alpha-Methylcinnamaldehyde supplier

Name
alpha-Methylcinnamaldehyde
EINECS 202-938-8
CAS No. 101-39-3
Article Data50
CAS DataBase
Density 1.015 g/cm³
Solubility Insoluble in water, but soluble in organic solvents such as ethanol.
Melting Point
Formula C₁₀H₁₀O
Boiling Point 254.604 °C at 760 mmHg
Molecular Weight 146.189
Flash Point 90.278 °C
Transport Information
Appearance yellow liquid
Safety 24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Cinnamaldehyde,a-methyl- (6CI,7CI,8CI);2-Methyl-3-phenyl-2-propen-1-al;2-Methyl-3-phenyl-2-propenal;2-Methyl-3-phenylacrolein;2-Methyl-3-phenylacrylaldehyde;2-Methyl-3-phenylpropenal;2-Methylcinnamic aldehyde;Methylcinnamaldehyde;NSC22283;NSC 49286;a-Methylcinnamic aldehyde;alpha-methyl cinnamaldehyde;alpha-Methylcinnamaldehyde;
PSA 17.07000
LogP 2.28880

Synthetic route

: 1504-55-8
2-methyl-3-phenylprop-2-en-1-ol

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With potassium phosphate; carbon dioxide In dimethyl sulfoxide at 90℃; for 48h;	92%
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile for 0.366667h; Heating;	86%
With trifluorormethanesulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In 1,4-dioxane at 20℃; for 0.433333h;	85%

: 71-23-8
propan-1-ol

: 100-52-7
benzaldehyde

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With Wilkinson's catalyst; boron trifluoride diethyl etherate In toluene at 30 - 80℃; Inert atmosphere;	90%

: 100-52-7
benzaldehyde

: 123-38-6
propionaldehyde

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
potassium fluoride on basic alumina In PEG400 at 30℃; for 4h;	89%
With KF-Al2O3 In PEG-400 at 30℃; for 4h;	89%
With sodium hydroxide at 0 - 20℃; for 6h;	89%

: C6H5CHCOSO2CF3CH3

: 201230-82-2
carbon monoxide

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; hydrogen; palladium diacetate In toluene at 60℃; under 3750.38 Torr; for 16h; Autoclave;	89%

: 78-85-3
2-methylpropenal

: 591-50-4
iodobenzene

A: 838-87-9
α-benzyl-cinnamaldehyde

B: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With 3-amino-3-methylbutanoic acid; palladium diacetate; silver trifluoroacetate In acetic acid at 80℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;	A 45% B 13%

...Expand

: 3-phenyl-2-methylpropen-1-tert-butyldimethylsilyl ether

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In acetonitrile at 40℃; for 72h;	44%

: 63163-76-8
(E)-1--2-methyl-1-propen

: 774-48-1
(diethoxymethyl)benzene

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at -78℃; for 16h;	30%
With titanium tetrachloride In dichloromethane at -78℃; for 5h; Product distribution; also reaction with benzaldehyde;	30%

: 60218-91-9
3-hydroxy-2-methyl-3-phenyl-propionaldehyde

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With sodium acetate at 120 - 130℃;

: 35811-93-9
3-chloro-2-methylcinnamaldehyde

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With zinc In ethanol

: 7422-93-7
1,1-dimethyl-2-propylidenehydrazine

: 100-52-7
benzaldehyde

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
Multistep reaction;

: 928-55-2
ethyl 1-propenyl ether

: 100-52-7
benzaldehyde

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
(i) BF3-Et2O, (ii) aq. HCl; Multistep reaction;

: 50259-54-6
4,4,6-trimethyl-2-(1-methyl-2-phenyl-vinyl)-5,6-dihydro-4H-[1,3]oxazine

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With sodium tetrahydroborate

: 61668-36-8
bromo-2 trimethylsilyloxy-1 propene-1

: 100-52-7
benzaldehyde

A: 32398-66-6
1-phenylbut-2-yn-1-ol

B: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With hydrogenchloride; tert.-butyl lithium 1.) THF, pentane, -70 deg C, 14.5 h; 2.) THF, pentane, -70 deg C, 20 min, then 0 deg C, 20 min; 3) THF, pentane, water 0 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 100-52-7
benzaldehyde

: 82215-51-8
4-((E)-2-Phenylsulfanyl-propenyl)-morpholine

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With ammonia; lithium 1.) ether, THF, -65 deg C, 15 min, 2.) ether, THF, -65 deg C, 1 h; Yield given. Multistep reaction;

: 64-17-5
ethanol

: 7732-18-5
water

: 100-52-7
benzaldehyde

: 123-38-6
propionaldehyde

: furan-2,3,5(4H)-trione pyridine (1:1)

: 101-39-3
2-methyl-3-phenyl-2-propenal

...Expand

: 100-52-7
benzaldehyde

: 123-38-6
propionaldehyde

alkali: alkali

: 101-39-3
2-methyl-3-phenyl-2-propenal

...Expand

: 100-52-7
benzaldehyde

: 123-38-6
propionaldehyde

alcoholic potash: alcoholic potash

A: 101-39-3
2-methyl-3-phenyl-2-propenal

B: 65-85-0
benzoic acid

...Expand

: 60218-91-9
3-hydroxy-2-methyl-3-phenyl-propionaldehyde

concentrated sodium acetate: concentrated sodium acetate

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
at 120 - 130℃;

: 100-52-7
benzaldehyde

buten-(2)-yl magnesium bromide: buten-(2)-yl magnesium bromide

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaH, 1,2-dimethoxy-ethane, (ii) /BRN= 471223/ 2: NaBH4 View Scheme
Multi-step reaction with 2 steps 1: (i) KOtBu, THF, (ii) /BRN= 471223/ 2: NaBH4 View Scheme

: 103-79-7
1-phenyl-acetone

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: POCl3 2: Zn / ethanol View Scheme
Multi-step reaction with 2 steps 1: lithium hexamethyldisilazane / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 2: palladium diacetate; N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; hydrogen / toluene / 16 h / 60 °C / 3750.38 Torr / Autoclave View Scheme

: 1504-55-8
2-methyl-3-phenylprop-2-en-1-ol

A: 1197-33-7
2-methyl-3-phenyl-acrylonitrile

B: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With ammonia; oxygen In tetrahydrofuran at 120℃; under 4560.31 Torr; for 5h;

: 1504-55-8, 39924-63-5, 55131-20-9
(E)-3-phenyl-2-methyl-2-propenol

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With silica gel; palladium at 90℃; for 24h; chemoselective reaction;

: 94-41-7
benzalacetophenone

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyrrolidine; water; trifluoroacetic acid / acetonitrile / 48 h / 50 °C / Inert atmosphere 2: acetonitrile / 12 h / 20 °C / Inert atmosphere View Scheme

: 86129-99-9
α-Methylcinnamaldehyde N-phenylimine

A: 101-39-3
2-methyl-3-phenyl-2-propenal

B: 62-53-3
aniline

Conditions

Conditions	Yield
With (R)-1,1'-binaphthyl-2,2'-phosphoric acid; yttrium(III) trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 18h;

: C30H30N4O6S

A: C19H18N4O5S

B: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With sodium hydroxide In water; dimethyl sulfoxide at 25 - 28℃; for 1h; pH=9.5;	A n/a B 100 mg

: 100-52-7
benzaldehyde

: 123-38-6
propionaldehyde

A: 60218-91-9
3-hydroxy-2-methyl-3-phenyl-propionaldehyde

B: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With 4-oxalocrotonate tautomerase from Pseudomonasputida mt-2, F50V mutant In aq. phosphate buffer at 20℃; for 5h; pH=7.6; Catalytic behavior; Time; Aldol Condensation; Enzymatic reaction;

...Expand

: 1199-77-5
α-methylcinnamic acid

A: 1504-55-8
2-methyl-3-phenylprop-2-en-1-ol

B: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With D-Glucose; Bacillus subtilis glucose dehydrogenase; Segniliparus rugosus carboxylic acid reductase; nicotinamide adenine dinucleotide phosphate; dimethyl sulfoxide; ATP; magnesium chloride In aq. phosphate buffer at 30℃; for 18h; pH=7.5; Enzymatic reaction;

: 30457-88-6
2-benzyl-2-propenal

: 101-39-3
2-methyl-3-phenyl-2-propenal

Conditions

Conditions	Yield
With palladium on silica; hydrogen at 80℃; under 375.038 Torr; Reagent/catalyst; Pressure; Flow reactor;

alpha-Methylcinnamaldehyde Consensus Reports

Reported in EPA TSCA Inventory.

alpha-Methylcinnamaldehyde Specification

The alpha-Methylcinnamaldehyde, with the CAS registry number 101-39-3, is also known as 3-Phenyl-2-methyl acrolein. It belongs to the product categories of Aldehydes; C10 to C21; Carbonyl Compounds. Its EINECS number is 202-938-8. This chemical's molecular formula is C₁₀H₁₀O and molecular weight is 146.19. What's more, its systematic name is 2-Methyl-3-phenylacrylaldehyde. Its classification code is Skin / Eye Irritant. This chemical should be sealed and stored in a cool and ventilated place. Moreover, it should be protected from heat and fire. It has been used in essence for household and personal care chemicals.

Physical properties of alpha-Methylcinnamaldehyde are: (1)ACD/LogP: 2.319; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.32; (4)ACD/LogD (pH 7.4): 2.32; (5)ACD/BCF (pH 5.5): 34.05; (6)ACD/BCF (pH 7.4): 34.05; (7)ACD/KOC (pH 5.5): 434.82; (8)ACD/KOC (pH 7.4): 434.82; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 17.07 Å²; (13)Index of Refraction: 1.563; (14)Molar Refractivity: 46.805 cm³; (15)Molar Volume: 144.036 cm³; (16)Polarizability: 18.555×10^-24cm³; (17)Surface Tension: 36.9 dyne/cm; (18)Density: 1.015 g/cm³; (19)Flash Point: 90.278 °C; (20)Enthalpy of Vaporization: 49.204 kJ/mol; (21)Boiling Point: 254.604 °C at 760 mmHg; (22)Vapour Pressure: 0.017 mmHg at 25°C.

Preparation: this chemical can be prepared by N,N-bis(trimethylsilyl)-(E)-propenylamine and diethoxymethyl-benzene at the temperature of -78 °C. This reaction will need reagent TiCl₄ and solvent CH₂Cl₂ with the reaction time of 16 hours. The yield is about 30%.

alpha-Methylcinnamaldehyde can be prepared by N,N-bis(trimethylsilyl)-(E)-propenylamine and diethoxymethyl-benzene at the temperature of -78 °C

Uses of alpha-Methylcinnamaldehyde: it can be used to produce 2-methyl-3-phenyl-acrylonitrile by heating. It will need reagents NH₂OH·HCl, NaI and solvent acetonitrile with the reaction time of 100 min. The yield is about 75%.

alpha-Methylcinnamaldehyde can be used to produce 2-methyl-3-phenyl-acrylonitrile by heating

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When using it, you must avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=CC(=Cc1ccccc1)C
(2)Std. InChI: InChI=1S/C10H10O/c1-9(8-11)7-10-5-3-2-4-6-10/h2-8H,1H3
(3)Std. InChIKey: VLUMOWNVWOXZAU-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		Food and Cosmetics Toxicology. Vol. 13, Pg. 853, 1975.
rat	LD50	oral	2050mg/kg (2050mg/kg)		Food and Cosmetics Toxicology. Vol. 13, Pg. 853, 1975.

Product Name

alpha-Methylcinnamaldehyde

Synthetic route

alpha-Methylcinnamaldehyde Consensus Reports

alpha-Methylcinnamaldehyde Specification

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