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11-BROMO-1-UNDECENE

11-BROMO-1-UNDECENE structure

CAS No:
7766-50-9
Formula:
C11H21Br
Chemical Name:
11-BROMO-1-UNDECENE
Synonyms:
11-Bromoundecene;UNDECYLENYL BROMIDE;1-BROMO-10-UNDECENE;11-BROMO-1-UNDECENE;10-Undecenyl bromide;W-UNDECYLENYL BROMIDE;UNDEC-10-ENYL BROMIDE;N-UNDECYLENIC BROMIDE;11-Undecen-1-yl bromide;11-BroMo-1-undecene 95%
Categories:
Organic Chemistry > Hydrocarbons and Derivatives

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Description

colourless liquid

11-BROMO-1-UNDECENE Basic Attributes

Molecular Weight：

233.19

Exact Mass：

232.082657

BRN：

1753231

NSC Number：

139878

DSSTox ID：

DTXSID90300900

HScode：

29033990

Characteristics

PSA：

XLogP3：

Density：

1.1±0.1 g/cm3

Melting Point：

55 °C

Boiling Point：

149-150 °C35 mm Hg(lit.)

Flash Point：

>110°C

Refractive Index：

1.466

Water Solubility：

soluble in water, 0.2422 mg/L @ 25°C (est).

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

Marks：

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

11-BROMO-1-UNDECENE Use and Manufacturing

A dichloromethane solution of 10-undecen-1-ol (30, 200 mg, 1.17 mmol) was treated with CBr4(403 mg, 1.29 mmol, 1.1 eq.) and Ph3P(340 mg, 1.29 mmol, 1.1 eq.) at 0 °C for2 h, and the reaction was quenched by addition of water. Thereaction mixture was extracted with dichloromethane andthe organic layer was dried over anhydrous Na2SO4powder.The organic solvent was evaporated in vacuo to obtain thecrude product. The crude product was used for the furtherreactions without chromatographic purification. The crudeproducts were purified by column chromatography on silicagel to obtain 1-bromo-10-undecene (31, 273 mg, quantitativeyield) [56] as colorless oil.11-Undecen-1-ol (140 g, 0.82 mol) and CBr4 (300 g, 0.90 mol)were dissolved in CH2Cl2 (500 mL) in Schlenk flask and triphenylphosphine(237 g, 0.90 mol) was then added dropwise over 15 minat 5 C. The systemwas stirred at 5 C for 2 h, and raised to room temperature for 12 h. The solution was concentrated and a white precipitate formed which was removed by filtration. The resultantsolution was fractionally distilled under reduced pressure to get apurified and colorless liquid product (177 g).To a solution of undec-10-en-1-ol (0.86 g, 5.0 mmol) in DMF (15 ML) was added triphenylphosphine (1.46 g, 5.6 mmol).The solution was cooled to 0° C. and NBS (0.96 g, 5.4 mmol) was added in portions.After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.5 ML).The solution was diluted with ether (80 ML), washed with water, saturated aqueous NaHCO3 and brine successively.The organic layer was dried and concentrated.The residue was purified by flash chromatography on silica gel, eluding with hexane to afford 11-bromo-undec-1-ene (0.96 g, 82percent) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.79 (1H, m), 4.93 (2H, m), 3.38 (2H, t, J=6.9 Hz), 2.02 (2H, m), 1.83 (2H, m), 1.20-1.55 (12H, m); 13C NMR (75 MHz, CDCl3) δ 139.36, 114.33, 34.27, 33.99, 33.01, 29.57*2, 29.27, 29.09, 28.94, 28.35. Phosphorus tribromide (5.3 g, 19.6 mmol, 1.84 ml) was added dropwise to a solution of 10-Undecen-1-ol (10 g, 58.7 mmol) in diethyl ether (100 ml) at −78° C. over a period of 10 min and then the mixture was allowed to warm to room temperature and stirred under Ar overnight. The reaction mixture was quenched with water and the layers were separated. The aqueous layer was extracted with ether (5×30 ml) and the combined organic layers were washed with brine and dried over sodium sulfate. After evaporation of the solvent in vacuo, the crude product was purified by chromatography column on silica gel (hexane) to give pure product 8.2 g (yield: 60percent). General procedure: To a stirred solution of n-dibromoalkane (1 equiv.) in anhydrous THF (0.1M) under an argon atmosphere was added tert-BuOK (1.15 equiv.) in portionwise over 30 min. After being stirred under reflux for 16h, the reaction was cooled and subsequently quenched with water. The resulting mixture was then diluted with diethylether, and the layers were separated. The aqueous layer was extracted several times with diethylether, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by flash column chromatography over silica gel using petroleum ether as eluent to afford the desired product.

Computed Properties

Molecular Weight:233.19
XLogP3:6
Rotatable Bond Count:9
Exact Mass:232.08266
Monoisotopic Mass:232.08266
Heavy Atom Count:12
Complexity:89
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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