Production Method 1

91-13-4

Reaction Conditions

1.1 Reagents: Bromine Solvents: Carbon tetrachloride ;  rt; 30 min, reflux

Reference

Application of monohydroxyphthalocyanines for selective preparation of homo- and heteroligand macrocyclic compounds

Tolbin, Alexander Yu.; Tomilova, Larisa G., Makrogeterotsikly, 2009, 2(3-4), 258-260

Production Method 2

91-13-4

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Diethyl ether ;  0 °C; rt → 40 °C
1.2 Reagents: Methanol
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 7
1.4 Reagents: Pyridine ,  Phosphorus tribromide Solvents: Diethyl ether ;  1 h, 0 °C; 0 °C → rt; 2 h, rt
1.5 Reagents: Water ;  cooled

Reference

Formal [5+1] annulation reactions of dielectrophilic peroxides: facile access to functionalized dihydropyrans

Zhong, Chen; Yin, Qi; Zhao, Yukun; Li, Qinfeng; Hu, Lin, Chemical Communications (Cambridge, 2020, 56(86), 13189-13192

Production Method 3

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Benzoyl peroxide Solvents: Carbon tetrachloride ;  8 h, reflux

Reference

Synthesis and crystal structure of novel benzimidazole cyclophanes

Hou, Xiaomeng; Xu, Linfei; Tang, Xuesong; Song, Yang; Bai, Yinjuan, Youji Huaxue, 2013, 33(3), 643-647

Production Method 4

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Carbon tetrachloride
1.2 Reagents: Benzoyl peroxide

Reference

Regioselectivity of diarylnitrilimines and methylarylnitrilimine with respect to isochromene

Chraibi, L.; Kitane, S.; Soufiaoui, M., Journal de la Societe Marocaine de Chimie, 1992, 1(1), 27-33

Production Method 5

91-13-4

Reaction Conditions

1.1 Reagents: N1,N1,N3,N3-Tetrabromo-1,3-benzenedisulfonamide Solvents: Ethyl acetate ;  8.5 h, reflux

Reference

Poly(N,N'-dibromo-N-ethyl-benzene-1,3-disulfonamide), N,N,N',N'-tetrabromobenzene-1,3-disulfonamide and novel poly(N,N'-dibromo-N-phenylbenzene-1,3-disulfonamide) as powerful reagents for benzylic bromination

Ghorbani-Vaghei, Ramin; Chegini, Mohammad; Veisi, Hojat; Karimi-Tabar, Mehdi, Tetrahedron Letters, 2009, 50(16), 1861-1865

Production Method 6

91-13-4

Reaction Conditions

1.1 Reagents: Bromine

Reference

Completely Regioselective, Highly Stereoselective Syntheses of cis-Bisfullerene[60] Adducts of 6,13-Disubstituted Pentacenes

Miller, Glen P.; Mack, James, Organic Letters, 2000, 2(25), 3979-3982

Production Method 7

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Benzoyl peroxide Solvents: Carbon tetrachloride ;  6 h, reflux

Reference

Joint experimental and density functional theory study of synthesis and electrochemical characterization of a new benzodioxocine-fused poly(N-methylpyrrole) derivative

Kurtay, Gulbin; Soganci, Tugba; Sarikavak, Kubra; Ak, Metin; Gullu, Mustafa, New Journal of Chemistry, 2020, 44(43), 18929-18941

Production Method 8

612-14-6

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide ,  Triphenylphosphine Solvents: Dichloromethane ;  -78 °C; 12 h, rt

Reference

Triphenylphosphine-N-Bromosuccinimide Mediated Chemoselective Cyclodehydration of Diols

Zhao, Shuo; Wu, You; Sun, Qi; Cheng, Tie-Ming; Li, Run-Tao, Synthesis, 2015, 47(8), 1154-1162

Production Method 9

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Benzoyl peroxide Solvents: Carbon tetrachloride ;  rt; 12 h, reflux

Reference

Benzosulfones as photochemically activated sulfur dioxide (SO2) donors

Malwal, Satish R.; Chakrapani, Harinath, Organic & Biomolecular Chemistry, 2015, 13(8), 2399-2406

Production Method 10

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Carbon tetrachloride

Reference

Regioselective bromination of activated aromatic substrates with N-bromosuccinimide over HZSM-5

Paul, Vincent; Sudalai, A.; Daniel, Thomas; Srinivasan, K. V., Tetrahedron Letters, 1994, 35(38), 7055-6

Production Method 11

91-13-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid ,  Sodium bromide ,  Sodium bromate Solvents: Dichloromethane ,  Water ;  6 h, rt; 30 min, rt

Reference

An alternative method for the regio- and stereoselective bromination of alkenes, alkynes, toluene derivatives and ketones using a bromide/bromate couple

Adimurthy, Subbarayappa; Ghosh, Sudip; Patoliya, Paresh U.; Ramachandraiah, Gadde; Agrawal, Manoj; et al, Green Chemistry, 2008, 10(2), 232-237

Production Method 12

612-14-6

91-13-4

Reaction Conditions

1.1 Reagents: Sulfuric acid ,  Hydrogen bromide ;  reflux

Reference

Potent MCH-1 receptor antagonists from cis-1,4-diaminocyclohexane-derived indane analogs

Qian, Yimin; Conde-Knape, Karin; Erickson, Shawn D.; Falcioni, Fiorenza; Gillespie, Paul; et al, Bioorganic & Medicinal Chemistry Letters, 2013, 23(14), 4216-4220

Production Method 13

91-13-4

Reaction Conditions

1.1 Reagents: Boron tribromide Solvents: Carbon tetrachloride ;  1 h, rt; 30 °C
1.2 Reagents: Water ;  cooled

Reference

A new method for α-bromination of methylarene

Shen, Litao; Chen, Hongbiao; Lin, Yuanbin, Youji Huaxue, 2010, 30(2), 272-275

Production Method 14

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Benzoyl peroxide Solvents: Chloroform ;  5 h, reflux

Reference

Design and synthesis of amide derivatives as S-adenosyl-L-homocysteine hydrolase inhibitors

Tan, Xiangduan; Wang, Panfeng; Nian, Siyun; Wang, Guoping, Chemical & Pharmaceutical Bulletin, 2014, 62(1), 112-117

Production Method 15

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Benzoyl peroxide Solvents: Dimethyl carbonate ;  15 min, 110 °C

Reference

Generation of (nonafluoro-tert-butoxy)methyl ponytails for enhanced fluorous partition of aromatics and heterocycles

Zhao, Xi; Ng, Wing Yan; Lau, Kai-Chung; Collis, Alana E. C.; Horvath, Istvan T., Physical Chemistry Chemical Physics, 2012, 14(11), 3909-3914

Production Method 16

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Acetonitrile ;  2 h, rt

Reference

2,3-Dihalo- and 2,3,6,7-Tetrahaloanthracenes by Vollhardt Trimerization

Hoffmann, Hendrik; Mukanov, Diana; Ganschow, Michael; Rominger, Frank; Freudenberg, Jan; et al, Journal of Organic Chemistry, 2019, 84(15), 9826-9834

Production Method 17

91-13-4

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Benzoyl peroxide Solvents: Carbon tetrachloride ;  20 min, reflux; 6 h, reflux

Reference

Synthesis and Computational Bandgap Engineering of New 3,4-Alkylenedioxypyrrole (ADOP) Derivatives and Investigation of Their Electrochromic Properties

Kurtay, Gulbin; Soganci, Tugba; Ak, Metin ; Gullu, Mustafa, Journal of the Electrochemical Society, 2016, 163(10),

1,2-Bis(bromomethyl)benzene Raw materials

• 1,2-Benzenedimethanol

1,2-Bis(bromomethyl)benzene Preparation Products

• 1,2-Bis(bromomethyl)benzene (91-13-4)

• 1. Alternative donor substrates for inverting and retaining glycosyltransferases?
  Luke L. Lairson,Warren W. Wakarchuk Chem. Commun., 2007, 365-367
• 2. Acenaphthenic hopanoids, a novel series of aromatised
  Teresita Carrillo-Hernández,Philippe Schaeffer,Pierre Albrecht Chem. Commun., 2001, 1976-1977
• 3. An approach to biodegradable star polymeric architectures using disulfide coupling?
  Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. Davis Chem. Commun., 2008, 6582-6584
• 4. An analysis of the WTC fires using CIB correlations and simple modeling
  JGQuintiere
• 5. An apparatus for testing water by measurement of its electrical conductivity
  Analyst, 1912,37, 538-543

• Solvents and Organic Chemicals Organic Compounds Organic Halides

1,2-Bis(bromomethyl)benzene: Properties, Applications, and Market Insights

1,2-Bis(bromomethyl)benzene (CAS No. 91-13-4), also known as o-xylylene dibromide, is an important organic compound widely used in synthetic chemistry and material science. This aromatic derivative features two bromomethyl groups attached to a benzene ring at the 1,2-positions, making it a versatile building block for various chemical transformations. The compound's molecular formula is C8H8Br2, with a molecular weight of 263.96 g/mol. Its unique structure allows it to participate in numerous reactions, including nucleophilic substitutions and polymerization processes.

The physical properties of 1,2-Bis(bromomethyl)benzene include a white to light yellow crystalline appearance with a melting point range of 70-73°C. It exhibits moderate solubility in organic solvents such as dichloromethane, chloroform, and toluene, but limited solubility in water. These characteristics make it particularly useful in organic synthesis where controlled reactivity is desired. Recent studies have highlighted its role in creating advanced materials, particularly in the development of polymeric networks and cross-linking agents for specialty polymers.

One of the most significant applications of 1,2-Bis(bromomethyl)benzene is in the synthesis of phthalocyanine derivatives, which are crucial for dyes, pigments, and electronic materials. Researchers have also explored its use in creating molecular cages and porous organic polymers for gas storage applications. In pharmaceutical intermediates, this compound serves as a precursor for various bioactive molecules, though all applications comply with international safety and regulatory standards.

The synthetic routes to 1,2-Bis(bromomethyl)benzene typically involve the bromination of o-xylene using N-bromosuccinimide (NBS) or elemental bromine under controlled conditions. Modern green chemistry approaches have focused on optimizing these processes to minimize byproducts and improve atom economy. Environmental considerations have led to the development of catalytic bromination methods that reduce bromine waste, aligning with current sustainability trends in chemical manufacturing.

Market analysis shows growing demand for 1,2-Bis(bromomethyl)benzene 91-13-4 in Asia-Pacific regions, particularly from the electronics and advanced materials sectors. The compound's role in producing high-performance polymers has attracted attention from research institutions and industrial developers alike. Quality specifications typically require ≥98% purity, with HPLC and NMR being standard analytical methods for verification. Proper storage recommendations include keeping the material in amber glass containers under inert atmosphere to prevent degradation.

Recent innovations have explored the use of 1,2-Bis(bromomethyl)benzene derivatives in organic electronics, particularly as precursors for conducting polymers and organic semiconductors. These applications capitalize on the compound's ability to form extended conjugated systems through various coupling reactions. The material science community has shown particular interest in its potential for creating microporous polymers with tunable pore sizes for selective molecular recognition.

Safety considerations for handling o-xylylene dibromide emphasize standard laboratory precautions, including the use of personal protective equipment and adequate ventilation. While not classified under stringent regulations, proper risk assessment is always recommended when working with brominated compounds. The scientific literature contains numerous references to its safe handling procedures and compatibility with various reaction conditions.

Looking forward, research trends suggest expanding applications of 1,2-Bis(bromomethyl)benzene CAS 91-13-4 in energy storage systems and catalytic materials. Its structural features make it an attractive candidate for designing metal-organic frameworks (MOFs) and other functional materials. The compound continues to be a subject of academic investigation, with recent publications exploring its photophysical properties and potential in optoelectronic devices.

For researchers and industrial users seeking high purity 1,2-Bis(bromomethyl)benzene, several specialty chemical suppliers offer the compound with detailed technical specifications. Quality control measures typically include rigorous testing for bromide content and thermal stability. The compound's shelf life can be extended through proper storage conditions, making it a reliable reagent for various synthetic applications.

The versatility of 1,2-Bis(bromomethyl)benzene ensures its continued importance in organic synthesis and materials science. As sustainable chemistry practices evolve, new methodologies for its production and application are likely to emerge, further expanding its utility across scientific disciplines while maintaining environmental responsibility.

• 35168-62-8(1,4-Bis(bromomethyl)-2,5-dimethylbenzene)
• 55231-61-3(Benzene, 2,4-bis(bromomethyl)-1,3,5-trimethyl-)
• 51678-43-4(Benzene,1,2,3,4-tetrakis(bromomethyl)-)
• 38622-14-9(Benzene, bis(bromomethyl)-)
• 28777-60-8(Benzene,(bromomethyl)methyl-)
• 4761-00-6(2-(Bromomethyl)-1,3,5-trimethylbenzene)
• 104155-11-5(Benzene,(bromomethyl)dimethyl- (9CI))
• 15442-91-8(1,2,4,5-Tetrakis(bromomethyl)benzene)
• 35168-64-0(3,6-Bis(bromomethyl)durene)
• 54757-29-8(Benzene, 2-(bromomethyl)-1,3,4-trimethyl-)