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1,6-Dibromohexane

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1,6-Dibromohexane Basic information
Product Name:1,6-Dibromohexane
Synonyms:1,6-Dibromohexan;1,6-dibromo-hexan;1,6-Dibromohexane,98%;1,6-DibroMohexane, 98% 100ML;1,6-DibroMohexane, 98% 500ML;Hexamethylene Bromide Hexamethylene Dibromide;1,6-DIBROMOHEXANE FOR SYNTHESIS;alpha,omega-dibromohexane
CAS:629-03-8
MF:C6H12Br2
MW:243.97
EINECS:211-067-2
Product Categories:Industrial/Fine Chemicals;DIBROMOALKANE;Bromine Compounds;alpha,omega-Bifunctional Alkanes;alpha,omega-Dibromoalkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;bc0001
Mol File:629-03-8.mol
1,6-Dibromohexane Structure
1,6-Dibromohexane 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.)
Fp 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 constant8.8900000000000006
Stability:Stable. Incompatible with strong oxidizing agents.
InChI1S/C6H12Br2/c7-5-3-1-2-4-6-8/h1-6H2
InChIKeySGRHVVLXEBNBDV-UHFFFAOYSA-N
SMILESBrCCCCCCBr
CAS DataBase Reference629-03-8(CAS DataBase Reference)
NIST Chemistry ReferenceHexane, 1,6-dibromo-(629-03-8)
EPA Substance Registry SystemHexane, 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 Class10 - Combustible liquids
Hazard ClassificationsAcute Tox. 4 Oral
Aquatic Chronic 2
Skin Sens. 1
ToxicityLD50 orally in Rabbit: 1800 mg/kg LD50 dermal Rabbit > 2000 mg/kg
MSDS Information
ProviderLanguage
1,6-Dibromohexane English
SigmaAldrich English
ACROS English
ALFA English
1,6-Dibromohexane Usage And Synthesis
Chemical Propertiescolourless 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.
Uses1,6-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.
Uses1,6-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.
Preparation1,6-Dibromohexane is synthesized from hexanediol by bromination.
Synthesis
1,6-Hexanediol

629-11-8

1,6-Dibromohexane

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
Tag:1,6-Dibromohexane(629-03-8) Related Product Information
Cyclohexane 1-Bromohexane Hexane Methylcyclohexane Cyclohexene oxide Butoxybenzene Quinhydrone 2,5-dibromohexane-3,4-dione 2,5-Dibromohexane, erythro + threo, 97%,2,5-DIBROMOHEXANE, 97%, MIXTURE OF DIASTEREOMERS,2,5-DIBROMOHEXANE (MIXTURE OF DIASTEREOMERS) 98+%,dibromohexan 3,4-DIBROMOHEXANE 1,2-DIBROMOHEXANE,1,2-DIBROMOHEXANE, 97+% PERFLUORO-1,6-DIBROMOHEXANE,1,6-Dibromodecafluorohexane~Perfluoro-1,6-dibromohexane 1,4-dibromohexane 2,3-DIBROMOHEXANE,2,3-dibromohexane,mixtureofdiastereomer 1,6-DIBROMOHEXANE-D12 1,5-dibromohexane 1,6-Dibromohexane 1,1-dibromohexane