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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.
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).
Hazard Statements: H302-H314
Harmful if swallowed. Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P270-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant