873-77-8

Basic information

• Product Name: 4-CHLOROPHENYLMAGNESIUM BROMIDE
• Synonyms: 4-CHLOROPHENYLMAGNESIUM BROMIDE;4-Chlorophenylmagnesium bromide solution;bromo(p-chlorophenyl)magnesium;4-CHLOROPHENYLMAGNESIUM BROMIDE, 1.0M SO LUTION IN DIETHYL ETHER;4-Chlorophenylmagnesium Bromide 1.0 M In Diethyl Ether;4-Chlorophenylmagnesium Bromide 1.0 M in Tetrahydrofuran;p-chlorophenylmagnesiumbromide;4-Chlorophenylmagnesium bromide, 0.9M solution in THF/toluene
• CAS NO: 873-77-8
• Molecular Formula: C₆H₄BrClMg
• Molecular Weight: 215.76
• EINECS: 212-853-8
• Product Categories: Aryl;Grignard Reagents;Organometallic Reagents;Grignard Reagent
• Mol File: 873-77-8.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 115 °C(Press: 0.04 Torr)
• Flash Point: −40 °F
• Appearance: Light gray to yellow to brown-black/Solution
• Density: 0.887 g/mL at 25 °C
• Storage Temp.: Flammables + water-Freezer (-20°C)e area
• Water Solubility: It reacts violently with water.
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: 4-CHLOROPHENYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLOROPHENYLMAGNESIUM BROMIDE(873-77-8)
• EPA Substance Registry System: 4-CHLOROPHENYLMAGNESIUM BROMIDE(873-77-8)

Safety Data

• Hazard Codes: F+,C,F
• Statements: 12-19-22-34-67-14-11
• Safety Statements: 9-16-26-29-33-36/37/39-45
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 1
• HazardClass: 3
• Hazardous Substances Data: 873-77-8(Hazardous Substances Data)

Usage

Chemical Properties

Light grey to brown-black solution when properly

Uses

4-Chlorophenylmagnesium bromide is used as a Grignard reagent in greener solvent, 2-methyltetrahydrofuran (2-MeTHF).

InChI:InChI=1/C6H4Cl.BrH.Mg/c7-6-4-2-1-3-5-6;;/h2-5H;1H;/q;;+1/p-1/rC6H4ClMg.BrH/c7-5-1-3-6(8)4-2-5;/h1-4H;1H/q+1;/p-1

Synthetic route

bromochlorobenzene (106-39-8) → (4-chlorphenyl)magnesium bromide (873-77-8)

Conditions	Yield
With magnesium In tetrahydrofuran at 20 - 25℃; for 5h;	95%
With magnesium In diethyl ether
With magnesium In tetrahydrofuran

bromochlorobenzene (106-39-8) + magnesium (7439-95-4) → (4-chlorphenyl)magnesium bromide (873-77-8)

Conditions	Yield
iodine In tetrahydrofuran at 70℃; for 1.5h; Heating / reflux;
In tetrahydrofuran at 20℃; for 2h;
In tetrahydrofuran Inert atmosphere;
With iodine In tetrahydrofuran at 20℃;
With lithium chloride In tetrahydrofuran at 0 - 25℃; for 0.5h; Inert atmosphere; Schlenk technique;

bromochlorobenzene (106-39-8) + 1-azaspiro[4.5]decan-4-one + ammonium chloride → (4-chlorphenyl)magnesium bromide (873-77-8)

Conditions	Yield
In toluene

bromochlorobenzene (106-39-8) + 1-azaspiro[5.5]undecan-5-one (158721-23-4) → 5-(4-chlorophenyl)-5-hydroxy-1-azaspiro[5.5]-undecane (158720-94-6) + (4-chlorphenyl)magnesium bromide (873-77-8)

Conditions	Yield
In toluene

bromochlorobenzene (106-39-8) + 6-azaspiro[4.5]decan-10-one (158721-26-7) → (4-chlorphenyl)magnesium bromide (873-77-8)

Conditions	Yield
With sodium hydroxide In water

bromochlorobenzene (106-39-8) + methyl 3-(1-benzyl-1H-imidazol-5-yl)propanoate (123261-02-9) → (4-chlorphenyl)magnesium bromide (873-77-8)

Conditions	Yield
With magnesium In tetrahydrofuran

2-chloro-N-methoxy-N-methyl-pyridine-3-carboxamide (488149-34-4) + (4-chlorphenyl)magnesium bromide (873-77-8) → 2-chloro-3-(4-chlorobenzoyl)-pyridine (80099-85-0)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 2h;	100%
In tetrahydrofuran; diethyl ether at 5 - 8℃; Inert atmosphere;	100%
In tetrahydrofuran; diethyl ether at 5 - 20℃; for 19.25h; Grignard reaction; Inert atmosphere;	100%
In tetrahydrofuran at 0 - 20℃; for 2h;

(4-chlorphenyl)magnesium bromide (873-77-8) + (Z)-3-(4-chloro-phenyl)-2-cyano-acrylic acid ethyl ester (29708-07-4) → ethyl 3,3-bis(4-chlorophenyl)-2-cyanoacrylate (14442-40-1)

Conditions	Yield
With hydrogenchloride In diethyl ether; toluene for 1h; Heating / reflux;	100%
Stage #1: (4-chlorphenyl)magnesium bromide; (Z)-3-(4-chloro-phenyl)-2-cyano-acrylic acid ethyl ester In diethyl ether; toluene for 1h; Heating / reflux; Stage #2: With hydrogenchloride; water In diethyl ether; toluene Stage #3: With sodium hydrogencarbonate In diethyl ether; ethyl acetate; toluene	100%

pivalaldehyde (630-19-3) + (4-chlorphenyl)magnesium bromide (873-77-8) → (+/-)-2,2-dimethyl-1-(p-chlorophenyl)propan-1-ol (6200-21-1)

Conditions	Yield
In diethyl ether	100%

Dimethylamino-(1,4-dioxa-spiro[4.5]dec-8-yl)-acetonitrile (943002-79-7) + (4-chlorphenyl)magnesium bromide (873-77-8) → [(4-Chlorophenyl)-(1,4-dioxa-spiro[4.5]dec-8-yl)-methyl]-dimethyl-amine (943030-31-7)

Conditions	Yield
In diethyl ether at 0 - 20℃; for 20h;	100%
In tetrahydrofuran at 0 - 20℃; for 20h;	100%
In diethyl ether at 0 - 20℃; for 20h;	100%
Stage #1: Dimethylamino-(1,4-dioxa-spiro[4.5]dec-8-yl)-acetonitrile; (4-chlorphenyl)magnesium bromide In diethyl ether at 20℃; for 20h; Stage #2: With ammonium chloride In diethyl ether; water at 0℃;	100%
Stage #1: Dimethylamino-(1,4-dioxa-spiro[4.5]dec-8-yl)-acetonitrile; (4-chlorphenyl)magnesium bromide In diethyl ether at 20℃; Inert atmosphere; Cooling with ice; Stage #2: With water; ammonium chloride In tetrahydrofuran Cooling with ice;	100%

(4-chlorphenyl)magnesium bromide (873-77-8) + N2-(tert-butoxycarbonyl)-N-methoxy-N-methyl-D,L-valinamide (293329-55-2) → tert-butyl 1-(4-chlorophenyl)-3-methyl-1-oxobutan-2-ylcarbamate (1394017-59-4)

Conditions	Yield
In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	100%
In tetrahydrofuran at -50 - 20℃; for 5.16667h;	3.6 g
In tetrahydrofuran at -50 - 20℃; for 5.16667h;

6-((triisopropylsilyl)oxy)hex-2-yn-1-yl methanesulfonate + (4-chlorphenyl)magnesium bromide (873-77-8) → ((4-(4-chlorophenyl)hexa-4,5-dien-1-yl)oxy)triisopropylsilane

Conditions	Yield
Stage #1: (4-chlorphenyl)magnesium bromide With copper(l) iodide; lithium bromide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 6-((triisopropylsilyl)oxy)hex-2-yn-1-yl methanesulfonate In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	100%

(4-chlorphenyl)magnesium bromide (873-77-8) + pentan-3-one (96-22-0) → 3-(4'-chlorophenyl)pentan-3-ol (76481-35-1)

Conditions	Yield
In dichloromethane at 0 - 20℃;	99%
In tetrahydrofuran for 0.5h;

(4-chlorphenyl)magnesium bromide (873-77-8) + (E)-1-(2-(methylthio)phenyl)-2-pyrrolidinyl-1-nitroethene (389838-02-2) → (E)-2-(4-chlorophenyl)-1-[2-(methylthio)phenyl]-1-nitroethylene (728895-74-7)

Conditions	Yield
In tetrahydrofuran at -78℃;	99%

Upstream product

• 106-39-8 bromochlorobenzene 
• 123261-02-9 methyl 3-(1-benzyl-1H-imidazol-5-yl)propanoate 
• 158721-26-7 6-azaspiro[4.5]decan-10-one 
• 158721-23-4 1-azaspiro[5.5]undecan-5-one 
• 7439-95-4 magnesium 

Downstream Products

• 27652-89-7 (4-chlorophenyl)-2-pyridylmethanol 
• 92299-60-0 1-butyl-3-(4-chloro-phenyl)-pyrrolidin-3-ol 
• 101697-11-4 2-(4-chlorobenzoyl)-1-naphtoic acid 
• 101697-12-5 1-(4-chlorobenzoyl)-2-naphtoic acid 
• 80-06-8 chlorfenethol 
• 3737-16-4 α-<4-Chlor-phenyl>-α-phenyl-4-pyridin-methanol 
• 4576-56-1 tris(p-chlorophenyl)phosphine oxide 
• 5431-35-6 4-chlorophenylphosphonic acid 
• 80268-72-0 2-chloro-1,1-bis-(4-chloro-phenyl)-ethanol 
• 854719-25-8 1-(4-chloro-phenyl)-2-methyl-cyclohexene 
• 35035-60-0 bis(4-chlorophenyl)(phenyl)phosphine 
• 6378-66-1 2-chloro-1-(4-chlorophenyl)ethanol 
• 856206-48-9 chloro-(4,4'-dichloro-benzhydryliden)-amine 
• 10557-71-8 4-chlorophenyltrimethylsilane 

Relevant articles and documents

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Nickel-Catalyzed Cross-Coupling of Functionalized Organo manganese Reagents with Aryl and Heteroaryl Halides Promoted by 4-Fluorostyrene

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