Conditions | Yield |
---|---|
Stage #1: 3,5-diamino-4-methylbenzoic acid With sulfuric acid; zinc(II) chloride; sodium nitrite In water at 2℃; for 5h; Stage #2: With sulfuric acid; sodium hydroxide In water for 1.75h; Reflux; | 98.9% |
Conditions | Yield |
---|---|
With 5 mol% Pd/C; hydrogen; potassium carbonate In N,N-dimethyl acetamide at 150℃; under 532.036 Torr; for 20h; | 92% |
palladium-carbon In 1,3,5-trimethyl-benzene | 71% |
69.9% |
Conditions | Yield |
---|---|
With SO42-/ZrO2-TiO2 at 350℃; Reagent/catalyst; | 66.1% |
Conditions | Yield |
---|---|
With pyridinium hydrobromide perbromide In xylene for 2h; Heating; | 65% |
2-methylcyclohexane-1,3-dione
A
2-methylbenzene-1,3-diol
B
3-hydroxy-2-methyl-1-cyclohexanone
Conditions | Yield |
---|---|
With bis(η5-cyclopentadienyl)hafnium dihydride In isopropyl alcohol at 80℃; for 8h; | A 39% B 52% |
ortho-cresol
A
4-methyl resorcinol
B
2-methylbenzene-1,4-diol
C
2-methylbenzene-1,3-diol
D
3-methylbenzene-1,2-diol
Conditions | Yield |
---|---|
With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride at -40℃; for 0.5h; Product distribution; | A 3% B 17% C 3% D 4% |
With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride at -40℃; for 0.5h; | A 3% B 17% C 3% D 4% |
Conditions | Yield |
---|---|
With hydrogen iodide |
Conditions | Yield |
---|---|
With hydrogenchloride; amalgamated zinc at 100℃; |
Conditions | Yield |
---|---|
at 220℃; |
methyl 2,4-dihydroxy-3-methylbenzoate
2-methylbenzene-1,3-diol
Conditions | Yield |
---|---|
With potassium hydroxide unter Wasserstoff; |
2-hydroxy-4-methoxy-3-methylbenzoic acid
2-methylbenzene-1,3-diol
Conditions | Yield |
---|---|
With hydrogen iodide |
6-acetoxy-6-methylcyclohexa-2,4-dienone
acetic acid
A
4-methyl resorcinol
B
2-methylbenzene-1,3-diol
C
3-methylbenzene-1,2-diol
Conditions | Yield |
---|---|
at 110℃; beim anschliessenden Erwaermen mit wss.-methanol. HCl; |
2-Chlor-2-methyl-cyclohexandion-(1,3)
2-methylbenzene-1,3-diol
Conditions | Yield |
---|---|
(i) HCl, DMF, (ii) aq. HCl; Multistep reaction; |
Conditions | Yield |
---|---|
(i) Ac2O, H2SO4, (ii) Py, (iii) aq. NaOH, MeOH; Multistep reaction; |
2-methylbenzene-1,3-diol
Conditions | Yield |
---|---|
With sulfuric acid Diazotization; |
2-hydroxy-4-methoxy-3-methylbenzoic acid
hydrogen iodide
2-methylbenzene-1,3-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium; methanol / dann die Mischung mit Methyljodid versetzen 2: hydriodic acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: aluminium chloride; diethyl ether / Einleiten von Chlorwasserstoff und anschliessendes Erwaermen mit Wasser 2: aq. NaOH solution 3: 100 - 110 °C 4: amalgamated zinc; aqueous HCl / 100 °C View Scheme |
5-carbomethoxy-6-hydroxysalicylaldehyde
2-methylbenzene-1,3-diol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aq. NaOH solution 2: 100 - 110 °C 3: amalgamated zinc; aqueous HCl / 100 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 100 - 110 °C 2: amalgamated zinc; aqueous HCl / 100 °C View Scheme |
MCPA
A
4,6-dichloro-2-methylphenol
B
2-methyl-4-chlorophenol
C
2-methylbenzene-1,4-diol
D
2-methylbenzene-1,3-diol
E
2,5-dihydroxy-3-methylbenzoaldehyde
F
2-Methyl-1,4-benzoquinone
G
ortho-cresol
H
3-methylbenzene-1,2-diol
I
2-chloro-6-methylphenol
Conditions | Yield |
---|---|
With water UV-irradiation; |
Conditions | Yield |
---|---|
Stage #1: 3-chloro-o-cresol With sodium formate; copper(l) chloride; sodium hydroxide; sodium sulfite In water at 195 - 200℃; under 7500.75 - 9000.9 Torr; Autoclave; Large scale; Stage #2: With hydrogenchloride In water Large scale; | |
Stage #1: 3-chloro-o-cresol With sodium formate; copper(l) chloride; sodium hydroxide at 195 - 200℃; for 1.5h; Autoclave; Stage #2: With hydrogenchloride In water at 30℃; pH=2 - 3; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: acetic acid; nitric acid / methanol / 3 h / 10 - 60 °C 2.1: iron(III) chloride; manganese(IV) oxide; hydrazine hydrate / diethyl ether / 4 h / 80 °C / Reflux 3.1: sulfuric acid; zinc(II) chloride; sodium nitrite / water / 5 h / 2 °C 3.2: 1.75 h / Reflux View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether at 20℃; | 100% |
With hydrogenchloride; water 1.) ether, 45 min, 2.) 40 deg C; Yield given. Multistep reaction; | |
With hydrogenchloride | |
With hydrogenchloride In diethyl ether at 20℃; Gattermann formylation; |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 100% |
4-hydroxyphenylacetate
2-methylbenzene-1,3-diol
2,4,4'-trihydroxy-3-methyldeoxybenzoin
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate at 110℃; for 0.5h; Heating / reflux; | 99% |
With boron trifluoride diethyl etherate at 60 - 70℃; for 5h; | 97% |
With boron trifluoride diethyl etherate at 110℃; for 2h; Inert atmosphere; |
2-methylbenzene-1,3-diol
4,6-dibromo-2-methylbenzene-1,3-diol
Conditions | Yield |
---|---|
With benzyltrimethylammonium tribromide In methanol; dichloromethane | 99% |
With benzyltrimethylammonium tribromide In methanol; dichloromethane for 1h; Ambient temperature; | 93% |
With benzyltrimethylammonium tribromide | 70% |
With bromine In acetic acid | |
With bromine In dichloromethane for 2h; | 5.54 g |
2-methylbenzene-1,3-diol
acetic anhydride
1-(2,4-dihydroxy-3-methylphenyl)ethanone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate at 80℃; for 6h; | 99% |
Stage #1: 2-methylbenzene-1,3-diol With boron trifluoride diethyl etherate at 70℃; Friedel-Crafts Acylation; Stage #2: acetic anhydride at 20 - 80℃; for 7h; | 95% |
Stage #1: 2-methylbenzene-1,3-diol With boron trifluoride diethyl etherate at 70℃; Stage #2: acetic anhydride at 80℃; for 6h; | 85% |
2-methylbenzene-1,3-diol
ethyl 2-oxocyclohexane carboxylate
3-Hydroxy-4-methyl-7,8,9,10-tetrahydro-6H-dibenzopyran-6-one
Conditions | Yield |
---|---|
With sulfuric acid at 0℃; for 2.5h; | 99% |
With sulfuric acid In ethanol at 0 - 20℃; Pechmann condensation; | 84% |
With sulfuric acid In water at 20℃; for 15h; Pechmann condensation; | 71% |
2-methylbenzene-1,3-diol
benzyl chloride
1,3-bisbenzyloxy-2-methylbenzene
Conditions | Yield |
---|---|
With potassium phosphate In dimethyl sulfoxide at 60℃; for 1.33333h; | 99% |
2-methylbenzene-1,3-diol
1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose
Conditions | Yield |
---|---|
With calcium sulfate; scandium tris(trifluoromethanesulfonate) In 1,2-dichloro-ethane at -30 - 0℃; for 2.5h; | 99% |
2-methylbenzene-1,3-diol
ethyl m-toluoylacetate
Conditions | Yield |
---|---|
With sulfuric acid at 0 - 20℃; for 3h; Pechmann Condensation; | 99% |
With sulfuric acid In water at 20℃; for 3h; Pechmann Condensation; | 88% |
2-methylbenzene-1,3-diol
N-(4,4-diethoxybutyl)-4-methylbenzenesulfonylamide
Conditions | Yield |
---|---|
With trifluoroacetic acid In chloroform at 20℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With cholin hydroxide In water at 20℃; for 0.833333h; | 99% |
With choline acetate at 20℃; for 12h; | 60% |
With choline acetate at 20℃; for 12h; | 60% |
2-methylbenzene-1,3-diol
Conditions | Yield |
---|---|
With trifluoroacetic acid Reflux; | 99% |
dimethylaminoacetaldehyde diethyl acetal
2-methylbenzene-1,3-diol
1-amino-2,2-bis(2,4-dihydroxy-3-methylphenyl)-N,N-dimethylethane hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 90℃; for 12h; | 98.5% |
2-methylbenzene-1,3-diol
2-methyl-4-nitrosobenzene-1,3-diol
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite In water | 98% |
With sulfuric acid; sodium nitrite In water at 0℃; for 0.5h; | |
With sulfuric acid; sodium nitrite In water at 20℃; for 0.75h; | |
With sulfuric acid; sodium nitrite In water at 0℃; for 2h; |
2-methylbenzene-1,3-diol
4-bromo-benzaldehyde
2,8,14,20-tetrakis(4-bromophenyl)-5,11,17,23-tetramethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaen-4,6,10,12,16,18,22,24-octol
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol Cyclization; Heating; | 98% |
Conditions | Yield |
---|---|
With sulfuric acid at 0 - 20℃; for 1.5h; Pechmann Condensation; | 98% |
2-methylbenzene-1,3-diol
acetic anhydride
2-methyl-1,3-phenylene diacetate
Conditions | Yield |
---|---|
With magnesium In neat (no solvent) at 25℃; for 18h; Temperature; | 98% |
2-methylbenzene-1,3-diol
ethyl acetoacetate
4,8-dimethyl-7-hydroxycoumarin
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; silica gel for 0.05h; Pechmann reaction; microwave irradiation; | 97% |
With bispyridine cobalt(II) chloride for 0.0333333h; Pechmann condensation; Microwave irradiation; neat (no solvent); | 97% |
With silica gel for 0.0416667h; Pechmann condensation; Microwave irradiation; | 97% |
2-methylbenzene-1,3-diol
ethyl 3-oxo-3-phenylpropionate
7-hydroxy-8-methyl-4-phenyl-chromen-2-one
Conditions | Yield |
---|---|
With sulfuric acid; silica gel at 80℃; for 0.5h; Pechmann condensation reaction; | 97% |
With potassium aluminum sulfate at 80℃; for 2h; Pechmann reaction; | 95% |
With sulfuric acid In water at 20℃; for 3h; Pechmann Condensation; | 93% |
2-methylbenzene-1,3-diol
4-chlorobenzaldehyde
malononitrile
2-amino-7-hydroxy-8-methyl-4-(4-chlorophenyl)-4H-chromene-3-carbonitrile
Conditions | Yield |
---|---|
With cholin hydroxide In water at 20℃; for 0.666667h; | 97% |
With choline acetate at 20℃; for 9h; | 70% |
With choline acetate at 20℃; for 9h; | 70% |
Conditions | Yield |
---|---|
With cholin hydroxide In water at 20℃; for 0.666667h; | 97% |
Conditions | Yield |
---|---|
With cholin hydroxide In water at 20℃; for 0.666667h; | 97% |
ethyl (2-chloroaceto)acetate
2-methylbenzene-1,3-diol
4-(chloromethyl)-7-hydroxy-8-methyl-2H-chromen-2-one
Conditions | Yield |
---|---|
zirconium(IV) chloride at 20℃; for 0.0833333h; | 96% |
With ammonium cerium(IV) nitrate; silica gel for 0.05h; Pechmann reaction; microwave irradiation; | 94% |
Stage #1: ethyl (2-chloroaceto)acetate With sulfuric acid at 0℃; Stage #2: 2-methylbenzene-1,3-diol at 20℃; | 91% |
Conditions | Yield |
---|---|
With cholin hydroxide In water at 20℃; for 4.5h; | 96% |
carbon dioxide
2-methylbenzene-1,3-diol
2,4-dihydroxy-3-methylbenzoic acid
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 30℃; under 15001.5 Torr; for 24h; Kolbe-Schmidt Synthesis; Autoclave; | 95% |
With potassium hydrogencarbonate In water for 5h; Heating; | 42% |
2-methylbenzene-1,3-diol
4,6-diiodo-2-methyl-1,3-benzenediol
Conditions | Yield |
---|---|
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; calcium carbonate In methanol; dichloromethane for 4h; Ambient temperature; | 95% |
ethyl 3,3-diethoxypropanoate
2-methylbenzene-1,3-diol
7-hydroxy-8-methyl-2H-chromen-2-one
Conditions | Yield |
---|---|
Stage #1: ethyl 3,3-diethoxypropanoate; 2-methylbenzene-1,3-diol at 120℃; Stage #2: With sulfuric acid; trifluoroacetic acid at 20℃; for 0.5h; | 95% |
2-methylbenzene-1,3-diol
acetoacetic acid methyl ester
4,8-dimethyl-7-hydroxycoumarin
Conditions | Yield |
---|---|
With Fe3O4-SiO2-HMTA nanomaterial In neat (no solvent) at 100℃; for 0.25h; Green chemistry; | 95% |
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate at 80℃; for 1.5h; Pechmann condensation; | 92% |
With potassium hydrogensulfate at 90℃; for 4h; Pechmann condensation; | 92% |
With poly(4-vinylpyridine)-supported copper iodide In neat (no solvent) at 80℃; for 0.25h; Pechmann Condensation; Green chemistry; | 87% |
2-methylbenzene-1,3-diol
Conditions | Yield |
---|---|
With ammonium hexafluorophosphate; potassium carbonate In water; N,N-dimethyl-formamide addn. of the Fe-complex and ligand to K2CO3 and DMF, stirring for 12 h at room temp. under N2, filtn. into aq. HCl, pptn., addn. of acetone, evapn. (vac.) and addn. of a aq. soln. of NH4PF6; filtn., washing with cold water, drying for several hours under vacuum, washing (Et2O), further drying, elem. anal.; | 95% |
IUPAC Name: 2-Methylbenzene-1,3-diol
Molecular Formula: C7H8O2
Molecular Weight: 124.14 g/mol
SMILES: Oc1cccc(O)c1C Copy
InChI: InChI=1/C7H8O2/c1-5-6(8)3-2-4-7(5)9/h2-4,8-9H,1H3
EINECS: 210-155-8
Product Categories: Intermediates of Dyes and Pigments; Aromatic Hydrocarbons (substituted) & Derivatives; Benzene derivates; Organic Chemicals; Dye Intermediate
Melting Point: 114-120 °C(lit.)
Index of Refraction: 1.594
Molar Refractivity: 34.84 cm3
Molar Volume: 102.5 cm3
Surface Tension: 51.6 dyne/cm
Density: 1.21 g/cm3
Flash Point: 142.9 °C
Enthalpy of Vaporization: 54.18 kJ/mol
Boiling Point: 282.1 °C at 760 mmHg
Vapour Pressure of 2-Methylresorcinol (CAS NO.608-25-3): 0.00201 mmHg at 25 °C
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | oral | 200mg/kg (200mg/kg) | Journal of the American College of Toxicology. Vol. 5(3), Pg. 167, 1986. |
Reported in EPA TSCA Inventory.
A poison by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: T, C
Risk Statements: 25-36/37/38-34-20/21/22
R25 :Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R34:Causes burns.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36-45-37/39-28A-36/37/39-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S37/39:Wear suitable gloves and eye/face protection.
S28:After contact with skin, wash immediately with plenty of soap-suds.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S27:Take off immediately all contaminated clothing.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: VH2009500
HazardClass: 6.1
PackingGroup of 2-Methylresorcinol (CAS NO.608-25-3): III
2-Methylresorcinol (CAS NO.608-25-3), its Synonyms are 1,3-Benzenediol, 2-methyl- ; 2-Methyl-1,3-benzenediol ; 1,3-Dihydroxy-2-methylbenzene ; 2,6-Dihydroxytoluene ; 2-Methyl-1,3-dihydroxybenzene ; 2-Methylresorcin . It is white to off-white crystal powder.
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