(E)-1,4-Dibromobut-2-ene Chemical Properties

Melting point:

48-51 °C(lit.)

Boiling point:

205 °C(lit.)

Density 

1.9393 (estimate)

refractive index 

1.5361 (estimate)

Flash point:

113°C

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Crystals or Crystalline Powder

color 

colorless to slightly brown

Water Solubility 

slightly soluble

BRN 

1719696

Stability:

Light Sensitive

InChIKey

RMXLHIUHKIVPAB-OWOJBTEDSA-N

CAS DataBase Reference

821-06-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Butene, 1,4-dibromo-, (E)-(821-06-7)

EPA Substance Registry System

2-Butene, 1,4-dibromo-, (2E)- (821-06-7)

Safety Information

Hazard Codes 

T,C

Risk Statements 

25-34-23/25

Safety Statements 

26-36/37/39-45-28A

RIDADR 

UN 2923 8/PG 2

WGK Germany 

2

RTECS 

EM4725000

F 

8-19

Hazard Note 

Toxic/Corrosive

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29033990

MSDS

• Language:English Provider:(E)-1,4-Dibromobut-2-ene

(E)-1,4-Dibromobut-2-ene Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(2E)-1,4-Dibromo-2-butene, is used as a reagent in the preparation of diaminoalkenes though copper-mediated diamination reaction.

Synthesis Reference(s)

The Journal of Organic Chemistry, 36, p. 3324, 1971 DOI: 10.1021/jo00821a012

General Description

Crystals or white crystalline solid.

Air & Water Reactions

(E)-1,4-Dibromobut-2-ene may be sensitive to exposure to light and air. Insoluble in water.

Reactivity Profile

(E)-1,4-Dibromobut-2-ene is incompatible with strong oxidizers and strong bases.

Fire Hazard

(E)-1,4-Dibromobut-2-ene is probably combustible.

Synthesis

Example 1 (E)-1,4-dibromo-2-butene (A) Synthesis: 1,3-butadiene (60 mL, 0.70 mol) was added to a 500 mL round-bottomed flask and the flask was placed in a -78 °C cooling bath. Carbon tetrachloride (CCl4, 100 mL) pre-cooled to -20 °C was slowly added to the flask to ensure that the temperature of the reaction mixture was maintained below -20 °C. Subsequently, bromine was added dropwise over a period of 2 hours. The reaction mixture was stirred vigorously at room temperature for 14 hours. After completion of the reaction, most of the solvent was evaporated under reduced pressure. The crude product was purified by recrystallization from cold hexane to afford white crystalline 1,4-dibromo-2-butene (A) (62.4 g, 0.29 mmol) in 58% yield. Thin layer chromatography (TLC) showed an Rf value of 0.74 (unfolding agent ratio hexane:ethyl acetate = 4:1). Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 300.40 MHz, CDCl3) data were as follows: δ 3.89-4.02 (m, 4H), 5.90-6.05 (m, 2H) ppm.

Purification Methods

Crystallise the dibromide from ligroin and/or distil it in a vacuum. [Beilstein 1 IV 79.]

References

[1] Journal of the American Chemical Society, 2014, vol. 136, # 43, p. 15403 - 15413
[2] Patent: US2008/262271, 2008, A1. Location in patent: Page/Page column 6
[3] Patent: WO2006/38764, 2006, A1. Location in patent: Page/Page column 9-10
[4] Chemische Berichte, 1938, vol. 71, p. 1679
[5] Angewandte Chemie, 1938, vol. 51, p. 919

(E)-1,4-Dibromobut-2-ene(821-06-7)Related Product Information

• CIS-BUTENEDIOIC ANHYDRIDE
• Maleic acid
• CIS-2-BUTENE
• Fumaric acid
• 1,3-Dibromo-5,5-dimethylhydantoin
• 1,3-Dibromopropane
• 2-Butene
• 3-METHYL-3-BUTEN-1-OL
• trans,trans-2,4-Undecadienal
• 1-BUTENE
• TRAUMATIC ACID
• TRANS-2-OCTENOIC ACID
• trans-2-Octenoic acid methyl ester
• trans-2-Pentenal
• (+/-)-trans-1,2-Diaminocyclohexane
• TRANS-1,4-CYCLOHEXANEDIOL
• trans-1,2-Cyclopentanediol
• TRANS-CYCLOBUTANE-1,2-DICARBOXYLIC ACID