1,10-Dibromodecane Chemical Properties

Melting point:

25-27 °C (lit.)

Boiling point:

160 °C/15 mmHg (lit.)

Density 

1.335 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4912(lit.)

Flash point:

26°C

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Low Melting Solid

Specific Gravity

1.335

color 

Beige to brown

Water Solubility 

insoluble

BRN 

506156

Dielectric constant

6.5599999999999996

InChIKey

GTQHJCOHNAFHRE-UHFFFAOYSA-N

CAS DataBase Reference

4101-68-2(CAS DataBase Reference)

NIST Chemistry Reference

Decane, 1,10-dibromo-(4101-68-2)

EPA Substance Registry System

Decane, 1,10-dibromo- (4101-68-2)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

TSCA 

Yes

HS Code 

29049090

MSDS

• Language:English Provider:1,10-Dibromodecane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,10-Dibromodecane Usage And Synthesis

Chemical Properties

beige to brown crystalline low melting mass

Uses

1,10-Dibromodecane is used as an alkylating agent and as synthetic organic intermediate.

Synthesis

The general procedure for the synthesis of 1,10-dibromodecane from 1,10-decanediol is as follows: 1,10-decanediol (1 eq.), 48% aqueous hydrobromic acid (ca. 3 eq./hydroxyl), and octane (ca. 7:1 volume-to-weight ratio to the diol) were added to a single-necked, round-bottomed flask and assembled with a fractionating column/Dean-Stark trap. The reaction mixture was placed in a heated oil bath (145-150°C) with rapid magnetic stirring. The aqueous (lower) layer at the initial boiling point (89-92°C) was condensed and gently separated, and subsequently collected at about half the theoretical volume of water; at this point the temperature of the azeotrope (still at head temperature) began to rise. The condenser was set to full reflux for a few hours, then turned back on and the aqueous-phase material continued to be collected for 1 hour (top temperature 96-100°C). The final volume of the aqueous phase distillate reaches 90-100% of the theoretical value (up to 24% hydrobromic acid in the high boiling distillate). When the octane phase (which is light tan in color) contains dibromides and brominated streptanols (e.g., 6 band 6c), it is washed with cold 85% v/v sulfuric acid (10 mL first, then 5 mL) to remove all color and brominated streptanols. For all three dibromides (3b, 4b, 6b), the neutralized octane solution was passed through a Vigreux column under reduced pressure to remove the solvent, and the residue (which was confirmed to be essentially pure by 1H NMR) was purified by Kugelrohr distillation. Trace amounts of 4-methyltetrahydropyran were detected prior to distillation of 4b.

References

[1] Tetrahedron Letters, 2015, vol. 56, # 4, p. 630 - 632
[2] Green Chemistry, 2014, vol. 16, # 2, p. 836 - 843
[3] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5386 - 5394
[4] Journal of the American Chemical Society, 1936, vol. 58, p. 488
[5] Journal of the Chemical Society, 1958, p. 2068

1,10-Dibromodecane(4101-68-2)Related Product Information

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