Lilial

Base Information

• Chemical Name: Lilial
• CAS No.: 80-54-6
• Deprecated CAS: 39390-70-0,75166-25-5,75166-25-5
• Molecular Formula: C14H20O
• Molecular Weight: 204.312
• Hs Code.: 2912.29
• European Community (EC) Number: 201-289-8
• NSC Number: 22275
• UNII: T7540GJV69
• DSSTox Substance ID: DTXSID9026500
• Nikkaji Number: J11.845A
• Wikipedia: Lilial
• Wikidata: Q209290
• RXCUI: 1307156
• Metabolomics Workbench ID: 123554
• ChEMBL ID: CHEMBL1496715
• Mol file: 80-54-6.mol

Synonyms:4-tert-butyl-alpha-methylhydrocinnamaldehyde;lilial;lily aldehyde

Chemical Property of Lilial

Chemical Property:

• Appearance/Colour: clear to slightly yellow liquid
• Vapor Pressure: 0.00444mmHg at 25°C
• Melting Point: 106-109 °C
• Refractive Index: 1.501 - 1.509
• Boiling Point: 277.7 °C at 760 mmHg
• Flash Point: 120.9 °C
• PSA: 17.07000
• Density: 0.93 g/cm³
• LogP: 3.36160
• Storage Temp.: 2-8°C
• Water Solubility.: 33mg/L at 20℃
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 204.151415257
• Heavy Atom Count: 15
• Complexity: 194

Purity/Quality:

99.9% ^*data from raw suppliers

3-(p-tert-Butylphenyl)isobutylaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-38-51/53-62-43
• Safety Statements: 60-61-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CC1=CC=C(C=C1)C(C)(C)C)C=O
• Description: Lily aldehyde (also known as lysmeral or Lilial) is a chemical compound commonly used as a perfume in cosmetic preparations and laundry powders1-3. It is fresh light green floral lily muguet lindenblossom aldehyde. Lilial is used in a wide variety of compositions where it confers a particularly recommended for floral notes such as muguet, linden-blossom and cyclamen2.
• Uses: In addition to its applications in the perfume and aroma industry, lilial is used mainly for the synthesis of substituted 3-(4-tert-butylphenyl)-2-methylpropylamines, a new class of substances with fungicidal properties. These compounds are effective against mildew in barley and wheat. 2-(4-tert-Butylbenzyl)propionaldehyde may be used as a reference standard for the determination of 2-(4-tert-butylbenzyl)propionaldehyde in:Human urine samples by ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) equipped with electrospray ionization (ESI) source and multiple reaction monitoring (MRM) mode of detection.Deodorants and air fresheners by sonication extraction coupled with gas chromatography-mass spectrometry (GC-MS).Scented consumer products by GC-MS as well as GC in combination with olfactometry.

Technology Process of Lilial

There total 42 articles about Lilial which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

3-(4-tert-butylphenyl)-2-methylprop-2-enal (180850-14-0) → lilial (80-54-6)

Guidance literature:

With calcium hydroxide; hydrogen; palladium/alumina; In methanol; for 4h; under 760 Torr; Ambient temperature;

Reference yield: 85.0%

diethyl<<3-<4-(1,1-dimethylethyl)phenyl>-2-methyl-1-propenyl>oxy>methylsilane (84472-74-2,84472-75-3) → lilial (80-54-6)

Guidance literature:

With potassium fluoride; In methanol; at 25 ℃; for 1h;

DOI:10.1021/ja00283a035

Reference yield: 83.3%

1-(bromomethyl)-4-(1,1-dimethylethyl)benzene (18880-00-7) + propionaldehyde (123-38-6) → lilial (80-54-6)

Guidance literature:

With sodium hydroxide; 4-tertbutylbenzyl triethylammonium iodide; In tetrahydrofuran; water; toluene; at 70 - 75 ℃; for 5h; Product distribution / selectivity;

upstream raw materials:

p-tert-butyl-α-methyl-3-phenylprop-2-enal

2-methylpropenal

tert-butylbenzene

diethyl<<3-<4-(1,1-dimethylethyl)phenyl>-2-methyl-1-propenyl>oxy>methylsilane

Downstream raw materials:

1-(4-t-Butylphenyl)-3-phenyl-2-methyl-propan

3-(p-tert-butylphenyl)-2-methyl-1-propanol

(1S,3R,S)-3-(1-(4-tert-butylphenyl)propan-2-yl)-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine

C₁₇H₂₄O

Refernces

• 1、 Wu, Fu-Peng,Li, Da,Peng, Jin-Bao,Wu, Xiao-Feng. "Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals". supporting information. p. 5699 - 5703. Retrieved 2019/08/01.
• 2、 Vrbková, Eva,Vysko?ilová, Eli?ka,Rott, Martin,Zapletal, Martin,?erveny, Libor. "A synthetic route to 4-alkyl-α-methylhydrocinnamylaldehydes". . p. 2603 - 2613. Retrieved 2017/03/22.