ChemicalBook Product Catalog Chemical Reagents Organic reagents Halogenated aliphatic hydrocarbons 1,6-Dibromohexane

1,6-Dibromohexane

Product Name1,6-Dibromohexane
CAS629-03-8
MFC6H12Br2
MW243.97
EINECS211-067-2
MOL File629-03-8.mol

Chemical Properties

Melting point	-2-2.5 °C (lit.)
Boiling point	243 °C (lit.)
Density	1.586 g/mL at 25 °C (lit.)
vapor pressure	<1 hPa (20 °C)
refractive index	n20/D 1.507(lit.)
Flash point	110 °C
storage temp.	Store below +30°C.
solubility	soluble in Chloroform, Ethyl Acetate
form	Liquid
color	colorless to brownish-yellow
Water Solubility	insoluble
BRN	1236322
Dielectric constant	8.8900000000000006
Stability	Stable. Incompatible with strong oxidizing agents.
InChI	1S/C6H12Br2/c7-5-3-1-2-4-6-8/h1-6H2
InChIKey	SGRHVVLXEBNBDV-UHFFFAOYSA-N
SMILES	BrCCCCCCBr
CAS DataBase Reference	629-03-8(CAS DataBase Reference)
NIST Chemistry Reference	Hexane, 1,6-dibromo-(629-03-8)
EPA Substance Registry System	Hexane, 1,6-dibromo- (629-03-8)

Safety Information

Hazard Codes	T,N,C
Risk Statements	25-51/53-43
Safety Statements	36-45-61-36/37
RIDADR	UN 2810 6.1/PG 3
WGK Germany	3
RTECS	MO1515000
TSCA	TSCA listed
HazardClass	9
PackingGroup	III
HS Code	29033036
Storage Class	10 - Combustible liquids
Hazard Classifications	Acute Tox. 4 Oral Aquatic Chronic 2 Skin Sens. 1
Toxicity	LD50 orally in Rabbit: 1800 mg/kg LD50 dermal Rabbit > 2000 mg/kg

MSDS

Provider	Language
1,6-Dibromohexane	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

colourless or pale yellow liquid. soluble in ethanol, ether, benzene and chloroform, insoluble in water. It is used in the synthesis of the hypotensive drug hexamethonium bromide.

Uses

1,6-Dibromohexane is used as a reagent in the synthesis of novel benzo[b]xanthone derivatives which have a potential antitumor activity. It is also used as a cross-linker for the cross-linking of glycuronans.

Uses

1,6-Dibromohexane is generally used to introduce C6 spacer in the molecular architecture. Some of the examples are:
Synthesis of solvent processable and conductive polyfluorene ionomers for alkaline fuel cell applications.
Synthesis of cross-linkable regioregular poly(3-(5-hexenyl)thiophene) (P3HNT) for stabilizing the film morphology in polymer photovoltaic cells.
Synthesis of pyrrolo-tetrathiafulvalene molecular bridge (6PTTF6) to study redox switching behavior of single molecules.
Synthesis of water-soluble thermoresponsive polylactides.

Preparation

1,6-Dibromohexane is synthesized from hexanediol by bromination.

Synthesis

629-11-8

629-03-8

The general procedure for the synthesis of 1,6-dibromohexane from 1,6-hexanediol was as follows: N-bromosuccinimide (NBS, 534 mg, 3 mmol) was dissolved in dichloromethane (CH2Cl2, 10 mL) in a 50 mL round-bottomed flask. Triphenylphosphine (Ph3P, 786 mg, 3 mmol) and 1,6-hexanediol (1 mmol) were added dropwise to the NBS solution at -78 °C. The reaction mixture was stirred at room temperature away from light for 12 h, during which the progress of the reaction was monitored by thin layer chromatography (TLC, eluent: petroleum ether-ethyl acetate, 20:1). Upon completion of the reaction, the mixture was concentrated under vacuum and purified by fast chromatography on silica gel column (eluent: petroleum ether-ethyl acetate, 30:1) to afford the target product 1,6-dibromohexane.

References

[1] Synthesis (Germany), 2015, vol. 47, # 8, p. 1154 - 1162
[2] Journal of the American Chemical Society, 1936, vol. 58, p. 488
[3] Archiv der Pharmazie (Weinheim, Germany), 1935, p. 323
[4] Zhurnal Obshchei Khimii, 1935, vol. 5, p. 1508
[5] Journal of the Chemical Society, 1948, p. 46

1,6-Dibromohexane

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