Conditions | Yield |
---|---|
With potassium carbonate In acetone at 50 - 60℃; for 27h; Time; Large scale; | 99% |
With potassium carbonate In acetone at 0 - 10℃; for 4h; Reflux; Inert atmosphere; | 91.1% |
With potassium carbonate In acetone at 20℃; for 3.16667h; Heating / reflux; | 80% |
Conditions | Yield |
---|---|
With thionyl chloride at 20℃; for 18h; Cooling with ice; Inert atmosphere; | 99% |
With Oxone In toluene at 60℃; for 48h; Green chemistry; | 97% |
With 2-(dimethoxymethylidene)propanedinitrile at 60℃; for 48h; | 95% |
methanol
2-bromoanisole
carbon monoxide
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II); triethylamine at 100℃; under 2585.74 Torr; for 16h; | 99% |
2-Methoxybenzoic acid
carbonic acid dimethyl ester
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With 5 wt percent zeolite NaY-Bf at 200℃; for 5h; Autoclave; Green chemistry; | 98% |
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry; | 96% |
carbonic acid dimethyl ester
salicylic acid
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With diiron nonacarbonyl at 180℃; for 1h; Sealed tube; | 97% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0208333h; microwave irradiation; | 92% |
With potassium carbonate at 150℃; for 10h; |
Conditions | Yield |
---|---|
With perchloric acid; sodium percarbonate; vanadia for 1.3h; Cooling; | 96% |
With dihydrogen peroxide at 20℃; for 20h; | 95% |
With aluminium(III) chloride hexahydrate; urea hydrogen peroxide adduct at 60℃; Green chemistry; | 90% |
methanol
4-iodoanisol
carbon monoxide
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere; | 96% |
With triethylamine; palladium on activated charcoal at 130℃; under 3750.38 Torr; for 2h; Sonogashira coupling; | 77% |
With triethylamine; G1-C2 PAMAM dendrimer*PPh2*PdCl2 at 105℃; under 5171.62 Torr; for 19h; | 100 % Chromat. |
Conditions | Yield |
---|---|
With bismuth(III) chloride; palladium diacetate; potassium carbonate at 20℃; for 2h; chemoselective reaction; | 95% |
With sodium methylate; potassium iodide at 15℃; Electrochemical reaction; | 85% |
With oxygen; potassium carbonate at 70℃; under 750.075 Torr; for 48h; | 53% |
Conditions | Yield |
---|---|
With potassium hydroxide In water at 15 - 20℃; Concentration; Temperature; | 94% |
With sodium hydroxide In water at 20 - 25℃; Temperature; | 94% |
With sodium hydroxide In water at 11 - 20℃; Temperature; Cooling; | 94% |
methyl 2-hydroxy-5-nitrobenzoate
2-Methoxybenzoic acid
A
2-methoxybenzoic acid methyl ester
B
5-nitrosalicylic acid
Conditions | Yield |
---|---|
Stage #1: 2-Methoxybenzoic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Stage #2: methyl 2-hydroxy-5-nitrobenzoate at 110℃; for 24h; | A 93% B n/a |
2-Methoxybenzoic acid
methyl salicylate
A
2-methoxybenzoic acid methyl ester
B
salicylic acid
Conditions | Yield |
---|---|
Stage #1: 2-Methoxybenzoic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Stage #2: methyl salicylate at 110℃; for 24h; Solvent; Reagent/catalyst; Temperature; | A 92% B n/a |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 91% |
With silver(l) oxide; benzene | |
With potassium hydroxide; Aliquat 336 1.) 60 deg C, 0.1 Torr, 6 h, 2.) room temp., 24 h; Yield given. Multistep reaction; | |
With potassium carbonate In N,N-dimethyl-formamide at 90℃; | |
With potassium carbonate In acetone at 20℃; Reflux; Darkness; |
methanol
N-(2-methoxybenzoyl)-N-phenylhydroxylamine
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With sodium perchlorate In acetonitrile electrolysis; | 87% |
Methyltrimethoxysilan
o-iodo-methyl-benzoic acid
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With oxygen; copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 145℃; under 760.051 Torr; for 18h; | 86% |
Methoxytrimethylsilane
2-bromobenzoic acid methyl ester
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With oxygen; copper diacetate; caesium carbonate In N,N-dimethyl-formamide at 145℃; under 760.051 Torr; for 18h; | 86% |
Conditions | Yield |
---|---|
In dichloromethane for 2h; Heating; | 85% |
With pyridine for 2h; Yield given; | |
With triethylamine In dichloromethane at 0℃; | |
With triethylamine In dichloromethane at 0℃; Inert atmosphere; | 1.56 g |
methanol
2-bromoanisole
carbon monoxide
A
2-methoxybenzoic acid methyl ester
B
2-Methoxybenzoic acid
Conditions | Yield |
---|---|
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 20h; Irradiation; | A 84.5% B 8% |
2-bromoanisole
carbon monoxide
A
2-methoxybenzoic acid methyl ester
B
2-Methoxybenzoic acid
Conditions | Yield |
---|---|
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 20h; Irradiation; | A 84.5% B 8% |
methanol
carbon monoxide
2-Chloroanisole
lithium methanolate
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; 5 mol% Pd/C; sodium fluoride In 1,4-dioxane at 150℃; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
Stage #1: methyl salicylate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 15h; | 81% |
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 4h; | 74% |
With potassium hydroxide In methanol for 3h; Reflux; | 53% |
With methanol; sodium methylate | |
With potassium carbonate; potassium iodide In acetone Reflux; |
diazomethyl-trimethyl-silane
methyl salicylate
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In methanol; hexane; acetonitrile for 15h; Ambient temperature; | 78% |
dihydroxy-methyl-borane
2-Methoxybenzoic acid
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With pyridine; copper (II) carbonate hydroxide at 90℃; for 24h; Chan-Lam Coupling; | 78% |
Conditions | Yield |
---|---|
With 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; palladium diacetate; potassium carbonate In dimethyl sulfoxide at 120℃; for 20h; Molecular sieve; | 74% |
tert.-butylhydroperoxide
2-methoxybenzylamine
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: tert.-butylhydroperoxide; 2-methoxybenzylamine In water; dimethyl sulfoxide Stage #2: In water; dimethyl sulfoxide at 100℃; for 20h; Sealed tube; | 74% |
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran at 70℃; for 0.5h; | 72% |
O-methyl S-p-methylphenyl thiocarbonate
2-Methoxyphenylboronic acid
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane In 1,4-dioxane at 60℃; for 16h; Sealed tube; Inert atmosphere; | 70% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); 1,1,3,3-Tetramethyldisiloxane; tricyclohexylphosphine In toluene at 110℃; for 12h; Glovebox; Inert atmosphere; Sealed tube; | 68% |
tert.-butylhydroperoxide
ortho-anisaldehyde
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
With copper (II)-fluoride In water; dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Inert atmosphere; Green chemistry; | 67% |
Conditions | Yield |
---|---|
With N-iodo-succinimide; 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 24h; Molecular sieve; | 60% |
With oxygen; potassium carbonate at 150℃; under 4500.45 Torr; for 24h; Autoclave; | 84 %Chromat. |
methanol
methoxybenzene
N,N-dimethyl-formamide
A
2-methoxybenzoic acid methyl ester
B
ortho-anisaldehyde
Conditions | Yield |
---|---|
Stage #1: methoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Stage #3: methanol Further stages; | A 53% B 6% |
pyrrolidine
2-methoxybenzoic acid methyl ester
(2-methoxyphenyl)(pyrrolidin-1-yl)methanone
Conditions | Yield |
---|---|
In acetonitrile at 35℃; under 6000480 Torr; for 96h; | 100% |
2-methoxybenzoic acid methyl ester
methyl 2-methoxy-5-iodobenzoate
Conditions | Yield |
---|---|
With iodine; silver sulfate In methanol at 20℃; for 0.5h; Inert atmosphere; | 99% |
With gold(III) chloride; N-iodo-succinimide In dichloromethane at 20℃; for 24h; Inert atmosphere; | 96% |
With N-iodo-succinimide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In dichloromethane; toluene at 20℃; for 14h; regioselective reaction; | 91% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; silver hexafluoroantimonate; 1-methylthiotriptycene In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 99% |
With gold(III) chloride; N-Bromosuccinimide In dichloromethane at 80℃; for 23h; Inert atmosphere; | 96% |
With iodine pentoxide; potassium bromide In water at 20℃; for 20h; regioselective reaction; | 92% |
acetic acid tert-butyl ester
2-methoxybenzoic acid methyl ester
tert-butyl 2-methoxybenzoate
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran Ambient temperature; | 98% |
2-methoxybenzoic acid methyl ester
dimethyl methane phosphonate
dimethyl [2-(2-methoxyphenyl)-2-oxoethyl]phosphonate
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran Barbier reaction; Cooling with ice; Inert atmosphere; | 97% |
With n-butyllithium In tetrahydrofuran at -78 - 0℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With platinum(IV) oxide; hydrogen at 60℃; under 750.075 - 1500.15 Torr; for 16h; Autoclave; Green chemistry; chemoselective reaction; | 97% |
Conditions | Yield |
---|---|
With aluminium trichloride; sodium iodide at 70 - 80℃; for 2h; | 95% |
With aluminum (III) chloride In dichloromethane at -5 - 25℃; | 94% |
With aluminium(III) iodide In carbon disulfide for 0.9h; Heating; | 76% |
With cerium(III) chloride; sodium iodide In acetonitrile for 20h; dealkylation; Heating; | 67% |
With niobium pentachloride In 1,2-dichloro-ethane for 6h; Heating; |
2-methoxybenzoic acid methyl ester
bis(pinacol)diborane
2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid methyl ester
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 2-(dimethyl(phenyl)silyl)-1-(6-methoxypyridin-2-yl)-2,3-dihydro-1H-naphtho[1,8-de]-[1,3,2]diazaborinine In hexane at 80℃; for 20h; Time; Schlenk technique; Inert atmosphere; | 95% |
With silica-SMAP-Ir(OCH3)(C8H12) In hexane ligand reacted with B-compound in hexane in presence of Ir-complex as catalyst at 25°C for 2 h; | 85% |
With Silica-SMAP-Ir(OMe)(cod) In hexane at 25℃; for 2h; Autoclave; regioselective reaction; | 85% |
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; (2-(diisopropylsilyl)phenyl)di-p-tolylphosphane In tetrahydrofuran at 80℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; | 82% |
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; (2-(diisopropylsilyl)phenyl)di-p-tolylphosphane In tetrahydrofuran at 80℃; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: 2-methoxybenzoic acid methyl ester With sodium hydroxide In methanol; water for 2h; Reflux; Stage #2: With hydrogenchloride In methanol; water pH=1; | 94% |
With sodium hydroxide In methanol at 40℃; for 2.5h; | 94.3% |
With potassium hydroxide In methanol at 35℃; for 1h; | 93% |
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 4h; Reflux; | 94% |
With hydrazine hydrate In ethanol at 80℃; for 1h; Inert atmosphere; | 92% |
With hydrazine hydrate for 5h; Heating; | 90% |
[hydroxy(tosyloxy)iodo]benzene
2-methoxybenzoic acid methyl ester
Conditions | Yield |
---|---|
In 2,2,2-trifluoroethanol at 20℃; for 17h; | 94% |
Diphenylmethane
2-methoxybenzoic acid methyl ester
A
benzophenone
B
methyl 5-benzhydryl-2-methoxybenzoate
C
1,1,2,2-tetraphenylethane
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; iron(II) chloride In 1,2-dichloro-ethane at 100℃; for 36h; Inert atmosphere; regioselective reaction; | A 0.14 mmol B 94% C 0.07 mmol |
1-methyl-4-(phenylmethyl)benzene
2-methoxybenzoic acid methyl ester
methyl 2-methoxy-5-(phenyl(p-tolyl)methyl)benzoate
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; iron(II) chloride In 1,2-dichloro-ethane at 100℃; for 36h; Inert atmosphere; regioselective reaction; | 94% |
methanesulfonic acid
hexamethylenetetramine
2-methoxybenzoic acid methyl ester
methyl 5-formyl-2-methoxybenzoate
Conditions | Yield |
---|---|
at 0 - 90℃; for 16h; Temperature; Large scale; | 94% |
Conditions | Yield |
---|---|
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h; | 93% |
With lithium chloride In N,N-dimethyl-formamide for 22h; Heating; | 90% |
With iodine; aluminium In cyclohexane at 80℃; for 18h; Solvent; Reagent/catalyst; | 86% |
2-methoxybenzoic acid methyl ester
(p-fluorophenyl)trimethylsilane
4'-fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With (Ph3P)Au(I)(OTs); [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid In methanol; chloroform at 20℃; | 92% |
Conditions | Yield |
---|---|
With iodine; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 6h; Sealed tube; | 92% |
With iodine; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 6h; | 92% |
With iodine; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 6h; | 92% |
2-methoxybenzoic acid methyl ester
1-methoxy-2-methoxymethylbenzene
Conditions | Yield |
---|---|
With aluminium(III) triflate; tris(2,4-pentanedionato)ruthenium(III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In deuteromethanol; toluene at 130℃; under 30402 Torr; for 12h; Autoclave; | 91% |
The Methyl 2-methoxybenzoate, with the CAS registry number 606-45-1, is also known as o-Methoxybenzoic acid methyl ester. It belongs to the product category of Aromatic Esters. Its EINECS registry number is 210-118-6. This chemical's molecular formula is C9H10O3 and molecular weight is 166.1739. Its IUPAC name is called methyl 2-methoxybenzoate. This chemical is clear colorless to slightly yellow liquid. The product should be sealed and stored in cool, dry place.
Physical properties of Methyl 2-methoxybenzoate: (1)H-Bond Donor: 0; (2)H-Bond Acceptor: 3; (3)Rotatable Bond Count: 3; (4)Exact Mass: 166.062994; (5)MonoIsotopic Mass: 166.062994; (6)Topological Polar Surface Area: 35.5; (7)Heavy Atom Count: 12; (8)Formal Charge: 0; (9)Complexity: 156; (10)Covalently-Bonded Unit Count: 1; (11)Feature 3D Acceptor Count: 2; (12)Feature 3D Ring Count: 1; (13)Effective Rotor Count: 3; (14)Conformer Sampling RMSD: 0.6; (15)CID Conformer Count: 4.
Preparation: this chemical can be prepared by 2-hydroxy-benzoic acid methyl ester and iodomethane. This reaction will need reagent sodium methylate and methanol.
Uses of Methyl 2-methoxybenzoate: it can be used to produce 2-methoxy-benzyl alcohol at temperature of 160 - 162 °C. This reaction will need reagents methanol, barium oxide and copper oxide-chromium oxide.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: COC1=CC=CC=C1C(=O)OC
(2)InChI: InChI=1S/C9H10O3/c1-11-8-6-4-3-5-7(8)9(10)12-2/h3-6H,1-2H3
(3)InChIKey: PFYHAAAQPNMZHO-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Food and Chemical Toxicology. Vol. 26, Pg. 385, 1988. | |
rat | LD50 | oral | 3800mg/kg (3800mg/kg) | Food and Chemical Toxicology. Vol. 26, Pg. 385, |
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