1,2-bis(bromomethyl)benzene

• ChemBase ID: 92379
• Molecular Formular: C8H8Br2
• Molecular Mass: 263.95712
• Monoisotopic Mass: 261.89927426
• SMILES: BrCc1c(cccc1)CBr
• Canonical SMILES: BrCc1ccccc1CBr
• InChI: InChI=1S/C8H8Br2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5-6H2
• InChIKey: KGKAYWMGPDWLQZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,2-bis(bromomethyl)benzene
• IUPAC Traditional name: benzene, 1,2-bis(bromomethyl)-
• Synonyms: alpha,alpha'-Dibromo-o-xylene; o-Xylylene dibromide; 1,2-Bis(bromomethyl)benzene; α,α′-Dibromo-o-xylene; omega,omega'-DIBROMO-o-XYLENE; o-Xylylene dibromide; 1,2-Bis(bromomethyl)benzene; 邻二溴亚二甲苯基; 1,2-二(溴甲基)苯; 二溴邻二甲苯; α,α′-二溴-邻二甲苯

Database IDs

• CAS Number: 622-24-2; 91-13-4
• EC Number: 202-042-7
• MDL Number: MFCD00000175
• Beilstein Number: 637159
• PubChem SID: 24861231; 24893875; 162079077; 24861229
• PubChem CID: 66665

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.5187206
• LogD (pH = 7.4): 3.5187206
• Log P: 3.5187206
• Molar Refractivity: 51.7588 cm^3
• Polarizability: 19.559998 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 91-94 °C; 91-94 °C(lit.); 91-95 °C; 92°C; 92-96°C
• Density: 1.96 g/mL at 25 °C(lit.); 1.960

Safety Information

• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 3448; UN3261
• German water hazard class: 2
• Hazard Class: 6.1; 8
• Packing Group: 2; II
• Risk Statements: 22-34; 34; R:36/37/38
• Safety Statements: 26-36/37/39-45; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H314; H314-H318
• GHS Precautionary statements: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3448 6.1/PG 2

Product Information

• Purity: ≥97.0% (AT); ≥98.5% (AT); 97%
• Grade: puriss.; purum
• Linear Formula: C6H4(CH2Br)2

DETAILS

Sigma Aldrich - D44405

Packaging
25, 100 g in glass bottle

REFERENCES

• 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).