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Cas Database

42498-44-2

42498-44-2

Identification

  • Product Name:[1,1'-Biphenyl]-3-carbonyl chloride

  • CAS Number: 42498-44-2

  • EINECS:

  • Molecular Weight:216.667

  • Molecular Formula: C13H9ClO

  • HS Code:2916399090

  • Mol File:42498-44-2.mol

Synonyms:3-biphenylcarbonyl chloride;3-phenylbenzoic acid chloride;Biphenyl-3-carbonyl chloride;[1,1'-biphenyl]-3-carbonyl chloride;

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Safety information and MSDS view more

  • Hazard Codes:C,N

  • 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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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Biphenyl-3-carbonyl chloride 97%
  • Packaging:1g
  • Price:$ 146
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Biphenyl-3-carbonyl chloride
  • Packaging:1g
  • Price:$ 294
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  • Manufacture/Brand:Crysdot
  • Product Description:[1,1'-Biphenyl]-3-carbonylchloride 95+%
  • Packaging:5g
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  • Manufacture/Brand:Atlantic Research Chemicals
  • Product Description:Biphenyl-3-carbonyl chloride 95%
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  • Price:$ 137.85
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:BIPHENYL-3-CARBONYL CHLORIDE 95.00%
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  • Price:$ 1280.66
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  • Manufacture/Brand:AK Scientific
  • Product Description:Biphenyl-3-carbonyl chloride
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  • Manufacture/Brand:AHH
  • Product Description:Biphenyl-3-carbonyl chloride 98%
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Relevant articles and documentsAll total 40 Articles be found

Identification and Optimization of Novel Small-Molecule Cas9 Inhibitors by Cell-Based High-Throughput Screening

Lee, Sang-Woo,Tran, Kim Tai,Vazquez-Uribe, Ruben,Gotfredsen, Charlotte Held,Clausen, Mads Hartvig,Mendez, Blanca Lopez,Montoya, Guillermo,Bach, Anders,Sommer, Morten Otto Alexander

, p. 3266 - 3305 (2022/02/23)

CRISPR/Cas9 has revolutionized several areas of life science; however, methods to control the Cas9 activity are needed for both scientific and therapeutic applications. Anti-CRISPR proteins are known to inhibit the CRISPR/Cas adaptive immunity; however, in vivo delivery of such proteins is problematic. Instead, small-molecule Cas9 inhibitors could serve as useful tools due to their permeable, proteolytically stable, and non-immunogenic nature. Here, we identified a small-molecule ligand with anti-CRISPR/Cas9 activity through a high-throughput screening utilizing an Escherichia coli selection system. Extensive structure-activity relationship studies, which involved a deconstruction-reconstruction strategy, resulted in a range of analogues with significant improvements in the inhibitory activity. Based on NMR and electrophoretic mobility shift assays, we propose that the inhibitory action of these compounds likely results from direct binding to apo-Cas9, preventing Cas9:gRNA complex formation. These molecules may find use as Cas9 modulators in various applications.

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul

supporting information, p. 5022 - 5037 (2021/05/04)

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Design and synthesis of N-(3-sulfamoylphenyl)amides as Trypanosoma brucei leucyl-tRNA synthetase inhibitors

Li, Zezhong,Xin, Weixiang,Wang, Qing,Zhu, Mingyan,Zhou, Huchen

, (2021/03/16)

The protozoan parasite Trypanosoma brucei (T. brucei) causes human African trypanosomiasis (HAT), which is a fatal and neglected disease in the tropic areas, and new treatments are urgently needed. Leucyl-tRNA synthetase (LeuRS) is an attractive target for the development of antimicrobial agents. In this work, starting from the hit compound thiourea ZCL539, we designed and synthesized a series of amides as effective T. brucei LeuRS (TbLeuRS) synthetic site inhibitors. The most potent compounds 74 and 91 showed IC50 of 0.24 and 0.25 μM, which were about 700-fold more potent than the starting hit compound. The structure-activity relationship was also discussed. These compounds provided a new scaffold and lead compounds for further development of antitrypanosomal agents.

Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction

Isshiki, Ryota,Kurosawa, Miki B.,Muto, Kei,Yamaguchi, Junichiro

supporting information, p. 10333 - 10340 (2021/07/21)

A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.

Facile Synthesis of Alkylidene Phthalides by Rhodium-Catalyzed Domino C?H Acylation/Annulation of Benzamides with Aliphatic Carboxylic Acids

Liu, Sien,He, Bangyue,Li, Hongyi,Zhang, Xiaofeng,Shang, Yaping,Su, Weiping

supporting information, p. 15628 - 15633 (2021/10/05)

The Rh-catalyzed ortho-C(sp2)?H functionalization of 8-aminoquinoline-derived benzamides with aliphatic acyl fluorides generated in situ from the corresponding acids has been developed. This reaction initiated with 8-aminoquinoline-directed ortho-C(sp2)?H acylation, which was accompanied by subsequent intramolecular nucleophilic acyl substitution of amide group to produce alkylidene phthalides This approach exhibits high stereo-selectivity for Z-isomer products, and tolerates a variety of functional groups as well as aliphatic carboxylic acids with diverse structural scaffolds.

Process route upstream and downstream products

Process route

3-phenylbenzoic acid
716-76-7

3-phenylbenzoic acid

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
3-phenylbenzoic acid; With N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; for 0.0833333h;
With oxalyl dichloride; In dichloromethane; at 20 ℃; for 12h;
100%
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at -5 - 20 ℃; for 16h; Inert atmosphere;
98%
With thionyl chloride; for 2h; Reflux;
87%
With phosphorus pentachloride;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 0.25h;
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; for 1h;
With oxalyl dichloride; N,N-dimethyl-formamide; In benzene; for 1h;
With thionyl chloride; N,N-dimethyl-formamide;
With thionyl chloride; Heating;
With thionyl chloride; N,N-dimethyl-formamide; for 3 - 6h; Product distribution / selectivity; Heating / reflux;
With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 20 ℃; for 2.66667h; Product distribution / selectivity;
With thionyl chloride; In toluene; at 60 ℃; for 2.5h; Product distribution / selectivity;
With thionyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; for 3.5h; Inert atmosphere;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 2h;
With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; at 20 - 60 ℃; for 2.66667 - 5h; Product distribution / selectivity;
With thionyl chloride;
With thionyl chloride; at 20 ℃;
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 5h; Inert atmosphere;
With thionyl chloride; for 1.5h; Reflux;
With thionyl chloride; In toluene; Reflux;
With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; Inert atmosphere;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;
With thionyl chloride; N,N-dimethyl-formamide; In N,N-dimethyl-formamide; toluene; at 80 ℃; for 3h;
With thionyl chloride; at 0 ℃; for 0.5h; Reflux;
With thionyl chloride; at 85 ℃; for 0.5h; Reflux;
With oxalyl dichloride; In dichloromethane; at 20 ℃;
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 1h; Inert atmosphere;
With thionyl chloride; for 2h; Reflux;
With thionyl chloride; for 1h; Heating / reflux;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; for 2h;
With oxalyl dichloride;
With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; toluene; for 4h;
With thionyl chloride; N,N-dimethyl-formamide; at 55 - 60 ℃; Temperature; Reagent/catalyst; Inert atmosphere;
3-phenylbenzoic acid; With N,N-dimethyl-formamide; In dichloromethane; at 0 ℃; for 0.0833333h; Inert atmosphere;
With oxalyl dichloride; In dichloromethane; Inert atmosphere;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃;
With thionyl chloride; at 90 ℃; for 3.5h;
With thionyl chloride; Reflux;
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20 ℃; Inert atmosphere;
With oxalyl dichloride; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;
phenylboronic acid
98-80-6

phenylboronic acid

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: potassium phosphate tribasic trihydrate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 7 h / 90 °C / Inert atmosphere
2: sodium hydroxide / water; methanol / 2 h / Reflux
3: thionyl chloride / 1.5 h / Reflux
With tetrakis(triphenylphosphine) palladium(0); thionyl chloride; potassium phosphate tribasic trihydrate; sodium hydroxide; In 1,4-dioxane; methanol; water;
Multi-step reaction with 2 steps
1: edetate disodium; palladium dichloride; sodium carbonate / water / 50 °C / Inert atmosphere; Reflux
2: thionyl chloride; N,N-dimethyl-formamide / 55 - 60 °C / Inert atmosphere
With thionyl chloride; edetate disodium; sodium carbonate; N,N-dimethyl-formamide; palladium dichloride; In water; 1: |Suzuki-Miyaura Coupling;
bromobenzene
108-86-1,52753-63-6

bromobenzene

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 1.) n-BuLi, 2.) ZnCl2, 3.) DIBAL-H, Ni(PPh3)2l2
2: 79.5 percent / 1 N NaOH / ethanol / 18 h / Ambient temperature
3: (COCl)2 / CH2Cl2; dimethylformamide / 1 h
With sodium hydroxide; n-butyllithium; oxalyl dichloride; bis(triphenylphosphine)nickel(II) diiodide; diisobutylaluminium hydride; zinc(II) chloride; In ethanol; dichloromethane; N,N-dimethyl-formamide;
3-iodobenzoic acid methyl ester
58313-23-8

3-iodobenzoic acid methyl ester

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 1.) n-BuLi, 2.) ZnCl2, 3.) DIBAL-H, Ni(PPh3)2l2
2: 79.5 percent / 1 N NaOH / ethanol / 18 h / Ambient temperature
3: (COCl)2 / CH2Cl2; dimethylformamide / 1 h
With sodium hydroxide; n-butyllithium; oxalyl dichloride; bis(triphenylphosphine)nickel(II) diiodide; diisobutylaluminium hydride; zinc(II) chloride; In ethanol; dichloromethane; N,N-dimethyl-formamide;
biphenyl-3-carboxylic acid ethyl ester
19926-50-2

biphenyl-3-carboxylic acid ethyl ester

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 79.5 percent / 1 N NaOH / ethanol / 18 h / Ambient temperature
2: (COCl)2 / CH2Cl2; dimethylformamide / 1 h
With sodium hydroxide; oxalyl dichloride; In ethanol; dichloromethane; N,N-dimethyl-formamide;
methyl 3-bromobenzoate
618-89-3

methyl 3-bromobenzoate

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: potassium phosphate tribasic trihydrate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 7 h / 90 °C / Inert atmosphere
2: sodium hydroxide / water; methanol / 2 h / Reflux
3: thionyl chloride / 1.5 h / Reflux
With tetrakis(triphenylphosphine) palladium(0); thionyl chloride; potassium phosphate tribasic trihydrate; sodium hydroxide; In 1,4-dioxane; methanol; water;
methyl 3-phenylbenzoate
16606-00-1

methyl 3-phenylbenzoate

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; methanol / 2 h / Reflux
2: thionyl chloride / 1.5 h / Reflux
With thionyl chloride; sodium hydroxide; In methanol; water;
m-bromobenzoic acid
585-76-2

m-bromobenzoic acid

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: edetate disodium; palladium dichloride; sodium carbonate / water / 50 °C / Inert atmosphere; Reflux
2: thionyl chloride; N,N-dimethyl-formamide / 55 - 60 °C / Inert atmosphere
With thionyl chloride; edetate disodium; sodium carbonate; N,N-dimethyl-formamide; palladium dichloride; In water; 1: |Suzuki-Miyaura Coupling;
3-bromobiphenyl
2113-57-7

3-bromobiphenyl

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
2: phosphorous pentachloride
With phosphorus pentachloride;
ethyl 3-bromobenzoate
24398-88-7

ethyl 3-bromobenzoate

3-phenylbenzoyl chloride
42498-44-2

3-phenylbenzoyl chloride

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 4 h / 90 °C / Inert atmosphere
2: sodium hydroxide / water; ethanol / 22 h / 20 °C
3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 0 °C
With tetrakis(triphenylphosphine) palladium(0); oxalyl dichloride; potassium carbonate; N,N-dimethyl-formamide; sodium hydroxide; In 1,4-dioxane; ethanol; dichloromethane; water;

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