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alpha,alpha'-Dibromo-p-xylene

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Products Intro: Product Name:alpha,alpha'-Dibromo-p-xylene
CAS:623-24-5
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Products Intro: Product Name:1,4-Bis(bromomethyl)benzene
CAS:623-24-5
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CAS:623-24-5
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alpha,alpha'-Dibromo-p-xylene manufacturers

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alpha,alpha'-Dibromo-p-xylene 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:623-24-5
MF:C8H8Br2
MW:263.96
EINECS:210-781-1
Product Categories:Aromatics;Miscellaneous Reagents;Aromatic Halides (substituted);Aryl;Building Blocks;C8;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
Mol File:623-24-5.mol
alpha,alpha'-Dibromo-p-xylene Structure
alpha,alpha'-Dibromo-p-xylene Chemical Properties
Melting point 143-145 °C(lit.)
Boiling point 245 °C(lit.)
density 2.012
refractive index 1.614
Fp 155-158°C/14mm
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility dioxane: soluble1g/10 mL (hot)
form Crystalline Powder and Coarse Crystals
color White to beige
Water Solubility soluble, hydrolyses
Sensitive Lachrymatory
BRN 1100019
InChI1S/C8H8Br2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H,5-6H2
InChIKeyRBZMSGOBSOCYHR-UHFFFAOYSA-N
SMILESBrCc1ccc(CBr)cc1
CAS DataBase Reference623-24-5(CAS DataBase Reference)
NIST Chemistry ReferenceBenzene, 1,4-bis(bromomethyl)-(623-24-5)
EPA Substance Registry System1,4-Bis(bromomethyl)benzene (623-24-5)
Safety Information
Hazard Codes C
Risk Statements 34-22
Safety Statements 26-36/37/39-45
RIDADR UN 3448 6.1/PG 2
WGK Germany 3
8-19-21
Hazard Note Corrosive/Lachrymatory
TSCA TSCA listed
HazardClass 8
PackingGroup III
HS Code 29039990
Storage Class6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
1,4-Bis(Bromomethyl)benzene English
ACROS English
SigmaAldrich English
ALFA English
alpha,alpha'-Dibromo-p-xylene Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powde
UsesIt is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals.
Synthesis Reference(s)Tetrahedron Letters, 35, p. 7055, 1994 DOI: 10.1016/0040-4039(94)88224-X
Synthesis
P-XYLENE

106-42-3

alpha,alpha'-Dibromo-p-xylene

623-24-5

2.3.2.1 Synthesis of 1,4-bis(bromomethyl)benzene 4 In a 250 mL round bottom flask, p-xylene 1 (5 mL, 40.78 mmol) and 70 mL carbon tetrachloride were added as solvents. The flask was heated in an oil bath. Subsequently, N-bromosuccinimide (29.86 g, 167.80 mmol) and benzoyl peroxide (5.83 g, 24.08 mmol) were added sequentially to the flask. The reaction mixture was refluxed at 70 °C for 12 hours. Upon completion of the reaction, the solution was cooled to room temperature, at which point a solid imide precipitated, which was removed by filtration. The filtrate was distilled under reduced pressure to remove the solvent to give the light yellow solid product 1,4-bis(bromomethyl)benzene 4 in 90% yield with a melting point of 142-144 °C. The product was analyzed by FT-IR (KBr, cm^-1) showing 568 (C-Br stretching vibration), 1625 (C=C stretching vibration); 1H NMR (300 MHz, CDCl3) showing 4.28 (s, 4H, methylene proton), 7.18 (s, 4H, aromatic proton).

Purification MethodsDistil 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.]
References[1] Tetrahedron Letters, 2000, vol. 41, # 32, p. 6241 - 6244
[2] Tetrahedron Letters, 2005, vol. 46, # 41, p. 7047 - 7050
[3] Synthetic Communications, 2009, vol. 39, # 13, p. 2304 - 2309
[4] Journal of Molecular Catalysis A: Chemical, 2012, vol. 363-364, p. 81 - 89,9
[5] Polyhedron, 2012, vol. 47, # 1, p. 151 - 164
Tag:alpha,alpha'-Dibromo-p-xylene(623-24-5) Related Product Information
Benzhydrylamine Diethylstilbestrol Decabromodiphenyl Ethane 4-Bromomethylbenzoic acid 1,3-Dibromo-5,5-dimethylhydantoin 1,2-Dibromopropane Benzyl bromide P-XYLENE 2,3,5,6-TETRAFLUORO-P-XYLENE Xylene 2,2-Bis(bromomethyl)propane-1,3-diol Musk xylene Benzene 1,4-BIS(BROMOMETHYL)NAPHTHALENE 4-BROMOMETHYL BENZOYL BROMIDE 96 1,2,4,5-TETRAKIS(BROMOMETHYL)BENZENE poly-p-xylene ALPHA,ALPHA,ALPHA',ALPHA'-TETRABROMO-P-XYLENE

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