenyl N-phenylcarbamates in the aminolysis reaction was rationalized using theoretical and experimental reactivity indexes: electrostatic potential at nuclei (EPN), Hirshfeld and NBO atomic charges, and Hammett constants. The obtained quantitative relationships between these property descriptors and experimental kinetic constants reported in the literature emphasize the usefulness of theoretical parameters (EPN, atomic charges) in characterizing chemical reactivity.

Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides

Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong

supporting information, p. 2820 - 2826 (2021/02/01)

A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.

Crystal form substance of plant growth regulator, and preparation method thereof

-

Paragraph 0046; 0048-0050, (2021/06/23)

The invention relates to a crystal form substance of a plant growth regulator, and a preparation method thereof. The crystal form substance comprises the following cell parameters: alpha = 90 DEG, beta = 90 DEG and gamma = 90 DEG. The preparation method of the crystal form substance comprises the following steps: 1) purifying a crude product of the plant growth regulator to obtain a purified substance; and 2) culturing crystals from the purified product in a mixed solvent. The crystal form substance of the plant growth regulator provided by the invention is a single crystal type compound, and due to the single crystal form, the stability is high, and the bioavailability is more obvious than a polycrystal effect; and the preparation method breaks through the technical bottleneck that technicians in the field cannot obtain the single crystal substance added with the plant growth regulator at the present stage, and the method is simple and easy to obtain.

Discovery of Potent EGFR Inhibitors With 6-Arylureido-4-anilinoquinazoline Derivatives

Li, Meng,Xue, Na,Liu, Xingang,Wang, Qiaoyun,Yan, Hongyi,Liu, Yifan,Wang, Lei,Shi, Xiaowei,Cao, Deying,Zhang, Kai,Zhang, Yang

, (2021/06/14)

According to the classical pharmacophore fusion strategy, a series of 6-arylureido-4-anilinoquinazoline derivatives (Compounds 7a–t) were designed, synthesized, and biologically evaluated by the standard CCK-8 method and enzyme inhibition assay. Among the title compounds, Compounds 7a, 7c, 7d, 7f, 7i, 7o, 7p, and 7q exhibited promising anti-proliferative bioactivities, especially Compound 7i, which had excellent antitumor activity against the A549, HT-29, and MCF-7 cell lines (IC50 = 2.25, 1.72, and 2.81?μM, respectively) compared with gefitinib, erlotinib, and sorafenib. In addition, the enzyme activity inhibition assay indicated that the synthesized compounds had sub-micromolar inhibitory levels (IC50, 11.66–867.1?nM), which was consistent with the results of the tumor cell line growth inhibition tests. By comparing the binding mechanisms of Compound 7i (17.32?nM), gefitinib (25.42?nM), and erlotinib (33.25?nM) to the EGFR, it was found that Compound 7i could extend into the effective region with a similar action conformation to that of gefitinib and interact with residues L85, D86, and R127, increasing the binding affinity of Compound 7i to the EGFR. Based on the molecular hybridization strategy, 14 compounds with EGFR inhibitory activity were designed and synthesized, and the action mechanism was explored through computational approaches, providing valuable clues for the research of antitumor agents based on EGFR inhibitors.

METHODS AND COMPOUNDS FOR RESTORING MUTANT p53 FUNCTION

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Paragraph 0530, (2021/11/20)

Mutations in oncogenes and tumor suppressors contribute to the development and progression of cancer. The present disclosure describes compounds and methods to recover wild-type function to p53 mutants. The compounds of the present disclosure can bind to mutant p53 and restore the ability of the p53 mutant to bind DNA and activate downstream effectors involved in tumor suppression. The disclosed compounds can be used to reduce the progression of cancers that contain a p53 mutation.

Process route upstream and downstream products

Process route

2-phenyl-3-phenylcarbamoyloxy-acrylic acid ethyl ester

2-phenyl-3-phenylcarbamoyloxy-acrylic acid ethyl ester

phenyl isocyanate
103-71-9

phenyl isocyanate

ethyl 3-oxo-2-phenylpropanoate
17838-69-6

ethyl 3-oxo-2-phenylpropanoate

Conditions
Conditions Yield
beim Erhitzen;
2-(phenylaminocarbonyloxy)benzonitrile
70792-83-5

2-(phenylaminocarbonyloxy)benzonitrile

salicylonitrile
611-20-1

salicylonitrile

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
Conditions Yield
at 150 ℃; for 2h; Equilibrium constant; further temperatures, further solvent;
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

N-phenyl-N-nitrosourea
6268-32-2

N-phenyl-N-nitrosourea

benzene diazonium chloride
100-34-5

benzene diazonium chloride

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
Conditions Yield
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

phenyl carbamate
64-10-8

phenyl carbamate

benzene diazonium chloride
100-34-5

benzene diazonium chloride

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
Conditions Yield
<i>N</i>-benzoyl-<i>O</i>-(4-methoxy-benzoyl)-hydroxylamine
59101-33-6

N-benzoyl-O-(4-methoxy-benzoyl)-hydroxylamine

carbon dioxide
124-38-9,18923-20-1

carbon dioxide

phenyl isocyanate
103-71-9

phenyl isocyanate

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

4-methoxy-N-phenylbenzamide
7465-88-5

4-methoxy-N-phenylbenzamide

Conditions
Conditions Yield
phenyl-carbamoyl bromide

phenyl-carbamoyl bromide

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
Conditions Yield
at 85 - 100 ℃;
carbon monoxide
201230-82-2

carbon monoxide

N-butylamine
109-73-9,85404-21-3

N-butylamine

aniline
62-53-3

aniline

N,N'-di-n-butylurea
1792-17-2

N,N'-di-n-butylurea

N-butyl-N'-phenylurea
3083-88-3

N-butyl-N'-phenylurea

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
Conditions Yield
With oxygen; gold; In acetonitrile; at 45 ℃; for 24h; under 760.051 Torr;
41%
25%
2%
1,4-diphenyl-azetidin-2-one
13474-22-1

1,4-diphenyl-azetidin-2-one

Ketene
463-51-4

Ketene

benzylidene phenylamine
538-51-2

benzylidene phenylamine

phenyl isocyanate
103-71-9

phenyl isocyanate

Conditions
Conditions Yield
at 680 ℃; under 0.002 Torr; Yields of byproduct given;
5%
at 680 ℃; under 0.002 Torr; Yield given. Title compound not separated from byproducts;
5%
Conditions
Conditions Yield
at 600 ℃; under 15 Torr;
3,3-dimethyl-1-phenyl-4-<N-(phenyl)-(1'-methyl)-azomethinyl>-2-azetidinone
53490-03-2

3,3-dimethyl-1-phenyl-4--2-azetidinone

dimethylketene
598-26-5

dimethylketene

N,N'-bis(phenyl)-1,2-dimethylethane-1,2-diimine
5393-49-7

N,N'-bis(phenyl)-1,2-dimethylethane-1,2-diimine

phenyl isocyanate
103-71-9

phenyl isocyanate

Phenyl-[1,2,3-trimethyl-but-2-en-(E)-ylidene]-amine

Phenyl-[1,2,3-trimethyl-but-2-en-(E)-ylidene]-amine

Conditions
Conditions Yield
at 680 ℃; under 0.002 Torr;
78%
18%

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