| Identification | More | [Name]
1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE | [CAS]
15442-91-8 | [Synonyms]
1,2,4,5-TETRA[BROMOMETHYL]BENZENE
1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE
ALPHA,ALPHA',ALPHA'',ALPHA'''-TETRABROMODURENE
TETRABROMODURENE
1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE, 95 % | [Molecular Formula]
C10H10Br4 | [MDL Number]
MFCD00009664 | [Molecular Weight]
449.8 | [MOL File]
15442-91-8.mol |
| Chemical Properties | Back Directory | [Appearance]
OFF-WHITE TO SLIGHTLY YELLOW CRYSTALLINE POWDER | [Melting point ]
159-161 °C(lit.) | [Boiling point ]
326.93°C (rough estimate) | [density ]
2.168 | [refractive index ]
1.7040 (estimate) | [storage temp. ]
Refrigerator, under inert atmosphere | [solubility ]
Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly) | [form ]
Crystalline Powder | [color ]
Off-white to light yellow | [InChI]
1S/C10H10Br4/c11-3-7-1-8(4-12)10(6-14)2-9(7)5-13/h1-2H,3-6H2 | [InChIKey]
UTXIKCCNBUIWPT-UHFFFAOYSA-N | [SMILES]
BrCc1cc(CBr)c(CBr)cc1CBr | [CAS DataBase Reference]
15442-91-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns.
R36/37:Irritating to eyes and respiratory system . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29039990 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Eye Dam. 1
Skin Corr. 1B
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
off-white to light yellow crystalline powder | [Uses]
1,2,4,5-Tetrakis(bromomethyl)benzene has been used in the synthesis of:
- tetrapodal imidazolium ligands as their PF6? salts
- 6,7-bis(bromomethyl)-2,11,18,21,24-pentaoxatetracyclo[23.4. 0.04,9.012,17]nonacosa-1(25),4(9),5,7,12 (17),13,15,26,28-nonaene
- conformationally constrained cyclic α-amino acid derivatives
- thiacyclophanes
- dendrimeric organoplatinum complexes
| [Synthesis]
General procedure for the synthesis of tetrabromotoluene from 1,2,4,5-tetramethylbenzene: 1,2,4,5-tetrakis(bromomethyl)benzene (2.8 g, 20 mmol) was prepared by reacting 1,2,4,5-tetramethylbenzene (2.8 g, 20 mmol) with N-bromosuccinimide (NBS, 14.4 g, 80 mmol) and benzoyl peroxide in 50 mL of tetrachloromethane (1c, 1 g, 5.9 mmol). The reaction mixture was heated at 77 °C for 50 min. After completion of the reaction, the precipitate was collected by filtration under reduced pressure and washed with hot tetrachloromethane. The filtrate was concentrated to a small volume and cooled to 4 °C. The crude product was filtered and purified by recrystallization from methanol. The reaction time was less than 1 hour to give a white solid product in 15% yield with a melting point of 159-160°C. The structure of the product was determined by 1H-NMR (CDCl3, δ: 7.37 ppm, 2H, a; 4.60 ppm, 8H, b), 13C-NMR (CDCl3, δ: 137.6 ppm, a; 133.6 ppm, h; 28.7 ppm, b), and FT-IR (KBr, νmax: 3026, 2980, 2933. 1504, 1456, 1210, 911, 797, 678, 598 cm-1) were characterized. | [References]
[1] Journal of the Chinese Chemical Society, 2002, vol. 49, # 1, p. 77 - 82
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 26, p. 4281 - 4286
[3] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 247, p. 23 - 30
[4] Heterocycles, 2015, vol. 90, # 1, p. 645 - 658
[5] Tetrahedron Letters, 2015, vol. 56, # 26, p. 3992 - 3995 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE(15442-91-8)MS
1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE(15442-91-8)1HNMR
1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE(15442-91-8)IR1
1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE(15442-91-8)IR2
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