2-methylundecanal

2-Methylundecanal

Names
IUPAC name 2-Methylundecanal
Identifiers
CAS Number	110-41-8 N
3D model (Jmol)	Interactive image
ChemSpider	54990 Y 5291693 (2R)-2-methyl Y 553128 (2S)-2-methyl Y
ECHA InfoCard	100.003.424
EC Number	203-765-0
PubChem	61031 6915922 (2R)-2-methyl 637522 (2S)-2-methyl
RTECS number	YQ1509000
InChI InChI=1S/C12H24O/c1-3-4-5-6-7-8-9-10-12(2)11-13/h11-12H,3-10H2,1-2H3 Y Key: NFAVNWJJYQAGNB-UHFFFAOYSA-N Y InChI=1/C12H24O/c1-3-4-5-6-7-8-9-10-12(2)11-13/h11-12H,3-10H2,1-2H3 Key: NFAVNWJJYQAGNB-UHFFFAOYAB
SMILES CCCCCCCCCC(C)C=O
Properties
Chemical formula	C12H24O
Molar mass	184.32 g·mol−1
Appearance	Colourless liquid
Density	830.3 mg cm−3
Boiling point	171 °C; 340 °F; 444 K
Refractive index (nD)	1.432
Hazards
R-phrases	R52, R53, R38
Flash point	93.4 °C (200.1 °F; 366.5 K)
Related compounds
Related alkyl aldehydes	Hexyl cinnamaldehyde Isobutyraldehyde Lilial
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Isobutyraldehyde
Lilial

2-Methylundecanal is an organic compound that is found naturally in kumquat peel oil. This compound smells herbaceous, orange, and ambergris-like. At high dilution it has a flavor similar to honey and nuts. It is a colorless or pale yellow liquid that is soluble in organic solvents such as ether and ethanol. It is used as a fragrance component in soaps, detergents, and perfumes.

The first synthesis of 2-methylundecanal was recorded by Georges Darzens in 1904 from methyl nonyl ketone and ethyl chloroacetate. This method of synthesis can be used to produce a variety of aldehydes and became known as the Darzens reaction and is still used today. 2-Methylundecanal is synthesized in industry by two main routes. The first route, like Darzens, involves converting methyl nonyl ketone to its glycidate by allowing it to react with alkyl chloroacetate. The glycidate then undergoes saponification followed by decarboxylation.

The second method for the synthesis of 2-methylundecanal begins with the conversion of undecanal to 2-methyleneundecanal by allowing it to react with formaldehyde in the presence of base. The 2-methyleneundecanal is then hydrogenated to give 2-methylundecanal. The required undecanal is generated from 1-decene by hydroformylation. The resulting solution is over 50% 2-methyleneundecanal. The double bond of this compound is hydrogenated and the resulting 2-methylundecanal is separated from the by-products using fractional distillation.