CHEBI:87138 - 9-methyldecan-1-ol

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ChEBI Name 9-methyldecan-1-ol
Definition A fatty alcohol that is decan-1-ol in which one of the hydrogens at position 9 has been replaced by a methyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Shi-qi An
Supplier Information
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Formula C11H24O
Net Charge 0
Average Mass 172.308
Monoisotopic Mass 172.183
InChI InChI=1S/C11H24O/c1-11(2)9-7-5-3-4-6-8-10-12/h11-12H,3-10H2,1-2H3
ChEBI Ontology
Outgoing 9-methyldecan-1-ol (CHEBI:87138) is a fatty alcohol (CHEBI:24026)
9-methyldecan-1-ol (CHEBI:87138) is a primary alcohol (CHEBI:15734)
Synonyms Sources
9-methyldecanol ChEBI
isoundecan-1-ol ChEBI
Note: (2016-01-07) Synonym provided by submitter.
Registry Numbers Types Sources
1736539 Reaxys Registry Number Reaxys
55505-28-7 CAS Registry Number NIST Chemistry WebBook
55505-28-7 CAS Registry Number ChemIDplus
Last Modified
07 January 2016
Submitter Remark
2015-07-24 14:03:11.0 Shi-qi An A solution of Mg turnings (403 mg, 16.57 mmoL) and i-pentyl bromide (2.5 g, 16.57 mmoL) were stirred in anhydrous THF (7 mL). The mixture was treated with solution of 6-bromohexan-1-ol (0.722 mL, 5.52 mmoL) and Li2CuCl4 (0.1 M, 2.1 mL in THF) and stirred for 1 h at rt. HCl(conc.) (5 mL) and Et2O (10 mL) were added. The sticky solid was washed with Et2O (3 x 10 mL), stirred and decanted. The organic layer was washed with NaHCO3 (30 mL) and brine (30 mL), dried over MgSO4 and the solvent removed under reduced pressure. Purification by column chromatography eluting with Hex:EtOAc (2:1) gave the product as a colourless oil (0.505 g, 53 %). 1H NMR (400 MHz, CDCl3) δ: 3.63 (t, 2H, J = 6.6 Hz), 1.62 - 1.46 (m, 4H), 1.36 - 1.20 (m, 9H), 1.17 – 1.12 (m, 2H), 0.86 (t, 6H, J = 6.6 Hz). 13C NMR (125 MHz, CDCl3) δ: 63.1, 39.0, 32.8, 29.8, 29.6, 29.4, 27.9, 27.3, 25.7, 22.6. ES-MS: m/z 171.4 [M-H]-, C11H23O-. IR (NaCl disk): 3440, 2925 cm-1.