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34440

Sigma-Aldrich

α,α′-Dibromo-p-xylene

purum, ≥98.0% (GC)

Synonym(s):

DMF, 1,4-Bis(bromomethyl)benzene, p-Xylylene dibromide

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About This Item

Linear Formula:
C6H4(CH2Br)2
CAS Number:
623-24-5
Molecular Weight:
263.96
Beilstein:
1100019
EC Number:
210-781-1
MDL number:
MFCD00000182
UNSPSC Code:
12352100
PubChem Substance ID:
329754742
NACRES:
NA.22

grade

purum

Quality Level

100

Assay

≥98.0% (GC)

form

crystals

bp

245 °C (lit.)

mp

143-145 °C (lit.)

solubility

dioxane: soluble 1 g/10 mL (hot)

SMILES string

BrCc1ccc(CBr)cc1

InChI

1S/C8H8Br2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H,5-6H2

InChI key

RBZMSGOBSOCYHR-UHFFFAOYSA-N

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Application

α, α′-Dibromo-p-xylene may be used in the preparation of:
  • third-generation bis(1-pyrazolyl)methane ligands
  • 5,5′-[(p-phenyl­enedimethyl­ene)dithio]bis­(1-phen­yl-1H-1,2,3,4-tetra­zole)
  • new bis 1,10-phenanthroline ligand (composed of two subunits of 7-(p-anisyl)-1,10-phenanthroline (phen) joined by p-(CH2)2C6H4(CH2)2 space groups at 4 positions), via Skraup synthesis
  • stereoisomers of α,α′-bis[3-(N,N-diethylcarbamoyl)-piperidino]-p-xylene

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jai Young Lee et al.
Acta crystallographica. Section E, Structure reports online, 65(Pt 10), o2369-o2370 (2009-01-01)
The title 22-crown-6 unit, C(26)H(28)O(6), comprising of three benzo groups and triethyl-ene glycol, was prepared by the reaction of α,α'-dibromo-p-xylene with 1,8-bis-(2-hydroxy-phen-oxy)-3,6-dioxaoctane in the presence of Cs(2)CO(3) with tetra-hydro-furan (THF) and recrystallized from dichloro-methane-hexane (1:20 v/v) at room temperature. In
5, 5'-[(p-Phenylenedimethylene) dithio] bis (1-phenyl-1H-1, 2, 3, 4-tetrazole).
Wang W, et al.
Acta Crystallographica Section E, Structure Reports Online, 61(4), 1163-1164 (2005)
D Pomeranc et al.
Journal of the American Chemical Society, 123(49), 12215-12221 (2001-12-06)
A bis-chelating ligand (L1), made of two 7-(p-anisyl)-1,10-phenanthroline (phen) subunits connected with a p-(CH(2))(2)C(6)H(4)(CH(2))(2) spacer through their 4 positions, has been prepared, using Skraup syntheses and reaction of the anion of 4-methyl-7-anisyl-1,10-phenanthroline with alpha,alpha'-dibromo-p-xylene. Its Fe(II) complex, [FeL1(dmbp)](PF(6))(2), was prepared
Daniel L Reger et al.
Inorganic chemistry, 48(3), 936-945 (2009-01-06)
The third-generation bis(1-pyrazolyl)methane ligands p-C(6)H(4)[CH(2)OCH(2)CH(pz)(2)](2) (L(p), pz = pyrazolyl ring) and m-C(6)H(4)[CH(2)OCH(2)CH(pz)(2)](2) (L(m)) have been synthesized by the reaction of (pz)(2)CHCH(2)OH with NaH followed by alpha,alpha'-dibromo-p-xylene or alpha,alpha'-dibromo-m-xylene. The reaction of L(p) with AgBF(4), AgPF(6), and AgO(3)SCF(3) yields the new
X Zheng et al.
Chirality, 7(2), 90-95 (1995-01-01)
The stereoisomers of alpha,alpha'-bis[3-(N,N-diethylcarbamoyl)-piperidino]-p-xylene (1) were synthesized. Rac ethyl nipecotate was resolved by diastereomeric (-)-D- and (+)-L-tartrate salt formation. The enantiomeric esters were hydrolyzed to the corresponding nipecotic acids, which were then converted into t-BOC derivatives. Treatment of the latter

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