13209-15-9

Basic information

• Product Name: ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE
• Synonyms: 1,2-bis(dibromomethyl)-benzen;Benzene,1,2-bis(dibromomethyl)-;O-XYLYLENE TETRABROMIDE;ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE;ALPHA,ALPHA,BETA,BETA-TETRABROMO-O-XYLENE;ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-2-XYLENE;A,A,A',A'-TETRABROMO-O-XYLENE;1,2-BIS(DIBROMOMETHYL)BENZENE
• CAS NO: 13209-15-9
• Molecular Formula: C₈H₆Br₄
• Molecular Weight: 421.75
• EINECS: 236-176-2
• Product Categories: Miscellaneous;Aryl;Building Blocks;C8;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 13209-15-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 114-116 °C(lit.)
• Boiling Point: 303.01°C (rough estimate)
• Flash Point: 157.8 °C
• Appearance: Clear colorless to yellow/Liquid or Low Melting Solid
• Density: 2.2654 (rough estimate)
• Refractive Index: 1.7040 (estimate)
• Storage Temp.: Store below +30°C.
• Water Solubility: Insoluble
• BRN: 2211698
• CAS DataBase Reference: ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE(13209-15-9)
• EPA Substance Registry System: ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-O-XYLENE(13209-15-9)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37-20/21/22
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 19-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 13209-15-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 13209-15-9 differently. You can refer to the following data:
1. α,α,α',α'-Tetrabromo-o-xylene reacts with 5endo,6endo-bis-chlormethyl-norborn-2-en to obtain trans/cis-2,3-bis(chloromethyl)-1,4-methano-1,2,3,4-tetrahydroanthracene. Further, it is involved in the preparation of 1-(3-butenyl)-2-(deuteriomethyl)benzene by reacting with allylmagnesium bromide. In addition this, it is used to prepare exo-benzocyclobuteno-1,2,3,4-tetrahydro-1,4-methanoanthracene by reacting with exo-1,4,4a,8b-tetrahydro-1,4-methanobiphenylene.
2. α,α,α′,α′-Tetrabromo-o-xylene can be employed as a precursor for the synthesis of: Poly(o-phenylene vinylene) (o-PPV) via electrochemical polymerization.A pentacene derivative by reacting with naphthalene moieties for the development of organic thin-film transistors (OTFTs).Bitopic pyrazole containing ligands.

Synthetic route

o-xylene (95-47-6) → 1,2-bis(dibromomethyl)benzene (13209-15-9) + 1-(dibromomethyl)-2-(tribromomethyl)benzene (95110-95-5)

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In dichloromethane for 19h; Irradiation;	A 72% B 6%
With N-Bromosuccinimide for 19h;	A 38% B 42%

1-(dibromomethyl)-2-(tribromomethyl)benzene (95110-95-5) → 1,2-bis(dibromomethyl)benzene (13209-15-9)

Conditions	Yield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 100℃;	40%

o-xylene (95-47-6) → 1,2-bis(dibromomethyl)benzene (13209-15-9)

Conditions	Yield
With bromine at 120 - 170℃; Irradiation;
With bromine at 140℃;
With bromine im Sonnenlicht;

1-chloromethyl-2-methylbenzene (552-45-4) → 1,2-bis(dibromomethyl)benzene (13209-15-9)

Conditions	Yield
With bromine at 140 - 160℃; Irradiation;

bromine (7726-95-6) + 1-chloromethyl-2-methylbenzene (552-45-4) → 1,2-bis(dibromomethyl)benzene (13209-15-9) + 2-chlorobromomethyl-1-dibromomethyl-benzene

Conditions	Yield
at 140 - 160℃; Irradiation;

1,2-bis(dibromomethyl)benzene (13209-15-9) + 1,2-Dicyanoethylene (764-42-1) → 2,3-dicyanonaphthalene (22856-30-0)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 75 - 80℃; for 8h;	97%
With sodium iodide In N,N-dimethyl-formamide at 75℃; for 7h;	88%
With sodium iodide In N,N-dimethyl-formamide at 75℃; for 5.5h;	78%

1,2-bis(dibromomethyl)benzene (13209-15-9) + phenylmagnesium bromide → 2-benzyltoluene (713-36-0)

Conditions	Yield
Stage #1: phenylmagnesium bromide With manganese(ll) chloride In tetrahydrofuran Metallation; Stage #2: 1,2-bis(dibromomethyl)benzene In tetrahydrofuran at 0℃; for 2.5h; Substitution; Stage #3: With water Substitution;	92%

1,2-bis(dibromomethyl)benzene (13209-15-9) + phenylmagnesium bromide → 1-benzyl-2-(deuteriomethyl)benzene (716-78-9)

Conditions	Yield
Stage #1: phenylmagnesium bromide With manganese(ll) chloride In tetrahydrofuran Metallation; Stage #2: 1,2-bis(dibromomethyl)benzene In tetrahydrofuran at 0℃; for 2.5h; Substitution; Stage #3: With water-d2 Substitution;	92%

1,2-bis(dibromomethyl)benzene (13209-15-9) → o-phthalic dicarboxaldehyde (643-79-8)

Conditions	Yield
Stage #1: 1,2-bis(dibromomethyl)benzene With sulfuric acid Stage #2: With water; sodium hydrogencarbonate Product distribution / selectivity;	91%
With sulfuric acid Product distribution / selectivity;	79%
With sulfuric acid

1,2-bis(dibromomethyl)benzene (13209-15-9) + p-benzoquinone (106-51-4) → 6,13-pentacenequinone (3029-32-1)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 120℃;	91%
With sodium iodide In N,N-dimethyl-formamide at 120℃; Inert atmosphere;	91%
Stage #1: p-benzoquinone With sodium iodide In N,N-dimethyl-formamide at 70℃; Inert atmosphere; Stage #2: 1,2-bis(dibromomethyl)benzene In N,N-dimethyl-formamide at 70℃; for 18h; Diels-Alder Cycloaddition; Inert atmosphere;	28%

7-methoxy-1H-inden-1-one (338989-51-8) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → 1-methoxy-11H-benzo[b]fluoren-11-one (1345090-10-9)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 24h;	90%

maleic anhydride (108-31-6) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → 2,3-Naphthalenedicarboxylic anhydride (716-39-2)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	87.6%
With sodium iodide In N,N-dimethyl-formamide at 70℃; for 4.5h; Diels-Alder Cycloaddition;	50%

1,4-dihydro-1,4-methanonaphthalene (4453-90-1) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → C19H14 (107426-42-6)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	87%

(4,4'-di-tert-butyl-2,2'-bipyridine)dimethylplatinum(II) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → trans-[PtMe2(CHBr-o-C6H4CHBr2)Br(4,4'-di-tert-butyl-2,2'-bipyridine)] (1359769-65-5)

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.16 mmol) added to soln. of Pt complex (0.16 mmol); stirred (4 h); evapd. (vac.); recrystd. from CH2Cl2/Et2O; elem. anal.;	87%

maleiimide (541-59-3) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → 2,3-Naphthalimide (4379-54-8)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 70 - 80℃; for 10h;	86%

(E)-2-styrylchromone (39103-38-3, 74719-73-6) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → 2-(3-phenylnaphth-2-yl)chromone

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide for 16h;	86%

1,2-bis(dibromomethyl)benzene (13209-15-9) + benzaldehyde (100-52-7) + allylmagnesium bromide (1730-25-2) → 2-[2-(3-butenyl)phenyl]-1-phenylethanol

Conditions	Yield
Stage #1: allylmagnesium bromide With manganese(ll) chloride In tetrahydrofuran Metallation; Stage #2: 1,2-bis(dibromomethyl)benzene In tetrahydrofuran at 0℃; for 2.5h; Substitution; Stage #3: benzaldehyde Substitution;	85%

1,2-bis(dibromomethyl)benzene (13209-15-9) + 6-(hydroxymethyl)naphthalene-1,4-dione (81402-06-4) → 2-(hydroxymethyl)-5,12-naphthacenequinone (1005001-34-2)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 80℃;	85%

dimethyl(2,2'-bipyridine)platinum(II) (52594-52-2) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → [PtMe2(CHBr-o-C6H4CHBr2)Br(2,2'-bipyridine)] (1359769-63-3)

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.14 mmol) added to soln. of Pt complex (0.14 mmol); stirred (24 h); evapd. (vac.); solidified with CH2Cl2/Et2O; elem. anal.;	85%

[(1,10-phenanthroline)dimethylplatinum(II)] (52594-55-5) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → [PtMe2(CHBr-o-C6H4CHBr2)Br(1,10-phenanthroline)] (1359769-64-4)

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.25 mmol) added to soln. of Pt complex (0.25 mmol); stirred (24 h); evapd. (vac.); solidified with CH2Cl2/Et2O; elem. anal.;	85%

n-butylmaleimide (2973-09-3) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → N-Butyl-β-naphthalimide (128600-23-7)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 85℃; for 12h; Diels-Alder Cycloaddition; Schlenk technique; Inert atmosphere;	85%

1,2-bis(dibromomethyl)benzene (13209-15-9) + trimethyl orthoformate (149-73-5) → phthalic aldehyde bis(dimethyl)acetal (37864-64-5)

Conditions	Yield
With zinc(II) chloride at 90℃; for 5h;	85%
With zinc(II) chloride at 90℃; for 5h;	85%

2-[(1E)-2-(4-chlorophenyl)ethenyl]-4H-1-benzopyran-4-one (55977-30-5, 133567-73-4) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → 2-[3-(4-chlorophenyl)naphth-2-yl]chromone

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide for 16h;	83%

1,2-bis(dibromomethyl)benzene (13209-15-9) + 9,10-Diacetoxy-1,4,5,8-tetrahydro-1,4:5,8-dimethanoanthracene (154968-64-6) → 7,16-diacetoxy-(6α,8α,15α,17α)-6,8,15,17-tetrahydro-6,17:8,15-dimethanoheptacene (288625-16-1)

Conditions	Yield
With calcium carbonate; sodium iodide In N,N-dimethyl-formamide at 20 - 55℃; for 5.5h;	83%

dimethyl(2,2'-bipyridine)platinum(II) (52594-52-2) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → [Pt2Me4Br2(μ-o-(CHBr)2C6H4)(2,2'-bipyridine)2] (1359769-66-6)

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.13 mmol) added to soln. of Pt complex (0.26 mmol); stirred (4 h); evapd. (vac.); recrystd. from CHCl3/hexane; elem. anal.;	80%

[(1,10-phenanthroline)dimethylplatinum(II)] (52594-55-5) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → [Pt2Me4Br2(μ-o-(CHBr)2C6H4)(1,10-phenanthroline)2] (1359884-75-5)

Conditions	Yield
In acetone under Ar; (C6H4)(CHBr2)2 (0.12 mmol) added to soln. of Pt complex (0.25 mmol); stirred (4 h); evapd. (vac.); recrystd. from CHCl3/hexane; elem. anal.;	80%

1,2-bis(dibromomethyl)benzene (13209-15-9) + C18H22 (107426-40-4) → DN-6 (107426-41-5)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	79%

1,2-bis(dibromomethyl)benzene (13209-15-9) + 5,12-Diacetoxy-1,4,7,10-tetrahydro-1,4:7,10-dimethanonaphthacene (189133-04-8) → 7,18-diacetoxy-(6α,9α,16α,19α)-6,9,16,19-tetrahydro-6,19:9,16-dimethanooctacene

Conditions	Yield
With calcium carbonate; sodium iodide In N,N-dimethyl-formamide at 20 - 55℃; for 5.5h;	79%

norborn-2-ene (498-66-8) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → C15H14 (32058-86-9)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	78%

1,2-bis(dibromomethyl)benzene (13209-15-9) + (1α,4α,4aβ,5α,8α,8aβ)-1,4,4a,5,8,8a-hexahydro-1,4:5,8-dimethanonaphthalene (83602-18-0) → C28H22 (107426-37-9)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	75%

1,2-bis(dibromomethyl)benzene (13209-15-9) + ((1R,4S,5R,8S)-10-Ethoxycarbonylmethoxy-1,4,5,8-tetrahydro-1,4;5,8-dimethano-anthracen-9-yloxy)-acetic acid ethyl ester (180134-63-8) → C40H34O6 (699018-43-4)

Conditions	Yield
With calcium carbonate; sodium iodide In N,N-dimethyl-formamide at 55℃; under 75.006 Torr; for 6h;	75%

1,2-bis(dibromomethyl)benzene (13209-15-9) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → 6,13-dihydro-6,13-methanopentacene

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 24h;	75%

1,2-bis(dibromomethyl)benzene (13209-15-9) + 6,7-dibromonaphthalene-1,4-dione (117157-38-7) → 2,3-dibromo-5,12-tetracenequinone

Conditions	Yield
With potassium iodide In N,N-dimethyl-formamide at 110℃; for 48h; Inert atmosphere; Sealed tube;	75%
With sodium iodide In N,N-dimethyl acetamide at 90℃; for 24h;	72%

1,2-bis(dibromomethyl)benzene (13209-15-9) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → C23H16 (107426-39-1)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 65℃; for 16h;	74%

5,8-diacetoxy-1,4-dihydro-1,4-methylenonaphthalene (7213-65-2) + 1,2-bis(dibromomethyl)benzene (13209-15-9) → 1,4-diacetoxy-5,12-dihydro-5,12-methylenotetracene (1233126-07-2)

Conditions	Yield
With calcium carbonate; sodium iodide In N,N-dimethyl-formamide at 20 - 55℃; under 75.0075 Torr; Diels-Alder reaction;	74%

Upstream product

• 95-47-6 o-xylene 
• 7726-95-6 bromine 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 95110-95-5 1-(dibromomethyl)-2-(tribromomethyl)benzene 

Downstream Products

• 2169-87-1 naphthalene-2,3-dicarboxylic acid 
• 21815-18-9 2-phenyl-1H-benzo[f]isoindole-1,3(2H)-dione 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 87-41-2 2-benzofuran-1(3H)-one 
• 22267-94-3 cis-diiodocyclobutabenzene 
• 6639-21-0 trans-diiodocyclobutabenzene 
• 14420-75-8 trans-1,2-dibromobenzocyclobutene 
• 109341-49-3 2,3-dihydro-1H-cyclopenta[b]naphthalen-1-one 
• 253-52-1 PHTHALAZINE 
• 6500-54-5 1,2-bis-diacetoxymethyl-benzene 
• 1359769-63-3 [PtMe₂(CHBr-o-C₆H₄CHBr₂)Br(2,2'-bipyridine)] 
• 1359769-64-4 [PtMe₂(CHBr-o-C₆H₄CHBr₂)Br(1,10-phenanthroline)] 
• 1359769-65-5 trans-[PtMe₂(CHBr-o-C₆H₄CHBr₂)Br(4,4'-di-tert-butyl-2,2'-bipyridine)] 
• 909806-50-4 α,α-dibromobenz[f]indanone 

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