2-(2-Bromoethyl)-1,3-dioxane Chemical Properties

Melting point:

157-161 °C

Boiling point:

67-70 °C2.8 mm Hg(lit.)

Density 

1.431 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.481(lit.)

Flash point:

206 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

ethanol: soluble50 (μg/mL)

form 

Liquid

color 

Clear colorless

Water Solubility 

It is not soluble in water but soluble in organic solvent such as ethanol.

BRN 

1421628

InChI

InChI=1S/C6H11BrO2/c7-3-2-6-8-4-1-5-9-6/h6H,1-5H2

InChIKey

WMDHQEHPOVOEOG-UHFFFAOYSA-N

SMILES

O1CCCOC1CCBr

CAS DataBase Reference

33884-43-4(CAS DataBase Reference)

NIST Chemistry Reference

2(2-Bromoethyl)-1,3-dioxane(33884-43-4)

EPA Substance Registry System

1,3-Dioxane, 2-(2-bromoethyl)- (33884-43-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-24/25

WGK Germany 

3

F 

8-10

TSCA 

Yes

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-(2-Bromoethyl)-1,3-dioxane Usage And Synthesis

Uses

2-(2-Bromoethyl)-1,3-dioxane was used in the synthesis of ketone adducts 2-[3-oxo-4(S)-(triphenylmethyl) amino-6-methylheptyl]-1,3-dioxane and 2-[3-oxo-4(S)-(triphenylmethyl)amino-6-methylheptyl]-1,3-dioxolane.

General Description

The reaction of Grignard reagent prepared from 2-(2-bromoethyl)-1,3-dioxane and N-tert-butanesulfinyl aldimines was studied.

Synthesis

A 2-L, three-necked flask has a mechanical stirrer, thermometer, and gas inlet tube. In the flask, 750 mL of dichloromethane, 112 g (2.00 mol) of acrolein (Note 1), and 0.10 g of dicinnamalacetone indicator are placed under nitrogen. The yellow solution is cooled to 0–5°C with an ice bath. Gaseous hydrogen bromide is bubbled into the solution with stirring until the indicator becomes deep red. The ice bath is removed, and 1.0 g of p-toluenesulfonic acid monohydrate and 152.2 g (2.00 mol, 144 mL) of 1,3-propanediol are added. The yellow solution is stirred at room temperature for 8 hr and then concentrated with a rotary evaporator. The residual oil is washed with two 250-mL portions of saturated aqueous sodium bicarbonate and dried over anhydrous potassium carbonate. Vacuum distillation through a 30-cm Vigreux column yields 252 g (65%) of 2-(2-Bromoethyl)-1,3-dioxane as a colourless liquid.

storage

This bromide is recognized to possess irritant properties and should therefore invariably be handled with gloved hands inside an efficient hood. It is also advisable that these reagents be refrigerated for long-term storage in order to minimize the potential for acid liberation.

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