2-methylundecanal dimethyl acetal
2-methylundecanal
Conditions | Yield |
---|---|
Stage #1: 2-methylundecanal dimethyl acetal With 2,4,6-trimethyl-pyridine; triethylsilyl trifluoromethyl sulfonate In dichloromethane at 0℃; Stage #2: With water In dichloromethane | 100% |
2-methyl-1,2-epoxyundecane
2-methylundecanal
Conditions | Yield |
---|---|
With methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide) In dichloromethane at -78℃; for 0.5h; | 96% |
With methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide) In dichloromethane at -78℃; Yield given; |
2-methylundecanal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80℃; for 4h; Temperature; | 93% |
1-bromo-2-methyl-undecane
2-methylundecanal
Conditions | Yield |
---|---|
With dimethyl sulfoxide for 0.0569444h; Kornblum oxidation; Microwave irradiation; | 92% |
2-methyl-1-undecanol
2-methylundecanal
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane for 3h; Ambient temperature; | 86% |
2-hydroxymethyl-1-undecen
2-methylundecanal
Conditions | Yield |
---|---|
With chloro(cyclopentadienyl)bis(triphenylphosphinyl) ruthenium(II); triethylammonium hexafluorophosphate In 1,4-dioxane for 3.5h; Heating; | 68% |
With chloro(cyclopentadienyl)bis(triphenylphosphinyl) ruthenium(II); triethylammonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3.5h; | 68% |
2,3-epoxy-3-methyl-dodecanoic acid ethyl ester
2-methylundecanal
Conditions | Yield |
---|---|
Verseifung und Erhitzen; |
1-ethoxy-2-methyl-undecan-2-ol
2-methylundecanal
Conditions | Yield |
---|---|
With formic acid |
Conditions | Yield |
---|---|
With manganese triacetate In acetic acid | |
With copper diacetate; air; cobalt(II) acetate In acetic acid at 50℃; for 5h; | 51 % Turnov. |
Diazoethan
caprinaldehyde
A
3-dodecanone
B
2-methylundecanal
C
2,3-epoxydodecane
Conditions | Yield |
---|---|
With bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In dichloromethane at -78℃; for 1h; Yield given. Yields of byproduct given; | |
In methanol; diethyl ether at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given; |
Diazoethan
caprinaldehyde
A
3-dodecanone
B
2-methylundecanal
C
2,3-epoxydodecane
Conditions | Yield |
---|---|
With trimethylaluminum In dichloromethane at -78℃; for 1h; Product distribution; other organoaluminum promotor; |
Conditions | Yield |
---|---|
In methanol; diethyl ether at 0℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given; | |
With trimethylaluminum In dichloromethane at -78℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given; |
2-methylundecanal
Conditions | Yield |
---|---|
man verseift und spaltet aus der dabei erhaltenen Glycidsaeure Kohlensaeure ab; |
undecylenic acid
acetic acid
A
2-methylundecanal
B
heneicosan-11-one
Conditions | Yield |
---|---|
at 420 - 425℃; |
Conditions | Yield |
---|---|
With [Rh(μ-S(CH2)10CO2Na)(cod)]2; hydrogen In water at 55℃; under 25858.1 Torr; for 22h; Title compound not separated from byproducts.; |
2-methylundecanoic acid methyl ester
2-methylundecanal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 94.6 percent / lithium aluminium hydride / diethyl ether; benzene / 6 h / Heating 2: 86 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
methyl 2-methylene-5,10-undecadienoate
2-methylundecanal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 97.5 percent / H2 / Cu/Cr / heptane / 10 h / 240 - 250 °C / 76000.1 Torr 2: 86 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: 97 percent / H2 / Raney nickel / heptane / 5 h / 90 °C / 76000.1 Torr 2: 94.6 percent / lithium aluminium hydride / diethyl ether; benzene / 6 h / Heating 3: 86 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Mg; HgCl; diethyl ether 2: formic acid View Scheme |
4-methyltridec-1-en-3-ol
2-methylundecanal
Conditions | Yield |
---|---|
With sodium hydroxide; ozone In water; toluene at -5℃; for 2h; | 80 %Chromat. |
(+/-)-2-(undecan-2-yl)imidazolidin-4-one
2-methylundecanal
Conditions | Yield |
---|---|
In ethanol; acetonitrile for 1h; pH=4.6; Inert atmosphere; aq. buffer; |
1-undecene
carbon monoxide
A
n-Undecane
B
Dodecanal
C
2-methylundecanal
Conditions | Yield |
---|---|
With (acetylacetonato)dicarbonylrhodium (l); hydrogen In tetrahydrofuran; toluene at 120℃; under 15.0015 Torr; for 5h; Catalytic behavior; Inert atmosphere; Schlenk technique; |
2-methylene-undecanal
2-methylundecanal
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen at 120℃; under 21002.1 Torr; |
Conditions | Yield |
---|---|
With piperidine; acetic acid In cyclohexane for 22h; Knoevenagel Condensation; Reflux; Dean-Stark; | 99% |
2-methylundecanal
glycinamide hydrochloride
(+/-)-2-(undecan-2-yl)imidazolidin-4-one
Conditions | Yield |
---|---|
With triethylamine In methanol for 18h; Inert atmosphere; Reflux; | 94% |
Conditions | Yield |
---|---|
With (triphenylphosphine)copper(I) hydride hexamer In toluene at 20℃; for 2h; | 92% |
Conditions | Yield |
---|---|
With piperidine at 20℃; under 75.0075 - 760.014 Torr; for 64h; Knoevenagel Condensation; | 92% |
Conditions | Yield |
---|---|
With piperidine at 20℃; for 48h; Knoevenagel Condensation; | 89% |
2-methylundecanal
Conditions | Yield |
---|---|
With pyrrolidine; Trichloromethanesulfonyl chloride; 2,6-di-tert-butyl-pyridine; water In 1,2-dimethoxyethane at 60℃; for 5h; | 79% |
2-methylundecanal
benzyltriphenylphosphonium bromide
(3-methyldodec-1-enyl)benzene
Conditions | Yield |
---|---|
Stage #1: benzyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 65℃; for 1h; Stage #2: 2-methylundecanal In tetrahydrofuran; hexane at 0 - 65℃; for 18h; | 76% |
Conditions | Yield |
---|---|
With pyridine; trichloroisocyanuric acid In acetonitrile | 75% |
2-methylundecanal
(S)-alaninamide hydrochloride
(5S)-5-methyl-2-(undecan-2-yl)imidazolidin-4-one
Conditions | Yield |
---|---|
With triethylamine In methanol for 18h; Inert atmosphere; Reflux; | 74% |
2-methylundecanal
1-methyl-4-(4-methyltridec-2-enyl)benzene
Conditions | Yield |
---|---|
Stage #1: triphenyl-β-p-tolylethylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 65℃; for 1h; Stage #2: 2-methylundecanal In tetrahydrofuran; hexane at 0 - 65℃; for 16h; | 69% |
2-methylundecanal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 7h; Dean-Stark; Reflux; | 69% |
2-(trimethylsilyl)-1,3-dithiane
2-methylundecanal
2-(2-methyl-undecylidene)-1,3-dithiane
Conditions | Yield |
---|---|
Stage #1: 2-(trimethylsilyl)-1,3-dithiane With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 5h; Inert atmosphere; Stage #2: 2-methylundecanal In tetrahydrofuran at -78 - 20℃; Inert atmosphere; | 65% |
2-methylundecanal
1-(2-ethyltriphenylphosphine)-4-methoxybenzene iodide
1-methoxy-4-(4-methyltridec-2-enyl)benzene
Conditions | Yield |
---|---|
Stage #1: 1-(2-ethyltriphenylphosphine)-4-methoxybenzene iodide With n-butyllithium In tetrahydrofuran; hexane at 0 - 65℃; for 1h; Stage #2: 2-methylundecanal In tetrahydrofuran; hexane at 0 - 70℃; for 14h; | 63% |
Conditions | Yield |
---|---|
In toluene at 60 - 65℃; | 62% |
piperidine
2-methylundecanal
phenylacetylene
4-methyl-3-(piperidin-1-yl)-1-phenyltridec-1-yne
Conditions | Yield |
---|---|
With CuI-USY zeolite at 80℃; for 15h; | 60% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 4h; Reflux; Dean-Stark; | 58% |
2-methylundecanal
Conditions | Yield |
---|---|
In toluene at 50℃; | 55% |
2-methylundecanal
undecanoic acid, 2-methyl
Conditions | Yield |
---|---|
Stage #1: 2-methylundecanal With Jones reagent In acetone at -25 - -5℃; for 0.583333h; Stage #2: With sodium hydroxide In water; acetone; toluene for 0.25h; Stage #3: With hydrogenchloride In water; toluene | 41% |
With potassium permanganate |
Conditions | Yield |
---|---|
In toluene at 45 - 55℃; | 20% |
2-methylundecanal
2-(4-methyltridec-2-enyl)naphthalene
Conditions | Yield |
---|---|
Stage #1: (2-(naphthalen-1-yl)ethyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 65℃; for 1h; Stage #2: 2-methylundecanal In tetrahydrofuran; hexane at 0 - 65℃; for 16h; | 14% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 4h; Dean-Stark; Reflux; | 7% |
Conditions | Yield |
---|---|
With potassium carbonate |
IUPAC Name: (2S)-2-Methylundecanal
Molecular Formula: C12H24O
Molecular Weight: 184.36
EINECS: 203-765-0
Density: 0.764 g/cm3
Boiling Point: 192.7 °C at 760 mmHg
Flash Point: 47.1 °C
Freely Rotating Bonds: 3
Polar Surface Area: 0 Å2
Index of Refraction: 1.435
Molar Refractivity: 57.47 cm3
Molar Volume: 220.1 cm3
Polarizability: 22.78 ×10-24 cm3
Surface Tension: 23.2 dyne/cm
Enthalpy of Vaporization: 41.13 kJ/mol
Vapour Pressure: 0.672 mmHg at 25°C
Appearance: slightly yellow
The Cas Register Number of 2-Methylundecanal is 110-41-8.The chemical synonyms of 2-Methylundecanal (CAS NO.110-41-8) are 2-Methyl-1-undecanal ; Undecanal, 2-methyl- ; 2-Methylhendecanal ; 2-Methylundecanal ; Methyl n-nonyl acetaldehyde ; Methyl n-nonyl acetic aldehyde ; Methyl nonyl acetaldehyde ; Methyl nonyl acetic aldehyde ; Methyl-n-nonylacetaldehyde ; Methylnonylacetaldehyde ; Methylnonylacetic aldehyde .Product categories of 2-Methylundecanal (CAS NO.110-41-8) are Industrial/Fine Chemicals ; Aldehydes ; C10 to C21 ; Carbonyl Compounds ; Alphabetical Listings ; Flavors and Fragrances ; M-N .The molecular structure of 2-Methylundecanal (CAS NO.110-41-8) is.
It is used as a fragrance component in soaps, detergents, and perfumes.
Georges Darzens recorded the synthesis of 2-methylundecanal in 1904 from methyl nonyl ketone and ethyl chloroacetate.
CH3(CH2)8C(O)CH3 + ClCH2CO2CH3 → CH3(CH2)8CH(CH3)OCH(CO2R) + HCl
CH3(CH2)8CCH3OCCO2CH3 + H2O → CH3(CH2)8CH(CH3)CHO + CO2 + ROH
1. | eye-rbt 500 mg | UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 12/13 ,1963. | ||
2. | orl-rat LD50:6690 mg/kg | UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 12/13 ,1963. | ||
3. | skn-rbt LD50:14 g/kg | UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 12/13 ,1963. |
Reported in EPA TSCA Inventory.
Mildly toxic by ingestion and skin contact. An eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
WGK Germany: 1
RTECS: YQ1509000
It smells herbaceous, orange, and ambergris-like. At high dilution it has a flavor similar to honey and nuts.
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