79832-89-6

Basic information

• Product Name: 1-Bromo-4-(trans-4-pentylcyclohexyl)benzene
• Synonyms: 1-Bromo-4-(4-pentylpropyl-cyclohexyl)-benzene;1-BROMO-4-(TRANS-4-N-PENTYLCYCLOHEXYL)BENZENE;4-PENTYL-CYCLOHEXYL BROMO PHENOL;1-Bromo-4-(4-Pentyl-Cyclohexyl)-Benzene,5PcbrC17H25Br;1-Bromo-4-(trans-4-pentylcyclohexyl)benzene;TRANS-4-(4-PENTYLCYCLOHEXYL)-1-BROMOBENZENE;1-broMo-4-((1s,4r)-4-pentylcyclohexyl)benzene;Benzene, 1-bromo-4-(trans-4-pentylcyclohexyl)-
• CAS NO: 79832-89-6
• Molecular Formula: C₁₇H₂₅Br
• Molecular Weight: 309.28
• EINECS: 616-745-5
• Product Categories: Liqiud crystal intermediates
• Mol File: 79832-89-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 363 °C at 760 mmHg
• Flash Point: 165.9 °C
• Appearance: /
• Density: 1.129 g/cm³
• Vapor Pressure: 3.89E-05mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-Bromo-4-(trans-4-pentylcyclohexyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-4-(trans-4-pentylcyclohexyl)benzene(79832-89-6)
• EPA Substance Registry System: 1-Bromo-4-(trans-4-pentylcyclohexyl)benzene(79832-89-6)

Safety Data

• Hazardous Substances Data: 79832-89-6(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

Intermediates of Liquid Crystals

InChI:InChI=1/C17H25Br/c1-2-3-4-5-14-6-8-15(9-7-14)16-10-12-17(18)13-11-16/h10-15H,2-9H2,1H3/t14-,15-

Synthetic route

1.4-dibromobenzene (106-37-6) + 4-n-pentylcyclohexylmagnesium bromide → 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In diethyl ether Ambient temperature;	86%

trans-4-pentylcyclohexylbenzene (66227-31-4) + iron (7439-89-6) + sodium hydrogensulfite → 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6)

Conditions	Yield
With bromine; iodine In dichloromethane

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) + (3,4-difluorophenyl)boronic acid (168267-41-2) → 3,4-difluoro-4'-(4-pentylcyclohexyl)-1,1'-biphenyl (134412-17-2)

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate In ethanol; water at 80℃; for 0.5h; Suzuki Coupling;	97%

4-fluoroboronic acid (1765-93-1) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 4-fluoro-4'-(4-pentylcyclohexyl)-1,1'-biphenyl

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate In ethanol; water at 80℃; for 0.5h; Suzuki Coupling;	95%

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) + phenylboronic acid (98-80-6) → 4-(4-pentylcyclohexyl)-1,1'-biphenyl

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate In ethanol; water at 80℃; for 0.166667h; Suzuki Coupling;	93%

4-trifluoromethylphenylboronic acid (128796-39-4) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 4-(4-pentylcyclohexyl)-4'-(trifluoromethyl)-1,1'-biphenyl (139047-78-2)

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate In ethanol; water at 80℃; for 1.25h; Suzuki Coupling;	93%

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) + 3,4,5-trifluorophenylboronic acid (143418-49-9) → 3,4,5-trifluoro-4'-(4-pentylcyclohexyl)-1,1'-biphenyl

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate In ethanol; water at 80℃; for 2.5h; Suzuki Coupling;	91%

cyclopent-3-enyl bromide (1781-66-4) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → bi-3-cyclopenten-1-yl + 1,1'-bis{4-[(trans-4-pentyl)cyclohexyl]phenyl} + 1-(cyclopenten-4-yl)-4-[(trans-4-pentyl)cyclohexyl]benzene

Conditions	Yield
Stage #1: cyclopent-3-enyl bromide With magnesium In diethyl ether Stage #2: 1-bromo-4-(trans-4-pentylcyclohexyl)benzene With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In diethyl ether at 20℃; for 12h; Further stages.;	A n/a B n/a C 75%

4-methoxyphenylboronic acid (5720-07-0) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 4-methoxy-4'-(trans-4-pentylcyclohexyl)biphenyl

Conditions	Yield
With sodium carbonate In ethanol; water; toluene at 90℃; for 6h; Inert atmosphere;	73%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water for 4h; Inert atmosphere; Reflux;	82 g

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) + 4-methoxyphenylacetylen (768-60-5) → 1-methoxy-4-((4-(4-pentylcyclohexyl)phenyl)ethynyl)benzene (372983-17-0)

Conditions	Yield
With Ph2P(CH2CH2O)22CH3; triethylamine; palladium dichloride In water at 80℃; for 8h; Sonogashira coupling; Inert atmosphere;	71%

Trimethyl borate (121-43-7) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 4-(trans-4-pentylcyclohexyl)phenylboronic acid (143651-26-7)

Conditions	Yield
Stage #1: 1-bromo-4-(trans-4-pentylcyclohexyl)benzene With magnesium In tetrahydrofuran at 20℃; for 3h; Stage #2: Trimethyl borate In tetrahydrofuran at 20 - 78℃; for 24h;	70%
With magnesium In tetrahydrofuran (Ar); dissolving Mg and aryl bromide in dry THF, stirring for 2 h at room temp., addn. of borate deriv. at -78°C, stirring for 5 h at room temp.; washing with HCl, water and chloroform, recrystn. (hexane);	52%

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) + (2,3-difluorophenyl)boronic acid (121219-16-7) → 2,3-difluoro-4'-(trans-4-pentylcyclohexyl)biphenyl

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; benzene for 6h; Heating / reflux;	69.9%

1-allyl-4-fluorobenzene (1737-16-2) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) + bis(pinacol)diborane (73183-34-3) → C32H46BFO2 + C32H46BFO2

Conditions	Yield
With [nickel(II)dichloride(dimethoxyethane)]; quinoline; lithium methanolate In 1,4-dioxane at 30℃; Inert atmosphere; Sealed tube; regioselective reaction;	A n/a B 68%

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 4-(trans-4-pentylcyclohexyl)phenylboronic acid (143651-26-7)

Conditions	Yield
Stage #1: 1-bromo-4-(trans-4-pentylcyclohexyl)benzene With magnesium In tetrahydrofuran at 20℃; for 2h; Stage #2: With Trimethyl borate In tetrahydrofuran at 20℃; for 5h; Further stages.;	52%

(-)-dimethy-2,3-O-isopropylidene-L-tartrate (37031-29-1) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → (4R,5R)-2,2-dimethyl-α,α,α',α'-tetra[4-(trans-4-n-pentylcyclohexyl)phenyl]-1,3-diox olane-4,5-dimethanol

Conditions	Yield
Stage #1: 1-bromo-4-(trans-4-pentylcyclohexyl)benzene With magnesium In tetrahydrofuran at 80℃; for 1h; Inert atmosphere; Stage #2: (-)-dimethy-2,3-O-isopropylidene-L-tartrate In tetrahydrofuran at 80℃; for 11.5h; Inert atmosphere;	51%

3-methyl-4-propyl-1-(4-bromophenyl)cyclohexane (136240-57-8) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 3r-methyl-4t-propyl-1c-<4'-(trans-4-amylcyclohexyl)-4-biphenylyl>cyclohexane (132640-45-0, 136315-98-5)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; magnesium 2.) THF, reflux, 1 h; Yield given. Multistep reaction;

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) + (3-bromocyclobutyl)benzene → trans-1-(4-Pentylcyclohexyl)-4-(3-phenylcyclobutyl)benzol + cis-1-(4-Pentylcyclohexyl)-4-(3-phenylcyclobutyl)benzol

Conditions	Yield
With lithium; zinc dibromide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 1.) THF, toluene, ultrasonic irradiation, 0-10 deg C, 3.3 h, 2.) THF, toluene, r.t., 3 d; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) + 3,4,5-trifluoro-1-bromobenzene (138526-69-9) → 3,4,5-trifluoro-4'-(4-pentylcyclohexyl)-1,1'-biphenyl

Conditions	Yield
Multistep reaction;

(2,6-difluoropyridin-3-yl)boronic acid (136466-94-9) + Na2 CO3 -solution + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 2,6-difluoro-3-[4-(trans-4-pentylcyclohexyl)phenyl]-pyridine (136466-93-8)

Conditions	Yield
Pd(PPh3)4 In ethanol; toluene

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 3-fluoro-5-octyloxy-2-[4-(trans-4-pentylcyclohexyl)phenyl]pyridine

4-n-pentylcyclohexanone (61203-83-6) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 1,4-bis-(trans-4-n-pentylcyclohexyl)-benzene

Conditions	Yield
With ammonium chloride; magnesium In tetrahydrofuran; ice-water; ethanol; potassium tert-butylate; water; palladium; dimethyl sulfoxide

Pd(PPh3)4 (4 x 10min4 mM) + 2,3-difluoro-pyridine-5-bromic acid + sodium carbonate (497-19-8) + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 2,3-difluoro-5-[4-(trans-4-pentylcyclohexyl)phenyl]-pyridine

Conditions	Yield
In ethanol; toluene

Na2CO3-solution + 2,3,6-trifluoro-pyridine-5-boronic acid + 1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 2,3,6-trifluoro-5-[4-(trans-4-pentylcyclohexyl)phenyl]-pyridine

Conditions	Yield
Pd(PPh3)4 In ethanol; toluene

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 4-(4-n-pentylcyclohexyl)benzeneboronic acid (136321-96-5)

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 4'-(trans-4-pentylcyclohexyl)-[1,1‘-biphenyl]-4-ol (91545-94-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate / toluene; ethanol; water / 6 h / 90 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 2 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water / 4 h / Inert atmosphere; Reflux 2: pyridine hydrochloride salt / 1 h / 200 °C View Scheme

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → C30H34N2O5

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium carbonate / toluene; ethanol; water / 6 h / 90 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 2 h / 0 °C / Inert atmosphere 3: sodium hydroxide / tetrahydrofuran; water; N,N-dimethyl-formamide / 4 h / 20 - 25 °C View Scheme

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → C30H38N2O

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium carbonate / toluene; ethanol; water / 6 h / 90 °C / Inert atmosphere 2: boron tribromide / dichloromethane / 2 h / 0 °C / Inert atmosphere 3: sodium hydroxide / tetrahydrofuran; water; N,N-dimethyl-formamide / 4 h / 20 - 25 °C 4: hydrogen; platinum(IV) oxide / 1,4-dioxane / 19 h / 20 - 80 °C View Scheme

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 6-((4’-(trans-4-pentylcyclohexyl)-[1,1’-biphenyl]-4-yl)oxy)hexan-1-ol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water / 4 h / Inert atmosphere; Reflux 2.1: pyridine hydrochloride salt / 1 h / 200 °C 3.1: potassium carbonate; potassium iodide / N,N-dimethyl acetamide / 90 °C / Inert atmosphere 3.2: 40 h / 90 °C / Inert atmosphere View Scheme

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → 6-((4'-(4-pentylcyclohexyl)[1,1'-biphenyl]-4-yl)oxy)hexyl 4-methylbenzenesulfonate

Conditions	Yield
Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water / 4 h / Inert atmosphere; Reflux 2.1: pyridine hydrochloride salt / 1 h / 200 °C 3.1: potassium carbonate; potassium iodide / N,N-dimethyl acetamide / 90 °C / Inert atmosphere 3.2: 40 h / 90 °C / Inert atmosphere 4.1: pyridine / dichloromethane / 24 h / 20 °C View Scheme

1-bromo-4-(trans-4-pentylcyclohexyl)benzene (79832-89-6) → C42H50O4

Conditions

Yield

Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water / 4 h / Inert atmosphere; Reflux 2.1: pyridine hydrochloride salt / 1 h / 200 °C 3.1: potassium carbonate; potassium iodide / N,N-dimethyl acetamide / 90 °C / Inert atmosphere 3.2: 40 h / 90 °C / Inert atmosphere 4.1: pyridine / dichloromethane / 24 h / 20 °C 5.1: potassium carbonate / acetone / 2 h / 70 °C / Inert atmosphere View Scheme

Upstream product

• 106-37-6 1.4-dibromobenzene 
• 66227-31-4 trans-4-pentylcyclohexylbenzene 
• 7439-89-6 iron 

Downstream Products

• 81793-59-1 4-fluoro-4'-(4-pentylcyclohexyl)-1,1'-biphenyl 
• 134412-17-2 3,4-difluoro-4'-(4-pentylcyclohexyl)-1,1'-biphenyl 
• 137019-95-5 3,4,5-trifluoro-4'-(4-pentylcyclohexyl)-1,1'-biphenyl 
• 79832-84-1 1,1'-bis{4-[(trans-4-pentyl)cyclohexyl]phenyl} 
• 372983-17-0 1-methoxy-4-((4-(4-pentylcyclohexyl)phenyl)ethynyl)benzene 
• 143651-26-7 4-(trans-4-pentylcyclohexyl)phenylboronic acid 
• 136321-96-5 4-(4-n-pentylcyclohexyl)benzeneboronic acid 
• 136466-93-8 2,6-difluoro-3-[4-(trans-4-pentylcyclohexyl)phenyl]-pyridine 

Relevant articles and documents

Cyclic hydrocarbon derivative and liquid crystal composition containing the same

A cyclic hydrocarbon derivative represented by formula (I): STR1 wherein each of Y1 and Y2 is independently F, Cl, CN, OCN, SCN, OCF3, OCF2 H, OCF2 CF3, CF3, R, --OR, --COOR or --OCOR, wherein R is alkyl, alkenyl or alkoxyalkyl, provided that at least one of Y1 and Y2 is R, --OR, --COOR or --OCOR; each of Z, Z1, Z2, Z3 and Z4 is independently a single bond, --CH2 CH2 --, --CH=CH--, --C C--, --COO--, --OCO--, --CH2 O--, OCH2 --, --(CH2)4 --, --(CH2)3 --O-- or --O--(CH2)3 --; ring A is group of formula (II): STR2 wherein each of X1, X2, X3, X4, X5, X6, X7, X8, X9, and X10 is independently H or D, provided that at least one of them is D; each of rings K, L, J, M and N is independently trans-1,4-cyclohexylene, 1,4-cyclohexenylene, substituted trans-1,4-cyclohexylene, 1,4-phenylene, substituted 1,4-phenylene, 1,3-dioxane-2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, pyarazine-2,5-diyl or a group of formula (III): STR3 wherein each of X11, X12, X13, X14, X15, X16, X17, X18, X19, and X20 is independently H or D, provided that at least one of them is D; in which the ring of formula (III) may be the same as or different from ring A; and k, l, m, and n each independently is 0 or 1, provided that the sum of k, l, m, and n is 0, 1 or 2. The compound is useful as an electro-optic liquid crystal display material.