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123-11-5

Basic Information
CAS No.: 123-11-5
Name: p-Anisaldehyde
Molecular Structure:
Molecular Structure of 123-11-5 (p-Anisaldehyde)
Formula: C8H8O2
Molecular Weight: 136.15 .
Synonyms: p-Formylanisole;p-Methoxybenzaldehyde;4-Anisaldehyde;4-Methoxybenzaldehyde;Anisaldehyde;Anisic aldehyde;Aubepine;Crategine;NSC 5590;Obepin;p-Anisic aldehyde;
EINECS: 204-602-6
Density: 1.088 g/cm3
Melting Point: -1 ºC
Boiling Point: 248 ºC at 760 mmHg
Flash Point: 108.9 ºC
Solubility: Miscible with acetone, alcohol, ether, chloroform and benzene. Immiscible with water.
Appearance: Clear to slight yellow liquid
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38-39-23/24/25-11
Safety: 26-45-36/37-16-7
Transport Information: UN 3316 9/PG 2
PSA: 26.30000
LogP: 1.50770
Synthetic route
105-13-5

4-Methoxybenzyl alcohol

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With 2,2'-bipyridylchromium peroxide In benzene for 0.8h; Heating;100%
With tris(4-methylphenyl)bismuthine oxide In toluene for 2h; Ambient temperature;100%
With 2,2'-bipyridylchromium peroxide In benzene for 0.8h; Product distribution; Heating; effect of various chromium(VI) based oxidants;100%
24588-72-5

2-(4-methoxyphenyl)-1,3-dithiane

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran Ambient temperature;100%
With silica gel; ferric nitrate In hexane at 50℃; for 0.166667h;100%
With silica gel; copper(II) nitrate In tetrachloromethane for 0.416667h; Ambient temperature;98%
2403-58-9

4-methoxybenzaldehyde diethylacetal

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With water at 80℃; for 2h;100%
With trifluoroacetic acid In dichloromethane at 25℃; for 20h;86%
With hydrogenchloride; sodium docusate In n-heptane at 25℃; Rate constant; variation of H3O(1+) concentration;
5422-47-9

1-(4-methoxyphenyl)-2-phenylethan-1-ol

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate; sodium acetate In water; acetonitrile Mechanism; Ambient temperature; other 2-aryl-1-(4-methoxyphenyl)ethanols;100%
2186-92-7

p-Anisaldehyde dimethyl acetal

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With polymer-supported dicyanoketene acetal; water In acetonitrile at 20℃; for 0.5h; Hydrolysis;100%
sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In water at 30℃; for 0.0833333h;100%
With iodine In dichloromethane at 0℃;100%
96181-80-5

(S)-1-benzyloxy-2-<(2R,5S,6R)-6-<(S)-1-(4-methoxybenzyloxymethyl)-ethyl>-5-methyltetrahydropyran-2-yl>butane

A

107207-23-8

(S)-2-<(2R,3S,6R)-6-<(S)-1-(benzyloxymethyl)propyl>-3-methyltetrahydropyran-2-yl>propan-1-ol

B

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water for 1h; Ambient temperature;A 100%
B n/a

Sodium; 6-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-hexanoate

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;100%
824-94-2

p-methoxybenzyl chloride

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation;100%
hydrotalcite In dimethyl sulfoxide at 140℃; for 1.5h; Kornblum reaction;96%
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 1.5h;95%
2746-25-0

p-Methoxybenzyl bromide

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; for 0.05h; Microwave irradiation;100%
With dihydrogen peroxide In ethanol for 4h; Reflux; Green chemistry;96%
With pyridine N-oxide for 0.0111111h; Irradiation; with microwave irradiation;92%
14202-31-4

4-methoxybenzaldehyde-1,1-diacetate

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With [NO(1+)*18-crown-6*H(NO3)2(1-)]; silica gel In dichloromethane at 20℃; for 0.0833333h;100%
With sulphated zirconia In acetonitrile at 60℃; for 0.3h; Microwave irradiation;100%
With iron(II) sulfate In dichloromethane for 0.166667h; Heating;99%
637-69-4

4-Methoxystyrene

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With sodium periodate; C31H29Br2N3Ru*CH2Cl2 In water; ethyl acetate; acetonitrile at 25℃; for 0.5h; Inert atmosphere; Schlenk technique;100%
With ruthenium trichloride; [bis(acetoxy)iodo]benzene In dichloromethane; water at 30℃; for 2.5h; Solvent;92.1%
With dihydrogen peroxide In acetonitrile at 65℃; for 6h;92%
120445-53-6

(E)-2-(4-methoxybenzylidene)hydrazine carboxamide

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With caro's acid; silica gel In dichloromethane for 0.583333h; Heating;100%
bismuth(III) chloride In tetrahydrofuran; water for 0.0833333h; catalysed cleavage; microwave irradiation;72%
123-08-0

4-hydroxy-benzaldehyde

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With sodium carbonate; dimethyl sulfate In water99.9%
With potassium carbonate In acetone
With halomethane In acetone
104-93-8

4-Methylanisole

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With oxygen In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 24h; Irradiation;99%
With cerium (IV) ammonium nitrate In methanol; benzene96.3%
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 2h; Irradiation; Green chemistry;96%
100-07-2

4-methoxy-benzoyl chloride

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; triphenylphosphine; indium(III) chloride In tetrahydrofuran at 0℃; for 2h; Reduction;99%
With pentacoordinated hydrogenosilane 191%
With hydrogenchloride; samarium; tributylphosphine In acetonitrile at -20℃; for 1h;90%
123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: p-methoxyl benzaldoxime With hexachlorodisilane; silica gel In toluene at 110℃; for 0.5h;
Stage #2: With water In toluene for 0.5h;
99%
With silica chromate; silica gel for 0.0333333h; microwave irradiation;98%
With 3-carboxypyridinium chlorochromate In dichloromethane for 0.75h; Heating;97%
123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With silica gel; periodic acid at 20℃; for 0.25h; Neat (no solvent);99%
With dimanganese decacarbonyl In toluene at 120℃; Sealed tube;93%
With aluminum oxide; potassium metaperiodate for 0.166667h; Microwave irradiation;92%
2393-23-9

4-methoxy-benzylamine

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccasefrom Trametes versicolor; oxygen In water at 30℃; for 24h; pH=4.5; Time; Enzymatic reaction;99%
With 2,6-dimethylpyridine; nitroxyl radical; sodium perchlorate In water; acetonitrile for 5h; Oxidation; Electrochemical reaction;98.2%
With cercosporin; oxygen In methanol at 20℃; Schlenk technique; Irradiation; Green chemistry; chemoselective reaction;97%
2403-50-1

2-(4-methoxyphenyl)-1,3-dioxolane

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With water at 80℃; for 0.25h; microwave irradiation;99%
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 1.5h; Heating;98%
With iron(III) chloride hexahydrate; acetaldehyde In dichloromethane at 20℃; for 0.25h;98%
174869-04-6

α-(2-cyanoethyl)-4,4'-dimethoxybenzoin

A

55234-56-5

4-(4-methoxy-phenyl)-4-oxo-butyronitrile

B

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With potassium cyanide In N,N-dimethyl-formamide at 80℃; for 1h;A 99%
B n/a

1-(4-Methoxy-phenyl)-1-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-2-phenyl-ethanol

A

53645-66-2

4-benzyl-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

B

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With potassium cyanide In N,N-dimethyl-formamide for 1h; Heating;A 99%
B n/a
105-13-5

4-Methoxybenzyl alcohol

A

2746-25-0

p-Methoxybenzyl bromide

B

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide In acetic acid for 10h; Ambient temperature;A 99%
B 1%
7465-86-3

4-methoxy-N,N-diethylbenzamide

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.25h;99%
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.5h; Product distribution / selectivity;99%
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.5h; Solvent; Inert atmosphere;99%
104-21-2

p-methoxybenzyl acetate

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With methanol; potassium permanganate In ethyl acetate at 25℃; for 24h;99%
Stage #1: p-methoxybenzyl acetate With NADPH; acetylesterase; Aryl alcohol oxidase; aryl alcohol dehydrogenase; water; oxygen at 37℃; for 0.0833333h; Enzymatic reaction; Borate buffer;
Stage #2: With 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one; horse radish peroxidase at 37℃; for 0.0666667h; Enzymatic reaction; Citric buffer;
Multi-step reaction with 2 steps
1: lipase B from Candida antarctica immobilized on Immobead 150 / aq. phosphate buffer / 0.33 h / 40 °C / pH 7.4
2: 9-azabicyclo<3.3.1>nonane-N-oxyl; copper(I) bromide; 1-methyl-1H-imidazole / water / 2 h / 20 °C
View Scheme
14429-02-8

benzyl-(4-methoxybenzyl)amine

A

100-52-7

benzaldehyde

B

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccasefrom Trametes versicolor; oxygen In water at 30℃; for 24h; pH=4.5; Enzymatic reaction;A n/a
B 99%
100-66-3

methoxybenzene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-formamide With pyridine; bis(trichloromethyl) carbonate In chloroform at 0 - 5℃; for 6h;
Stage #2: With aluminum (III) chloride at 20 - 30℃; for 0.7h;
Stage #3: methoxybenzene at 80 - 85℃; for 12h; Time; Temperature;
98.2%
With methanesulfonyl chloride at 20 - 100℃; for 1h;91.1%
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In acetonitrile at -5℃; for 1h;
Stage #2: methoxybenzene With copper(II) nitrate In acetonitrile at 20℃; for 12h; Vilsmeier-Haack Formylation;
Stage #3: With water In acetonitrile Kinetics; Mechanism; Catalytic behavior; Reagent/catalyst; Time; Solvent; Temperature; Vilsmeier-Haack Formylation; Heating;
67%
14629-56-2

trimethyl(4-methoxybenzyloxy)silane

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.166667h; Heating;98%
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate In acetonitrile for 0.1h; Reflux;96%
With Montmorillonite K10; ferric nitrate Oxidation; deprotection; Irradiation;95%
6712-20-5

2-(4-methoxyphenyl)-[1,3]dithiolane

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With silica gel; copper(II) nitrate In tetrachloromethane for 0.25h; Ambient temperature;98%
With silica gel In neat (no solvent) at 20℃; for 0.0333333h;98%
With ferric nitrate Ambient temperature;97%
23837-10-7

((4-methoxyphenyl)methylene)bis(phenylsulfane)

123-11-5

4-methoxy-benzaldehyde

Conditions
ConditionsYield
With bismuth(III) nitrate In benzene for 12h; Ambient temperature;98%
With thionyl chloride; dihydrogen peroxide In acetonitrile at 25℃; for 0.0166667h;95%
With β‐cyclodextrin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetone at 20℃; for 0.5h;89%
With sodium perborate In acetic acid at 25℃; for 1h;85%
With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 1h; Ambient temperature;78%
1076-38-6

4-hydroxy[1]benzopyran-2-one

123-11-5

4-methoxy-benzaldehyde

10172-75-5

3,3-(4'-methoxybenzylidene)bis(4-hydroxycoumarin)

Conditions
ConditionsYield
With 4-sulfophthalic acid In water at 80℃; for 0.416667h; Catalytic behavior; Green chemistry;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; for 16h;99%
With phosphotungstic acid In water at 80℃; for 0.383333h; domino Knoevenagel type condensation/Michael reaction;99%
118-93-4

o-hydroxyacetophenone

123-11-5

4-methoxy-benzaldehyde

3327-24-0

1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water Claisen-Schmidt Condensation;100%
Stage #1: o-hydroxyacetophenone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: 4-methoxy-benzaldehyde In ethanol; water
100%
With sodium hydroxide In ethanol at 20℃;95%
79-24-3

Nitroethane

123-11-5

4-methoxy-benzaldehyde

17354-63-1

4-(2-nitro-propenyl)-anisole

Conditions
ConditionsYield
With ammonium acetate at 110℃; for 72h;100%
With ammonium acetate Henry reaction; Reflux;94%
With ammonium acetate at 120℃; for 2h;93%
13329-40-3

4-Iodoacetophenone

123-11-5

4-methoxy-benzaldehyde

92855-02-2

(E)-1-(4-iodophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water at 20℃; for 4.25h; Cooling with ice;100%
With sodium hydroxide In methanol at 0 - 20℃; for 4h; Claisen-Schmidt condensation;91%
With SiO2-H3PO4 Aldol Condensation; Microwave irradiation;88%
139-65-1

4,4'-thiobisaniline

123-11-5

4-methoxy-benzaldehyde

3430-65-7

bis-[4-(4-methoxy-benzylidenamino)-phenyl]-sulfide

Conditions
ConditionsYield
With piperidine In ethanol100%
With ethanol; zinc(II) chloride
123-11-5

4-methoxy-benzaldehyde

126-81-8

dimedone

19419-25-1

9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione

Conditions
ConditionsYield
With poly[(2-acrylamido-2-methylpropane sulfonic acid)-co-(acrylic acid)-co-(vinyl functionalized halloysite clay)] In water at 20℃; for 3h;100%
With N-sulfonic acid poly(4-vinylpyridinium) chloride at 100℃; for 0.166667h;98%
With phospho sulphonic acid In neat (no solvent) at 110℃; for 0.5h; Green chemistry;98%
123-11-5

4-methoxy-benzaldehyde

104-94-9

4-methoxy-aniline

1749-08-2

N-(4-methoxy benzylidene)-4-methoxyaniline

Conditions
ConditionsYield
In ethanol for 1h; Sonication;100%
With magnesium sulfate In dichloromethane at 20℃; for 72h;99%
In ethyl 2-hydroxypropionate; water at 20℃; for 0.05h;93%
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    123-11-5

    p-Anisaldehyde

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    p-Anisaldehyde

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    p-Anisaldehyde Molecular weight: 136.15 Density: 1.1192 (25℃) CAS : 123-11-5; 50984-52-6 Melting point (℃): 2.5 Boiling point (℃): 249.5 Refractive index: 1.5710- 1.5740 (20℃) Flash point (℃): 121 Property: colorless or light yellow

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    123-11-5 p-Anisaldehyde

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Chemistry

IUPAC Name: 4-Methoxybenzaldehyde
Synonyms of p-Anisaldehyde (CAS NO.123-11-5): 4-Anisaldehyde ; 4-Methoxybenzaldehyde ; AI3-00223 ; Anisic aldehyde ; Aubepine ; Benzaldehyde, 4-methoxy- ; CCRIS 821 ; Caswell No. 051E ; Crategine ; EINECS 204-602-6 ; FEMA No. 2670 ; Formylanisole, p- ; HSDB 2641 ; NSC 5590 ; Obepin ; UNII-9PA5V6656V ; p-Anisic aldehyde ; p-Formylanisole ; p-Methoxybenzaldehyde ; p-Methoxybenzaldehyde (natural) ; Anisaldehyde
CAS NO: 123-11-5
Classification Code: Mutation data ; Natural Product ; Skin / Eye Irritant ;
Molecular Formula of p-Anisaldehyde (CAS NO.123-11-5): C8H8O2
Molecular Weight: 136.1479
Molecular Structure:

Melting Point: -1 °C
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.547
Molar Refractivity: 39.68 cm3
Molar Volume: 125.1 cm3
Surface Tension: 37.2 dyne/cm
Density of p-Anisaldehyde (CAS NO.123-11-5): 1.088 g/cm3
Flash Point: 108.9 °C
Enthalpy of Vaporization: 48.52 kJ/mol
Boiling Point: 248 °C at 760 mmHg
Vapour Pressure: 0.0249 mmHg at 25°C

Uses

  p-ANISALDEHYDE(123-11-5) is mainly used for the preparation of vanilla, spices, apricot, butter, cinnamon and chocolate, caramel, cherry, walnuts, raspberry, strawberry, mint flavor. It can also be used for daily Flavor and Flavors. The pharmaceutical industry for the manufacture of anti-microbial drugs hydroxyl ammonia benzyl penicillin, is the anti-histamine drug intermediates.

Production

 p-Anisaldehyde (CAS NO.123-11-5) is made by the oxidation of anethole (the chief constituent of anise, star anise, and fennel oils).
  CH3OC6H4CH=CHCH3 → CH3OC6H4CH=O
Anethole is obtained from the higher-boiling fractions of pine oil.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 1260mg/kg (1260mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
mouse LD50 oral 1859mg/kg (1859mg/kg) GASTROINTESTINAL: NECROTIC GHANGES

GASTROINTESTINAL: OTHER CHANGES

LIVER: FATTY LIVER DEGERATION
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 58(8), Pg. 20, 1993.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 12, Pg. 823, 1974.
rat LD50 oral 1510mg/kg (1510mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn,IrritantXi,ToxicT,FlammableF
Risk Statements: 22-36/37/38-39-23/24/25-11 
R22: Harmful if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R39: Danger of very serious irreversible effects. 
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed. 
R11: Highly flammable.
Safety Statements: 26-45-36/37-16-7 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37: Wear suitable protective clothing and gloves. 
S16: Keep away from sources of ignition. 
S7: Keep container tightly closed.
RIDADR: UN 3316 9/PG 2
WGK Germany: 1
RTECS: BZ2625000
F: 10-23
HazardClass: IRRITANT
HS Code: 29124900
Moderately toxic by ingestion. A skin irritant. Mutation data reported. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Specification

Precautions: Do not ingest. Do not breathe gas/fumes/vapor/spray. Keep away from heat. Keep away from sources of ignition. Avoid contact with skin and eyes. Empty containers pose a fire risk, evaporate the residue under a fume hood. Ground all equipment containing material. Wear suitable protective clothing. In case of insufficient ventilation, wear suitable respiratory equipment. If ingested, seek medical advice immediately and show the container or the label.
Storage: Keep container in a cool, well-ventilated area. Keep container tightly closed.