4812-20-8

Basic information

• Product Name: 2-Isopropoxyphenol
• Synonyms: 2-(1-methylethoxy)-pheno;Phenol, 2-(1-methylethoxy)-;Phenol, 2-isopropoxy;propoxurphenol;o-Isopropoxyphenol;2-ISOPROPOXYPHENOL;2-(1-methylethoxy)phenol;1-Hydroxy-2-isopropoxybenzene
• CAS NO: 4812-20-8
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• EINECS: 225-379-1
• Product Categories: Aromatic Phenols;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 4812-20-8.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 100-102 °C11 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: Clear light yellow to light red-brown/Liquid
• Density: 1.03 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0798mmHg at 25°C
• Refractive Index: n20/D 1.514(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 9.99±0.35(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1937063
• CAS DataBase Reference: 2-Isopropoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropoxyphenol(4812-20-8)
• EPA Substance Registry System: 2-Isopropoxyphenol(4812-20-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4812-20-8(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow to light red-brown liquid

Uses

2-Isopropoxyphenol was used as a target chemical in developing a method to measure the urinary phenolic metabolites of pesticides.

General Description

2-Isopropoxyphenol is a metabolite of propoxur.

InChI:InChI=1/C9H12O2/c1-7(2)11-9-6-4-3-5-8(9)10/h3-7,10H,1-2H3

Synthetic route

2,2-dimethyl-1,3-benzodioxole (14005-14-2) → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
With aluminium trichloride; sulfuric acid	88%
With sulfuric acid; diisobutylaluminium hydride In methanol; water; toluene	72%

benzene-1,2-diol (120-80-9) + isopropyl bromide (75-26-3) → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
With potassium carbonate In acetone for 24h; Williamson synthesis; Reflux;	88%
With potassium hydroxide In dimethyl sulfoxide for 0.5h;	53%
With potassium hydroxide In dimethyl sulfoxide at 18℃; for 2h;

2-isopropoxybenzoic acid (63635-26-7) + isopropyl bromide (75-26-3) → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
With potassium hydroxide In methanol for 21h; Ambient temperature;	78.5%

o-methoxyphenyl i-propyl ether (2539-21-1) → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
With sodium In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 2h;	78%
With sodium In N,N,N,N,N,N-hexamethylphosphoric triamide at 100℃; for 2h; Mechanism;	78%
With ammonia; sodium

benzene-1,2-diol (120-80-9) + isopropyl bromide (75-26-3) → 2-Isopropoxyphenol (4812-20-8) + Brenzcatechindi-isopropylether (1698-98-2)

Conditions	Yield
With sodium In methanol for 3h; Condensation; Heating;	A 63% B 16%

(2-isopropoxybenzyl)trimethylsilane → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
With sodium persulfate; oxygen In acetonitrile at 55℃; for 9h;	56%

2,2-dimethyl-1,3-benzodioxole (14005-14-2) → 2-Isopropoxyphenol (4812-20-8) + benzene-1,2-diol (120-80-9)

Conditions	Yield
With sodium di(ethyl)amine In N,N,N,N,N,N-hexamethylphosphoric triamide; benzene for 12h; Product distribution; Heating; other metal amide, other reagent-substrate ratio;	A 48% B 30%
With sodium di(ethyl)amine In N,N,N,N,N,N-hexamethylphosphoric triamide; benzene for 12h; Heating;	A 48% B 30%

o-methoxyphenyl i-propyl ether (2539-21-1) + ammonia (7664-41-7) + sodium → 2-Isopropoxyphenol (4812-20-8)

Propoxur (114-26-1) → carbon dioxide (124-38-9) + 2-Isopropoxyphenol (4812-20-8) + methylamine (74-89-5)

Conditions	Yield
With borate buffer; cetyltrimethylammonim bromide In water at 100℃; for 0.00833333h; pH=9.0; Product distribution; Further Variations:; Temperatures; Decomposition;

Propoxur (114-26-1) → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
With sodium hydroxide at 20℃; for 0.0833333h;

salicylaldehyde (90-02-8) + hydrochloride of 2-nitro-4-methyl-phenylhydrazine → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / K2CO3 / dimethylformamide / 48 h / Ambient temperature 2: 6.30 g / selenium dioxide, H2O2 / CH2Cl2 / 72 h / Ambient temperature 3: 78.5 percent / KOH / methanol / 21 h / Ambient temperature View Scheme

2-isopropoxybenzaldehyde (22921-58-0) → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 6.30 g / selenium dioxide, H2O2 / CH2Cl2 / 72 h / Ambient temperature 2: 78.5 percent / KOH / methanol / 21 h / Ambient temperature View Scheme

1,2-dimethoxybenzene (91-16-7) → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / Na / hexamethylphosphoric acid triamide / 100 °C 2: 78 percent / Na / hexamethylphosphoric acid triamide / 2 h / 100 °C View Scheme

triethylsilane (617-86-7) + 2,2-dimethyl-1,3-benzodioxole (14005-14-2) → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
With trifluoroacetic acid

2,2-dimethyl-1,3-benzodioxole (14005-14-2) + sodium bis(2-methoxyethoxy)aluminum dihydride → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
With aluminium trichloride In toluene

2,2-dimethyl-1,3-benzodioxole (14005-14-2) + sodium diethyl aluminum hydride → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
With aluminium trichloride; sulfuric acid In methanol; water; toluene

1-(bromomethyl)-2-(propan-2-yloxy)benzene → 2-Isopropoxyphenol (4812-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium; iodine / tetrahydrofuran / 0.25 h / Inert atmosphere 2: sodium persulfate; oxygen / acetonitrile / 9 h / 55 °C View Scheme

2-Isopropoxyphenol (4812-20-8) + allyl bromide (106-95-6) → 2-isopropoxyallylphenol (186743-35-1)

Conditions	Yield
With potassium carbonate In acetone for 12h;	100%

2-Isopropoxyphenol (4812-20-8) + methyl isocyanate (624-83-9) → Propoxur (114-26-1)

Conditions	Yield
With N,N'-dimethylbenzylamine at 60 - 90℃; for 3h; Reagent/catalyst; Temperature;	99%
In Dimethyldisulphide at 20℃; for 1h;

carbon monoxide (201230-82-2) + 2-Isopropoxyphenol (4812-20-8) + buta-1,3-diene (106-99-0) → C18H24O3

Conditions	Yield
With palladium diacetate; triphenylphosphine; benzoic acid In tetrahydrofuran at -40 - 80℃; under 15001.5 Torr; Autoclave; Inert atmosphere;	99%

2-Isopropoxyphenol (4812-20-8) + propargyl bromide (106-96-7) → 1-Isopropoxy-2-prop-2-ynyloxy-benzene (200286-21-1)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2.5h;	97%

2-Isopropoxyphenol (4812-20-8) → 5-iodo-2-isopropoxyphenol (900174-04-1)

Conditions	Yield
Stage #1: 2-Isopropoxyphenol With potassium iodide; sodium hydroxide In methanol at 20℃; Stage #2: With sodium hypochlorite In methanol	96%

2-Isopropoxyphenol (4812-20-8) → 4-bromo-2-isopropoxy-phenol (916228-69-8)

Conditions	Yield
With pyridinium hydrobromide perbromide In dichloromethane at 20℃; for 6h;	94%
With bromine In dichloromethane at -70 - -10℃; for 1h;	94%
With bromine In dichloromethane; water at -70 - -10℃; for 4h;

2-Isopropoxyphenol (4812-20-8) → benzene-1,2-diol (120-80-9)

Conditions	Yield
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;	94%
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h;	94%
With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18h;	94%

2-Isopropoxyphenol (4812-20-8) + 4-(4-chlorophenyl)-5-(3-hydroxypropyl)-2-(2-methylimidazol-1-yl)oxazole (198064-22-1) → 4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-[3-[2-(2-propyloxy)phenoxy]propyl]oxazole

Conditions	Yield
With tributylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; Mitsunobu reaction;	93%

2-Isopropoxyphenol (4812-20-8) + 5-chloro-6-(thiophen-2-yl)pyrazine-2,3-dicarbonitrile (77858-55-0) → 5-(2-isopropyloxyphenoxy)-6-(thiophen-2-yl)pyrazine-2,3-dicarbonitrile (1259925-63-7)

Conditions	Yield
With triethylamine In acetone at 20℃; for 2h;	89%

2-Isopropoxyphenol (4812-20-8) + 3-monochloro-1,2-propanediol (96-24-2) → rac-3-(2-isopropoxyphenoxy)-propane-1,2-diol

Conditions	Yield
	88%

2-(3-bromopropyl)isoindole-1,3-dione (5460-29-7) + 2-Isopropoxyphenol (4812-20-8) → 2-[3-(2-isopropoxy-phenoxy)-propyl]-isoindole-1,3-dione (748772-62-5)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 25 - 80℃; for 18.25h;	87%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 18h;	87%

2-Isopropoxyphenol (4812-20-8) + 5-chloropyrazine-2,3-dicarbonitrile (72111-57-0) → 5-(2-isopropyloxyphenoxy)pyrazine-2,3-dicarbonitrile (1259925-59-1)

Conditions	Yield
With triethylamine In acetone at 20℃; for 2h;	86%

2-Isopropoxyphenol (4812-20-8) → 2-hydroxy-3-isopropoxyphenyl bromide (350792-40-4)

Conditions	Yield
With bromine; tert-butylamine In dichloromethane; toluene at -78 - 20℃; for 5h;	85%
With bromine; tert-butylamine In dichloromethane; toluene at -60 - 20℃; for 0.5h;	39%
With bromine; tert-butylamine In toluene at -78 - 18℃; for 14h;

diethyl ether (60-29-7) + ethyl-magnesium tetrahydroborate (6077-70-9, 18129-13-0) + 2-Isopropoxyphenol (4812-20-8) → 2-isopropoxyphenolato-magnesium tetrahydroborate diethyl ether (1/2) (862776-00-9)

Conditions	Yield
In diethyl ether byproducts: C2H6; all manipulations under anhydrous conditions and under N2 atm.; soln. oforg. compd. added dropwise to stirred soln. of Mg compd.; filtered, washed with Et2O, dried in vac.; elem. anal.;	83.5%

2-Isopropoxyphenol (4812-20-8) + allyl halide → 2-isopropoxyallylphenol (186743-35-1)

Conditions	Yield
With potassium carbonate In acetone	79%

2-Isopropoxyphenol (4812-20-8) + (S)-3-chloropropan-1,2-diol (60827-45-4) → (S)-3-(2-isopropoxyphenoxy)-propane-1,2-diol

Conditions	Yield
	79%

2-Isopropoxyphenol (4812-20-8) + 2-(N-tert-butoxycarbonylamino)ethanol (26690-80-2) → [2-(2-isopropoxy-phenoxy)-ethyl]-carbamic acid tert-butyl ester (748772-58-9)

Conditions	Yield
With triphenylphosphine polystyrene; di-tert-butyl-diazodicarboxylate In tetrahydrofuran at 0 - 25℃; for 18h;	78%
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 25℃; for 18h;	78%

2-Isopropoxyphenol (4812-20-8) + ethylene dibromide (106-93-4) → 1-(2-bromoethoxy)-2-isopropoxybenzene (1262059-05-1)

Conditions	Yield
With potassium carbonate; potassium iodide In acetone at 60℃;	67%
With potassium hydroxide In ethanol for 75h; Reflux;	45%
With potassium carbonate; potassium iodide In acetone Reflux;

2-Isopropoxyphenol (4812-20-8) + 1,3-chlorobromopropane (109-70-6) → 1-(3-chloropropoxy)-2-(1-methylethoxy)benzene (117022-42-1)

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;	62%
With potassium hydroxide; potassium carbonate In acetone; benzene	232 g (62%)

2-Isopropoxyphenol (4812-20-8) + 2-(4-methoxyphenyl)cyclobutan-1-one O-(4-(trifluoromethyl)benzoyl)oxime → 4-(2-isopropoxyphenoxy)-4-(4-methoxyphenyl)butanenitrile

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; copper(l) chloride In dichloromethane at 20℃; for 5h; Irradiation; Inert atmosphere;	61%

formaldehyd (50-00-0) + 2-Isopropoxyphenol (4812-20-8) → 2-hydroxy-3-isopropoxybenzaldehyde

Conditions	Yield
Stage #1: 2-Isopropoxyphenol With triethylamine; magnesium chloride In acetonitrile at 20℃; for 1h; Stage #2: formaldehyd In acetonitrile for 4h; Reflux;	57%
Stage #1: 2-Isopropoxyphenol With triethylamine; magnesium chloride In acetonitrile at 20℃; for 1h; Stage #2: formaldehyd In acetonitrile at 82℃; for 4h;	57%

Propyl isocyanate (110-78-1) + 2-Isopropoxyphenol (4812-20-8) → Propyl-carbamic acid 2-isopropoxy-phenyl ester (60309-52-6)

Conditions	Yield
With triethylamine

Upstream product

• 2539-21-1 o-methoxyphenyl i-propyl ether 
• 120-80-9 benzene-1,2-diol 
• 75-26-3 isopropyl bromide 
• 14005-14-2 2,2-dimethyl-1,3-benzodioxole 
• 924904-20-1 1-(bromomethyl)-2-(propan-2-yloxy)benzene 
• 91-16-7 1,2-dimethoxybenzene 
• 22921-58-0 2-isopropoxybenzaldehyde 
• 90-02-8 salicylaldehyde 
• 114-26-1 Propoxur 
• 7664-41-7 ammonia 
• 63635-26-7 2-isopropoxybenzoic acid 
• 617-86-7 triethylsilane 

Downstream Products

• 64381-57-3 Methoxymethyl-carbamic acid 2-isopropoxy-phenyl ester 
• 60309-51-5 Ethyl-carbamic acid 2-isopropoxy-phenyl ester 
• 60309-53-7 Butyl-carbamic acid 2-isopropoxy-phenyl ester 
• 117022-42-1 1-(3-chloropropoxy)-2-(1-methylethoxy)benzene 
• 130631-91-3 2-(2-Isopropoxy-phenoxy)-2-methyl-benzo[1,3]dioxin-4-one 
• 130632-01-8 2-Acetoxy-benzoic acid 2-isopropoxy-phenyl ester 
• 200286-21-1 1-Isopropoxy-2-prop-2-ynyloxy-benzene 
• 350792-40-4 2-hydroxy-3-isopropoxyphenyl bromide 
• 186743-35-1 2-isopropoxyallylphenol 
• 748772-62-5 2-[3-(2-isopropoxy-phenoxy)-propyl]-isoindole-1,3-dione 
• 915921-87-8 1-(2-chloroethoxy)-2-isopropoxybenzene 
• 114-26-1 Propoxur 

Relevant articles and documents

Direct oxidation of the C(sp2)-C(sp3) bond from benzyltrimethylsilanes to phenols

A novel pathway for direct conversion of benzylsilanes to phenols by oxidation with Na2S2O8 and oxygen is efficiently developed under mild and neutral conditions. The reaction shows good functional group tolerance to afford phenols in moderate yields. The possible mechanism is proposed based on the isotopic labeling trials.

Chemoenzymatic total syntheses of ribisins A, B, and D, polyoxygenated benzofuran derivatives displaying NGF-potentiating properties

Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.

Facile and sensitive spectrophotometric determination of propoxur in formulations and environmental samples

A facile, rapid, and sensitive spectrophotometric method for the determination of propoxur in insecticidal formulations, fortified water, vegetables, agricultural wastewater, and agricultural soil samples has been elaborated. The proposed method is based on the hydrolysis of propoxur under basic conditions, followed by instantaneous azo coupling of the resulting 2-isopropoxyphenol with the anilines 2a - c. This yielded the orange-red chromophore 3a (λmax = at 470 nm). the pale-red coupling product 3b (490 nm), or the red derivative 3c (478 nm), which are stable for 46 h, 38 h, and 24 h, respectively, and could be readily analyzed spectrophotometrically.