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Anisole

Basic information Product Features Toxicity Limited use Chemical properties Uses Production method Category Toxicity grading Acute toxicity Stimulus data Flammability hazard characteristics Storage feature Extinguishing agents Occupational standards Safety Related Supplier

Anisole Basic information

Product Name:
Anisole
CAS:
100-66-3
MF:
C7H8O
MW:
108.14
EINECS:
202-876-1
Mol File:
100-66-3.mol
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Anisole Chemical Properties

Melting point:
-37 °C
Boiling point:
154 °C(lit.)
Density 
0.995 g/mL at 25 °C(lit.)
vapor density 
3.7 (vs air)
vapor pressure 
10 mm Hg ( 42.2 °C)
FEMA 
2097 | ANISOLE
refractive index 
n20/D 1.516(lit.)
Flash point:
125 °F
storage temp. 
Store at RT.
solubility 
1.71g/l
form 
Liquid
color 
Clear colorless
Relative polarity
0.198
Odor
phenol, anise odor
Odor Threshold
0.057ppm
explosive limit
0.34-6.3%(V)
Water Solubility 
1.6 g/L (20 ºC)
JECFA Number
1241
Merck 
14,669
BRN 
506892
Stability:
Stable. Flammable. Incompatible with strong oxidizing agents.
InChIKey
RDOXTESZEPMUJZ-UHFFFAOYSA-N
CAS DataBase Reference
100-66-3(CAS DataBase Reference)
NIST Chemistry Reference
Benzene, methoxy-(100-66-3)
EPA Substance Registry System
Anisole (100-66-3)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
10-38-20-36/37
Safety Statements 
37/39-26-16-24/25
RIDADR 
UN 2222 3/PG 3
WGK Germany 
2
RTECS 
BZ8050000
Autoignition Temperature
887 °F
TSCA 
Yes
HazardClass 
3
PackingGroup 
III
HS Code 
29093090
Hazardous Substances Data
100-66-3(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 3700 mg/kg (Taylor)

MSDS

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Anisole Usage And Synthesis

Product Features

Anisole, also known as anise ether, methoxybenzene methyl phenyl ether, is a colorless liquid with an odor of anise, sweet, naturally present in the tarragon oil, insoluble in water, soluble in alcohol, ether, acetone, soluble in benzene. It irritates the eyes and mucous membranes. It is obtained originally from distilled methyl salicylate or methoxybenzoate, is now mainly produced through the reaction of methylating agent of dimethyl sulfate with phenol in alkaline aqueous solution. Anisole is prone to start Electrophilic substitution reaction in aromatic nucleus, and condensed with formaldehyde to produce viscous oil or resin material, reacts with phosphorus trichloride to produce chlorine anisole and a small amount of o-chloro product, reacts with thionyl chloride to produce 2,4,6-trichloroanisole. In addition, anisole is heated to react with hydrobromic or hydroiodic, carbon-oxygen bond cleaves, phenol and halogenated methane is produced, which is an important method for determining methoxy group of benzene ring.
The above information is edited by the chemicalbook of Yan Yanyong.

Toxicity

GRAS (FEMA).
LD50 3700 mg/kg (rat, oral).

Limited use

FEMA (mg/kg): Soft drinks 9.0, cold 16, confectionery51, bakery 34.
limited in moderation (FDA§172.515,2000).

Chemical properties

It is a colorless liquid, with an aromatic odor, insoluble in water, soluble in alcohol, ether.

Uses

1. GB2760-1996 stipulates it as allowable usable spices in food. It is mainly used for the preparation of vanilla, fennel and beer flavor.
2. It is used for analyzing the reagents, solvents, and used for preparing perfumery and enteral pesticides.
3. It is used for the production of perfumes, dyes, pharmaceuticals, pesticides, also used as a solvent.
4. It is used in organic synthesis, also used as solvents, perfume and insect repellent.
5. It is used as solvents for recrystallization, fillers of thermostat, and used for measuring refractive index, as spices and organic synthesis intermediates.

Production method

It is produced through the reaction of methylating agent of dimethyl sulfate with phenol in alkaline aqueous solution. Phenol was mixed with sodium hydroxide solution, dimethyl sulfate was slowly added at below 10 ℃. And then heat to 40 ℃, reflux for 18h, then stand for separation of the oil and dried with anhydrous calcium chloride, vacuum distillation to obtain anisole.
It is derived by introducing the methyl chloride into the sodium phenol of liquid ammonia to react.
It is generated from heating phenol and methanol.
It is obtained from the reaction of phenol with dimethyl sulfate in the presence of sodium hydroxide.

Category

Flammable liquid

Toxicity grading

Moderate toxicity

Acute toxicity

Oral-rat LD50: 3700 mg/kg. Oral-Mouse LD50: 2800 mg/kg

Stimulus data

Skin-rabbit 500 mg/24 hours moderate

Flammability hazard characteristics

In case of fire, high temperature, strong oxidants, it is combustible. Burning discharges irritative smoke.

Storage feature

complete package, with care, warehouse ventilation, away from open flame, heat, and stored separately from oxidants

Extinguishing agents

Foam, carbon dioxide, dry sandy, soil

Occupational standards

STEL 10 mg/m3

Chemical Properties

Clear straw colored liquid

Chemical Properties

Anisole is a colorless to yellowish liquid with an agreeable, aromatic, spicy-sweet odor.

Chemical Properties

Anisole has a characteristic pleasant, anise-like, agreeable aromatic odor.

Occurrence

Reported found in apple juice and in the oil of Artemisia dracunculus var. turkestanica; also reported found in butter, Camembert cheese, roasted beef, olive (Olea europae), Malay apple, Jerusalem artichoke (Helianthus tuberosus), Bourbon vanilla, truffles, crab and sopadilla fruit (Achras sapota L.).

Uses

A biochemical for proteomics research.

Uses

In perfumery, in organic syntheses.

Definition

ChEBI: A monomethoxybenzene that is benzene substituted by a methoxy group.

Preparation

By reacting phenol and dimethyl sulfate in the presence of aqueous NaOH; by passing methyl chloride into a suspension of sodium phenolate in liquid ammonia

Aroma threshold values

Detection: 50 ppb

Synthesis Reference(s)

Canadian Journal of Chemistry, 40, p. 441, 1962 DOI: 10.1139/v62-070
Journal of the American Chemical Society, 88, p. 4271, 1966 DOI: 10.1021/ja00970a037
Organic Syntheses, Coll. Vol. 1, p. 58, 1941

General Description

A clear straw-colored liquid with an aromatic odor. Insoluble in water and the same density as water. Vapors heavier than air. Flash point 125°F. Boiling point 307°F. Moderately toxic by ingestion. A skin irritant. Used to make perfumes, flavorings and as a solvent.

Air & Water Reactions

Flammable. Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Insoluble in water

Reactivity Profile

Ethers, such as Anisole can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Safety Profile

Moderately toxic by ingestion and inhalation. A skin irritant. A flammable liquid. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid fumes.

Potential Exposure

Anisole is used as a solvent; a flavoring, vermicide, making perfumes; and in organic synthesis.

Shipping

UN2222 Anisole, Hazard Class: 3; Labels: 3- Flammable liquid.

Purification Methods

Shake anisole with half its volume of 2M NaOH, and the emulsion is allowed to separate. Repeat three times, then wash twice with water, dry over CaCl2, filter, dry over sodium wire and finally distil it from fresh sodium under N2 using a Dean-Stark trap (samples in the trap being rejected until free from turbidity) [Caldin et al. J Chem Soc, Faraday Trans 1 72 1856 1976]. Alternatively dry it with CaSO4 or CaCl2, or by refluxing with sodium or BaO with crystalline FeSO4 or by passage through an alumina column. Traces of phenols are removed by prior shaking with 2M NaOH, followed by washing with water. It has been be purified by zone refining. [Beilstein 6 IV 548.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

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AnisoleSupplierMore

HUAIAN DEPON CHEMICAL CO., LTD. Gold
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Shanghai Aladdin Bio-Chem Technology Co.,LTD Gold
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Ningbo Bingxing Chemical Co., Ltd. Gold
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13738829766
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Shanghai Guoyuan Chemical Co., Ltd. Gold
Tel:
13913095008 0512-55170668-
Email:
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Basic information Product Features Toxicity Limited use Chemical properties Uses Production method Category Toxicity grading Acute toxicity Stimulus data Flammability hazard characteristics Storage feature Extinguishing agents Occupational standards Safety Related Supplier