4-(bromomethyl)benzo[d][1,3]dioxole

4-(bromomethyl)benzo[d][1,3]dioxole Property

Melting point:

62-62.5 °C(Solv: ethyl ether (60-29-7))

Boiling point:

274.8±19.0 °C(Predicted)

Density 

1.652±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

White to off-white Solid

InChI

InChI=1S/C8H7BrO2/c9-4-6-2-1-3-7-8(6)11-5-10-7/h1-3H,4-5H2

InChIKey

NXSORIZRMNGQNL-UHFFFAOYSA-N

SMILES

O1C2=CC=CC(CBr)=C2OC1

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

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

P321Specific treatment (see … on this label).

P330Rinse mouth.

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

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

4-(bromomethyl)benzo[d][1,3]dioxole Chemical Properties,Usage,Production

Synthesis

General procedure: An ethyl ether solution of phosphorus tribromide is prepared by dissolving 3.1 ml (0.033 mol) of phosphorus tribromide in 15 ml of ether. This solution was slowly added dropwise to an ether solution containing 4.5 g (0.03 mol) of 1,3-benzodioxolane-4-alkylmethanol at 0°C in an ice bath. After the dropwise addition was completed, the reaction was continued with stirring at 0°C for 3 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium carbonate solution, the organic phase was separated and washed with saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate for 8 hours and then filtered to remove the desiccant. The filtrate was distilled under reduced pressure to remove the solvent to obtain the crude product. The crude product was purified by fast silica gel column chromatography using petroleum ether: ethyl acetate (19:1) as eluent to give 5.8 g of the yellow oily target product 4-(bromomethyl)benzo[d][1,3]dioxole in 90.6% yield.

References

[1] Australian Journal of Chemistry, 1985, vol. 38, # 10, p. 1481 - 1489
[2] Patent: CN103804341, 2018, B. Location in patent: Paragraph 0064; 0072; 0073
[3] Patent: CN108690016, 2018, A. Location in patent: Paragraph 0555; 0557; 0558
[4] Patent: WO2007/44796, 2007, A2. Location in patent: Page/Page column 108-109
[5] Journal of the American Chemical Society, 1957, vol. 79, p. 6033