Guaiacol

Iupac Name：2-methoxyphenol

CAS No.: 90-05-1

Molecular Weight：124.139

Modify Date.: 2022-11-11 20:15

Introduction: Guaiacol has a characteristic sweet odor. It is slightly phenolic.Guaiacol is obtained from hardwood tar or synthetically from onitrophenolvia o-anisidine. View more+

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1. Names and Identifiers

1.1 Name: Guaiacol
1.2 Synonyms: 1H-Indole, 6-fluoro-2,3-dihydro- 2,3-dihydro-6-fluoro-1H-indole 2,3-dihydro-6-fluoroindole 2-Hydroxyanisole 2-Methoxyphenol 2-Methoxy-phenol 5-fluoro-2,3-dihydro-1h-isoindole 6-Fluor-indolin 6-fluoro-2,3-dihydro-indole 6-Fluoroindoline CATECHOL MONOMETHYL ETHER Catechol, Methyl EINECS 201-964-7 GUAJACOL Gulaiacol Indoline, 6-fluoro- Indoline,6-fluoro methoxyphenol Methylcatechol MFCD00002185 O-HYDROXYANISOLE o-methoxy catechol O-METHOXYPHENOL o-methoxy-Phenol O-Methyl catechol O-METHYLCATECHOL ORTHO-METHOXYPHENOL Phenol, 2-methoxy- PYROCATECHOL MONOMETHYL ETHER PYROGUAIAC ACID

1.3 CAS No.: 90-05-1

1.4 CID: 460

1.5 EINECS(EC#): 201-964-7; 232-287-5; 232-419-1

1.6 Molecular Formula: C7H8O2 (isomer)

1.7 Inchi: InChI=1S/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3

1.8 InChkey: LHGVFZTZFXWLCP-UHFFFAOYSA-N

1.9 Canonical Smiles: COC1=CC=CC=C1O

1.10 Isomers Smiles: COC1=CC=CC=C1O

2. Properties

2.1 Density: 1.09 g/mL at 20 °C

2.1 Melting point: -20

2.1 Boiling point: less than -4° F (NTP, 1992)

2.1 Refractive index: 1.534

2.1 Flash Point: 165° F (NTP, 1992)

2.2 PSA: 29.46000

2.2 logP: 1.40080

2.2 Solubility: H2O: insoluble

2.3 VaporDensity: 4.27 (vs air)

2.4 Appearance: off-white crystals

2.5 Storage: Air Sensitive. Light Sensitive. Ambient temperatures.

2.6 Chemical Properties: It appears as white or slightly yellow crystals or colorless to pale yellow transparent oily liquid. It has a special aromatic smell. It is slightly soluble in water and benzene. It is easily soluble in glycerol. It is miscible with ethanol, ether, chloroform, oil and glacier acetic acid.

2.7 Color/Form: Faintly yellowish, limpid, oily liquid or yellow crystals
White or slightly yellow crystalline mass or colorless to yellowish, very refractive liquid
Hexagonal prisms

2.8 Odor Threshold: 0.0074ppm

2.9 PH: 5.4 (10g/l, H2O, 20℃)

2.10 pKa: 9.98(at 25℃)

2.11 Water Solubility: 17 g/L (15 oC)

2.12 Spectral Properties: Index of refraction: 1.5429 at 20 deg C/D
MAX ABSORPTION (ALCOHOL): 274 NM (LOG E= 3.41)
IR: 3218 (Coblentz Society Spectral Collection)
UV: 36 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 3149 (Sadtler Research Laboratories Spectral Collection)
MASS: 20585 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 1081(Atlas of Mass Spectral Data, John Wiley & Sons, New York)

2.13 Stability: Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents.

2.14 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.

3.2 Purification Methods: Crystallise guaiacol from *benzene/pet ether or distil it in a vacuum. [Beilstein 6 H 768, 6 IV 5563.] Guaiacol Preparation Products And Raw materials Raw materials

3.3 Usage: Guaiacol is a precursor of vanillin and santalidol (a synthetic sandal-wood fragrance). it is obtained from wood tar by the destructive distillation of hardwood, by the distillation of the phenol fraction of coal tar, or through the use of o-dichlorobenzene. it is processed to yield vanillin.

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn,T,Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R23/24/25

4.1 Safety Statements: Confirmed carcinogen. When heated to decomposition it emits acrid smoke and irritating fumes.

4.1 Packing Group: II

4.1 Octanol/Water Partition Coefficient: log Kow = 1.32

4.2 Fire Hazard: Guaiacol is combustible.

4.3 Other Preventative Measures: SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Engineering controls such as exhaust ventilation are recommended.

4.4 Hazard Class: 6.1(b)

4.4 Hazard Declaration: H302-H315-H319

4.4 Cleanup Methods: Wear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing vapor or dust. Ventilate area and wash spill site. Place spillage in appropriately labelled container for disposal.

4.5 DisposalMethods: SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

4.6 RIDADR: 30kgs

4.6 Fire Fighting Procedures: As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
Water spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials.

4.7 FirePotential: This material is combustible when exposed to heat or flame.

4.8 Caution Statement: P280-P301 + P312 + P330-P305 + P351 + P338-P337 + P313

4.8 Formulations/Preparations: Oral solution: Codeine BP: 7.0 mg/5 mL and Guaiacol (1949) BPC /Boots Company plc/ 75.0 mg/5 mL, Pulmo Bailly (DDD Limited, United Kingdom)

4.9 WGK Germany: 1

4.9 RTECS: SL7525000

4.9 Protective Equipment and Clothing: Gloves: Chemically compatible. Eye protection: Safety goggles or glasses. Protective clothing: Protect exposed skin.
Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. If material is in solid form, the use of an approved dust mask is recommended.

4.10 Skin, Eye, and Respiratory Irritations: Eye, skin, gastrointestinal, and/or respiratory tract irritation ... .

4.11 Safety: Hazard Codes:?Xn,T,Xi
Risk Statements: 22-36/38?
R22:Harmful if swallowed.?
R36/38:Irritating to eyes and skin.
Safety Statements: 26?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 2810
WGK Germany: 1
RTECS: SL7525000
Hazard Note: Toxic/Irritant
HazardClass: 6.1(b)
PackingGroup of Guaiacol (CAS NO.90-05-1): II

4.12 Sensitive: Air Sensitive

4.13 Specification: ?Guaiacol (CAS NO.90-05-1), its Synonyms are o-Methoxyphenol ; 1-Hydroxy-2-methoxybenzene ; 2-Hydroxyanisole ; 2-Methoxyphenol ; Guaiastil ; Guaicol ; Guaicolina ; Guajacol ; Phenol, 2-methoxy- ; Phenol, o-methoxy- ; Propenylguaiacol ; Pyrocatechol methyl ester ; Pyrocatechol monomethyl ether ; Pyroguaiac acid . It is colorless to amber crystals or liquid.

4.14 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	oral	1500mg/kg (1500mg/kg)	?	Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982.
guinea pig	LDLo	subcutaneous	900mg/kg (900mg/kg)	?	Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982.
human	LDLo	oral	43mg/kg (43mg/kg)	BEHAVIORAL: TREMOR GASTROINTESTINAL: OTHER CHANGES	"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 295, 1969.
mouse	LC50	inhalation	7570mg/m3 (7570mg/m3)	?	Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982.
mouse	LD50	intravenous	170mg/kg (170mg/kg)	?	Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982.
mouse	LD50	oral	621mg/kg (621mg/kg)	?	Drugs of the Future. Vol. 5, Pg. 539, 1980.
pigeon	LDLo	subcutaneous	400mg/kg (400mg/kg)	?	Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982.
rabbit	LD50	skin	4600mg/kg (4600mg/kg)	?	Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982.
rabbit	LDLo	intravenous	3700ug/kg (3.7mg/kg)	?	Journal of Agricultural and Food Chemistry. Vol. 17, Pg. 497, 1969.
rabbit	LDLo	oral	2gm/kg (2000mg/kg)	?	Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982.
rabbit	LDLo	subcutaneous	1250mg/kg (1250mg/kg)	?	Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982.
rat	LD50	oral	520mg/kg (520mg/kg)	BEHAVIORAL: GENERAL ANESTHETIC	Folia Medica Cracoviensia. Vol. 32, Pg. 309, 1991.
rat	LDLo	subcutaneous	900mg/kg (900mg/kg)	?	Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : CCl4 solution

IR : liquid film

Raman : 4880 A,100M,liquid

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

90-05-1Total: 93 Synthesis Route

91-16-7 263 Suppliers

90-05-1 332 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 62, # 12 p. 4097 - 4104
Yield: ~97%

91-16-7 263 Suppliers

120-80-9 163 Suppliers

90-05-1 332 Suppliers

Literatures:
Australian Journal of Chemistry, , vol. 38, # 5 p. 777 - 792
Yield: ~8%

135-02-4 162 Suppliers

90-05-1 332 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 49, # 24 p. 4740 - 4741
Yield: ~95%

View all

8. Precursor and Product

precursor:

100-66-3

5720-06-9

121-33-5

1835-09-2

1847-84-3

1847-92-3

274-09-9

1655-70-5

7382-59-4

1774-10-3

91-16-7

529-28-2

578-57-4

486-29-3

135-02-4

835-79-0

View all

product :

4542-41-0

1125-74-2

617-05-0

881-68-5

1655-71-6

120-80-9

1655-70-5

2880-58-2

2570-43-6

877-22-5

7368-78-7

87-16-1

563-03-1

645-56-7

931-17-9

2539-21-1

4097-63-6

2772-46-5

531-37-3

934-00-9

501-19-9

766-51-8

5922-56-5

621-59-0

7309-51-5

View all

9. Other Information

9.0 Merck: 14,4553

9.1 BRN: 508112

9.2 Chemical properties: It appears as white or slightly yellow crystals or colorless to pale yellow transparent oily liquid. It has a special aromatic smell. It is slightly soluble in water and benzene. It is easily soluble in glycerol. It is miscible with ethanol, ether, chloroform, oil and glacier acetic acid.

9.3 Application: Used for pharmaceuticals, dyes and spices intermediates
Mainly used for the preparation of coffee, vanilla, fumigation and tobacco flavor.
Used for the synthesis of dyes, also used as analytical reagents
In medicine, it can be used for the manufacture of calcium guaiacol sulfonate; in the spice industry, it is used the manufacture of vanillin and artificial musk; Used for test copper, hydrocyanic acid and nitrite

9.4 Preparative methods: It can be obtained by diazotization and hydrolysis of anthranium anisole.
Obtained from fractionated of wood oil.
In the nature of guaiacol is presented in the guaiacum or pine oil. In the creosote oil obtained from wood dry distillation, guaiacol is the major ingredient. This product could be obtained through fractional distillation of creosote oil. Japan Osaka Refining Company takes o-nitrochlorobenzene as raw material, first synthesizes o-nitroanisole, and then reduces it to o-anisidine, and finally obtains the goods. China's production method is roughly the same. Ingredient consumption quota: 1250 kg / t of amino-containing anisole, 1500 kg / t of sulfuric acid (93%), 700 kg / t of sodium nitrite and 400 kg / t of copper sulfate.

9.5 Toxicity: LD50:900 mg / kg (rat, subcutaneous).
LD50: 3.7 mg / kg (rabbit, intravenously).
Oral administration of large amount can stimulate the esophagus and stomach, resulting in heart failure, collapse and death.

9.6 Description: Guaiacol has a characteristic sweet odor. It is slightly phenolic. Guaiacol is obtained from hardwood tar or synthetically from onitrophenol via o-anisidine.

9.7 Chemical Properties: Guaiacol has a characteristic sweet odor. It is slightly phenolic.

9.8 Chemical Properties: Light Yellow Oil

9.9 Occurrence: Detected in the distillation product from guaiac resin; guaiacol is found in castoreum oil, in the essential oil from fowers of Pandanus odoratissimus L , in the distillation waters of orange leaves, in the essential oil of Ruta Montana L and in the essential oil of tobacco leaves Also reported found in lemon peel oil, bog blueberry, asparagus, cabbage, celery, onion, chive, tomato, peppermint oil, rye bread, Parmesan cheese, butter, smoked fsh, meats, barley, dried bonito, malt, hardwood smoke, cognac, beer, brandy, rum, whiskies, sherry, grape wines, cocoa, coffee, tea, peanuts, popcorn, soybeans, avocado, beans, mushroom, sesame seed, mango, tamarind, rice dill, licorice, corn oil, cuttlefsh and other sources

9.10 Uses: Guaiacol is a precursor of vanillin and santalidol (a synthetic sandal- wood fragrance). it is obtained from wood tar by the destructive distillation of hardwood, by the distillation of the phenol fraction of coal tar, or through the use of o-dichlorobenzene. it is processed to yield vanillin.

9.11 Uses: Synthetic flavors, medicine (expectorant).

9.12 Uses: A phenolic natural product and reducing co-substrate for COX reactions.

9.13 Definition: ChEBI: A monomethoxybenzene that consists of phenol with a methoxy substituent at the ortho position.

9.14 Aroma threshold values: Detection: 3 to 31 ppb; aroma characteristics at 1.0%: phenolic, smoky, spicy, medicinal, vanilla, savory meaty, woody with a bourbon whiskey casky nuance.

9.15 Taste threshold values: Taste characteristics at 2.0 ppm: woody, phenolic, bacon, savory, smoky and medicinal.

9.16 General Description: Colorless to amber crystals or liquid. Density (of solid) 1.129 g / cm3. Solidifies at 28°C (82.4°F), but may remain liquid for a long time even at a much lower temperature. Slightly water soluble . Soluble in aqueous sodium hydroxide. Used medicinally as an expectorant. Used, because of its anti-oxidant properties, as an anti-skinning agent for paints.

9.17 Air & Water Reactions: Sensitive to air and light (darkens). Slightly water soluble.

9.18 Reactivity Profile: Guaiacol may react with oxidizing materials. Guaiacol forms salts readily with bases.

9.19 Hazard: Toxic by ingestion and skin absorption.

9.20 Fire Hazard: Guaiacol is combustible.

9.21 Biochem/physiol Actions: Guaiacol, along with 2,4,6-trichloroanisole, is responsible for cork taint in wine. A method has been developed for extraction and quantitation of the two compounds.

9.22 Chemical Synthesis: Obtained from hardwood tar or synthetically from o-nitrophenol via o-anisidine.

9.23 Purification Methods: Crystallise guaiacol from *benzene/pet ether or distil it in a vacuum. [Beilstein 6 H 768, 6 IV 5563.]

9.24 Usage: 2-Methoxyphenol acts as an expectorant. It is used as an anti-oxidant as well as an anti-skinning agent for paints. It serves as a precursor to flavorants such as eugenol and vanillin. Further, it is used as an intermediate in the chemical synthesis of active pharmaceuticals, flavoring and perfumery products. In addition to this, it is also used as an indicator in chemical reactions that produce oxygen.

10. Computational chemical data

Molecular Weight: 124.139g/mol
Molecular Formula: C₇H₈O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 124.052429494
Monoisotopic Mass: 124.052429494
Complexity: 83
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 29.5
Heavy Atom Count: 9
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBgMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAACASAkAIyBoAABgCAACBCAAACCAAgIAAIiAAGiIgNJiKGMRqAcCMkwBELuAeAQAAAAAAAAAAAQAAAAAAAAACAAAAAAAAAAA==

11. Question & Answer

The uses of Guaiacol Jan 21 2021
Guaiacol is a naturally-occurring organic compound with the formula C 6 H 4 (OH)(OCH 3 ), first isolated by Otto Unverdorben in 1826. Although it is biosynthesized by a variety of organisms,this yellowish aromatic oil is usually derived from guaiacum or wood creosote. Samples darken upon exposure t...

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