3-Bromocumene

3-Bromocumene Property

Melting point:

-10°C (estimate)

Boiling point:

52-53°C 0,8mm

Density 

1,285 g/cm³

refractive index 

1.5302

Flash point:

52-53°C/0.8mm

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

color 

Colorless to Light orange to Yellow

Water Solubility 

Difficult to mix in water.

BRN 

1858092

InChI

InChI=1S/C9H11Br/c1-7(2)8-4-3-5-9(10)6-8/h3-7H,1-2H3

InChIKey

GBSGGFCCQZUXNB-UHFFFAOYSA-N

SMILES

C1(Br)=CC=CC(C(C)C)=C1

CAS DataBase Reference

5433-01-2(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,N,Xn

Risk Statements 

22-50/53-51/53-36/38

Safety Statements 

24/25-61-60-36-26

RIDADR 

3082

HS Code 

29039990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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).

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

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

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

3-Bromocumene Chemical Properties,Usage,Production

Chemical Properties

Clear colorless to yellow liquid

Uses

3-Bromocumene is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 1691, 1960 DOI: 10.1021/jo01080a001

Synthesis

2-Bromo-4-isopropylaniline (2.65 g, 12.4 mmol, 1.0 eq.) was added to a mixed solution consisting of 96% ethanol (23 mL) and concentrated sulfuric acid (2.5 mL) over 15 min. The reaction system was cooled to -5 °C under vigorous stirring and an aqueous solution of sodium nitrite (1.42 g, 20.7 mmol, 1.67 eq.) was added dropwise over 1 h (3 mL). After the dropwise addition, stirring was continued at -5 °C for 30 min. Subsequently, copper powder (12.0 g) was added and the reaction mixture was refluxed for 4 hours. After the reaction was completed, the reaction mixture was filtered through a glass sand core funnel. The filtrate was poured into cold water (60 mL) and the organic product was extracted with dichloromethane (4 x 50 mL). The organic extracts were combined, dried with anhydrous potassium carbonate and concentrated under reduced pressure. The residue was purified by fractional distillation under reduced pressure (11 mmHg, 89-90 °C) to give 3-isopropylbromobenzene (1.91 g, 77% yield) as a yellow oil.

References

[1] Synthesis (Germany), 2016, vol. 48, # 19, p. 3301 - 3308
[2] Journal of the Chemical Society, 1939, p. 1299,1301
[3] Journal of Organic Chemistry, 1939, vol. 4, p. 20,26
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 794 - 797