Product Features Uses Toxicity Production method Limited use
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Anisole

Product Features Uses Toxicity Production method Limited use
Product Name
Anisole
CAS No.
100-66-3
Chemical Name
Anisole
Synonyms
METHOXYBENZENE;ANISOL;MOB;METHYL PHENYL ETHER;Anizol;ANISLOE;ANISOLE;Amisale;FEMA 2097;7) ANISOLE
CBNumber
CB5100716
Molecular Formula
C7H8O
Formula Weight
108.14
MOL File
100-66-3.mol
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Anisole Property

Melting point:
-37 °C (lit.)
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)
refractive index 
n20/D 1.516(lit.)
FEMA 
2097 | ANISOLE
Flash point:
125 °F
storage temp. 
Store below +30°C.
solubility 
1.71g/l
form 
Liquid
color 
Clear colorless
Relative polarity
0.198
Odor
phenol, anise odor
Odor Type
phenolic
Odor Threshold
0.057ppm
explosive limit
0.34-6.3%(V)
Water Solubility 
1.6 g/L (20 ºC)
Merck 
14,669
JECFA Number
1241
BRN 
506892
Dielectric constant
4.3（20℃）
Stability:
Stable. Flammable. Incompatible with strong oxidizing agents.
InChIKey
RDOXTESZEPMUJZ-UHFFFAOYSA-N
LogP
2.62 at 30℃
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

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H226Flammable liquid and vapour

H336May cause drowsiness or dizziness

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W209708
Product name
Anisole
Purity
≥99%, FCC, FG
Packaging
1kg
Price
$67.7
Updated
2024/03/01
Sigma-Aldrich
Product number
W209708
Product name
Anisole
Purity
≥99%, FCC, FG
Packaging
10Kg
Price
$408
Updated
2024/03/01
Sigma-Aldrich
Product number
8.01452
Product name
Anisole
Purity
for synthesis
Packaging
100mL
Price
$38.9
Updated
2024/03/01
Sigma-Aldrich
Product number
96109
Product name
Anisole
Purity
analytical standard
Packaging
5ml
Price
$70.2
Updated
2024/03/01
Sigma-Aldrich
Product number
8.01452
Product name
Anisole
Purity
for synthesis
Packaging
500mL
Price
$56.4
Updated
2024/03/01
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Anisole Chemical Properties,Usage,Production

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.

Uses

1. Anisole is a solvent used in the synthesis of organic compounds and in large-scale applications such as the production of perfumes.
2. GB2760-1996 stipulates it as allowable usable spices in food. It is mainly used for the preparation of vanilla, fennel and beer flavor.
3. It is used for analyzing the reagents, solvents, and used for preparing perfumery and enteral pesticides.
4. Anisole has been used directly in the synthesis of the marine pyrrole alkaloids polycitone A and B and the nonylphenol isomer 4-(3',6'-dimethyl-3-heptyl)phenol.
5. It is used as solvents for recrystallization, fillers of thermostat, and used for measuring refractive index, as spices and organic synthesis intermediates.

Toxicity

Anisole has acute toxicity, LD50: 3700mg/kg (oral in rats); 2800mg/kg (oral in mice). Rabbit percutaneous: 500mg (24h), moderate stimulation. Anisole is also mutagenic, causing DNA inhibition, 25 μmol/L in human lymphocytes.

Production method

Anisole 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°C. And then heat to 40 °C, 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.

Limited use

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

Description

Anisole is a colorless liquid with a spicy-sweet smell. Anisole can be produced by all the aforementioned methods. It is an important intermediate in the synthesis of organic compounds, for example fragrances and pharmaceuticals. The compound is also used as a solvent and as a heat transfer medium.

Chemical Properties

Anisole is a colorless to yellowish liquid with a characteristic pleasant, anise-like, agreeable, aromatic, spicy-sweet odor. It is used in perfumery.

Occurrence

Anisole is a natural product 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

Anisole is widely used as a solvent for the synthesis of various organic compounds, anethole, nonylphenol isomer 4-(3',6'-dimethyl-3-heptyl)phenol, perfumes, insect pheromones and pharmaceuticals. It finds application in the preparation of inorganic complexes and materials such as tin-core/tin oxide nanoparticles.

Application

Anisole is an organic compound with the chemical formula C7H8O with a pleasant anise-like aroma, used in organic synthesis and also as a solvent, fragrance and insect repellent. For organic synthesis, it is also used as solvent, fragrance and insect repellent.

Preparation

Anisole is synthesized 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.

Definition

ChEBI: Anisole is a monomethoxybenzene that is benzene substituted by a methoxy group. It has a role as a plant metabolite.

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.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

storage

Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet away from ignition sources and corrosive and reactive materials.Prior to working with this chemical you should be trainedon its proper handling and storage. Before enteringconfined space where anisole may be present, check tomake sure that an explosive concentration does not exist.Store in tightly closed containers in a cool, well-ventilated,fireproof area. Metal containers involving the transfer ofthis chemical should be grounded and bonded. Wherepossible, automatically pump liquid from drums or otherstorage containers to process containers. Drums must beequipped with self-closing valves, pressure vacuum bungs,and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers ofthis chemical. Sources of ignition, such as smoking andopen flames, are prohibited where this chemical is used,handled, or stored in a manner that could create a potentialfire or explosion hazard.

Shipping

Anisole requires a shipping label of“FLAMMABLE LIQUID.” Anisole falls in Hazard Class 3,Packing Group III.[19, 20]

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.

Anisole Preparation Products And Raw materials

Raw materials

Dimethyl ester Phenol Sodium hydroxide Dimethyl ether Dimethyl sulfate

Preparation Products

cleaner LS 4,5-Imidazoledicarboxylic acid 6-METHOXY-1-NAPHTHOIC ACID 4-chloro-4'-methoxybenzophenone 6-Hydroxy-1-naphthoic acid PYRIDIN-2-YLMETHYL-HYDRAZINE Fast Scarlet Base LG 3-(4-METHOXYBENZOYL)PROPIONIC ACID Diaveridine 1-Methyl-1H-imidazole-4-carboxylic acid METHOXYCHLOR Imidazole-4-methanol 4,5-DICARBOXY-1-METHYL-1H-IMIDAZOLE Cefcapene pivoxil PYRIDIN-3-YLMETHYL-HYDRAZINE Methyldopa 4,5-Dicyanoimidazole Verapamil 1H-Imidazole-4-carboxylic acid trisodium [5-acetamido-4-hydroxy-3-[[2-hydroxy-5-[[2-(sulphooxy)ethyl]sulphonyl]phenyl]azo]naphthalene-2,7-disulphonato(5-)]cuprate(3-) 1-CHLOROMETHYL-2,3,4-TRIMETHOXYBENZENE 1,5-Diazabicyclo[4.3.0]non-5-ene Anisyl acetate 2-Bromoanisole PYRIDIN-4-YLMETHYL-HYDRAZINE Ceftibuten 2,4,6-TRIBROMOANISOLE Cefdinir Lawesson's Reagent Anoxomer ALLURA RED AC Fenofibrate 4-Fluoro-4'-methoxybenzophenone 4-Chloro-4'-hydroxybenzophenone Disperse Blue BGL 1-METHYL-1H-IMIDAZOLE-5-CARBOXYLIC ACID Bunazosin hydrochloride Alacepril CHLOROTRIANISENE 1-METHYL-1H-IMIDAZOLE-4,5-DICARBONITRILE
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View Lastest Price from Anisole manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Anisole 100-66-3
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100 mt
Release date
2024-11-01
Qingdao RENAS Polymer Material Co., Ltd.
Product
Anisole 100-66-3
Price
US $0.00/kg
Min. Order
20kg
Purity
99%
Supply Ability
20 tons
Release date
2024-09-03
Hebei Yanxi Chemical Co., Ltd.
Product
Anisole 100-66-3
Price
US $30.00-10.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
30 tons
Release date
2023-10-25

100-66-3, AnisoleRelated Search:

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