1-Bromo-4-chlorobutane Chemical Properties

Melting point:

96-97 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))

Boiling point:

80-82 °C/30 mmHg (lit.)

Density 

1.488 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4875(lit.)

Flash point:

140 °F

storage temp. 

Store below +30°C.

solubility 

soluble in Chloroform

form 

Liquid

color 

Clear

Water Solubility 

SLIGHTLY SOLUBLE

BRN 

1098275

InChIKey

NIDSRGCVYOEDFW-UHFFFAOYSA-N

CAS DataBase Reference

6940-78-9(CAS DataBase Reference)

NIST Chemistry Reference

Butane, 1-bromo-4-chloro-(6940-78-9)

EPA Substance Registry System

Butane, 1-bromo-4-chloro- (6940-78-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-37/39-26

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29034980

MSDS

• Language:English Provider:1-Bromo-4-chlorobutane
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1-Bromo-4-chlorobutane Usage And Synthesis

Chemical Properties

clear liquid

Uses

1-Bromo-4-chlorobutane is used as a reagent in the synthesis of a novel spirohydantoin derivative as a potent multireceptor-active antipsychotic and antidepressant agent.

Synthesis

1. n-Butyllithium (1.6 M hexane solution, 5.0 mL, 8.0 mmol) was added slowly and dropwise to a tetrahydrofuran (THF, 10 mL) solution of diisopropylamine (1.1 mL, 8.0 mmol) at -30 °C and stirred continuously for 30 min at this temperature. 2. the reaction system was cooled down to -70 °C, a solution of (benzyloxy)acetic acid (0.60 g, 3.6 mmol) in THF (5 mL) was added slowly dropwise and stirred for 30 min at the same temperature. 3. Maintaining the -70 °C condition, 1-bromo-3-chloropropane (3.6 mL, 36 mmol) was added to the reaction mixture and stirring was continued for 30 minutes before the reaction system was slowly warmed to room temperature and stirred for 2 hours. 4. The reaction mixture was poured into ice-cold water and washed with ethyl acetate. 5. The pH of the aqueous layer was adjusted to 3-4 with 6 M hydrochloric acid and the mixture was subsequently extracted with ethyl acetate. 6. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. 7. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 100/0 to 50/50 gradient elution) to afford 1-bromo-4-chlorobutane as a colorless oil (0.28 g, 32% yield). 8. The structure of the product was investigated by 1H NPD analysis. 8. The structure of the product was confirmed by 1H NMR (CDCl3): δ 1.91-2.06 (4H, m), 3.54 (2H, t, J=5.1 Hz), 4.08 (1H, t, J=6.6 Hz), 4.55 and 4.74 (2H, d, J=11.4 Hz), 7.34-7.39 (5H, m).

References

[1] Patent: EP2455380, 2012, A1. Location in patent: Page/Page column 79

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