1,3-Dibromopropane

Synonym(s):1,3-Dibromopropane;Trimethylene bromide;Trimethylene dibromide

CAS NO.：109-64-8
Empirical Formula: C3H6Br2
Molecular Weight: 201.89
MDL number: MFCD00000255
EINECS: 203-690-3
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-24 19:19:26

What is 1,3-Dibromopropane?

Chemical properties

1,3-Dibromopropane is a colourless to slightly yellow liquid with sweet odor. soluble in ether, acetone and chloroform, insoluble in water. Decomposes when exposed to heat for a long time and is partially converted to 1,2-dibromopropane. Boiling with water produces propylene glycol. It is used substrate specificity of haloalkane dehalogenases.

The Uses of 1,3-Dibromopropane

1,3-Dibromopropane is used to prepare C3-bridged compounds through C-N coupling reactions. It is used in the preparation of 2,3,4,5-tetrahydro-7,7-diphenylimidazo- [2,1-b]-thiazine-6(7H)-one by reacting with potassium salt of 5,5-diphenyl-2-thiohydantoin.

General Description

1,3-Dibromopropane is a dihalogenated propane. It undergoes reduction catalyzed by electrogenerated solution-phase nickel(I) salen and nickel(I) salen confined in a polymer film on the surface of a carbon electrode to afford cyclopropane and propylene, respectively.

Hazard

Colorless liquid; sweet odor. Insoluble in water; soluble in organic solvents. Combustible.

Synthesis

1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide. It can derived from the reaction of propylene glycol with brominated hydrochloric acid.

Chemical properties

1,3-Dibromopropane is a colorless liquid with sweet odor. It was used in the first cyclopropane synthesis in 1881, known as the Freund reaction.

Preparation

1,3-Dibromopropane can be prepared via the free radical addition between allyl bromide and hydrogen bromide.

synthesis of 1,3-Dibromopropane

Purification Methods

1,3-Dibromopropane [109-64-8] M 201.9, f -34.4o, b 63 -63.5o/26mm, 76 -77o/40mm, 9 0o/80mm, 165o/atm, d 4 1.977, n 1.522. Wash the dibromide with dilute aqueous Na2CO3, then water. Dry and fractionally distil it under reduced pressure. [Beilstein 1 IV 216.]

Properties of 1,3-Dibromopropane

Melting point:	-34 °C (lit.)
Boiling point:	167 °C (lit.)
Density	1.989 g/mL at 25 °C (lit.)
vapor density	7 (vs air)
vapor pressure	2.6 hPa (20 °C)
refractive index	n20/D 1.524(lit.)
Flash point:	54 °C
storage temp.	Store below +30°C.
solubility	1.68g/l
form	Liquid
color	Clear colorless to yellow
Water Solubility	1.7 g/L (30 ºC)
Merck	14,9713
BRN	635662
Dielectric constant	4.3（20℃）
Stability:	Stable. Incompatible with strong oxidizing agents, strong bases. Flammable.
CAS DataBase Reference	109-64-8(CAS DataBase Reference)
NIST Chemistry Reference	Propane, 1,3-dibromo-(109-64-8)
EPA Substance Registry System	Propane, 1,3-dibromo- (109-64-8)

Safety information for 1,3-Dibromopropane

Signal word	Warning
Pictogram(s)	Flame Flammables GHS02 Exclamation Mark Irritant GHS07 Environment GHS09
GHS Hazard Statements	H226:Flammable liquids H302:Acute toxicity,oral H315:Skin corrosion/irritation H411:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P240:Ground/bond container and receiving equipment. P273:Avoid release to the environment. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.