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Basic Information

Molecular Structure:
CAS No.:	123-11-5
Name:	p-Anisaldehyde
Article Data:	1962

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:	Xn
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With [NO(1+)18-crown-6H(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%

Downstream Products

836-41-9

106-51-4

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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: Harmful Xn, Irritant Xi, Toxic T, Flammable F
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.