1-(3-bromopropyl)-4-chlorobenzene

1-(3-bromopropyl)-4-chlorobenzene Property

Boiling point:

92 °C(Press: 0.3 Torr)

Density 

1.424

storage temp. 

Sealed in dry,Room Temperature

Appearance

light yellow liquid

InChI

InChI=1S/C9H10BrCl/c10-7-1-2-8-3-5-9(11)6-4-8/h3-6H,1-2,7H2

InChIKey

OVXYDNVSUOXGQG-UHFFFAOYSA-N

SMILES

C1(CCCBr)=CC=C(Cl)C=C1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

1-(3-bromopropyl)-4-chlorobenzene Chemical Properties,Usage,Production

Synthesis

1. Preparation of 1-(3-bromopropyl)-4-chlorobenzene a. Triphenylphosphine (7.42 g, 28.3 mmol) was dissolved in dichloromethane (200 mL) and cooled at 0 °C. b. A solution of bromine (1.46 mL, 28.3 mmol) in dichloromethane (40 mL) was slowly added to the above cooled solution over 30 min. c. A dichloromethane (20 mL) solution of 3-(4-chlorophenyl)propan-1-ol (4.6 g, 27 mmol) was added. d. Gradually warm the reaction mixture to room temperature with continuous stirring for 24 hours. e. The reaction mixture was transferred to a partition funnel and washed sequentially with saturated sodium bicarbonate solution, water and brine. f. The organic layer was dried with anhydrous sodium sulfate and subsequently concentrated. g. The residue was purified by silica gel column chromatography (silica gel size: 230-400 mesh, 350 g; eluent: 7.5% ethyl acetate/hexane) to afford 6.15 g (97% yield) of the target product 1-(3-bromopropyl)-4-chlorobenzene as a clear, colorless oil. h. Product characterization data: - NMR hydrogen spectrum (400 MHz, CDCl3) δ 2.16 (2H, m), 2.77 (2H, t), 3.41 (2H, t), 7.15 (2H, d), 7.27 (2H, d). h. Product characterization data. - HPLC retention time: 5.1 min (Method A).

References

[1] Patent: WO2011/126567, 2011, A1. Location in patent: Page/Page column 164
[2] Patent: US6407298, 2002, B1. Location in patent: Page column 5
[3] Patent: WO2010/146111, 2010, A1. Location in patent: Page/Page column 114
[4] Journal of Medicinal Chemistry, 2002, vol. 45, # 16, p. 3549 - 3557
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4752 - 4756