101-86-0

Basic information

• Product Name: alpha-Hexylcinnamaldehyde
• Synonyms: FEMA 2569;HCA;JASMONAL H;HEXYLCINNAMALDEHYDE;HEXYL CINNAMIC ALDEHYDE;A-N-HEXYL-B-PHENYLACROLEIN;ALPHA-HEXYLCINNAMIC ALDEHYDE;ALPHA-HEXYLCINNAMALDEHYDE
• CAS NO: 101-86-0
• Molecular Formula: C₁₅H₂₀O
• Molecular Weight: 216.32
• EINECS: 202-983-3
• Product Categories: Pharmaceutical Intermediates;aldehyde Flavor;Aldehydes;C10 to C21;Carbonyl Compounds;Alphabetical Listings;Flavors and Fragrances;G-H
• Mol File: 101-86-0.mol

Chemical Properties

• Boiling Point: 174-176 °C15 mm Hg(lit.)
• Flash Point: 200 °F
• Appearance: /
• Density: 0.95 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000697mmHg at 25°C
• Refractive Index: n20/D 1.55(lit.)
• Storage Temp.: 2-8°C
• Solubility: water: soluble0.005g/L at 25°C
• CAS DataBase Reference: alpha-Hexylcinnamaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Hexylcinnamaldehyde(101-86-0)
• EPA Substance Registry System: alpha-Hexylcinnamaldehyde(101-86-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 36/37/38-34-43-52/53
• Safety Statements: 26-36/37/39-45-36-36/37-61
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 2
• RTECS: GD6560000
• Hazardous Substances Data: 101-86-0(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
α-Hexylcinnamaldehyde is used as a fragrance ingredient for its typical floral scent, particularly suitable for personal care products such as perfumes, creams, and shampoos, as well as household products.
Used in Food and Pharmaceutical Industry:
α-Hexylcinnamaldehyde is also used as a flavoring additive in the food and pharmaceutical industry, providing a sweet, waxy, floral, green, citrus, and fruity taste at 5 ppm.
Used in Soap Perfumes:
Due to its stability to alkali, α-hexylcinnamaldehyde is widely used in flower compositions, such as jasmine and gardenia, and is particularly useful in soap perfumes.
Used in Solubilization Studies:
The solubilization of α-hexylcinnamaldehyde by ionic surfactants, such as sodium dodecyl sulfate and dodecyltrimethylammonium chloride, and a non-ionic surfactant like dodecyl polyoxyethylene ethers, has been investigated for various applications.

Preparation

By condensation of octylaldehyde with benzaldehyde

Hazard

Combustible.

Contact allergens

Hexyl cinnamic aldehyde is a fragrance allergen. Its presence has to be mentioned by name in cosmetics within the EU.

InChI:InChI=1/C15H20O/c1-2-3-4-6-11-15(13-16)12-14-9-7-5-8-10-14/h5,7-10,12-13H,2-4,6,11H2,1H3/b15-12-

Synthetic route

Octanal (124-13-0) + benzaldehyde (100-52-7) → α-hexylcinnamaldehyde (101-86-0)

Conditions	Yield
With benzoic acid; L-proline In neat (no solvent) at 125℃; for 1h; Aldol Condensation; Inert atmosphere;	97%
With nitrogen; potassium hydroxide In methanol; water at 30℃; for 6h;	93.8%
With pyrrolidine In neat (no solvent) at 120℃; for 0.25h; Microwave irradiation;	90%

Octanal (124-13-0) + benzaldehyde (100-52-7) → 2-hexyl-2-decenal (13893-39-5) + α-hexylcinnamaldehyde (101-86-0)

Conditions	Yield
With p-toluene sulfonic acid impregnated on MCM-41 In neat (no solvent) at 125℃; for 13h; Inert atmosphere; Green chemistry;

α-hexylcinnamaldehyde (101-86-0) → α-hexylcinnamyl alcohol (53892-67-4)

Conditions	Yield
With tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; hydrogen; potassium carbonate In water; isopropyl alcohol at 100℃; under 22502.3 Torr; for 17h; Inert atmosphere;	98%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol at 82℃; for 6h; Inert atmosphere; Schlenk technique; chemoselective reaction;	96%
With Cp*Ir(6,6'-dionato-2,2'-bipyridine)(H2O); isopropyl alcohol at 82℃; for 6h; Inert atmosphere; Green chemistry;	96%

α-hexylcinnamaldehyde (101-86-0) → (±)-2-benzyl-1-octanol (107613-28-5)

Conditions	Yield
With sodium tetrahydroborate; palladium diacetate In methanol at 20℃; for 1h;	95%

α-hexylcinnamaldehyde (101-86-0) + anthranilic acid amide (28144-70-9) → 3-phenyl-propionaldehyde (104-53-0)

Conditions	Yield
With bismuth (III) nitrate pentahydrate In ethanol at 100℃; for 12h; Temperature;	92%

α-hexylcinnamaldehyde (101-86-0) → α-hexylcinnamaldehyde-α-d1

Conditions	Yield
With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; water-d2; potassium acetate In dichloromethane at 50℃; for 12h;	92%

α-hexylcinnamaldehyde (101-86-0) → (±)-2-benzyl-1-octanol (107613-28-5) + trans-α-n-hexylcinnamic alcohol (53892-67-4)

Conditions	Yield
With chlorine[2-(4,5-dihydro-1H-imidazol-2-yl)-6-methoxypyridine](pentamethylcyclopentadienyl)iridium(III) chloride; sodium formate In water at 80℃; for 0.5h; Schlenk technique; chemoselective reaction;	A 91% B n/a

α-hexylcinnamaldehyde (101-86-0) + anthranilic acid amide (28144-70-9) → 2-(1-phenyl-2-octyl)quinazolin-4(3H)-one

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In toluene at 120℃; for 12h; Inert atmosphere;	88%

α-hexylcinnamaldehyde (101-86-0) + aniline (62-53-3) + propynoic acid ethyl ester (623-47-2) → ethyl 5-hexyl-1,4-diphenyl-1,4-dihydropyridine-3-carboxylate

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate) In toluene at 70℃; for 6h; Schlenk technique; Inert atmosphere;	84%

α-hexylcinnamaldehyde (101-86-0) + N-benzyloxy-α-methyl-α-bromopropionamide (1303507-75-6) → C26H33NO3

Conditions	Yield
With potassium hydroxide at 20℃;	84%

α-hexylcinnamaldehyde (101-86-0) + N-benzyloxy-α-methyl-α-bromopropionamide (1303507-75-6) → (E)-3-(benzyloxy)-5,5-dimethyl-2-(1-phenyloct-1-en-2-yl)-oxazolidin-4-one

Conditions	Yield
With potassium carbonate at 20℃;	84%

α-hexylcinnamaldehyde (101-86-0) + toluene-4-sulfonamide (70-55-3) → N-(2-hexyl-1H-inden-1-yl)-4-methylbenzenesulfonamide (1589518-79-5)

Conditions	Yield
With aluminum (III) chloride In nitromethane at 80℃; for 6h;	75%

3,5-dimethoxyphenol (500-99-2) + α-hexylcinnamaldehyde (101-86-0) → 3-hexyl-5,7-dimethoxy-2-phenyl-2H-chromene

Conditions	Yield
With [(C6H6)(PCy3)(CO)RuH]+*BF4−; potassium carbonate; triphenylphosphine In chlorobenzene at 120℃; for 16h; Schlenk technique; regioselective reaction;	72%

α-hexylcinnamaldehyde (101-86-0) + 2-Hydroxybenzoylhydrazine (936-02-7) → N'-(2-benzylideneoctylidene)-2-hydroxybenzohydrazide

Conditions	Yield
In ethanol at 60 - 70℃; for 8h;	69%

α-hexylcinnamaldehyde (101-86-0) + anthranilic acid amide (28144-70-9) → 2-(1-benzylideneheptyl)-3H-quinazolin-4-one

Conditions	Yield
With bismuth (III) nitrate pentahydrate In ethanol at 100℃; for 12h;	68%

O-methylresorcine (150-19-6) + α-hexylcinnamaldehyde (101-86-0) → C22H26O2

Conditions	Yield
With [(C6H6)(PCy3)(CO)RuH]+*BF4−; potassium carbonate; triphenylphosphine In chlorobenzene at 130℃; for 16h; Schlenk technique; regioselective reaction;	63%

α-hexylcinnamaldehyde (101-86-0) + (E)-MeZnC(CH(Ph))B(pin) → C29H39BO3

Conditions	Yield
at -10℃; for 12h;	60%

α-naphthol (90-15-3) + α-hexylcinnamaldehyde (101-86-0) → C25H26O

Conditions	Yield
With [(C6H6)(PCy3)(CO)RuH]+*BF4−; potassium carbonate; triphenylphosphine In chlorobenzene at 130℃; for 12h; Schlenk technique; regioselective reaction;	59%

α-hexylcinnamaldehyde (101-86-0) + 4-hydroxybenzoic acid hydrazide (5351-23-5) → N'-(2-benzylideneoctylidene)-4-hydroxybenzohydrazide

Conditions	Yield
In ethanol at 60 - 70℃; for 8h;	30%

α-hexylcinnamaldehyde (101-86-0) + benzyl alcohol (100-51-6) → 2-hexyl-3-phenyl-allyl alcohol (53892-67-4)

Conditions	Yield
With sodium hydroxide at 100℃;

1,5-dimethylhexylamine (543-82-8) + α-hexylcinnamaldehyde (101-86-0) → (1,5-Dimethyl-hexyl)-[2-[1-phenyl-meth-(E)-ylidene]-oct-(E)-ylidene]-amine (30121-85-8)

α-hexylcinnamaldehyde (101-86-0) + allyl bromide (106-95-6) → 1-Phenyl-2-hexyl-1,5-hexadien-3-ol (103826-27-3)

Conditions	Yield
With bismuth 1) DMF, r.t., 4 h, 2) r.t., 3 h; Yield given. Multistep reaction;
With bismuth 1.) DMF, room temperature, 2 h, 2.) DMF, room temperature, 2 h; Yield given. Multistep reaction;

α-hexylcinnamaldehyde (101-86-0) → allophanic acid-(2-hexyl-3-phenyl-allyl ester)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / 100 °C View Scheme

bromobenzene (108-86-1) + α-hexylcinnamaldehyde (101-86-0) → 1,3-diphenyl-2-n-hexyl-2-propen-1-ol

Conditions	Yield
With sodium hydrogencarbonate; magnesium In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water

α-hexylcinnamaldehyde (101-86-0) → C29H39BO5

Conditions	Yield
Multi-step reaction with 2 steps 1: 12 h / -10 °C 2: bis(acetylacetonate)oxidovanadium(IV); tert.-butylhydroperoxide / dichloromethane / 2 h / 0 °C View Scheme

α-hexylcinnamaldehyde (101-86-0) → C29H39BO4

Conditions	Yield
Multi-step reaction with 2 steps 1: 12 h / -10 °C 2: bis(acetylacetonate)oxidovanadium(IV); tert.-butylhydroperoxide / dichloromethane / 0 °C View Scheme

α-hexylcinnamaldehyde (101-86-0) → C23H28O4

Conditions	Yield
Multi-step reaction with 3 steps 1: 12 h / -10 °C 2: bis(acetylacetonate)oxidovanadium(IV); tert.-butylhydroperoxide / dichloromethane / 2 h / 0 °C 3: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 0 °C View Scheme

α-hexylcinnamaldehyde (101-86-0) → C23H28O4

Conditions	Yield
Multi-step reaction with 4 steps 1: 12 h / -10 °C 2: bis(acetylacetonate)oxidovanadium(IV); tert.-butylhydroperoxide / dichloromethane / 2 h / 0 °C 3: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 0 °C 4: boron trifluoride diethyl etherate / tetrahydrofuran / 20 °C View Scheme

Triethoxysilane (998-30-1) + α-hexylcinnamaldehyde (101-86-0) → C21H36O4Si

Conditions	Yield
With C24H41FFeNP3 In tetrahydrofuran at 60℃; for 7h; Inert atmosphere; Schlenk technique;
With C18H37F5FeP4 In tetrahydrofuran at 40℃; Schlenk technique; Inert atmosphere;
With o-Ph2P(C6H4)Si(Me)2Fe(H)(PMe3)3 In tetrahydrofuran at 50℃; for 4h; Schlenk technique;
With 2C4H8O*C42H47FeOP5 In tetrahydrofuran at 60℃; for 36h; Inert atmosphere; Schlenk technique;

α-hexylcinnamaldehyde (101-86-0) → C30H33NO3S

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 1 h / 0 °C 2.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C 3.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C 4.1: potassium carbonate; gold(I) chloride / 1,2-dichloro-ethane / 60 °C View Scheme

α-hexylcinnamaldehyde (101-86-0) → C37H39NO6S2

Conditions	Yield
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C 1.2: 1 h / 0 °C 2.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C 3.1: n-butyllithium / tetrahydrofuran / -78 - 20 °C 4.1: potassium carbonate; gold(I) chloride / 1,2-dichloro-ethane / 60 °C View Scheme

Upstream product

• 124-13-0 Octanal 
• 100-52-7 benzaldehyde 

Downstream Products

• 30121-85-8 (1,5-Dimethyl-hexyl)-[2-[1-phenyl-meth-(E)-ylidene]-oct-(E)-ylidene]-amine 
• 103826-27-3 1-Phenyl-2-hexyl-1,5-hexadien-3-ol 
• 107613-28-5 (±)-2-benzyl-1-octanol 
• 53892-67-4 α-hexylcinnamyl alcohol 
• 1589518-79-5 N-(2-hexyl-1H-inden-1-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Α, β - production of unsaturated aldehydes

The present invention aims to provide a method for preparing an aldehyde, which can prepare a target aldehyde with high selectivity and can also suppress the production of by-products. The present invention relates to a method for preparing an α,β-unsaturated aldehyde. The method includes a step of reacting a compound of formula (I) with a compound of formula (II) to provide an α,β-unsaturated aldehyde of formula (III). An alkali metal hydroxide and an alkanol having 1 to 4 carbon atoms are used in the step. The amount of the alkali metal hydroxide is 8 mol% or more and 12 mol% or less with respect to the compound of formula (I). The total amount of water contained in materials that are used in the reaction is 10 mol% or more and 50 mol% or less with respect to the compound of formula (I).

Bifunctional organocatalysts for the synthesis of jasminaldehyde and their derivatives

L-Proline in the presence of benzoic acid is found to be an effective catalytic system for the cross-aldol condensation of benzaldehyde with 1-heptanal under solvent free condition amongst the several amino acids screened for this reaction. Under the optimized reaction conditions, the desired product (e.g. jasminaldehyde) is formed up to 96% selectivity in one hour using the desired arylaldehyde: 1-alkanaldehyde ratio as low as 2:1 under controlled addition of 1-alkanaldehyde.

P-Toluene sulfonic acid (PTSA)-MCM-41 as a green, efficient and reusable heterogeneous catalyst for the synthesis of jasminaldehyde under solvent-free condition

This paper reports the synthesis of p-Toluene sulfonic acid (PTSA)-MCM-41 by impregnation method and its characterization XRD, FT-IR, TGA, N2 adsorption-desorption isotherms, SEM, and TEM. The impregnated catalysts were used to catalyse cross-aldol condensation of active methylene bearing aliphatic aldehydes with aromatic aldehydes under solvent and metal-free condition particularly in the synthesis perfumery chemical-jasminaldehyde and related compounds. The as synthesized catalyst PTSA-MCM-41 has displayed high efficiency (selectivity up to 91%) in catalyzing cross-aldol condensation reaction and was reusable (5 cycles) with no apparent loss in activity. The catalytic performance of PTSA-MCM-41 was compared with other catalysts viz., ZnO, proline, proline-LDH, PTSA, PTSA-zirconia and PTSA-zeolite where PTSA-MCM-41 showed better performance particularly in synthesis of jasminaldehyde.

Microwave-assisted organocatalytic cross-aldol condensation of aldehydes

An environmentally benign organocatalytic cross-aldol condensation of aldehydes under microwave irradiation in the absence of solvent is described. Using pyrrolidine as a catalyst, an efficient and sustainable atom economic method was developed for the cross-aldol condensation of various aldehydes with excellent results. Among the products, jasmine aldehyde, α-hexyl cinnamaldehyde and cyclamen aldehyde, three compounds of great industrial demand, were synthesised.