33240-34-5

Basic information

• Product Name: CYCLOPENTYLMAGNESIUM BROMIDE
• Synonyms: CYCLOPENTYLMAGNESIUM BROMIDE: (18% IN TETRAHYDROFURAN, CA. 1MOL/L);Cyclopentylbromomagnesium;Einecs 251-420-8;Magnesium, bromocyclopentyl-;Cyclopentylmagnesium bromide solution 2.0 in diethyl ether;Cyclopentylmagnesium bromide, 2.0M solution in diethyl ether, AcroSeal;CyclopentylMagnesiuM BroMide, 2M in THF;CYCLOPENTYLMAGNESIUM
• CAS NO: 33240-34-5
• Molecular Formula: C₅H₉BrMg
• Molecular Weight: 173.33
• EINECS: 251-420-8
• 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: 33240-34-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 35 °C
• Flash Point: −36 °F
• Appearance: Gray/Solution
• Density: 0.996 g/mL at 25 °C
• Vapor Pressure: 314mmHg at 25°C
• CAS DataBase Reference: CYCLOPENTYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOPENTYLMAGNESIUM BROMIDE(33240-34-5)
• EPA Substance Registry System: CYCLOPENTYLMAGNESIUM BROMIDE(33240-34-5)

Safety Data

• Hazard Codes: F+,C
• Statements: 12-14-22-34-66-67-19-17
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 1
• HazardClass: 4.3/3
• PackingGroup: I
• Hazardous Substances Data: 33240-34-5(Hazardous Substances Data)

Usage

Chemical Properties

Grey to light brown to dark brown liquid

InChI:InChI=1/C5H9.BrH.Mg/c1-2-4-5-3-1;;/h1H,2-5H2;1H;/q-1;;+2/p-1

Synthetic route

Cyclopentyl bromide (137-43-9) → bicyclopentyl (1636-39-1) + cyclopentylmagnesium bromide (33240-34-5)

Conditions	Yield
With tetrahydrofuran; magnesium chloride at 37℃; Product distribution; Mechanism; effect of solvent deuteration, other reagents;	A 2% B 71%

Cyclopentyl bromide (137-43-9) → Cyclopentane (287-92-3) + bicyclopentyl (1636-39-1) + cyclopentene (142-29-0) + cyclopentylmagnesium bromide (33240-34-5)

Conditions	Yield
With magnesium In diethyl ether at 0℃; Mechanism; Rate constant; reaction rate dependence on angular velocity of disk, solution viscosity;	A 13 % Chromat. B 21 % Chromat. C 13 % Chromat. D 50%

Cyclopentyl bromide (137-43-9) → cyclopentylmagnesium bromide (33240-34-5)

Conditions	Yield
With magnesium In diethyl ether
With magnesium In diethyl ether Thermodynamic data; -ΔH(reaction);
With magnesium In tetrahydrofuran at 23℃; Kinetics;

cyclopentylmagnesium bromide (33240-34-5) + Carbonic acid ethyl ester (E)-non-2-enyl ester → (1-Vinyl-heptyl)-cyclopentane

Conditions	Yield
CuCl - N-heterocyclic carbene In diethyl ether at 0℃;	100%

5,7-di-tert-butyl-1,2,3,3a-tetrahydrobenzo[d]pyrrolo[2,1-b]oxazole + cyclopentylmagnesium bromide (33240-34-5) → 2,4-di-tert-butyl-6-(2-cyclopentylpyrrolidin-1-yl)phenol

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

phenyldimethylsilyl chloride (768-33-2) + cyclopentylmagnesium bromide (33240-34-5) → cyclopentyldimethyl(phenyl)silane

Conditions	Yield
With (DrewPhos)2PdI2 In diethyl ether at 20℃; for 24h;	99%

cyclopentylmagnesium bromide (33240-34-5) → cyclopentyldimethyl(phenyl)silane

Conditions	Yield
With (DrewPhos)2PdI2 In diethyl ether at 20℃; for 24h; Inert atmosphere; Schlenk technique;	99%

cyclopentylmagnesium bromide (33240-34-5) → Cyclopentane (287-92-3)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butyl alcohol In diethyl ether at 34℃;	98%

C19H25N2S(1+)*F6Sb(1-) + cyclopentylmagnesium bromide (33240-34-5) → C13H14S

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78℃; for 2h; Schlenk technique; Inert atmosphere;	98%

[(η(5)-C5H4SiMe3)2Ti(C.tplbond.CSiMe3)2Cu(SC6H4(CH2N(CH3)2))] + cyclopentylmagnesium bromide (33240-34-5) → (C5H4Si(CH3)3)2Ti(CCSi(CH3)3)2CuC5H9

Conditions	Yield
In diethyl ether (N2); addn. of a soln. of magnesium compd. in Et2O to a soln. of copper complex in Et2O at -50°C, stirring for 90 min; filtration through Kieselgur, evapn. at -30°C, dissolving in a mixt. of CH2Cl2/petroleum ether 1:5 at -30°C, filtration through Kieselgur, evapn.;	96%

(2S,4S)-4-isopropyl-2-p-toluene-4,5-dihydro-<1,2λ6,3>oxathiazole 2-oxide (145624-62-0, 145679-46-5) + cyclopentylmagnesium bromide (33240-34-5) → C17H27NO2S (145624-67-5)

Conditions	Yield
In tetrahydrofuran; diethyl ether 1) -78 deg C, 5 min, 2) 0 deg C, 45 min;	94%

Ni(2+)*C36H44N4C3H2O(2-) + cyclopentylmagnesium bromide (33240-34-5) → Ni(II) meso-(3-hydroxy-3-cyclopentyl-propenyl)octaethylporphyrin

Conditions	Yield
In tetrahydrofuran; diethyl ether at -30℃; for 0.166667h;	94%

1-Fluoronaphthalene (321-38-0) + cyclopentylmagnesium bromide (33240-34-5) → 1-cyclopentylnaphthalene (92578-67-1)

Conditions	Yield
Stage #1: 1-Fluoronaphthalene With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(diphenylphosphino)ethane In di-isopropyl ether for 0.05h; Sealed tube; Glovebox; Stage #2: cyclopentylmagnesium bromide In diethyl ether; di-isopropyl ether at 100℃; for 24h; Sealed tube; Glovebox;	94%
Stage #1: 1-Fluoronaphthalene With C30H36NiOP2 In tetrahydrofuran for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: cyclopentylmagnesium bromide In tetrahydrofuran at 60℃; for 16h; Inert atmosphere; Schlenk technique;	79%

cyclohexenone (930-68-7) + cyclopentylmagnesium bromide (33240-34-5) → 1-cyclopentyl-cyclohex-2-enol

Conditions	Yield
With lanthanum(III) chloride; lithium chloride In tetrahydrofuran at 0℃; for 0.5h;	93%
LaCl3-2LiCl In tetrahydrofuran	93%

isochromane (493-05-0) + cyclopentylmagnesium bromide (33240-34-5) → 3,4-dihydro-1-cyclopentyl-1H-2-benzopyran

Conditions	Yield
Stage #1: isochromane With 2-azatricyclo[3.3.1.13,7]decan-2-ol; [bis-(trifluoroacetoxy)iodo]benzene In 1,2-dichloro-ethane at 50℃; for 15h; Inert atmosphere; Stage #2: cyclopentylmagnesium bromide With 2-azatricyclo[3.3.1.13,7]decan-2-ol; [bis-(trifluoroacetoxy)iodo]benzene In diethyl ether; 1,2-dichloro-ethane at -30℃; for 3h; Inert atmosphere;	93%

Gallium trichloride (13450-90-3) + cyclopentylmagnesium bromide (33240-34-5) → tricyclopentylgallium (149063-84-3)

Conditions	Yield
In diethyl ether room temp, 16h; evapn.; extn. (hexane); distn. (150-155°C, 0.1 mmHg);	92.4%

N,N-dibenzylformamide (5464-77-7) + cyclopentylmagnesium bromide (33240-34-5) → 6-exo-(N,N-dibenzylamino)bicyclo[3.1.0]hexane

Conditions	Yield
With titanium(IV) isopropylate In tetrahydrofuran; benzene Reflux;	92%

1-naphthyl tosylate (68211-49-4) + cyclopentylmagnesium bromide (33240-34-5) → 1-cyclopentylnaphthalene (92578-67-1)

Conditions	Yield
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 23℃; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;	92%

(μ-dithio)bis(tricarbonyliron) (14243-23-3) + cyclopentylmagnesium bromide (33240-34-5) → (CH3S)(C5H9S)Fe2(CO)6 (102844-59-7, 102918-27-4, 102918-28-5)

Conditions	Yield
With methyl iodide In tetrahydrofuran N2; dropwise addn. of Grignard reagent to Fe-complex (-78°C), stirring (15-20 min), addn. of MeI, stirring (30 min, then 2-3 h, room temp.); solvent removal (reduced pressure), chromy. (silicic acid), distn. (reduced pressure); elem. anal.;	91%

9-ethyl-6-methoxypurine (1338696-09-5) + cyclopentylmagnesium bromide (33240-34-5) → 8-cyclopentyl-9-ethyl-6-methoxy-9H-purine (1383483-98-4)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 1,2-dichloro-ethane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	91%

benzyl 4-oxoquinoline-1(4H)-carboxylate (172538-83-9) + cyclopentylmagnesium bromide (33240-34-5) → (2R)-benzyl 2-cyclopentyl-4-oxo-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions	Yield
Stage #1: benzyl 4-oxoquinoline-1(4H)-carboxylate With copper(I) bromide dimethylsulfide complex; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane In dichloromethane at 18 - 25℃; for 0.333333h; Inert atmosphere; Schlenk technique; Stage #2: cyclopentylmagnesium bromide In dichloromethane at -78℃; for 2h; Inert atmosphere; Schlenk technique; enantioselective reaction;	91%

tert-Butyl 4-(5-(6-(3-Bromo-5-methylphenoxy)pyridin-2-yl)-4-methyl-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate + cyclopentylmagnesium bromide (33240-34-5) → tert-Butyl 4-(5-(6-(3-Cyclopentyl-5-methylphenoxy)pyridin-2-yl)-4-methyl-1H-1,2,3-triazol-1-yl)piperidine-1-carboxylate

Conditions	Yield
With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In diethyl ether at 20 - 60℃; for 1h;	91%

1-(2-(tert-butylsulfinyl)phenyl)-3-(2-formylphenyl)-1,3-dimethylurea (1114451-19-2) + cyclopentylmagnesium bromide (33240-34-5) → C25H34N2O3S (1114451-42-1)

Conditions	Yield
With N,N'-dimethylpropylideneurea In tetrahydrofuran; hexane at -78℃; Inert atmosphere; diastereoselective reaction;	90%

5-chloro-6-[(triisopropyl)oxy]-1,3-benzoxazol-2(3H)-one + cyclopentylmagnesium bromide (33240-34-5) → N-{5-chloro-2-hydroxy-4-[(triisopropylsilyl)oxy]phenyl}cyclopentanecarboxamide

Conditions	Yield
In tetrahydrofuran at 70℃;	89%

anthranilic acid nitrile (1885-29-6) + cyclopentylmagnesium bromide (33240-34-5) → (2-aminophenyl)-cyclopentyl methanone (106718-47-2)

Conditions	Yield
Stage #1: anthranilic acid nitrile; cyclopentylmagnesium bromide With copper(I) bromide dimethylsulfide complex In tetrahydrofuran; diethyl ether at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In water Cooling with ice;	89%
With hydrogenchloride In diethyl ether; water; ethyl acetate
Stage #1: anthranilic acid nitrile; cyclopentylmagnesium bromide In tetrahydrofuran at 0 - 20℃; Grignard reaction; Stage #2: With hydrogenchloride; water In tetrahydrofuran Grignard reaction; Stage #3: With sodium hydroxide In tetrahydrofuran; water at 0℃;
Stage #1: anthranilic acid nitrile; cyclopentylmagnesium bromide In tetrahydrofuran at 0 - 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran Stage #3: With sodium hydroxide In tetrahydrofuran; water at 0℃;
In tetrahydrofuran at 0 - 20℃;

(2S)-2,3-Epoxy-1-(triisopropylsilyloxy)propane (185140-87-8) + cyclopentylmagnesium bromide (33240-34-5) → (S)-1-cyclopentyl-3-(triisopropylsilyloxy)propan-2-ol (1254212-40-2)

Conditions	Yield
With dilithium tetrachlorocuprate In tetrahydrofuran at -40℃; for 0.5h; Inert atmosphere;	89%

9-benzyl-6-(4-ethylphenyl)-9H-purine (1346993-67-6) + cyclopentylmagnesium bromide (33240-34-5) → 9-benzyl-8-cyclopentyl-6-(4-ethylphenyl)-9H-purine (1383484-01-2)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 1,2-dichloro-ethane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	89%

N-Phenyl-2-(trimethylsilyl)propenamide (153035-24-6) + cyclopentylmagnesium bromide (33240-34-5) → 3-Cyclopentyl-N-phenyl-2-trimethylsilanyl-propionamide (153035-37-1)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 20℃; for 4h;	88%

(E)-2-Hexenal (6728-26-3) + cyclopentylmagnesium bromide (33240-34-5) → (E)-1-cyclopentylhex-2-en-1-ol

Conditions	Yield
In tetrahydrofuran at -20 - 20℃; Inert atmosphere;	88%

isoprene epoxide (1838-94-4) + cyclopentylmagnesium bromide (33240-34-5) → (E)-4-cyclopentyl-2-methylbut-2-en-1-ol (1067637-10-8)

Conditions	Yield
With copper(I) bromide In tetrahydrofuran; diethyl ether at -30℃; for 1h;	87%

3-(dimethoxymethyl)-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine (1190770-72-9) + cyclopentylmagnesium bromide (33240-34-5) → C26H31NO3 (1195045-90-9)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; regioselective reaction;	87%

6-methoxy-9-methyl-9H-purine (38917-25-8) + cyclopentylmagnesium bromide (33240-34-5) → 8-cyclopentyl-6-methoxy-9-methyl-9H-purine (1383483-97-3)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 1,2-dichloro-ethane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	87%

benzyl bromide (100-39-0) + cyclopentylmagnesium bromide (33240-34-5) → ((cyclopentylsulfonyl)methyl)benzene (14633-48-8)

Conditions	Yield
Stage #1: cyclopentylmagnesium bromide With 1,4-diazabicyclo[2.2.2]octane-triethylenediamine-bis(sulfur dioxide) In tetrahydrofuran at -40℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 120℃; for 3h; Inert atmosphere; Microwave irradiation;	86%

Upstream product

• 137-43-9 Cyclopentyl bromide 

Downstream Products

• 766-00-7 2-cyclopentyl-ethanol 
• 767-05-5 3-cyclopentyl-1-propanol 
• 77-39-4 cycrimine 
• 110480-94-9 cyclopentylphenylmethanol 
• 3400-41-7 N-phenylcyclopentanecarboxamide 
• 5422-88-8 phenyl cyclopentyl ketone 
• 15831-52-4 cyclopentyl(4-methoxyphenyl)methanone 
• 17932-68-2 dicyclopentyl-phenyl-silane 
• 142-29-0 cyclopentene 
• 3524-75-2 allylcyclopentane 
• 872-53-7 cyclopentanealdehyde 
• 427-49-6 2-cyclopentyl-2-hydroxy-2-phenylacetic acid 
• 2690-19-9 3-cyclopentylcyclohex-1-ene 
• 5773-56-8 1,2-Diphenylethanol 

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