All Photos(1)

34440

Sigma-Aldrich

α,α′-Dibromo-p-xylene

purum, ≥98.0% (GC)

Synonym(s):
DMF, p-Xylylene dibromide, 1,4-Bis(bromomethyl)benzene
Linear Formula:
C6H4(CH2Br)2
CAS Number:
Molecular Weight:
263.96
Beilstein:
1100019
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

purum

assay

≥98.0% (GC)

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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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