2-[5-(1,1-dimethyl-1-silaethyl)-3-methylphenyl]-2-methyl-2-silapropane
orcinol
Conditions | Yield |
---|---|
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.1h; Green chemistry; | 99% |
3-Trimethylstannyl-2-<(trimethylstannyl)methyl>propene
malonoyl dichloride
orcinol
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 4h; | 93% |
5-methyl-2-(2-pyridinylsulfonyl)-1,3-phenylene diacetate
orcinol
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20 - 50℃; | 81% |
orcinol
Conditions | Yield |
---|---|
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran at 0℃; for 4h; | 73% |
Conditions | Yield |
---|---|
With BBr*(CH3)2 In 1,2-dichloro-ethane at 83.5℃; for 24h; | 63.7% |
Conditions | Yield |
---|---|
With ethene; 5%-palladium/activated carbon; ammonium acetate In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; under 760.051 Torr; for 6h; Schlenk technique; Molecular sieve; | A 13% B 58% |
5-methyl-2-bromocyclohex-2-en-3-ol-1-one
A
orcinol
B
4-bromo-5-methyl-1,3-benzenediol
C
4,6-dibromo-5-methylresorcinol
D
2,4-dibromo-5-methyl-resorcinol
Conditions | Yield |
---|---|
In diphenylether heating to 170-174 deg C during 1 h; | A 25% B 45% C 14% D 10% |
1,7-Bis(2-methyl-1,3-dioxolan-2-yl)-2,4,6-heptantrion
orcinol
Conditions | Yield |
---|---|
With barium dihydroxide at 100℃; for 24h; | 25% |
methanol
umbilicaric acid
A
orcinol
B
methyl orsellinate
C
4-Hydroxy-2-methoxy-6-methylbenzoesaeure-methylester
Conditions | Yield |
---|---|
at 140℃; |
methanol
diploschistesic acid
A
orcinol
B
methyl 3-hydroxy orsellinate
Conditions | Yield |
---|---|
at 150 - 160℃; |
Conditions | Yield |
---|---|
at 280 - 300℃; durch Kalischmelze; | |
With potassium hydroxide at 200℃; |
Conditions | Yield |
---|---|
With potassium hydroxide at 320℃; |
Conditions | Yield |
---|---|
With water | |
bei der Destillation; |
Conditions | Yield |
---|---|
beim Schmelzen; | |
With water | |
With calcium hydroxide |
Conditions | Yield |
---|---|
With sodium hydroxide at 90℃; kurzes Kochen der angesaeuerten Reaktionsloesung; |
3-bromo-5-methylphenol
orcinol
Conditions | Yield |
---|---|
durch Kalischmelze; |
ethyl 2,6-dihydroxy-4-methylbenzoate
orcinol
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid at 20℃; |
Conditions | Yield |
---|---|
With calcium hydroxide man leitet in das Filtrat CO2 oder neutralisiert mit Schwefelsaeure; |
buta-1,3-diene
A
orcinol
B
1,2,3,4-butanetetrol
Conditions | Yield |
---|---|
With barytes | |
With methyllithium; calcium carbonate |
Conditions | Yield |
---|---|
With sodium hydroxide at 150℃; |
methanol
isoelecanoric acid
A
orcinol
B
methyl orsellinate
C
orsellinic acid
Conditions | Yield |
---|---|
for 20h; Heating; | A 2 mg B 23 mg C 22 mg |
for 20h; Product distribution; Heating; | A 2 mg B 23 mg C 22 mg |
methyl crotonate
1-(phenylsulfinyl)propan-2-one
orcinol
Conditions | Yield |
---|---|
With magnesium methanolate Heating; |
Conditions | Yield |
---|---|
at 180℃; Product distribution; pyrolysis; rate of decarboxylation; | A 0.065 g B 0.033 g |
atranorin
A
orcinol
B
atranol
C
2,5-dimethyl-1,3-benzenediol
D
2,4-dihydroxy-3,6-dimethyl-benzoic acid methyl ester
E
methyl haematommate
Conditions | Yield |
---|---|
at 230 - 250℃; for 0.75h; Product distribution; pyrolysis; |
evernic acid
A
orcinol
B
O-methylorcinol
C
2-hydroxy-4-methoxy-6-methylbenzoic acid
Conditions | Yield |
---|---|
at 180℃; for 1h; Product distribution; pyrolysis; rate of decarboxylation; |
isoelecanoric acid
A
orcinol
B
methyl orsellinate
C
orsellinic acid
Conditions | Yield |
---|---|
With methanol for 20h; Heating; | A 2 mg B 23 mg C 22 mg |
chromyl acetate
1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-5-one
A
orcinol
B
1,3,3-trimethyl-2-oxabicyclo<2.2.2>octane-5,8-dione
Conditions | Yield |
---|---|
In acetic acid a) 10 deg C, 10 h, b) RT, overnight; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
dmap at 100℃; for 2.5h; | 100% |
With tin(IV) tetraphenylporphyrin perchlorate at 20℃; for 0.0833333h; | 99% |
With triethylamine In dichloromethane at 0 - 20℃; for 60h; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 6h; Heating; | 100% |
With potassium carbonate In acetone Reflux; Inert atmosphere; | 89% |
With potassium carbonate In acetone for 6h; Heating; | 76% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile Heating; | 100% |
Stage #1: orcinol With sodium hydride In tetrahydrofuran at 20℃; for 2h; Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran at 20℃; for 8h; | 95% |
Conditions | Yield |
---|---|
With perchloric acid at 20℃; Pechmann condensation; | 98% |
With 2-amino pyrimidine nanocellulose-supported palladium nanoparticles In neat (no solvent) at 130℃; for 2h; Pechmann Condensation; | 97% |
With sulfonic acid supported on the silica coated Fe3O4 nanoparticles In neat (no solvent) at 130℃; for 0.416667h; Pechmann Condensation; Green chemistry; chemoselective reaction; | 94% |
orcinol
N,N-dimethyl-formamide
2,4-dihydroxy-6-methylbenzaldehyde
Conditions | Yield |
---|---|
Stage #1: orcinol; N,N-dimethyl-formamide With trichlorophosphate Stage #2: With sodium hydroxide | 98% |
Stage #1: orcinol; N,N-dimethyl-formamide With trichlorophosphate Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride; water | 98% |
With trichlorophosphate at 20℃; for 1h; | 93% |
orcinol
1,1,1,3,3,3-hexamethyl-disilazane
2-[5-(1,1-dimethyl-1-silaethyl)-3-methylphenyl]-2-methyl-2-silapropane
Conditions | Yield |
---|---|
With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry; | 98% |
With 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0833333h; Neat (no solvent); | 96% |
With succinimide-N-sulfonic acid In acetonitrile at 20℃; for 0.0833333h; | 96% |
In toluene Heating; | 91% |
Conditions | Yield |
---|---|
With triethylamine In toluene heating; | 98% |
Stage #1: orcinol With dmap; triethylamine In tetrahydrofuran for 0.0833333h; Inert atmosphere; Stage #2: chloro-diphenylphosphine In tetrahydrofuran for 16h; Inert atmosphere; Reflux; |
Conditions | Yield |
---|---|
With 1-(4-ferrocenylbutyl)-3-{3-[dihydroxy(methoxy)silyl]propyl}benzimidazol-3-ium chloride supported on Fe3O4(at)SiO2 core-shell/BiOCl nano-composite In ethanol; water at 20℃; for 0.1h; Sonication; | 98% |
orcinol
1,3-dihydroxy-2-iodo-5-methylbenzene
Conditions | Yield |
---|---|
With iodine; sodium hydrogencarbonate In tetrahydrofuran; water at 0℃; for 1h; | 97% |
With N-iodo-succinimide In acetonitrile at 0℃; for 0.166667h; Inert atmosphere; | 94.6% |
With N-iodo-succinimide In acetonitrile at 0℃; for 0.25h; | 93% |
orcinol
ethyl 3-oxo-3-phenylpropionate
5-hydroxy-7-methyl-4-phenyl-2H-chromen-2-one
Conditions | Yield |
---|---|
With copper(ll) bromide at 80℃; for 0.333333h; Pechmann reaction; neat (no solvent); | 97% |
With nanosilica molybdic acid 2 In neat (no solvent) at 80℃; for 0.333333h; Pechmann Condensation; Green chemistry; | 88% |
With Ag supported on the hydroxyapatite-core-shell magnetic γ-Fe2O3 nanoparticles In neat (no solvent) at 80℃; for 0.7h; Pechmann Condensation; Green chemistry; | 85% |
orcinol
2,4-dichloroquinazoline
3,5-bis(2-chloroquinazolin-4-yloxy)toluene
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone at 20℃; for 48h; Inert atmosphere; regioselective reaction; | 97% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; | 97% |
With triethylamine In tetrahydrofuran at 20℃; for 1h; | 85% |
Stage #1: orcinol With triethylamine In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: Chlorodiisopropylphosphane In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique; Glovebox; |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 18h; Inert atmosphere; Reflux; | 97% |
Conditions | Yield |
---|---|
With nanosilica molybdic acid 2 In neat (no solvent) at 80℃; for 0.333333h; Pechmann Condensation; Green chemistry; | 96% |
With Polyvinylpolypyrrolidone supported BF3 complex In ethanol for 2h; Pechmann condensation; Reflux; | 95% |
With copper(ll) bromide at 80℃; for 0.166667h; Pechmann reaction; neat (no solvent); | 93% |
Conditions | Yield |
---|---|
With 1-(4-ferrocenylbutyl)-3-{3-[dihydroxy(methoxy)silyl]propyl}benzimidazol-3-ium chloride supported on Fe3O4(at)SiO2 core-shell/BiOCl nano-composite In ethanol; water at 20℃; for 0.133333h; Sonication; | 96% |
Conditions | Yield |
---|---|
With benzyltriphenylphosphonium tribromide; calcium carbonate In methanol; dichloromethane at 20℃; for 0.5h; | 95% |
With 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane bromide; calcium carbonate In methanol at 20℃; for 0.166667h; | 95% |
With benzyltrimethylammonium tribromide In methanol; dichloromethane for 1h; Ambient temperature; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Reflux; | 95% |
With potassium carbonate In acetone for 24h; Heating; | 92% |
With potassium carbonate In acetone for 24h; Heating; | 92% |
Conditions | Yield |
---|---|
With hydrogenchloride; aluminium trichloride; dicyanozinc In diethyl ether for 2h; | 95% |
With hydrogenchloride; water; dicyanozinc 1.) Et2O, 25 deg C, 2.) 60 deg C; Yield given. Multistep reaction; |
orcinol
chloromethyl methyl ether
1,3-bis(methoxymethoxy)-5-methylbenzene
Conditions | Yield |
---|---|
Stage #1: orcinol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil for 18h; Inert atmosphere; | 95% |
With sodium hydride In N,N-dimethyl-formamide at 18℃; for 18h; | 93% |
Stage #1: orcinol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.666667h; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide; mineral oil for 16h; | 93% |
orcinol
2-(2-(2-chloroethoxy)ethoxy)tetrahydro-2H-pyran
3,5-Bis(5-tetrahydropyranyloxy-3-oxa-1-pentyloxy)toluene
Conditions | Yield |
---|---|
With sodium hydroxide In butan-1-ol Substitution; | 95% |
Conditions | Yield |
---|---|
With sodium acetate; NaNO2 In ethanol; water addn. of resorcinol (in EtOH) to soln. of NaOAc and NiCl2 (in H2O), addn. of NaNO2 (in H2O), stirring (1 week); filtration, washing (H2O, EtOH, several h), drying (50°C, 0.1 mm); elem. anal.; | 95% |
orcinol
4,6-Dichloro-2-(methylthio)pyrimidine
1,3-bis(6-chloro-2-methylpyrimidin-4-yloxy)benzene
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone at 20℃; for 48h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With nano Fe3O4(at) SiO2(at)BenzIm-Fc[Cl]/ZnCl2 In ethanol; water at 20℃; for 0.333333h; Sonication; | 95% |
Conditions | Yield |
---|---|
With 1-(4-ferrocenylbutyl)-3-{3-[dihydroxy(methoxy)silyl]propyl}benzimidazol-3-ium chloride supported on Fe3O4(at)SiO2 core-shell/BiOCl nano-composite In ethanol; water at 20℃; for 0.133333h; Sonication; | 95% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 40℃; under 15001.5 Torr; for 24h; Kolbe-Schmidt Synthesis; Autoclave; | 95% |
orcinol
2,2,6-trimethyl-4H-1,3-dioxin-4-one
4,5-dimethyl-7-hydroxycoumarin
Conditions | Yield |
---|---|
Stage #1: 2,2,6-trimethyl-4H-1,3-dioxin-4-one With dihydroxy-poly(ethylene glycol) of MW = 4000 In toluene for 5h; Heating; Stage #2: orcinol With titanium tetrachloride In tetrahydrofuran at 20℃; for 0.583333h; von Pechmann reaction; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate; dimethyl sulfate In acetone for 24h; Reflux; | 94% |
With potassium carbonate; dimethyl sulfate In acetonitrile | 82% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In chlorobenzene at 40 - 70℃; for 1.5h; Inert atmosphere; | 94% |
With aluminum (III) chloride In chlorobenzene at 20 - 70℃; Friedel Crafts acylation; | 89% |
With aluminum (III) chloride In chlorobenzene at 0 - 70℃; for 2.5h; | 75% |
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere; | |
With aluminum (III) chloride In chlorobenzene at 70℃; Friedel-Crafts Acylation; |
orcinol
ethyl (2-chloroaceto)acetate
4-(chloromethyl)-7-hydroxy-5-methyl-2H-chromen-2-one
Conditions | Yield |
---|---|
Stage #1: ethyl (2-chloroaceto)acetate With sulfuric acid at 0℃; Stage #2: orcinol at 20℃; | 94% |
With sulfuric acid at 0 - 20℃; for 3h; | 94% |
With silica gel supported zirconyl chloride octahydrate at 90℃; for 0.133333h; Pechmann condensation reaction; | 81% |
With sulfuric acid In water at -5℃; | 80% |
Molecular Structure of Orcinol (CAS NO.504-15-4):
IUPAC Name: 5-methylbenzene-1,3-diol
CAS Number: 504-15-4
Molecular Formula: C7H8O2
Molecular Weight: 124.14
EINECS: 225-193-0
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 40.46 Å2
Index of Refraction: 1.594
Molar Refractivity: 34.84 cm3
Molar Volume: 102.5 cm3
Surface Tension: 51.6 dyne/cm
Enthalpy of Vaporization: 55.06 kJ/mol
Vapour Pressure: 0.00122 mmHg at 25°C
Density: 1.21g/cm3
Melting Point: 108 - 111°C
Boiling Point: 287 - 290°C
Flash Point: 159°C
liansport Information: 25kgs
Sensitive: Air Sensitive
Merck: 14,6864
BRN: 1071903
Product Categories: Alcohols and Derivatives; Aromatic Phenols
1. | orl-rat LD50:844 mg/kg | GTPPAF Gigiena Truda i Professionalnaya Patologiya v Estonskoi SSR. Labor Hygiene and Occupational Pathology in the Estonian SSR. 8 (1972),145. | ||
2. | scu-rat LDLo:1000 mg/kg | RMSRA6 Revue Medicale de la Suisse Romande. 15 (1895),561. | ||
3. | orl-mus LD50:772 mg/kg | HYSAAV Hygiene and Sanitation: English Translation of Gigiena Sanitariya. 34 (4-6),(1969),16. | ||
4. | ipr-mus LD50:405 mg/kg | CTYAD8 Zhongcaoyao. Chinese Herbal Medicine. 12 (1981),410. | ||
5. | ivn-mus LD50:290 mg/kg | CTYAD8 Zhongcaoyao. Chinese Herbal Medicine. 12 (1981),410. | ||
6. | orl-rbt LD50:2400 mg/kg | HYSAAV Hygiene and Sanitation: English Translation of Gigiena Sanitariya. 34 (4-6),(1969),16. | ||
7. | orl-gpg LD50:1687 mg/kg | HYSAAV Hygiene and Sanitation: English Translation of Gigiena Sanitariya. 34 (4-6),(1969),16. | ||
8. | scu-gpg LDLo:600 mg/kg | RMSRA6 Revue Medicale de la Suisse Romande. 15 (1895),561. | ||
9. | scu-frg LDLo:50 mg/kg | RMSRA6 Revue Medicale de la Suisse Romande. 15 (1895),561. | ||
10. | skn-mam LD50:7800 mg/kg | &nb |
EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.
Poison by subcutaneous and intravenous routes. Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by skin contact. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety Information of Orcinol (CAS NO.504-15-4):
Hazard Codes: Xn
Risk Statements: 22-36/37/38-41-37/38-20/21/22
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R41:Risk of serious damage to the eyes.
R37/38:Irritating to respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-26-36-37/39
S22:Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
RIDADR: 2811
WGK Germany: 3
RTECS: VH2100000
PackingGroup: III
HS Code: 29072900
Orcinol , with CAS number of 504-15-4, can be called 1,3-Dihydroxy-5-methylbenzene ; 1,5-Dihydroxy-3-methylbenzene ; 3,5-Dihydroxytoluene ; 3-Hydroxy-5-methylphenol ; 5-Methyl-1,3-benzenediol ; 5-Methyl-1,3-dihydroxybenzene ; 5-Methylresorcinol ; Orcin . It is a pink-grey to pink-brown cryst. powder or crystal. Orcinol (CAS NO.504-15-4) can be used in organic synthesis, pharmaceutical intermediate and also can used as analytical reagent.
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