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Phenylmagnetic chloride (PhMgCl) is a versatile organometallic compound, primarily used as a Grignard reagent in organic synthesis. It is a yellowish-brown to dark brown solution and has been enhanced for energy efficiency.

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  • 100-59-4 Structure
  • Basic information

    1. Product Name: PHENYLMAGNESIUM CHLORIDE
    2. Synonyms: PHENYLMAGNESIUM CHLORIDE, 2.0M SOLUTION IN TETRAHYDROFURAN;Phenylmagnesium Chloride 2.0 M In Tetrahdyrofuran;PHENYLMAGNESIUM CHLORIDE 25 WT% IN THF;Phenylmagnesium chloride, 25 wt% solution in tetrahydrofuran;PHENYLMAGNESIUM CHLORIDE, 1 M in DIBUTYL ETHER;PHENYLMAGNESIUM CHLORIDE, 2 M in TETRAHYDROFURAN;Phenylmagnesiumchloride,2-3MinTHF;PHENYLMAGNESIUMCHLORIDE,25%INTETRAHYDROFURAN
    3. CAS NO:100-59-4
    4. Molecular Formula: C6H5ClMg
    5. Molecular Weight: 136.86
    6. EINECS: 202-868-8
    7. Product Categories: Organometallics;Classes of Metal Compounds;Grignard Reagents;Grignard Reagents & Alkyl Metals;Mg (Magnesium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;Aryl;Grignard Reagents;Organometallic Reagents;grignard reagent
    8. Mol File: 100-59-4.mol
  • Chemical Properties

    1. Melting Point: 89-90℃
    2. Boiling Point: 230℃ (8 Torr)
    3. Flash Point: 1 °F
    4. Appearance: yellowish-brown to dark brown solution
    5. Density: 0.98 g/mL at 20 °C
    6. Vapor Pressure: 101mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: water-free area
    9. Solubility: N/A
    10. Water Solubility: It reacts violently with water.
    11. Sensitive: Air & Moisture Sensitive
    12. Merck: 14,7298
    13. BRN: 3587900
    14. CAS DataBase Reference: PHENYLMAGNESIUM CHLORIDE(CAS DataBase Reference)
    15. NIST Chemistry Reference: PHENYLMAGNESIUM CHLORIDE(100-59-4)
    16. EPA Substance Registry System: PHENYLMAGNESIUM CHLORIDE(100-59-4)
  • Safety Data

    1. Hazard Codes: F,C
    2. Statements: 14-19-20/21/22-34-67-65-63-48/20-11-40-37
    3. Safety Statements: 26-36/37/39-45-62-33-16
    4. RIDADR: UN 2924 3/PG 2
    5. WGK Germany: 2
    6. RTECS:
    7. F: 10
    8. TSCA: Yes
    9. HazardClass: 8
    10. PackingGroup: II
    11. Hazardous Substances Data: 100-59-4(Hazardous Substances Data)

100-59-4 Usage

Uses

Used in Organic Synthesis:
Phenylmagnetic chloride is used as a Grignard reagent for the production of hydrocarbons, alcohols, ketones, organic acids, amines, silicones, and boranes. It plays a crucial role in various cross-coupling reactions, facilitating the formation of carbon-carbon bonds and enabling the synthesis of complex organic molecules.
Used in Pharmaceutical Synthesis:
Phenylmagnetic chloride is used as a reagent in the synthesis of specific pharmaceutical compounds, such as (?)-phenserine and stephacidin B. Its ability to form carbon-carbon bonds makes it a valuable tool in the development of novel drugs and therapeutic agents.
Used in Energy Storage:
Phenylmagnetic chloride can be used as an electrolyte solution, in combination with aluminium chloride (AlCl3), in the development of rechargeable magnesium batteries. This application highlights its potential in the energy storage industry, contributing to the advancement of more efficient and sustainable battery technologies.
Used in Green Chemistry:
Phenylmagnetic chloride is also employed as a Grignard reagent in greener solvents, such as 2-methyltetrahydrofuran (2-MeTHF). This application demonstrates its utility in promoting environmentally friendly and sustainable chemical processes, reducing the environmental impact of organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 100-59-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 100-59:
(5*1)+(4*0)+(3*0)+(2*5)+(1*9)=24
24 % 10 = 4
So 100-59-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H5.ClH.Mg/c1-2-4-6-5-3-1;;/h1-5H;1H;/q-1;;+2/p-1

100-59-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (P1381)  Phenylmagnesium Chloride (27% in Tetrahydrofuran, ca. 2mol/L)  

  • 100-59-4

  • 250g

  • 640.00CNY

  • Detail
  • Alfa Aesar

  • (H51157)  Phenylmagnesium chloride, 1M in MeTHF   

  • 100-59-4

  • 100ml

  • 483.0CNY

  • Detail
  • Alfa Aesar

  • (H51157)  Phenylmagnesium chloride, 1M in MeTHF   

  • 100-59-4

  • 500ml

  • 1208.0CNY

  • Detail
  • Aldrich

  • (775045)  Phenylmagnesiumchloridesolution  1.0 M in 2-methyltetrahydrofuran

  • 100-59-4

  • 775045-100ML

  • 331.11CNY

  • Detail
  • Aldrich

  • (775045)  Phenylmagnesiumchloridesolution  1.0 M in 2-methyltetrahydrofuran

  • 100-59-4

  • 775045-4X25ML

  • 387.27CNY

  • Detail
  • Aldrich

  • (775045)  Phenylmagnesiumchloridesolution  1.0 M in 2-methyltetrahydrofuran

  • 100-59-4

  • 775045-800ML

  • 1,645.02CNY

  • Detail
  • Aldrich

  • (257125)  Phenylmagnesiumchloridesolution  2.0 M in THF

  • 100-59-4

  • 257125-200ML

  • 1,503.45CNY

  • Detail
  • Aldrich

  • (224448)  Phenylmagnesiumchloridesolution  2.0 M in THF

  • 100-59-4

  • 224448-100ML

  • 714.87CNY

  • Detail
  • Aldrich

  • (224448)  Phenylmagnesiumchloridesolution  2.0 M in THF

  • 100-59-4

  • 224448-800ML

  • 2,597.40CNY

  • Detail

100-59-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Phenylmagnesium chloride

1.2 Other means of identification

Product number -
Other names Phenylmagnesium chloride

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:100-59-4 SDS

100-59-4Relevant articles and documents

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

Adamo, Andrea,Berton, Mateo,McQuade, D. Tyler,Sheehan, Kevin

, p. 1343 - 1356 (2020)

Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a batch-to-batch variability. Tubular reactors of solid reagents combined with solution-phase reagents enable the continuous-flow preparation of organomagnesium reagents. The use of stratified packed-bed columns of magnesium metal and lithium chloride for the synthesis of highly concentrated turbo Grignards is reported. A low-cost pod-style synthesizer prototype, which incorporates single-use prepacked perfluorinated cartridges and bags of reagents for the automated on-demand lab-scale synthesis of carbon, nitrogen, and oxygen turbo magnesium bases is presented. This concept will provide access to fresh organomagnesium reagents on a discovery scale and will do so independent from the operator’s experience in flow and/or organometallic chemistry.

A method for preparing substituted biphenyl

-

Paragraph 0073; 0074; 0075, (2018/08/03)

The invention discloses a preparation method of substituted biphenyl. The preparation method includes the steps that under the anhydrous condition, a compound 2 and a compound 3 are subjected to a coupled reaction in solvent in the presence of Ni salt and ZnX3X4, and then substituted biphenyl is obtained, wherein Ni salt is one or more of NiX5X6(PPh3)2, NiX7X8(dppp), NiX9X10(dppf), NiX11X12(dppe) and acetylacetone nickel, the temperature of the coupled reaction is 0-30 DEG C, and ZnX3X4 is mixed with the compound 3 before the compound 2 is mixed with the compound 3. According to the method, reaction conditions are mild, the process is simple, operation is safe, requirements for equipment are low, aftertreatment is simple, pollution to the environment is small, industrial production is easy, the usage quantity of zinc halides is small, the cost is low, the yield is high, and the product purity is high.

Movel photoacid generators, resist compositons, and patterning processes

-

Page/Page column 65, (2009/04/23)

Photoacid generators generate sulfonic acids of formula (1a) or (1c) upon exposure to high-energy radiation. ????????R1-COOCH(CF3)CF2SO3-H+?????(1a) ????????R1-O-COOCH(CF3)CF2SO3-H+?????(1c) R1 is a C20-C50 hydrocarbon group having a steroid structure. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.

Novel fluorosulfonyloxyalkyl sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process

-

Page 32, (2008/06/13)

Sulfonate salts have the formula: R1SO3-CH(Rf)-CF2SO3-M+ wherein R1 is alkyl or aryl, Rf is H or trifluoromethyl, and M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.

Novel fluorohydroxyalkyl sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process

-

Page/Page column 29, (2010/11/27)

Sulfonate salts have the formula: CF3-CH(OH)-CF2SO3-M+ wherein M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Because of inclusion within the molecule of a hydroxyl group which is a polar group, the sulfonic acids are effective for restraining the length of acid diffusion through hydrogen bond or the like. The photoacid generators that generate these sulfonic acids perform well during the device fabrication process including coating, pre-baking, exposure, post-exposure baking, and developing steps. The photoacid generators are little affected by water left on the wafer during the ArF immersion lithography.

Process safety evaluation of a magnesium-iodine exchange reaction

Reeves, Jonathan T.,Sarvestani, Max,Song, Jinhua J.,Tan, Zhulin,Nummy, Laurence J.,Lee, Heewon,Yee, Nathan K.,Senanayake, Chris H.

, p. 1258 - 1262 (2012/12/23)

An unexpected highly exothermic decomposition was observed during routine safety analysis of the magnesium-iodine exchange reaction of 2-iodo-4-fluorotoluene (3) with commercially available i-PrMgCl (2.0 M solution in THF). When the reaction mixture was scanned in an adiabatic calorimeter with the use of a 2 °C/min temperature ramp, a rapid exothermic decomposition with an onset temperature of approximately 80 °C was observed. The system temperature rapidly rose to 210 °C at a peak rate of 200 °C/min. Subsequent testing of three simplified substrates showed the same type of exothermic decomposition for all cases. Control experiments indicated that the decomposition requires both aryl iodide and i-PrMgCl (or arylMgCl and i-PrI). While the onset temperatures for all cases studied were generally well above the typical operating temperature for these reactions (0-10 °C), it is nonetheless important to cautiously evaluate these types of processes and install proper engineering controls for analogous decomposition events.

Formation of phenylmagnesium halides in toluene

Simuste, Hannes,Panov, Dmitri,Tuulmets, Ants,Nguyen, Binh T.

, p. 3061 - 3066 (2007/10/03)

Formation reactions of phenylmagnesium chloride and bromide in toluene in the presence of one or two equivalents of diethyl ether or THF were investigated kinetically. Also, the reaction in diethyl ether and in chlorobenzene was addressed. Kinetic features of the reactions are similar to those found previously for the formation of alkylmagnesium halides in toluene and consist of rapid formation of a disolvated Grignard reagent followed by a slower formation of a monosolvated reagent. The latter is able of catalyzing the conversion of different halides into Grignard reagents. However, the contribution of Wurtz-type side reactions is considerable except when THF is used in toluene. Involving the kinetic data and the activation parameters some details of the reaction mechanism were discussed.

Kinetics and Thermodynamics of Oxidation of Magnesium with Phenyl Halides in Benzene in the Presence of Diethyl Ether

Maslennikov,Spirina

, p. 274 - 276 (2007/10/03)

The equilibrium constants and the enthalpies and entropies of adsorption of phenyl chloride and phenyl iodide on the surface of magnesium during oxidation in benzene were determined. The reaction scheme explaining acceleration of conversion and increase in the fraction of products of the Wuertz reaction with increasing concentration of oxidant was suggested.

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