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91-13-4 - o-Xylylene dibromide, 97% - 1,2-Bis(bromomethyl)benzene - alpha,alpha'-Dibromo-o-xylene - A17241 - Alfa Aesar

A17241 o-Xylylene dibromide, 97%

CAS Number
91-13-4
Synonyms
1,2-Bis(bromomethyl)benzene
alpha,alpha'-Dibromo-o-xylene

Size Price ($) Quantity Availability
5g 16.48
25g 56.65
100g 146.26
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o-Xylylene dibromide, 97%

MDL
MFCD00000175
EINECS
202-042-7

Chemical Properties

Formula
C8H8Br2
Formula Weight
263.96
Melting point
92-96°
Density
1.960
Solubility
Solubility in toluene is almost transparent and ethanol. Insoluble in water.

Applications

1,2-Bis(bromomethyl)benzene is used in the synthesis of isothioureas involved in the inhibition of human nitric oxide synthases. Also used in the synthesis of tridentate carbene ligands.

Notes

Store away from oxidizing agents. Keep the container tightly closed and place it in a cool, dry and well ventilated condition.

Literature References

Gary D. Ewing, et al. Efficient synthesis of 4,5-benzotropone from o-xylylene dibromide.J. Org. Chem.,1975,40(20), 2965-2966.

C. E. Griffin, et al. Synthesis of a Macrocycle by Application of the Wittig Reaction.J. Org. Chem.,1962,27(5), 1627-1631.

Reductive debromination with activated Ni provides a simple route to o-xylylene, which can be trapped by dienophiles: J. Org. Chem., 53, 339 (1988):

o-Xylylene can also be generated using Zn metal and ultrasound: J. Org. Chem., 47, 751 (1982), or NaI in DMF: Chem. Pharm. Bull., 22, 2159 (1974).

Dialkylating agent for the formation of a variety of benzo-fused carbocyclic and heterocyclic ring systems, e.g. five-membered with Meldrum's acid (Isopropyl­idene malonate, A15603): Org. Prep. Proced. Int., 24, 185 (1992), 7-membered with Dimethyl­ acetone-1,3-dicarboxyl­ate, A14969: J. Org. Chem., 54, 5237 (1989), as well as macrocycles and cryptands; see, e.g.: J. Org. Chem., 57, 6112 (1992). Reaction with 1,2- and 1,3-diols has been used a method of protection; the diol can be regenerated by hydrogenolysis: Synth. Commun., 19, 3363 (1989).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P280-P305+P351+P338-P309-P310

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician.

Other References

Beilstein
637159
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2903.99
TSCA
Yes

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