10-Bromdecanol

Bezeichnung:10-Bromdecanol

CAS-Nr53463-68-6

Englisch Name:10-Bromodecanol

CBNumberCB2490678

SummenformelC10H21BrO

Molgewicht237.18

MOL-Datei53463-68-6.mol

Synonyma

10-Bromdecanol

10-Bromdecanol physikalisch-chemischer Eigenschaften

Siedepunkt	165-169 °C/10 mmHg (lit.)
Dichte	1.19 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.476(lit.)
Flammpunkt	>230 °F
storage temp.	Inert atmosphere,Store in freezer, under -20°C
Löslichkeit	Chloroform (Sparingly)
pka	15.20±0.10(Predicted)
Aggregatzustand	Liquid
Farbe	Clear yellow
Wasserlöslichkeit	It is miscible with water.
BRN	1738593
Stabilität	Moisture Sensitive
InChI	1S/C10H21BrO/c11-9-7-5-3-1-2-4-6-8-10-12/h12H,1-10H2
InChIKey	LGZMUUBPTDRQQM-UHFFFAOYSA-N
SMILES	OCCCCCCCCCCBr
CAS Datenbank	53463-68-6(CAS DataBase Reference)
EPA chemische Informationen	1-Decanol, 10-bromo- (53463-68-6)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
TSCA	TSCA listed
HS Code	29055900
Speicherklasse	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

10-Bromodecanol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
Clear yellow liquid
Verwenden
10-Bromodecanol can be used to synthesize rotaxane dendrimers. It can also be used to synthesize J2326, a molecule that induces neurite outgrowth in neuronal cells.
Verwenden
10-Bromo-1-decanol is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It was also used in the synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm (Amyelois transitella).
Definition
ChEBI: 10-Bromo-1-decanol is a primary alcohol.
Synthese

112-47-0

53463-68-6

General procedure for the synthesis of 10-bromo-1-decanol from 1,10-decanediol: 1,10-decanediol (10 g, 57.47 mmol) was dissolved in toluene (600 mL) and transferred to a 1 L two-necked, round-bottomed flask fitted with a Dean-Stark separator. 48% hydrobromic acid (7.15 mL, 63.21 mmol) was slowly added to the reaction system and subsequently heated to reflux for 16 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was washed sequentially with 1 N hydrochloric acid, 2 M aqueous sodium hydroxide, deionized water and saturated saline. The organic phase was separated, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 15% ethyl acetate/hexane) to afford 10-bromo-1-decanol as a colorless transparent oil (12.7 g, 93% yield). Thin layer chromatography (TLC) Rf = 0.45 (unfolding agent: 20% ethyl acetate/hexane); 1H NMR (500 MHz, CDCl3): δ 3.63 (t, J = 5.8 Hz, 2H), 3.39 (t, J = 6.8 Hz, 2H), 1.85 (m, 2H), 1.56 (m, 2H), 1.42 (m, 2H), 1.38- 1.27 (m, 10H); 13C NMR (125 MHz, CDCl3): δ 62.9, 33.9, 32.7, 32.6, 29.3, 29.2, 29.2, 28.6, 28.0, 25.6; infrared spectra (neat sample): νmax 2927, 2856, 1738, 1593, 1449, 1367, 1241 cm-1; high-resolution mass spectrum (ESI): calculated value C10H22BrO [M + H]+ 237.0854, measured value 237.0845.
Einzelnachweise
[1] Tetrahedron, 2015, vol. 71, # 7, p. 1058 - 1067
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1083 - 1092
[3] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 6, p. 273 - 276
[4] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[5] Patent: EP1818336, 2007, A1. Location in patent: Page/Page column 7

10-Bromodecanol Upstream-Materialien And Downstream Produkte

10-Bromdecanol Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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