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Cas Database

4903-36-0

4903-36-0

Identification

Synonyms:N-Phenyl-benzimidoyl chloride;N-phenylbenzenecarboxyimidoyl chloride;(N-phenyl)(benzyliden)(chloro)imine;N-PHENYLBENZIMIDOYL CHLORIDE;

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Safety information and MSDS view more

  • Hazard Codes:C

  • Signal Word:Danger

  • Hazard Statement:H314 Causes severe skin burns and eye damage

  • 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

Supplier and reference price

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  • Product Description
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:N-Phenylbenzimidoyl chloride 95%
  • Packaging:5g
  • Price:$ 241
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:N-Phenylbenzimidoyl chloride 95%
  • Packaging:1g
  • Price:$ 54.1
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:N-PHENYLBENZIMIDOYL CHLORIDE 95.00%
  • Packaging:5MG
  • Price:$ 504.24
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  • Manufacture/Brand:Adipogen Life Sciences
  • Product Description:N-Phenylbenzimidoyl chloride ≥95%(NMR)
  • Packaging:2.5 g
  • Price:$ 153
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Relevant articles and documentsAll total 56 Articles be found

Novel Conjugated s-Tetrazine Derivatives Bearing a 4H-1,2,4-Triazole Scaffold: Synthesis and Luminescent Properties

?wiatkowski, Marcin,Kudelko, Agnieszka,Maj, Anna

, (2022/01/20)

A series of new symmetrical s-tetrazine derivatives, coupled via a 1,4-phenylene linkage with a 4H-1,2,4-triazole ring, were obtained. The combination of these two rings in an extensively coupled system has significant potential applications, mainly in op

Br?nsted Base-Catalyzed Formal Reductive [3+2] Annulation of 4,4,4-Trifluorocrotonate and α-Iminoketones

Kondoh, Azusa,Terada, Masahiro

supporting information, p. 585 - 588 (2020/12/07)

A formal reductive [3+2] annulation of 4,4,4-trifluorocrotonate and α-iminoketones was developed under Br?nsted base catalysis. A single phosphazene base efficiently catalyzes the one-pot tandem reaction involving two mechanistically different elementary processes, namely the chemoselective reduction of an imine moiety of α-iminoketones with thiols as the reductant and the subsequent intermolecular Michael addition of an enolate of α-aminoketones concomitant with lactam formation. This operationally simple method provides β-trifluoromethyl-substituted γ-lactams with a tetrasubstituted carbon as a single diastereomer.

Synthesis of Imidoyl Chlorides Using Phosphorus Trichloride

Nguyen, T. L.,Popov, Yu. V.,Shishkin, E. V.,Shishkin, V. E.,Vo, T. L. Q.,Zotov, Yu. L.

, p. 849 - 851 (2021/06/12)

Abstract: The reaction of carboxamides with phosphorus trichloride under heating at 75–80°C for 1 h in the presence of a 4-dimethylaminopyridine catalyst was used to synthesize imidoyl chlorides in yields of 63–99%.

Regioselective Synthesis of Trisubstituted Quinoxalines Mediated by Hypervalent Iodine Reagents

Ito, Ryota,Miura, Kasumi,Suzuki, Noriyuki,Suzuki, Yumiko,Takehara, Ren

, p. 16892 - 16900 (2021/12/06)

A facile and regioselective synthesis of quinoxalines, an important motif in medicinal chemistry and materials sciences, was developed. Despite their prospective utility, the regioselective preparation of trisubstituted quinoxalines has not been previously established. In the reported system, hypervalent iodine reagents catalyzed the annulation between α-iminoethanones ando-phenylenediamines in a chemo/regioselective manner to afford trisubstituted quinoxalines. Excellent regioselectivities (6:1 to 1:0) were achieved using [bis(trifluoroacetoxy)iodo]benzene and [bis(trifluoroacetoxy)iodo]pentafluorobenzene as annulation catalysts.

Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis

K?ring, Laura,Sitte, Nikolai A.,Bursch, Markus,Grimme, Stefan,Paradies, Jan

supporting information, p. 14179 - 14183 (2021/09/03)

The metal-free catalytic hydrogenation of secondary carboxylic acid amides is developed. The reduction is realized by two new catalytic reactions. First, the amide is converted into the imidoyl chloride by triphosgene (CO(OCCl3)2) using novel phosphorus(V) catalysts. Second, the in situ generated imidoyl chlorides are hydrogenated in high yields by an FLP-catalyst. Mechanistic and quantum mechanical calculations support an autoinduced catalytic cycle for the hydrogenation with chloride acting as unusual Lewis base for FLP-mediated H2-activation.

Process route upstream and downstream products

Process route

phosphorus pentachloride
10026-13-8,874483-75-7

phosphorus pentachloride

N-Phenyl-benzimidic acid ethyl ester
6780-41-2

N-Phenyl-benzimidic acid ethyl ester

chloroethane
75-00-3

chloroethane

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

Conditions
Conditions Yield
thionyl chloride
7719-09-7

thionyl chloride

N-methyl-N-phenyl-benzamide
1934-92-5

N-methyl-N-phenyl-benzamide

methylene chloride
74-87-3

methylene chloride

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

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

hydrogenchloride

diethyl ether
60-29-7,927820-24-4

diethyl ether

(Z)-benzophenone O-(phenyl(phenylimino)methyl) oxime

(Z)-benzophenone O-(phenyl(phenylimino)methyl) oxime

N-phenyl benzoyl amide
93-98-1,5705-51-1

N-phenyl benzoyl amide

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

Conditions
Conditions Yield
N-phenyl benzoyl amide
93-98-1,5705-51-1

N-phenyl benzoyl amide

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

Conditions
Conditions Yield
With thionyl chloride; for 2h; Reflux;
100%
With thionyl chloride; at 70 ℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox;
100%
With thionyl chloride; for 4h; Heating;
99%
With phosphorus pentachloride; at 90 ℃; for 0.333333h; under 700 Torr;
92%
With thionyl chloride; In toluene; for 12h; Inert atmosphere; Reflux;
90%
With thionyl chloride; at 65 ℃; for 2h; Inert atmosphere;
90%
With thionyl chloride;
89%
With thionyl chloride; In toluene; for 12h; Inert atmosphere; Reflux;
88%
With thionyl chloride; In toluene; for 11h; Inert atmosphere; Reflux;
88%
With phosphorus pentachloride; at 80 ℃; for 0.5h;
86%
With thionyl chloride; Heating;
79%
With dmap; phosphorus trichloride; at 75 - 80 ℃; for 1h; Reagent/catalyst;
72%
With phosphorus pentachloride;
With phosphorus pentachloride; steam bath;
With trichlorophosphate; In toluene; Heating;
With phosphorus pentachloride; In toluene; Ambient temperature;
With phosphorus pentachloride; at 100 - 120 ℃; for 0.5h;
With thionyl chloride; at 75 - 80 ℃; for 1h;
1.07 g
With thionyl chloride; at 75 - 80 ℃; for 1.5h;
With thionyl chloride; at 75 - 80 ℃; for 1.5h;
With phosphorus pentachloride; In benzene; at 40 ℃; for 15h;
With phosphorus pentachloride; In benzene; at 50 - 60 ℃;
With thionyl chloride; at 75 - 80 ℃; for 1h;
With phosphorus pentachloride; In benzene; at 50 ℃;
With phosphorus pentachloride; at 85 ℃;
With phosphorus pentachloride; trichlorophosphate; for 1h; Heating;
With phosphorus pentachloride; In toluene; for 2h; Heating;
With thionyl chloride; for 1h; Heating;
With thionyl chloride;
With thionyl chloride; at 90 ℃;
With thionyl chloride; at 80 ℃; for 1h;
With phosphorus pentachloride; In benzene; for 2h; Heating;
With thionyl chloride; for 3h; Reflux;
With thionyl chloride; at 80 ℃; for 1h;
With thionyl chloride; for 2h; Reflux;
With thionyl chloride; at 135 ℃; for 4h;
With thionyl chloride; at 80 ℃; for 6h;
With thionyl chloride; In toluene; at 100 ℃; for 12h; Inert atmosphere;
With thionyl chloride; Reflux;
With phosphorus pentachloride; In toluene;
With thionyl chloride; at 80 ℃; for 6h;
With thionyl chloride; for 24h; Inert atmosphere; Reflux;
With thionyl chloride; for 10h; Heating;
With bis(trichloromethyl) carbonate;
With thionyl chloride;
With thionyl chloride; for 16h; Reflux;
With thionyl chloride; at 70 ℃; for 2h; Inert atmosphere;
With thionyl chloride; at 80 ℃; for 4h;
With thionyl chloride; at 80 ℃; for 4h;
With thionyl chloride; Inert atmosphere;
With bis(trichloromethyl) carbonate; tris(naphthalen-1-yl)phosphine oxide; In chloroform-d1; at 90 ℃; for 15h; Glovebox;
With thionyl chloride; In toluene; Reflux;
benzoyl chloride
98-88-4

benzoyl chloride

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine / ethyl acetate / 20 °C
2: thionyl chloride / 4 h / 135 °C
With thionyl chloride; triethylamine; In ethyl acetate;
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique; Glovebox
2: thionyl chloride / 2 h / 70 °C / Inert atmosphere; Schlenk technique; Glovebox
With thionyl chloride; triethylamine; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane
2: phosphorus pentachloride / toluene
With phosphorus pentachloride; triethylamine; In dichloromethane; toluene;
Multi-step reaction with 2 steps
1: dichloromethane / 2 h / 20 °C
2: thionyl chloride / 6 h / 80 °C
With thionyl chloride; In dichloromethane;
Multi-step reaction with 2 steps
1: pyridine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
2: thionyl chloride / toluene / 12 h / Inert atmosphere; Reflux
With pyridine; thionyl chloride; In tetrahydrofuran; toluene;
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 1 h / 20 °C
2: phosphorus pentachloride / toluene / 2 h / Inert atmosphere
With phosphorus pentachloride; triethylamine; In dichloromethane; toluene;
Multi-step reaction with 2 steps
1: dichloromethane
2: bis(trichloromethyl) carbonate
With bis(trichloromethyl) carbonate; In dichloromethane;
Multi-step reaction with 2 steps
1: dichloromethane
2: thionyl chloride
With thionyl chloride; In dichloromethane;
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 20 °C
2: thionyl chloride / 16 h / Reflux
With thionyl chloride; triethylamine; In dichloromethane;
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 12 h / 0 - 20 °C
2: thionyl chloride / 4 h / 80 °C
With thionyl chloride; triethylamine; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: trialkylamine / tetrahydrofuran / 12 h / 0 - 20 °C
2: thionyl chloride / 4 h / 80 °C
With thionyl chloride; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: triethylamine / chloroform
2: thionyl chloride / toluene / Reflux
With thionyl chloride; triethylamine; In chloroform; toluene;
aniline
62-53-3

aniline

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: triethylamine / ethyl acetate / 20 °C
2: thionyl chloride / 4 h / 135 °C
With thionyl chloride; triethylamine; In ethyl acetate;
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique; Glovebox
2: thionyl chloride / 2 h / 70 °C / Inert atmosphere; Schlenk technique; Glovebox
With thionyl chloride; triethylamine; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane
2: phosphorus pentachloride / toluene
With phosphorus pentachloride; triethylamine; In dichloromethane; toluene;
Multi-step reaction with 2 steps
1: dichloromethane / 2 h / 20 °C
2: thionyl chloride / 6 h / 80 °C
With thionyl chloride; In dichloromethane;
Multi-step reaction with 2 steps
1: pyridine / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
2: thionyl chloride / toluene / 12 h / Inert atmosphere; Reflux
With pyridine; thionyl chloride; In tetrahydrofuran; toluene;
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 1 h / 20 °C
2: phosphorus pentachloride / toluene / 2 h / Inert atmosphere
With phosphorus pentachloride; triethylamine; In dichloromethane; toluene;
Multi-step reaction with 2 steps
1: dichloromethane
2: bis(trichloromethyl) carbonate
With bis(trichloromethyl) carbonate; In dichloromethane;
Multi-step reaction with 2 steps
1: dichloromethane
2: thionyl chloride
With thionyl chloride; In dichloromethane;
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 20 °C
2: thionyl chloride / 16 h / Reflux
With thionyl chloride; triethylamine; In dichloromethane;
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 12 h / 0 - 20 °C
2: thionyl chloride / 4 h / 80 °C
With thionyl chloride; triethylamine; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: trialkylamine / tetrahydrofuran / 12 h / 0 - 20 °C
2: thionyl chloride / 4 h / 80 °C
With thionyl chloride; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: triethylamine / chloroform
2: thionyl chloride / toluene / Reflux
With thionyl chloride; triethylamine; In chloroform; toluene;
Benzophenone oxime
574-66-3

Benzophenone oxime

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

Conditions
Conditions Yield
With phosphorus pentachloride;
Multi-step reaction with 2 steps
1: 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione / acetonitrile / 0.33 h / 80 °C / Inert atmosphere; Schlenk technique
2: thionyl chloride / 2 h / 65 °C / Inert atmosphere
With thionyl chloride; 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione; In acetonitrile; 1: |Beckmann Rearrangement;
N-methyl-N-phenyl-benzamide
1934-92-5

N-methyl-N-phenyl-benzamide

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

Conditions
Conditions Yield
With phosphorus pentachloride; at 150 - 160 ℃;
With thionyl chloride;
N-phenyl benzoyl amide
93-98-1,5705-51-1

N-phenyl benzoyl amide

chlore-methylene-di(tert-butyle)phosphorane
76711-20-1

chlore-methylene-di(tert-butyle)phosphorane

di-tert-butyl-methylphosphine oxide
18351-81-0

di-tert-butyl-methylphosphine oxide

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

Conditions
Conditions Yield
In diethyl ether; added at -20 deg C, then temp. was raised.;
80%
80%
benzophenone
119-61-9

benzophenone

<i>N</i>-phenyl-benzimidoyl chloride
4903-36-0

N-phenyl-benzimidoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: alcohol; hydrochloric acid; hydroxylamine hydrochloride
2: PCl5
With hydrogenchloride; ethanol; phosphorus pentachloride; hydroxylamine hydrochloride;
Multi-step reaction with 3 steps
1: hydroxylamine hydrochloride; sodium acetate / ethanol; water / 80 °C / Inert atmosphere
2: 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione / acetonitrile / 0.33 h / 80 °C / Inert atmosphere; Schlenk technique
3: thionyl chloride / 2 h / 65 °C / Inert atmosphere
With thionyl chloride; hydroxylamine hydrochloride; sodium acetate; 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione; In ethanol; water; acetonitrile; 2: |Beckmann Rearrangement;

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