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| CAS No.: | 90-05-1 |
|---|---|
| Name: | Guaiacol |
| Article Data: | 608 |
| Molecular Structure: | |
|
|
|
| Formula: | C7H8O2 |
| Molecular Weight: | 124.139 |
| Synonyms: | Phenol,o-methoxy- (8CI);1-Hydroxy-2-methoxybenzene;2-Hydroxyanisole;2-Methoxyphenol;Anastil;Guaiastil;Methylcatechol;Phenol,2-methoxy-;O-Methyl catechol;Pyrocatechol monomethyl ether;Pyroguaiac acid;o-Guaiacol;o-Hydroxyanisole;o-Methoxyphenol;Guaiacol (JAN); |
| EINECS: | 201-964-7 |
| Density: | 1.109 g/cm3 |
| Melting Point: | 26-29 ºC(lit.) |
| Boiling Point: | 205 ºC at 760 mmHg |
| Flash Point: | 82.2 ºC |
| Solubility: | Slightly soluble |
| Appearance: | off-white crystals |
| Hazard Symbols: |
 Xn, T, Xi
|
| Risk Codes: | R22;R36/38 |
| Safety: | Human poison by ingestion. Experimental poison by intravenous route. Mildly toxic by skin contact and inhalation. Human systemic effects by ingestion: tremors and gastrointestinal changes. Human mutation data reported. An eye and severe skin irritant. Ingestion produces burning in the mouth and throat. Flammable when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. Protect from light. Used as an expectorant. When heated to decomposition it emits acrid smoke and irritating fumes. |
| PSA: | 29.46000 |
| LogP: | 1.40080 |
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2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
A
- 90-05-1
2-methoxy-phenol
B
- 100-06-1
1-(4-methoxyphenyl)ethanone
| Conditions | Yield |
|---|---|
| With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere; | A 99% B 99% |
| With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction; | A 95% B 72% |
| With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; Reagent/catalyst; Irradiation; chemoselective reaction; | A 89% B 88% |
| Conditions | Yield |
|---|---|
| With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique; | 95% |
| Stage #1: 4-iodoanisol With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In water; dimethyl sulfoxide at 20 - 100℃; Inert atmosphere; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; Inert atmosphere; | 94% |
| Stage #1: 4-iodoanisol With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 100℃; for 10h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; | 94% |
| Conditions | Yield |
|---|---|
| With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere; | 88% |
| Stage #1: 2-bromoanisole With copper(l) iodide; cesium hydroxide; 5-bromo-2-(1H-imidazol-2-yl)pyridine In water; dimethyl sulfoxide; tert-butyl alcohol at 120℃; for 36h; Inert atmosphere; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide; tert-butyl alcohol pH=1 - 2; Inert atmosphere; | 83% |
| With tert.-butylhydroperoxide; n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h; | 78% |
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 1h; | A 95% B 99% |
| With 5%-palladium/activated carbon; ammonium formate In water at 80℃; for 1h; | A n/a B 98% |
| With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; | A 89% B 86% |
| Conditions | Yield |
|---|---|
| With oxygen; copper(II) nitrate In acetonitrile at 120℃; under 4500.45 Torr; for 10h; | A n/a B 99% |
| With sodium hydroxide for 2h; Reagent/catalyst; Time; Milling; Green chemistry; | A 95 %Chromat. B 80 %Chromat. |
- 92409-23-9
1-(4-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
A
- 90-05-1
2-methoxy-phenol
| Conditions | Yield |
|---|---|
| With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; Irradiation; Flow reactor; chemoselective reaction; | A 94% B 93% |
| With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; | A 82% B 90% |
| With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 15h; Irradiation; chemoselective reaction; | A 88% B 85% |
| With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction; | A 56% B 34% |
| With formic acid; 10-phenyl-10H-phenothiazine; N-ethyl-N,N-diisopropylamine In acetone at 20℃; for 96h; Inert atmosphere; Irradiation; | A 28 mg B 42 mg |
- 10548-77-3
1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
A
- 104397-78-6
1-(3,4-dimethoxyphenyl)-3-hydroxypropan-1-one
B
- 90-05-1
2-methoxy-phenol
| Conditions | Yield |
|---|---|
| With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere; | A 98% B 97% |
| With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 48h; Irradiation; chemoselective reaction; | A 90% B 95% |
| With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; | A 90% B 80% |
| Conditions | Yield |
|---|---|
| With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 3h; Inert atmosphere; | 96% |
| With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere; | 96% |
| With sulfosuccinic acid functionalized mesoporous silica In ethanol at 100℃; |
- 106534-23-0
1-(4-Hydroxyphenyl)-2-(2-methoxyphenoxy)-1-ethanol
A
- 90-05-1
2-methoxy-phenol
B
- 99-93-4
4-Hydroxyacetophenone
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 4h; | A n/a B 97% |
| With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; | A 90% B 76% |
| With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry; | A 90% B 76% |
| With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere; |
- 7382-68-5
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol
A
- 90-05-1
2-methoxy-phenol
B
- 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 14h; | A n/a B 96% |
| With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; | A 86% B 82% |
| With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry; | A 86% B 82% |
| With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere; |
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Chemistry
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IUPAC Name: 2-Methoxyphenol
Molecular Formula: C7H8O2
Molecular Weight: 124.13 g/mol
SMILES: c1(c(cccc1)O)OC
InChI: InChI=1/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
EINECS: 201-964-7
Classification Code: Human Data; Mutation data; Skin / Eye Irritant
Product Categories: Pharmaceutical Intermediates; Aromatic Ethers; Aromatics Compounds; Antioxidant; Biochemistry; Aromatics
Melting Point: 26-29 °C(lit.)
Water Solubility: 17 g/L (15 °C)
FreezingPoint: 28 °C
Sensitive: Air Sensitive
Stability: Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents.
Index of Refraction: 1.534
Molar Refractivity: 34.81 cm3
Molar Volume: 111.8 cm3
Polarizability: 13.8×10-24 cm3
Surface Tension: 38.6 dyne/cm
Density: 1.109 g/cm3
Flash Point: 82.2 °C
Enthalpy of Vaporization: 45.92 kJ/mol
Boiling Point: 205 °C at 760 mmHg
Vapour Pressure of Guaiacol (CAS NO.90-05-1): 0.179 mmHg at 25 °C
Uses
Guaiacol is a precursor to various flavorants such as eugenol and vanillin. Its derivatives are used medicinally as an expectorant, antiseptic, and local anesthetic. It also can be used as a dye in chemical reactions as oxygen will turn guaiacol from colorless to brown.
Production
Guaiacol is produced industrially by methylation of catechol, using potash and dimethyl sulfate:
C6H4(OH)2 + (CH3O)2SO2 → C6H4(OH)(OCH3) + HO(CH3O)SO2
Toxicity Data With Reference
| 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. |
Safety Profile
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
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.