6921-34-2

Basic information

• Product Name: Benzylmagnesium chloride
• Synonyms: chloro(phenylmethyl)-magnesiu;BENZYLMAGNESIUM CHLORIDE;Benzylmagnesium chloride solution;BENZYLMAGNESIUM CHLORIDE, 1.0M SOLUTION IN DIETHYL ETHER;BENZYLMAGNESIUM CHLORIDE, 2.0M SOLUTION IN TETRAHYDROFURAN;BENZYLMAGNESIUM CHLORIDE SOLUTION, ~1.3 M IN THF;BENZYLMAGNESIUM CHLORIDE SOL., ~1 M IN D IETHYL ETHER;Benzylmagnesium Chloride 0.9 M In Dibutyl Ether
• CAS NO: 6921-34-2
• Molecular Formula: C₇H₇ClMg
• Molecular Weight: 150.89
• EINECS: 230-039-0
• Product Categories: Classes of Metal Compounds;Grignard Reagents;Grignard Reagents & Alkyl Metals;Mg (Magnesium) Compounds;Synthetic Organic Chemistry;Typical Metal Compounds;Alkyl;Grignard Reagents;Organometallic Reagents;grignard reagent
• Mol File: 6921-34-2.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 182 °C(Press: 16 Torr)
• Flash Point: 1 °F
• Appearance: Brown to purple/Liquid
• Density: 1.031 g/mL at 25 °C
• Storage Temp.: water-free area
• Water Solubility: Severe reaction
• Sensitive: Air & Moisture Sensitive
• BRN: 878506
• CAS DataBase Reference: Benzylmagnesium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Benzylmagnesium chloride(6921-34-2)
• EPA Substance Registry System: Benzylmagnesium chloride(6921-34-2)

Safety Data

• Hazard Codes: F+,C,Xi,F
• Statements: 12-14-34-66-67-36/37-19-11-14/15-40-37-17-22
• Safety Statements: 16-29-33-7/8-45-43-36/37/39-26-6A-43B
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 1
• F: 1-3-10
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: II
• Hazardous Substances Data: 6921-34-2(Hazardous Substances Data)

Usage

Chemical Properties

Light gray to dark amber-grey slurry or solution

Uses

Different sources of media describe the Uses of 6921-34-2 differently. You can refer to the following data:
1. Benzyl magnesium chloride is used as a Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF). It is also used as organic chemical synthesis intermediate.
2. Benzylmagnesium chloride (Grignard reagent) can be used as an alkylating reagent:For alkylating quinolyl-functionalized Cp?chromium(III) complexes which are used as precursors for the preparation of active olefin polymerization catalysts. In the synthesis of 2,3-disubstituted benzopyran-4-ones, 6-chloro-8-methylpurine derivative, and phenylalanine derivatives.

Application

Benzylmagnesium chloride (Grignard reagent) can be used as an alkylating reagent:For alkylating quinolyl-functionalized Cp?chromium(III) complexes which are used as precursors for the preparation of active olefin polymerization catalysts.In the synthesis of 2,3-disubstituted benzopyran-4-ones, 6-chloro-8-methylpurine derivative, and phenylalanine derivatives.

General Description

This product has been enhanced for energy efficiency.

Research

Grignard reagents are organometallic compounds discovered by a French chemist, Victor Grignard in 1900. These compounds can be obtained as a formula “RMgX” by the reaction of halogenated hydrocarbons with magnesium metal in anhydrous solvents such as diethyl ether,1) and have been widely used in organic synthesis.Grignard reagents are usually used as solutions, and they are typically grayish white ~ light brown clear solutions. They generally exist in an equilibrium between alkyl magnesium halides (RMgX) and dialkyl magnesium (R2Mg), which form equilibrium mixtures with complicated compositions (called “Schlenk equilibrium”).2) Furthermore, some of these species may cause precipitation due to their lower solubility. However, there is no problem in actual use.In the case of precipitation being formed:Please use it after gently shaking the bottle to fully disperse the suspension (If the amount of precipitation is very small, you can use the top clear layer of the suspension). Especially in cold conditions such as in winter, a large amount of precipitate may frequently form. In this case, please use it after crushing the solid with a dried glass stick. Alternatively, you can also use it the following. The bottle is put into a plastic bag and soaking in a water bath with warming at 40 degree C to dissolve the solid. Please be careful of volatilization of the organic solvent when the bottle is unsealing.

Precautions

It reacts violently with water. Air & moisture sensitive. Incompatible with oxidizing agents and bases.

InChI:InChI=1/C7H7.ClH.Mg/c1-7-5-3-2-4-6-7;;/h2-6H,1H2;1H;/q;;+1/p-1/rC7H7Mg.ClH/c8-6-7-4-2-1-3-5-7;/h1-5H,6H2;1H/q+1;/p-1

Synthetic route

benzyl chloride (100-44-7) → benzylmagnesium chloride (6921-34-2)

Conditions	Yield
With bromine; magnesium In tetrahydrofuran; tert-butyl methyl ether at 20 - 35℃; Product distribution / selectivity; Inert atmosphere;	99%
With magnesium In tetrahydrofuran at 20 - 23℃;	95%
With polymer supported 'magnesium(anthracene)'	90%

benzyl chloride (100-44-7) → 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7) + benzylmagnesium chloride (6921-34-2)

Conditions	Yield
With magnesium In tetrahydrofuran; 2-methyltetrahydrofuran at 60℃; under 5171.62 Torr; Solvent; Temperature; Inert atmosphere; Flow reactor;	A n/a B 83%

{C5H5FeC5H4CH2N(CH3)2CH2CHCH2}(1+)*Br(1-)={C5H5FeC5H4CH2N(CH3)2CH2CHCH2}Br + 1-propylmagnesium chloride (2234-82-4) → N,N'-dimethylbenzylamine (103-83-3) + N,N-dimethylaminomethylferrocene (1271-86-9) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7) + benzylmagnesium chloride (6921-34-2)

Conditions	Yield
With CoCl2	A n/a B 70% C 10% D 61%
With CoCl2	A n/a B 70% C 10% D 61%

(3-Methyl-2-phenyl-3,6-dihydro-2H-selenopyran-2-yl)-phenyl-methanone (114272-48-9, 114272-57-0) → (±)2-methyl-1-phenylpentan-1-one (31366-05-9) + 1,2-diphenyl-3-methylhexane (114272-51-4) + benzylmagnesium chloride (6921-34-2)

Conditions	Yield
With nickel In ethanol Heating;	A n/a B 57% C n/a

9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium (86901-19-1) + benzyl chloride (100-44-7) → 9,10-dibenzyl-9,10-dihydroanthracene (3613-43-2) + 9-benzyl-9,10-dihydroanthracene (2294-89-5) + 2-Benzyl-1,2-dihydro-anthracene (126695-08-7) + benzylmagnesium chloride (6921-34-2)

Conditions	Yield
In tetrahydrofuran for 3h; Ambient temperature; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium (86901-19-1) + benzyl chloride (100-44-7) → 9-benzyl-9,10-dihydroanthracene (2294-89-5) + 2-Benzyl-1,2-dihydro-anthracene (126695-08-7) + 1,2-Dibenzyl-1,2-dihydro-anthracene + benzylmagnesium chloride (6921-34-2)

Conditions	Yield
In tetrahydrofuran for 3h; Ambient temperature; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium (86901-19-1) + benzyl chloride (100-44-7) → 9-benzyl-9,10-dihydroanthracene (2294-89-5) + 2-Benzyl-1,2-dihydro-anthracene (126695-08-7) + 1,4-Dibenzyl-1,4-dihydro-anthracene + benzylmagnesium chloride (6921-34-2)

Conditions	Yield
In tetrahydrofuran for 3h; Ambient temperature; Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

benzyl chloride (100-44-7) → 2-methylanthracene (613-12-7) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7) + toluene (108-88-3) + benzylmagnesium chloride (6921-34-2)

Conditions	Yield
With magnesium 9,10-dimethylanthracene * 3 THF In tetrahydrofuran for 3h; Yield given. Yields of byproduct given;

benzyl chloride (100-44-7) → 9,10-dibenzyl-9,10-dihydroanthracene (3613-43-2) + 9-benzyl-9,10-dihydroanthracene (2294-89-5) + 2-Benzyl-1,2-dihydro-anthracene (126695-08-7) + benzylmagnesium chloride (6921-34-2)

Conditions	Yield
With magnesium anthracene * 3 THF In diethyl ether for 1h; Ambient temperature; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

diethyl ether (60-29-7) + benzyl chloride (100-44-7) + magnesium → benzylmagnesium chloride (6921-34-2)

2-(Dimethyl-λ4-sulfanylidene)-1,2-diphenyl-ethanone (60014-28-0) → benzylmagnesium chloride (6921-34-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: Se / toluene / 1.5 h / Heating 2: Raney nickel / ethanol / Heating View Scheme

4-(chloroacetyl)biphenyl (635-84-7) → 2-(4-biphenylyl)-3-chloro-1-phenylpropan-2-ol (75450-68-9) + benzylmagnesium chloride (6921-34-2)

benzyl bromide (100-39-0) → benzylmagnesium chloride (6921-34-2)

Conditions	Yield
With iodine; magnesium In tetrahydrofuran at 20 - 50℃; for 0.5h; Inert atmosphere;

benzyl chloride (100-44-7) → benzylmagnesium chloride (6921-34-2)

Conditions	Yield
With diethyl ether; magnesium

acetophenone (98-86-2) + benzylmagnesium chloride (6921-34-2) → 1,2-diphenylpropane-2-ol (5342-87-0)

Conditions	Yield
In dichloromethane at 0 - 20℃;	100%

truxenone (4430-15-3) + benzylmagnesium chloride (6921-34-2) → 5,10,15-triol-5,10,15-tribenzyl-10,15-dihydro-5H-diindeno[1,2-a;1',2'-c]fluorene

Conditions	Yield
In tetrahydrofuran for 8h; Ambient temperature;	100%

(3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxole (2457-93-4) + benzylmagnesium chloride (6921-34-2) → 6-benzyl-3,6-dideoxy-1,2-O-isopropylidene-D-glucose (125218-34-0)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	100%

2-(2-bromoethyl)isoindoline-1,3-dione (574-98-1) + benzylmagnesium chloride (6921-34-2) → 9b-benzyl-2,3-dihydrooxazolo[2,3-a]isoindol-5-(9bH)-one (876065-74-6)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 48h;	100%

((CH3)5C5)Co((C2H5)2C2B3H3)Ta(Cl)2(C5H5) + benzylmagnesium chloride (6921-34-2) → ((CH3)5C5)Co((C2H5)2C2B3H3)Ta(CH2C6H5)2(C5H5)

Conditions	Yield
In tetrahydrofuran; diethyl ether stirring (2 h); evapn., CH2Cl2 addn., filtering, evapn., washing (petroleum ether); elem. anal.;	100%

(1RS,4SR)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enyl picolinate + benzylmagnesium chloride (6921-34-2) → C18H28OSi

Conditions	Yield
With copper(I) bromide dimethylsulfide complex; zinc dibromide In tetrahydrofuran; diethyl ether at 0℃; for 1h; regioselective reaction;	100%

benzylmagnesium chloride (6921-34-2) + 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester (475095-03-5) → 4-benzyl-4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester (911228-42-7)

Conditions	Yield
Stage #1: benzylmagnesium chloride With copper(l) cyanide In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: 4-(cyano-ethoxycarbonyl-methylene)-piperidine-1-carboxylic acid benzyl ester In tetrahydrofuran at -10 - 20℃;	100%

α-methoxy-N-methoxycarbonylazocane (1227635-41-7) + benzylmagnesium chloride (6921-34-2) → α-benzyl-N-methoxycarbonylazocane (1227635-47-3)

Conditions	Yield
Stage #1: α-methoxy-N-methoxycarbonylazocane; benzylmagnesium chloride In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -78℃; Inert atmosphere;	100%

benzyl 2-methoxyazepane-1-carboxylate (1227635-42-8) + benzylmagnesium chloride (6921-34-2) → α-benzyl-N-benzyloxycarbonylazepane (1227635-50-8)

Conditions	Yield
Stage #1: benzyl 2-methoxyazepane-1-carboxylate; benzylmagnesium chloride In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -78℃; Inert atmosphere;	100%

α-methoxy-N-benzyloxycarbonylazocane (1227635-43-9) + benzylmagnesium chloride (6921-34-2) → α-benzyl-N-benzyloxycarbonylazocane (1227635-51-9)

Conditions	Yield
Stage #1: α-methoxy-N-benzyloxycarbonylazocane; benzylmagnesium chloride In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -78℃; Inert atmosphere;	100%

benzyl 2-methoxypyrrolidine-1-carboxylate (88001-42-7) + benzylmagnesium chloride (6921-34-2) → α-benzyl-N-benzyloxycarbonylpyrrolidine (1227635-48-4)

Conditions	Yield
Stage #1: benzyl 2-methoxypyrrolidine-1-carboxylate; benzylmagnesium chloride In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -78℃; Inert atmosphere;	100%

2-methoxypiperidine-1-carboxylic acid benzyl ester (66893-75-2) + benzylmagnesium chloride (6921-34-2) → α-benzyl-N-benzyloxycarbonylpiperidine (1227635-49-5)

Conditions	Yield
Stage #1: 2-methoxypiperidine-1-carboxylic acid benzyl ester; benzylmagnesium chloride In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -78℃; Inert atmosphere;	100%

2-methoxy-piperidine-1-carboxylic acid methyl ester (56475-86-6) + benzylmagnesium chloride (6921-34-2) → α-benzyl-N-methoxycarbonylpiperidine (144688-84-6)

Conditions	Yield
Stage #1: 2-methoxy-piperidine-1-carboxylic acid methyl ester; benzylmagnesium chloride In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -78℃; Inert atmosphere;	100%

1-Carbomethoxy-2-methoxy-hexamethylenimine (84839-66-7) + benzylmagnesium chloride (6921-34-2) → α-benzyl-N-methoxycarbonylazepane (1227635-46-2)

Conditions	Yield
Stage #1: 1-Carbomethoxy-2-methoxy-hexamethylenimine; benzylmagnesium chloride In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -78℃; Inert atmosphere;	100%

methyl 2-methoxypyrrolidine-1-carboxylate (56475-88-8) + benzylmagnesium chloride (6921-34-2) → α-benzyl-N-methoxycarbonylpyrrolidine (144688-80-2)

Conditions	Yield
Stage #1: methyl 2-methoxypyrrolidine-1-carboxylate; benzylmagnesium chloride In dichloromethane at -78℃; for 1h; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at -78℃; Inert atmosphere;	100%

acetylacetone (123-54-6) + benzylmagnesium chloride (6921-34-2) + spiro[adamantane-2,3'-diazirine] (41736-95-2) → 2-Adamantanone (700-58-3) + 1-benzyl-3,5-dimethyl-1H-pyrazole (1134-81-2)

Conditions	Yield
Stage #1: benzylmagnesium chloride; spiro[adamantane-2,3'-diazirine] In diethyl ether at 0℃; for 2h; Inert atmosphere; Stage #2: acetylacetone With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;	A 84% B 100%

2,2,6,6-tetramethyl-piperidine (768-66-1) + zinc trimethylacetate + benzylmagnesium chloride (6921-34-2) → TMPZnCl*Mg(OPiv)2, TMP - 2,2,6,6-tetramethylpiperidyl, OPiv -pivalate

Conditions	Yield
Stage #1: 2,2,6,6-tetramethyl-piperidine; benzylmagnesium chloride In tetrahydrofuran at 40℃; Inert atmosphere; Schlenk technique; Stage #2: zinc trimethylacetate In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere; Schlenk technique;	100%
Stage #1: 2,2,6,6-tetramethyl-piperidine; benzylmagnesium chloride In tetrahydrofuran at 20 - 40℃; for 12h; Inert atmosphere; Schlenk technique; Stage #2: zinc trimethylacetate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;

C20H32N3O2P + benzylmagnesium chloride (6921-34-2) → (3aR,7aR)-1,3-diisopropyl-2-(((S)-1-(3-methoxyphenyl)-2-phenylethyl)amino)octahydrobenzo[d][1,3,2]diazaphosphole 2-oxide

Conditions	Yield
In dichloromethane at -48℃; for 6h; Inert atmosphere;	100%

benzylmagnesium chloride (6921-34-2) → 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Conditions	Yield
With ethylene dibromide; silver(I) 4-methylbenzenesulfonate In tetrahydrofuran at 20℃; for 0.5h;	99%
With dilithium tetrachlorocuprate; N,N'-di-tert-butyldiaziridinone In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	98%
With trifluoromethanesulfonic acid anhydride In diethyl ether for 0.333333h; Heating;	95%

(S)-3-(1H-indol-3-yl)-N-methoxy-N-methyl-2-(triethylsilyloxy)-propanamide (1155864-28-0) + benzylmagnesium chloride (6921-34-2) → (S)-4-(1H-indol-3-yl)-1-phenyl-3-(triethylsilyloxy)butan-2-one (1155864-29-1)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	99%

(Z)-5<(tert-butyldimethylsilyl)oxy>3,4-epoxy-3-methyl-1-pentyne + benzylmagnesium chloride (6921-34-2) → 1-(t-butyldimethylsilyloxy)-3-methyl-6-phenylhexa-3,4-dien-2-ol

Conditions	Yield
Stage #1: benzylmagnesium chloride With copper(I) bromide dimethylsulfide complex; lithium bromide In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere; Stage #2: (Z)-5<(tert-butyldimethylsilyl)oxy>3,4-epoxy-3-methyl-1-pentyne In tetrahydrofuran at -80 - -50℃; for 4h; Inert atmosphere; optical yield given as %de;	99%

tert-butyl N-[(1R)-2-[methoxy(methyl)amino]-1-methyl-2-oxo-ethyl]carbamate (146553-06-2) + benzylmagnesium chloride (6921-34-2) → ((R)-1-methyl-2-oxo-3-phenyl-propyl)-carbamic acid tert-butyl ester (1426421-61-5)

Conditions	Yield
In tetrahydrofuran; diethyl ether at -16 - 20℃;	99%

(1RS,2SR,7SR)-4-[2-(1H-indol-3-yl)ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione + benzylmagnesium chloride (6921-34-2) → (1RS,2SR,7SR)-5-benzyl-5-hydroxy-4-[2-(1H-indol-3-yl)ethyl]-4-azatricyclo[5.2.1.02,6]dec-8-ene-3-one

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78 - 20℃; diastereoselective reaction;	99%

C25H31NO3 + benzylmagnesium chloride (6921-34-2) → (1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl (4-methoxyphenyl)-L-phenylalaninate

Conditions	Yield
Stage #1: benzylmagnesium chloride With zinc(II) chloride In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Stage #2: C25H31NO3 In tetrahydrofuran at -78℃; for 2h; Schlenk technique; diastereoselective reaction;	99%

(5S,2E)-ethyl 4,4-dichloro-5-(1,1-dimethylethylsulfonamido)-6-methylhept-2-enoate + benzylmagnesium chloride (6921-34-2) → (2S,5S,3Z)-ethyl 2-benzyl-4-chloro-5-(1,1-dimethylethylsulfonamido)-6-methylhept-3-enoate

Conditions	Yield
Stage #1: benzylmagnesium chloride With copper(l) cyanide; lithium chloride In tetrahydrofuran at -78 - 0℃; for 0.166667h; Inert atmosphere; Stage #2: (5S,2E)-ethyl 4,4-dichloro-5-(1,1-dimethylethylsulfonamido)-6-methylhept-2-enoate In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; diastereoselective reaction;	99%

5,7-di-tert-butyl-1,2,3,3a-tetrahydrobenzo[d]pyrrolo[2,1-b]oxazole + benzylmagnesium chloride (6921-34-2) → 2-(2-benzylpyrrolidin-1-yl)-4,6-di-tert-butylphenol

Conditions	Yield
In diethyl ether; 1,2-dichloro-ethane at 0℃; Solvent; Inert atmosphere;	99%

3-(4’-methoxy-1,1’-biphenyl-4-yl)-2-(methylsulfanyl)benzofuran + benzylmagnesium chloride (6921-34-2) → 2-benzyl-3-(4’-methoxy-1,1’-biphenyl-4-yl)benzofuran

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride In toluene at 50℃; for 4h; Schlenk technique; Inert atmosphere;	99%

1,3-chlorobromopropane (109-70-6) + benzylmagnesium chloride (6921-34-2) → 1-Chloro-4-phenylbutane (4830-93-7)

Conditions	Yield
In tetrahydrofuran at 0 - 5℃; for 6h;	98.6%
In tetrahydrofuran at 0 - 5℃; for 6h;	94.1%

2-[(1-phenylmethyl)sulfinyl]pyridine (87577-90-0) + benzylmagnesium chloride (6921-34-2) → 2-Benzylpyridine (101-82-6)

Conditions	Yield
With phenylmagnesium bromide In tetrahydrofuran for 0.25h; Ambient temperature;	98%

Upstream product

• 100-44-7 benzyl chloride 
• 60-29-7 diethyl ether 
• 60014-28-0 2-(Dimethyl-λ⁴-sulfanylidene)-1,2-diphenyl-ethanone 
• 114272-48-9 (3-Methyl-2-phenyl-3,6-dihydro-2H-selenopyran-2-yl)-phenyl-methanone 
• 100-39-0 benzyl bromide 
• 2234-82-4 1-propylmagnesium chloride 
• 635-84-7 4-(chloroacetyl)biphenyl 
• 86901-19-1 9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium 

Downstream Products

• 122-97-4 3-Phenyl-1-propanol 
• 3360-41-6 4-phenyl-butan-1-ol 
• 10309-79-2 1-benzyl-2-methylhydrazine 
• 54813-58-0 2-phenyl-1-(pyridin-4-yl)ethanol 
• 1202-49-9 (E)-2-styrylfuran 
• 3783-65-1 (E)-2-(2-phenylethenyl)thiophene 
• 41010-30-4 (E)-2-styrylselenophene 
• 36707-30-9 2-(2-phenylethyl)furan 
• 857580-91-7 N-(1-benzyl-2-phenyl-ethyl)-anthranilic acid anilide 
• 1745-77-3 2-benzylquinoline 
• 112119-93-4 1,2-dihydro-1-benzylisoquinoline 
• 122-78-1 phenylacetaldehyde 
• 14627-92-0 2-phenyl-1-(pyridin-3-yl)ethanone 
• 51859-08-6 2-benzylidene-1-methyl-1,2-dihydro-pyridine 

Relevant articles and documents

Highly variable Zr-CH2-Ph bond angles in tetrabenzylzirconium: Analysis of benzyl ligand coordination modes

Analysis of a monoclinic modification of Zr(CH2Ph)4 by single-crystal X-ray diffraction reveals that the bond angles Zr-CH 2-Ph in this compound span a range of 25.1° , which is much larger than previously observed for the orthorhombic form (12.1°). In accord with this large range, density functional theory calculations demonstrate that little energy is required to perturb the Zr-CH2-Ph bond angles in this compound. Furthermore, density functional theory calculations on Me 3ZrCH2Ph indicate that bending of the Zr-CH2-Ph moiety in the monobenzyl compound is also facile, thereby demonstrating that a benzyl ligand attached to zirconium is intrinsically flexible, such that its bending does not require a buffering effect involving another benzyl ligand.

Scalable Continuous Synthesis of Grignard Reagents from in Situ-Activated Magnesium Metal

The continuous synthesis of Grignard reagents has been investigated under continuous processing conditions using Mg turnings at variable liquid throughputs and concentrations. A novel process window easily accessible through continuous processing was employed, namely, using a large molar access of Mg turnings within the reactor and achieving Mg activation by mechanical means. A laboratory and a 10-fold-increased pilot-scale reactor setup were built and evaluated, including integrated inline analytics via ATR-IR measurements. The main goal of this work was to explore the full potential of classic Grignard reagent formation through the use of scalable flow chemistry and to allow for fast and safe process optimization. It was found that on both the laboratory and pilot scales, full conversion of the employed halides could be achieved with a single passage through the reactor. Furthermore, Grignard reagent yields of 89-100% were reached on the laboratory scale.

Redox-Active Ligand-Assisted Two-Electron Oxidative Addition to Gallium(II)

The reaction of digallane (dpp-bian)Ga?Ga(dpp-bian) (2) (dpp-bian=1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene) with allyl chloride (AllCl) proceeded by a two-electron oxidative addition to afford paramagnetic complexes (dpp-bian)Ga(η1-All)Cl (3) and (dpp-bian)(Cl)Ga?Ga(Cl)(dpp-bian) (4). Treatment of complex 4 with pyridine induced an intramolecular redox process, which resulted in the diamagnetic complex (dpp-bian)Ga(Py)Cl (5). In reaction with allyl bromide, complex 2 gave metal- and ligand-centered addition products (dpp-bian)Ga(η1-All)Br (6) and (dpp-bian-All)(Br)Ga?Ga(Br)(dpp-bian-All) (7). The reaction of digallane 2 with Ph3SnNCO afforded (dpp-bian)Ga(SnPh3)2 (8) and (dpp-bian)(NCO)Ga?Ga(NCO)(dpp-bian) (9). Treatment of GaCl3 with (dpp-bian)Na in diethyl ether resulted in the formation of (dpp-bian)GaCl2 (10). Diorganylgallium derivatives (dpp-bian)GaR2 (R=Ph, 11; tBu, 14; Me, 15; Bn, 16) and (dpp-bian)Ga(η1-All)R (R=nBu, 12; Cp, 13) were synthesized from complexes 3, 10, Bn2GaCl, or tBu2GaCl by salt metathesis. The salt elimination reaction between (dpp-bian)GaI2 (17) and tBuLi was accompanied by reduction of both the metal and the dpp-bian ligand, which resulted in digallane 2 as the final product. Similarly, the reaction of complex 10 with MentMgCl (Ment=menthyl) proceeded with reduction of the dpp-bian ligand to give the diamagnetic complex [(dpp-bian)GaCl2][Mg2Cl3(THF)6] (18). Compounds 11, 12, 13, 15, and 16 were thermally robust, whereas compound 14 decomposed when heated at reflux in toluene to give complex (dpp-bian-tBu)GatBu2 (19). Both complexes 7 and 19 contain R-substituted dpp-bian ligand: in the former compound the allyl group was attached to the imino-carbon atom, whereas in complex 19, the tBu group was situated on the naphthalene ring. Crystal structures of complexes 3, 8, 9, 10, 13, 14, 18, and 19 were determined by single-crystal X-ray analysis. The presence of dpp-bian radical anions in 3, 6, 8, and 10–16 was determined by ESR spectroscopy.