623-24-5

Basic information

• Product Name: alpha,alpha'-Dibromo-p-xylene
• Synonyms: 1,4-bis(bromomethyl)-benzen;1,4-Di(brommethyl)-benzen;1,4-Dibromomethylbenzene;p-(Bromomethyl)benzene;p-alpha,alpha'-Dibromoxylene;p-Bis(bromomethyl)benzene;p-Xylene, alpha,alpha'-dibromo-;P-XYLYLENE BROMIDE
• CAS NO: 623-24-5
• Molecular Formula: C₈H₈Br₂
• Molecular Weight: 263.96
• EINECS: 210-781-1
• Product Categories: Aromatic Halides (substituted);Aromatics;Miscellaneous Reagents;Aryl;Building Blocks;C8;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 623-24-5.mol
• Article Data: 54

Chemical Properties

• Melting Point: 143-145 °C(lit.)
• Boiling Point: 245 °C(lit.)
• Flash Point: 155-158°C/14mm
• Appearance: White to beige/Crystalline Powder and Coarse Crystals
• Density: 2.012
• Refractive Index: 1.614
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: dioxane: soluble1g/10 mL (hot)
• Water Solubility: soluble, hydrolyses
• Sensitive: Lachrymatory
• BRN: 1100019
• CAS DataBase Reference: alpha,alpha'-Dibromo-p-xylene(CAS DataBase Reference)
• NIST Chemistry Reference: alpha,alpha'-Dibromo-p-xylene(623-24-5)
• EPA Substance Registry System: alpha,alpha'-Dibromo-p-xylene(623-24-5)

Safety Data

• Hazard Codes: C
• Statements: 34-22
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3448 6.1/PG 2
• WGK Germany: 3
• F: 8-19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 623-24-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Purification Methods

Distil it under a vacuum and recrystallise it from EtOH, *benzene or chloroform. [Wenner Org Chem 17 527 1952, Beilstein 5 H 385, 5 I 187, 5 II 301, 5 III 859, 5 IV 970.]

Synthetic route

p-xylylene glycol (589-29-7) → 1,4-bis(bromomethyl)benzene (623-24-5)

Conditions	Yield
With Silphos; bromine In acetonitrile for 0.166667h; Heating;	97%
With hydrogen bromide bei der Destillation;

para-xylene (106-42-3) → 1,4-bis(bromomethyl)benzene (623-24-5)

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4h; Bromination; Heating;	90%
With hydrogen bromide; sodium bromide In chloroform; water at 0 - 2℃; Electrolysis;	90%
With hydrogen bromide; sodium bromide In chloroform; water at 15℃; Electrolysis;	90%

terephthalaldehyde, (623-27-8) → 1,4-bis(bromomethyl)benzene (623-24-5)

Conditions	Yield
With isopinocampheyl-boron dibromide dimethylsulfide complex In hexane at 20℃; for 5h; Reduction; bromination;	81%

para-xylene (106-42-3) → 1,4-bis(bromomethyl)benzene (623-24-5) + 4-Methylbenzyl bromide (104-81-4)

Conditions	Yield
With sodium bromate; sodium hydrogensulfite In water; ethyl acetate at 20℃; for 4h; Bromination;	A 70% B 6%
With N-Bromosuccinimide In water at 25℃; for 22h; Wohl-Ziegler bromination;	A 3% B 66%
With hydrogen bromide; dihydrogen peroxide In water at 20℃; Irradiation;	A 10% B 62%

4-dimethylamino-benzaldehyde (100-10-7) → 1,4-bis(bromomethyl)benzene (623-24-5)

Conditions	Yield
With [2,5-Me2C6H3SO2N(Br)CH2]2; dibenzoyl peroxide In tetrachloromethane at 77℃; for 1.5h; Bromination;	62%

formaldehyd (50-00-0) + benzyl bromide (100-39-0) → 1,4-bis(bromomethyl)benzene (623-24-5)

Conditions	Yield
With phosphoric acid; hydrogen bromide; acetic acid at 95 - 110℃; Einleiten von HBr;

formaldehyd (50-00-0) + benzene (71-43-2) → 1,4-bis(bromomethyl)benzene (623-24-5)

Conditions	Yield
With tetrachloromethane; hydrogen bromide; zinc dibromide
With hydrogen bromide; acetaldehyde

bis(bromomethyl) ether (4497-29-4) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) + benzene (71-43-2) → 1,4-bis(bromomethyl)benzene (623-24-5) + benzyl bromide (100-39-0)

bis(bromomethyl) ether (4497-29-4) + benzene (71-43-2) → 1,4-bis(bromomethyl)benzene (623-24-5)

Conditions	Yield
With zinc(II) chloride

bis(bromomethyl) ether (4497-29-4) + benzene (71-43-2) → 1,4-bis(bromomethyl)benzene (623-24-5) + benzyl bromide (100-39-0)

Conditions	Yield
With zinc(II) chloride

p-xylylene (502-86-3) → 1,4-bis(bromomethyl)benzene (623-24-5)

Conditions	Yield
With bromine

para-xylene (106-42-3) → 1,4-bis(bromomethyl)benzene (623-24-5) + ω.ω.ω'-tribromo-p-xylene

Conditions	Yield
With bromine

para-xylene (106-42-3) → 1,4-bis(bromomethyl)benzene (623-24-5) + 1-(dibromomethyl)-4-methylbenzene (4076-57-7) + 1-methyl-4-(tribromomethyl)benzene

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); 1,3,4,6-Tetrabromo-3α,6α-diphenylglycoluril In tetrachloromethane at 81℃; for 2h; Inert atmosphere;	A 61 %Chromat. B 30 %Chromat. C 9 %Chromat.

1,4-bis(bromomethyl)benzene (623-24-5) + 1-(5-Phenoxy-pentyl)-4-aza-1-azonia-bicyclo[2.2.2]octane; bromide → C42H62N4O2(4+)*4Br(1-)

Conditions	Yield
In methanol; chloroform Heating;	100%

1H-imidazole (288-32-4) + 1,4-bis(bromomethyl)benzene (623-24-5) → 1,4-bis(imidazol-l-yl-methyl)benzene (56643-83-5)

Conditions	Yield
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: 1,4-bis(bromomethyl)benzene In tetrahydrofuran; mineral oil for 6h; Reflux; Inert atmosphere;	100%
Stage #1: 1H-imidazole With potassium hydroxide In acetonitrile at 20℃; for 2h; Stage #2: 1,4-bis(bromomethyl)benzene In acetonitrile at 20℃; for 1.5h;	88%
With potassium hydroxide In isopropyl alcohol	80%

1,4-bis(bromomethyl)benzene (623-24-5) + triphenylphosphine (603-35-0) → p-xylenebis(triphenylphosphonium) dibromide (40817-03-6)

Conditions	Yield
In N,N-dimethyl-formamide for 3h; Heating;	100%
In N,N-dimethyl-formamide at 20℃; for 4h;	98%
In dichloromethane at 40℃; for 4h;	95%

1,4-bis(bromomethyl)benzene (623-24-5) → poly(p-xylylene)

Conditions	Yield
With chromium chloride; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Electrolysis;	100%

1,4-bis(bromomethyl)benzene (623-24-5) → p-xylylene diazide (102437-81-0)

Conditions	Yield
With sodium azide In dimethyl sulfoxide at 20℃; for 18h;	100%
With sodium azide In dimethyl sulfoxide at 20℃; for 1h;	98%
With sodium azide In N,N-dimethyl-formamide at 60℃; for 10h;	97%

1,4-bis(bromomethyl)benzene (623-24-5) + cis-4,7,11,14-tetraazaperhydropyrene (74199-16-9) → C32H52N8(2+)*2Br(1-)

Conditions	Yield
In acetonitrile at 20℃; for 168h;	100%

1,4-bis(bromomethyl)benzene (623-24-5) → 1,4-bis(mercaptomethyl)benzene (105-09-9)

Conditions	Yield
Stage #1: 1,4-bis(bromomethyl)benzene With thiourea In ethanol for 4h; Inert atmosphere; Stage #2: With water; sodium hydroxide for 0.5h; Inert atmosphere; Reflux;	100%
With potassium carbonate; tiolacetic acid In methanol at 20℃; for 1h;	100%
With thioacetic acid; potassium carbonate In methanol at 20℃; for 0.5h;	98%

1,4-bis(bromomethyl)benzene (623-24-5) + bis(tert-butoxyaminoethyl)amine → 1,4-bis<<(2-aminoethyl)amino>methyl>benzene (71277-17-3)

Conditions	Yield
Stage #1: 1,4-bis(bromomethyl)benzene; bis(tert-butoxyaminoethyl)amine With potassium carbonate In acetonitrile at 60℃; for 12h; Stage #2: With hydrogenchloride In diethyl ether	100%

1,4-bis(bromomethyl)benzene (623-24-5) + 6-(3,4-dimethoxy-phenyl)-2,3,4,5-tetrahydropyridazin-3-one (39499-66-6) → 2-[4-(bromomethyl)benzyl]-6-(3,4-dimethoxyphenyl)-4,5-dihydropyridazin-3(2H)-one

Conditions	Yield
Stage #1: 6-(3,4-dimethoxy-phenyl)-2,3,4,5-tetrahydropyridazin-3-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Stage #2: 1,4-bis(bromomethyl)benzene In N,N-dimethyl-formamide; mineral oil for 0.25h;	100%

1,4-bis(bromomethyl)benzene (623-24-5) + (R,R)-4,4'-diisopropyl-2,2'-methylenebis(1,3-oxazoline) (131833-90-4) → 1,4-bis[2,2-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)ethyl]benzene (1381949-76-3)

Conditions	Yield
Stage #1: 2,2'-methylenebis[(4S)-4-isopropyl-4,5-dihydro-oxazole] With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 1,4-bis(bromomethyl)benzene In tetrahydrofuran at 80℃; for 10h; Inert atmosphere;	100%
Stage #1: 2,2'-methylenebis[(4S)-4-isopropyl-4,5-dihydro-oxazole] With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 1,4-bis(bromomethyl)benzene In tetrahydrofuran for 10h; Inert atmosphere; Heating;	100%
Stage #1: 2,2'-methylenebis[(4S)-4-isopropyl-4,5-dihydro-oxazole] With potassium tert-butylate Stage #2: 1,4-bis(bromomethyl)benzene

1,4-bis(bromomethyl)benzene (623-24-5) + 2,2-bis[(4S)-4-isopropyloxazolin-2-yl]propane (131833-92-6) → 1,4-bis[2,2-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)ethyl]benzene (1381949-76-3)

Conditions	Yield
Stage #1: 2,2-bis[(4S)-4-isopropyloxazolin-2-yl]propane With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 1,4-bis(bromomethyl)benzene In tetrahydrofuran at 77℃; Inert atmosphere; Heating;	100%

1,4-bis(bromomethyl)benzene (623-24-5) + tetrakis(4-thiylphenyl)methane (361344-97-0) → C41H32S4

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;	100%

1,4-bis(bromomethyl)benzene (623-24-5) + 5-bromo-1H-indole-3-carboxaldehyde (877-03-2) → C26H18Br2N2O2

Conditions	Yield
Stage #1: 5-bromo-1H-indole-3-carboxaldehyde With potassium hydroxide In dimethyl sulfoxide at 20℃; for 1h; Stage #2: 1,4-bis(bromomethyl)benzene In dimethyl sulfoxide for 1h;	100%

1,4-bis(bromomethyl)benzene (623-24-5) + methyl 3-pyridinecarboxylate (93-60-7) → α,α'-bis(3-methoxycarbonylpyridiniumyl)-p-xylene dibromide

Conditions	Yield
In acetone for 10h; Substitution; Heating;	99.6%

1,4-bis(bromomethyl)benzene (623-24-5) + 1-methyl-4-(4-pyridyl)pyridinium iodide (38873-01-7) → 1-methyl-[4,4']bipyridinyl-1-ium iodide

Conditions	Yield
In acetonitrile at 130℃; for 0.166667h; Microwave irradiation;	99%

1,4-bis(bromomethyl)benzene (623-24-5) + dibenzylamine (103-49-1) → C36H36N2 (36997-16-7)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 0.25h;	99%

1,4-bis(bromomethyl)benzene (623-24-5) + N,N-dimethylaminododecane (112-18-5) → N,N'-didodecyl-N,N,N',N'-tetramethyl-N,N'-(p-xylenediyl)diammonium dibromide

Conditions	Yield
In acetone for 12h; Reflux;	99%
In propan-1-ol for 9h;	95%
In ethanol for 48h; Reflux;	73%

1,4-bis(bromomethyl)benzene (623-24-5) + (S,S)-2,2'-methylenebis(4-tert-butyl-2-oxazoline) (132098-54-5) → 1,4-bis{2,2-bis[(S)-4-tert-butyl-4,5-dihydrooxazol-2-yl]ethyl}benzene (1593634-91-3)

Conditions	Yield
Stage #1: (S,S)-2,2'-methylenebis(4-tert-butyl-2-oxazoline) With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 1,4-bis(bromomethyl)benzene In tetrahydrofuran for 10h; Inert atmosphere; Heating;	99%
Stage #1: (S,S)-2,2'-methylenebis(4-tert-butyl-2-oxazoline) With potassium tert-butylate Stage #2: 1,4-bis(bromomethyl)benzene

1,4-bis(bromomethyl)benzene (623-24-5) + (S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline) (132098-59-0) → 1,4-bis{2,2-bis[(4S)-4-phenyl-4,5-dihydrooxazol-2-yl]ethyl}benzene (1593634-96-8)

Conditions	Yield
Stage #1: (S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline) With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 1,4-bis(bromomethyl)benzene In tetrahydrofuran for 10h; Inert atmosphere; Heating;	99%
Stage #1: (S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline) With potassium tert-butylate Stage #2: 1,4-bis(bromomethyl)benzene

1,4-bis(bromomethyl)benzene (623-24-5) + C32H22N4 → C64H54Br4N4(4+)*4F6P(1-)

Conditions	Yield
Stage #1: 1,4-bis(bromomethyl)benzene; C32H22N4 In N,N-dimethyl-formamide at 20℃; for 48h; Stage #2: With ammonium hexafluorophosphate In water; N,N-dimethyl-formamide	99%

1,4-bis(bromomethyl)benzene (623-24-5) + N1-trityl-N2-(2-(tritylamino)ethyl)ethane-1,2-diamine (145901-58-2) → N-[4-({Bis-[2-(trityl-amino)-ethyl]-amino}-methyl)-benzyl]-N'-trityl-N-[2-(trityl-amino)-ethyl]-ethane-1,2-diamine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile for 50h; Heating;	98.6%

1,4-bis(bromomethyl)benzene (623-24-5) + (E)-1-(4-pyridyl)-2-(3,4,5-trimethoxyphenyl)ethene (118160-75-1) → 1-(4-Bromomethyl-benzyl)-4-[(E)-2-(3,4,5-trimethoxy-phenyl)-vinyl]-pyridinium; bromide (118160-64-8) + C40H42N2O6(2+)*2Br(1-)

Conditions	Yield
In various solvent(s) for 1h; Heating;	A 98% B n/a

1,4-bis(bromomethyl)benzene (623-24-5) + potassium selenocyanate (3425-46-5) → 1,4-bis(selenocyanatomethyl)benzene (85539-83-9)

Conditions	Yield
In acetone for 4h; Ambient temperature;	98%
In N,N-dimethyl-formamide for 0.75h; Inert atmosphere;	96%
In acetone at 20℃; for 4h; Inert atmosphere;	95.1%

1,4-bis(bromomethyl)benzene (623-24-5) + 4,4'-bipyridine (553-26-4) → 1,1-[1,4-phenylenebis(methylene)]bis-4,4'-pyridylpiridinium bis(hexafluorophosphate) (108861-20-7)

Conditions	Yield
Stage #1: 1,4-bis(bromomethyl)benzene; 4,4'-bipyridine In acetonitrile Stage #2: With ammonium hexafluorophosphate In water	98%
With ammonium hexafluorophosphate In chloroform; acetonitrile for 5h; Heating;	96%
Stage #1: 1,4-bis(bromomethyl)benzene; 4,4'-bipyridine In acetonitrile at 60℃; for 8h; Sealed tube; Stage #2: With ammonium hexafluorophosphate In water	45%

1,4-bis(bromomethyl)benzene (623-24-5) + 4-[(E)-2-(4-pyridinyl)ethenyl]phenol (67882-97-7) → 1-(4-Bromomethyl-benzyl)-4-[(E)-2-(4-hydroxy-phenyl)-vinyl]-pyridinium; bromide (118160-74-0) + C34H30N2O2(2+)*2Br(1-)

Conditions	Yield
In various solvent(s) for 1h; Heating;	A 98% B n/a

1,4-bis(bromomethyl)benzene (623-24-5) + Tetraethylene glycol (112-60-7) → 1,4-bis(13-hydroxy-2,5,8,11-tetraoxatridecyl)benzene (168211-62-9)

Conditions	Yield
With sodium Williamson etherification;	98%
With sodium hydride at 40℃; for 48h;	71%
With potassium carbonate In acetone for 15h; Heating;	53%
With sodium 1.) 50 deg C; 2.) 60 deg C, 18 h; Yield given. Multistep reaction;

1,4-bis(bromomethyl)benzene (623-24-5) + cis-13-1,4,7,10-tetraazatetracyclo<5.5.2.04,14010,13>tetradecane (74199-09-0, 79236-92-3) → C28H44N8(2+)*2Br(1-)

Conditions	Yield
In acetonitrile at 20℃; for 24h;	98%

1,4-bis(bromomethyl)benzene (623-24-5) + betacarboline (244-63-3) → 2-[4-(β-carboline-2-ium-2-ylmethyl)benzyl]-β-carboline-2-ium dibromide

Conditions	Yield
In N,N-dimethyl-formamide Reflux; Inert atmosphere;	98%
In ethyl acetate at 78℃; for 48h;	54%

2-pyridinealdoxime (873-69-8) + 1,4-bis(bromomethyl)benzene (623-24-5) → 1-(2-bromomethylbenzyl)-4-hydroxyiminomethylpyridinium bromide (78282-91-4)

Conditions	Yield
With acetone for 2h; Reflux;	98%
In acetone Reflux;
In acetone at 20℃;

1,4-bis(bromomethyl)benzene (623-24-5) + 3-pyridinealdoxime (1193-92-6) → 1-(3-bromomethylbenzyl)-4-hydroxyiminomethylpyridinium bromide (951126-25-3)

Conditions	Yield
With acetone for 2h; Reflux;	98%
In acetone Reflux;
In acetone at 20℃;

Upstream product

• 106-42-3 para-xylene 
• 50-00-0 formaldehyd 
• 100-39-0 benzyl bromide 
• 71-43-2 benzene 
• 4497-29-4 bis(bromomethyl) ether 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 613-33-2 (4,4'-dimethyl-1,1'-biphenyl) 
• 502-86-3 p-xylylene 
• 589-29-7 p-xylylene glycol 
• 623-27-8 terephthalaldehyde, 

Downstream Products

• 63885-00-7 1,1'-dimethyl-1,1'-p-xylylene-bis-pyrrolidinium; dibromide 
• 102207-40-9 1,1'-(1,4-phenylene-bis(methylene))bis(1-ethylpiperidinium) dibromide 
• 64038-54-6 4,4'-dimethyl-4,4'-p-xylylene-bis-morpholinium; dibromide 
• 14208-10-7 1,1'-[1,4-phenylenebis(methylene)]bis(pyridinium) dibromide 
• 110491-35-5 3,3'-dihydroxy-1,1'-p-xylylene-bis-pyridinium; dibromide 
• 63915-82-2 1,1'-dimethyl-1,1'-p-xylylene-bis-piperidinium; dibromide 
• 118226-14-5 1,4-bis<(propylamino)methyl>benzene 
• 102956-12-7 3,3'-p-xylylene-bis-carbazic acid dibenzyl ester 
• 112039-24-4 1,4-bis-ethoxymethyl-benzene 
• 35293-09-5 1,4-bis((4-nitrophenoxy)methyl)benzene 
• 53658-03-0 4,4′-((1,4-phenylenebis(methylene))bis(oxy))dibenzonitrile 
• 622-75-3 1,4-phenylenediacetonitrile 
• 2962-72-3 1,4-bis<2-(4-methylphenyl)ethyl>benzene 
• 589-29-7 p-xylylene glycol 

Relevant articles and documents

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Synthesis of 2,24-Diene-12,13,15,16,34,35,37,38-octaphenyl[44]triphenylparacyclophane

A new octaphenyl[4.4]triphenylparacyclophanediene was readily synthesized in six steps from p -xylene via the installment of bromine atoms, replacement with a vinyl group, carbonylative coupling, intermolecular followed by intramolecular double Grubbs olefin metathesis, Knoevenagel condensation, and Diels-Alder cycloaddition. The belt-shaped structure and trans -stereochemistry of the alkene moieties of the octaphenyl[4.4]triphenylparacyclophane and a synthetic intermediate, 2,21-dioxo-11,30-diene[3.4.3.4]paracyclophane, were determined by X-ray crystallography. The synthetic methodology leading to octaphenyl[4.4]triphenylparacyclophane is applicable for the synthesis of substituted triphenylparacyclophanes and possibly their corresponding bis-hexabenzocoronenylparacyclophanes via a Scholl-Mullen oxidative aryl-aryl coupling reaction.

Synthesis and photophysics of new pyridyl end-capped 3D-dithia[3.3]paracyclophane-based Janus tectons: Surface-confined self-assembly of their model pedestal on HOPG

Surface-confined supramolecular self-assembly is currently a promising strategy to create well-organised 2D-networks on conducting surfaces. However, using such substrates tends to quench any electronic properties of the adsorbed molecules. In this context, new pyridyl end-capped 3D-dithia[3.3]paracyclophane-based molecules were designed, along with their model compound (pedestal), with the objective of self-assembling these tectons on any substrate. The synthesis of these new molecules was not straightforward and is consequently described in detail. Once the materials were successfully isolated, their optoelectronic properties were investigated to study potential non-covalent interactions: through pH-dependent absorption and emission measurements, and infra-red spectrometry. We evidenced that both ionic bonding and coordination bonding are compatible with the molecules design. Finally, preliminary scanning tunneling microscopy (STM) studies were performed to study the supramolecular self-assembly properties of the model lower-deck (pedestal) on highly oriented pyrolytic graphite (HOPG): we observed a quasi-square lattice of self-assembled 2D-networks that appear to form independently of the underlying HOPG lattice.

SYSTEM AND METHOD FOR PREPARING AROMATIC DERIVATIVE

A system for preparing an aromatic derivative is provided, including: a photo-bromination reaction section for performing a photocatalytic reaction of an aromatic hydrocarbon and a brominating agent to form an aromatic hydrocarbon bromide; a substitution reaction section for performing a substitution reaction of the an aromatic hydrocarbon bromide from the photo-bromination reaction section with an alkali base compound or an alkali carboxylate compound to form an aromatic derivative; and a regeneration unit for reacting an alkali metal bromide formed by the substitution reaction section with an acid to form a hydrobromic acid. The regeneration unit is in fluid communication with the photo-bromination reaction section, such that the hydrobromic acid is recycled to the photo-bromination reaction section. A method for preparing the aromatic derivative is also provided.