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3,4-Dimethylanisole, also known as 1-methoxy-3,4-dimethylbenzene, is an organic compound with the chemical formula C9H12O. It is a colorless liquid with a pleasant, sweet, and woody odor. It is commonly found in essential oils and is used as a fragrance ingredient in various products.

4685-47-6

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4685-47-6 Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dimethylanisole is used as a starting reagent in the synthesis of 3and 4-methoxy-N-hydroxyphthalimide, which are important intermediates in the production of pharmaceuticals.
Used in Flavor and Fragrance Industry:
3,4-Dimethylanisole is used as a fragrance ingredient in perfumes, soaps, and other personal care products due to its pleasant and woody scent.
Used in Essential Oils:
3,4-Dimethylanisole is found in essential oils extracted from various plants, such as basil and anise. It contributes to the characteristic aroma and flavor of these oils, which are used in aromatherapy, food flavoring, and other applications.

Check Digit Verification of cas no

The CAS Registry Mumber 4685-47-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,6,8 and 5 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4685-47:
(6*4)+(5*6)+(4*8)+(3*5)+(2*4)+(1*7)=116
116 % 10 = 6
So 4685-47-6 is a valid CAS Registry Number.
InChI:InChI=1/C9H12O/c1-7-4-5-9(10-3)6-8(7)2/h4-6H,1-3H3

4685-47-6 Well-known Company Product Price

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  • Alfa Aesar

  • (B22735)  3,4-Dimethylanisole, 99%   

  • 4685-47-6

  • 50g

  • 554.0CNY

  • Detail
  • Alfa Aesar

  • (B22735)  3,4-Dimethylanisole, 99%   

  • 4685-47-6

  • 250g

  • 2326.0CNY

  • Detail

4685-47-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,4-DIMETHYLANISOLE

1.2 Other means of identification

Product number -
Other names Benzene, 4-methoxy-1,2-dimethyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4685-47-6 SDS

4685-47-6Synthetic route

3,4-Dimethylphenol
95-65-8

3,4-Dimethylphenol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

Conditions
ConditionsYield
With dimanganese decacarbonyl at 180℃; for 1h; Reagent/catalyst;99%
3,4-Dimethylphenol
95-65-8

3,4-Dimethylphenol

dimethyl sulfate
77-78-1

dimethyl sulfate

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

Conditions
ConditionsYield
With sodium hydroxide at 0 - 50℃; for 2h;96%
With aluminum oxide; potassium hydroxide for 10h; microwave irradiation;75%
With sodium hydroxide at 90℃;
4-bromo-o-xylene
583-71-1

4-bromo-o-xylene

sodium methylate
124-41-4

sodium methylate

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

Conditions
ConditionsYield
With copper(I) bromide In methanol at 125 - 130℃; for 4h; Autoclave;96%
3,4-Dimethylphenol
95-65-8

3,4-Dimethylphenol

methyl iodide
74-88-4

methyl iodide

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

Conditions
ConditionsYield
With potassium hydroxide In methanol; water81%
3,4-Dimethylphenol
95-65-8

3,4-Dimethylphenol

potassium methyl sulfate
562-54-9

potassium methyl sulfate

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

Conditions
ConditionsYield
With sodium hydroxide
4-methoxysalicylaldehyde
52289-54-0

4-methoxysalicylaldehyde

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate; diethylene glycol
2-methyl-4-methoxybenzyl chloride
84658-09-3

2-methyl-4-methoxybenzyl chloride

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

Conditions
ConditionsYield
palladium on activated charcoal
4-chloro-1,2-dimethylbenzene
615-60-1

4-chloro-1,2-dimethylbenzene

potassium methanolate
865-33-8

potassium methanolate

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

Conditions
ConditionsYield
With 18-crown-6 ether; iodine; chromium(0) hexacarbonyl 1.) diglyme, cyclohexane, reflux, 75 h, 2.) benzene, 60 deg C, 2.0 h, 3.) THF, R.T., 30 min; Yield given. Multistep reaction;
1-methoxy-3-methyl-benzene
100-84-5

1-methoxy-3-methyl-benzene

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POCl3
2: N2H4+H2O; KOH; diethylene glycol
View Scheme
Multi-step reaction with 2 steps
1: (chloromethylation)
2: Pd-C
View Scheme
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

4-methoxysalicylaldehyde
52289-54-0

4-methoxysalicylaldehyde

Conditions
ConditionsYield
With dipotassium peroxodisulfate; copper(ll) sulfate pentahydrate In water; acetonitrile at 90℃; for 0.5h;100%
With dipotassium peroxodisulfate; copper(II) sulfate In water; acetonitrile for 0.5h; Heating;92%
With ammonium cerium(IV) nitrate In methanol at 27 - 28℃; for 0.0833333h;86%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

3-methyl-4-anisaldehyde
32723-67-4

3-methyl-4-anisaldehyde

Conditions
ConditionsYield
With dipotassium peroxodisulfate; copper(II) sulfate In water; acetonitrile for 0.5h; Heating / reflux;100%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

4-methoxy-2-methylbenzonitrile
21883-13-6

4-methoxy-2-methylbenzonitrile

Conditions
ConditionsYield
With tert.-butylnitrite; N-hydroxyphthalimide; palladium diacetate In acetonitrile at 80℃; for 24h; Concentration; Inert atmosphere; Sealed tube;99%
With sodium azide; copper(ll) sulfate pentahydrate; [bis(acetoxy)iodo]benzene In acetonitrile at -40 - 25℃; Inert atmosphere;76%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

2,6-Dibromo-1-methoxy-3,4-dimethylbenzene
129633-42-7

2,6-Dibromo-1-methoxy-3,4-dimethylbenzene

Conditions
ConditionsYield
With benzyltrimethylazanium tribroman-2-uide; zinc(II) chloride In acetic acid for 1h; Ambient temperature;95%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

A

3,4-Dimethylphenol
95-65-8

3,4-Dimethylphenol

B

3,4-dimethyl-cyclohex-2-enone
10463-42-0

3,4-dimethyl-cyclohex-2-enone

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium In tetrahydrofuran; ethanol at -30℃; for 2h;A 3%
B 94%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

1,2-bis(bromomethyl)-4-methoxybenzene
36132-96-4

1,2-bis(bromomethyl)-4-methoxybenzene

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 4h; Heating;94%
With N-Bromosuccinimide; dibenzoyl peroxide In dimethyl sulfoxide68%
With N-Bromosuccinimide; Perbenzoic acid In tetrachloromethane for 15h; Heating;65%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

benzoyl chloride
98-88-4

benzoyl chloride

(4,5-dimethyl-2-methoxyphenyl)(phenyl)methanone
4072-15-5

(4,5-dimethyl-2-methoxyphenyl)(phenyl)methanone

Conditions
ConditionsYield
With lithium perchlorate; scandium tris(trifluoromethanesulfonate) In nitromethane at 20℃; for 72h;93%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

2-iodo-4,5-dimethyl-anisole
50772-82-2

2-iodo-4,5-dimethyl-anisole

Conditions
ConditionsYield
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 0.5h; Ambient temperature;92%
Multi-step reaction with 3 steps
1: acetic acid; concentrated aqueous HNO3
2: Raney nickel; ethanol
3: aqueous H2SO4; NaNO2 / Diazotization.Erwaermen der erhaltenen Diazoniumsalz-Loesung mit KI auf dem Dampfbad
View Scheme
With iron(III) chloride; N-iodo-succinimide; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In toluene at 70℃; for 5h; Inert atmosphere; regioselective reaction;
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

1-bromo-2-methoxy-4,5-dimethylbenzene
33500-88-8

1-bromo-2-methoxy-4,5-dimethylbenzene

Conditions
ConditionsYield
With bromine In dichloromethane at -70℃; Inert atmosphere;91%
With bromine In dichloromethane at -70℃; for 1h;91%
With tetra-N-butylammonium tribromide In methanol; dichloromethane at 20℃;75%
With N-Bromosuccinimide In acetonitrile at 35℃; for 20h; Inert atmosphere;45%
With carbon disulfide; bromine
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

3,4-dimethyl-2,6-dinitroanisole
160754-06-3

3,4-dimethyl-2,6-dinitroanisole

Conditions
ConditionsYield
Stage #1: 3,4-dimethylanisole With nitric acid In 1,2-dichloro-ethane at 20 - 25℃; for 5h;
Stage #2: With sulfuric acid; nitric acid at 55 - 60℃; for 5h;
90%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

chromium(0) hexacarbonyl
199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

(η6-3,4-dimethylanisole)tricarbonyl chromium
77490-94-9

(η6-3,4-dimethylanisole)tricarbonyl chromium

Conditions
ConditionsYield
With THF (catalyst) In tetrahydrofuran; dibutyl ether under N2, educts heated under reflux in n-Bu2O-THF for 21 h in the dark; cooled soln. filtered through Kieselguhr, evapd. in vac., solid dissolved in acetone, filtered, pptd. by addn. of light petroleum, recrystd. from acetone/light petroleum; elem. anal.;87%
In tetrahydrofuran at 150℃; for 48h; Inert atmosphere;87%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

1-methoxy-4,5-dimethylcyclohexa-1,4-diene
43087-42-9

1-methoxy-4,5-dimethylcyclohexa-1,4-diene

Conditions
ConditionsYield
With ethanol; ammonia; sodium In tetrahydrofuran for 3h;84%
Birch reduction;67%
With methanol; ammonia; sodium
(i) Li, liq. NH3, Et2O, (ii) EtOH; Multistep reaction;
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

C12H20F2

C12H20F2

C21H29FO

C21H29FO

Conditions
ConditionsYield
With 1-oxothiolane; dimethyldiacetoxysilane; cesium adamantane-1-carboxylate; C44H34Cl4F12Ir2; oxygen; copper diacetate In para-xylene at 85℃; Sealed tube; diastereoselective reaction;80%
1-[(4-methoxyphenyl)sulfanyl]pyrrolidine-2,5-dione
80172-73-2

1-[(4-methoxyphenyl)sulfanyl]pyrrolidine-2,5-dione

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

(2-methoxy-4,5-dimethylphenyl)(4′-methoxyphenyl)sulfane

(2-methoxy-4,5-dimethylphenyl)(4′-methoxyphenyl)sulfane

Conditions
ConditionsYield
With iron(III) chloride; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide In chloroform at 40℃; for 5h; regioselective reaction;76%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

triethyloxonium fluoroborate
368-39-8

triethyloxonium fluoroborate

chromium(0) hexacarbonyl
199620-14-9, 13007-92-6

chromium(0) hexacarbonyl

(CO)5CrC(OC2H5)C6H2(CH3)2OCH3

(CO)5CrC(OC2H5)C6H2(CH3)2OCH3

Conditions
ConditionsYield
With n-butyl lithium In diethyl ether aryllithium (10-20°C, n-BuLi, (C2H5)2O, 20 h at room temp.) was treated with Cr(CO)6 in (C2H5)2O, the temp. was raised to 20-25°C for 30 min, evapd., dissolved in min cold H2O, a soln. of (C2H5)3OBF4 inCH2Cl2 was added (Ar); extd. with petroleum ether, filtered through silica;69%
2-Methoxy-4-methylphenol
93-51-6

2-Methoxy-4-methylphenol

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

2',3-dimethoxy-2-hydroxy-4',5,5'-trimethylbiphenyl

2',3-dimethoxy-2-hydroxy-4',5,5'-trimethylbiphenyl

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol at 50℃; Electrolysis;63%
cyclohexene-1-carboxylic acid
636-82-8

cyclohexene-1-carboxylic acid

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

(4aR,9aS)-8-Methoxy-5,6-dimethyl-1,2,3,4,4a,9a-hexahydro-fluoren-9-one
118104-49-7

(4aR,9aS)-8-Methoxy-5,6-dimethyl-1,2,3,4,4a,9a-hexahydro-fluoren-9-one

Conditions
ConditionsYield
With PPA; Polyphosphoric acid (PPA) at 100℃; for 3h;60%
1,3-dimethoxy-2-hydroxy-benzene
91-10-1

1,3-dimethoxy-2-hydroxy-benzene

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

2',3,5-trimethoxy-4',5'-dimethyl-[1,1'-biphenyl]-4-ol

2',3,5-trimethoxy-4',5'-dimethyl-[1,1'-biphenyl]-4-ol

Conditions
ConditionsYield
With dipotassium peroxodisulfate; tetra(n-butyl)ammonium hydrogensulfate; trifluoroacetic acid at 20℃; for 2h; Schlenk technique; regioselective reaction;60%
1,2,4,5-Tetrafluorobenzene
327-54-8

1,2,4,5-Tetrafluorobenzene

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

2,3,5,6-tetrafluoro-2'-methoxy-4',5'-dimethyl-1,1'-biphenyl

2,3,5,6-tetrafluoro-2'-methoxy-4',5'-dimethyl-1,1'-biphenyl

Conditions
ConditionsYield
With (triphenylphosphine)gold(I) chloride; 1-pivaloyloxy-1,2-benziodoxol-3(1H)-one; silver pivalate; dimethyl sulfoxide In 1,4-dioxane at 120℃; for 16h; Inert atmosphere; regioselective reaction;59%
carbon dioxide
124-38-9

carbon dioxide

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

4-methoxy-2-methylphenylacetic acid
942-97-2

4-methoxy-2-methylphenylacetic acid

Conditions
ConditionsYield
With bis(2-pyridyl)methane; xanth-9-one; nickel(II) chloride hexahydrate; potassium tert-butylate In benzene at 20℃; under 760.051 Torr; for 4h; Irradiation; Schlenk technique;58%
3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

4,5-dimethyl-2-nitro-anisole
18087-11-1

4,5-dimethyl-2-nitro-anisole

Conditions
ConditionsYield
With trifluoroacetic acid; sodium nitrite In water55%
With nitric acid; acetic acid
With nitric acid; acetic anhydride
methanol
67-56-1

methanol

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

methyl 4-methoxy-2-methylbenzoate
35598-05-1

methyl 4-methoxy-2-methylbenzoate

Conditions
ConditionsYield
With tetradecyl(tributyl)phosphonium methanesulfonate at 20℃; for 18h; Inert atmosphere; Electrolysis; Sealed tube; Green chemistry;53%
cyclopent-1-enecarboxylic acid
1560-11-8

cyclopent-1-enecarboxylic acid

3,4-dimethylanisole
4685-47-6

3,4-dimethylanisole

(3aR,8aS)-7-Methoxy-4,5-dimethyl-2,3,3a,8a-tetrahydro-1H-cyclopenta[a]inden-8-one
124703-10-2

(3aR,8aS)-7-Methoxy-4,5-dimethyl-2,3,3a,8a-tetrahydro-1H-cyclopenta[a]inden-8-one

Conditions
ConditionsYield
With PPA; Polyphosphoric acid (PPA) at 100℃; for 3h;50%

4685-47-6Relevant articles and documents

A 4-methoxy-2-methyl-benzyl cyanide synthesis method

-

Paragraph 0032; 0033, (2019/02/02)

The invention relates to a synthesis method for 4-methoxy-2-methyl benzyl cyanide. The synthesis method takes 3, 4-dimethylphenol which is cheap and simple and easy to purchase as the raw material, and comprises six steps: methylation, oxidation, Witting reaction, alkene ether hydrolysis, oximation and dehydration. The synthesis method uses the simple and cheap raw material, is simple to operate, is easy for industrial production, has short production cycle, only needs purification in the last step of the six so as to obtain high-quality 4-methoxy-2-methyl benzyl cyanide, and avoids using extremely toxic substances like NaCN and KCN, thus filling the blank home and abroad.

Methylation of phenol and its derivatives with dimethyl carbonate in the presence of Mn2(CO)10, W(CO)6, and Co2(CO)8

Khusnutdinov,Shchadneva,Mayakova, Yu. Yu.

, p. 330 - 334 (2015/05/04)

Aryl methyl ethers were synthesized by reactions of phenol, substituted phenols, and α- and β-naphthols with dimethyl carbonate in the presence of manganese, tungsten, and cobalt carbonyls. Optimal reactant and catalyst ratios and reaction conditions were found to ensure selective formation of aryl methyl ethers.

Synthesis and blocking activities of isoindolinone- and isobenzofuranone-containing phenoxylalkylamines as potent α1- adrenoceptor antagonists

Zhang, Shou-Hua,Wang, Chun-Ye,Jiang, Zhen-Zhou,Ni, Pei-Zhou,Zhou, Jin-Pei,Xi, Bao-Min,Chen, Wen-Hua

scheme or table, p. 96 - 99 (2011/03/19)

This paper describes the synthesis and blocking activities of twelve new isoindolinone- and isobenzofura-none-containing phenoxylalkylamines as potent α1-Adrenoceptor antagonists. These compounds were synthesized in moderate to good yields starting from 3,4-dimethylphenol, and characterized with 1H-NMR, MS, IR and elemental analysis. Their blocking activities toward α1-Adrenoceptors were evaluated on isolated rat anococcygeus muscles. The results indicated that these compounds were very strong in blocking α1-Adrenoceptors, and most of them exhibited activities that were comparable to that of known potent α1- Adrenoceptor antagonist 1-(2,6-dimethylphenoxy)-2-(3,4- dimethoxyphenylethylamino)propane hydrochloride (DDPH).

Solid state S-methylation of thiols and O-methylation of phenols and naphthols with dimethyl sulfate under microwave irradiation

Heravi, Majid M.,Ahari, Neda Zamani,Oskooie, Hossein A.,Ghassemzadeh, Mitra

, p. 1701 - 1712 (2007/10/03)

Mild and efficient S-methylation of thiols and o-methylation of phenols and naphthals occurs with dimethyl sulfate (DMS) supported on basic alumina under microwave irradiation in solventless system. Copyright Taylor & Francis Inc.

New synthetic route to [bis-1,2-(aminomethyl)benzene]dichloroplatinum(II) complexes, screening for cytotoxic activity in cisplatin-sensitive and resistant human cancer cell lines, and reaction with glutathione

Rinke,Gruenert,Bednarski

, p. 763 - 769 (2007/10/03)

A new synthetic route to [bis-1,2-(aminomethyl)benzene]dichloroplatinum(II) complexes is described. o-Xylene and the 4-methoxy substituted derivative were used as starting points for the synthesis: benzylic bromination with N-bromosuccinamide /benzoylperoxide followed by the substitution of the benzyl bromides for azide and finally a catalytic hydrogenation with Pd/C of the diazides gave the desired diamines ligands. An attempt to synthesize the 4,6-dimethoxy derivative was unsuccessful due to the bromination of the aromatic ring. The diamines were complexed with K2PtCl4 to give the target Pt(II) complexes: [1,2-bis(aminomethyl)benzene]dichloroplatinum(II) (4a) and [1,2-bis(aminomethyl)-4-methoxy-benzene]dichloroplatinum(II) (4b). Screening for cytotoxic activity was done in comparison to cisplatin in a panel of eight human cancer cell lines; in all cases, the 4-methoxy derivative 4b was less active than the unsubstituted analog, 4a. In four cell lines 4a was as potent as cisplatin, while in the other four lines cisplatin was considerably more potent then 4a. The 5637 bladder cancer cell line was made 4-5 fold resistant to either cisplatin or [d,l-trans-1,2-diaminocyclohexane]dichloroplatinum(II); 4a showed some cross resistance (2-3 fold) to both resistant cell lines. The reactivity of 4a towards substitutions with glutathione (GSH), a biological thiol involved in intrinsic and acquired resistance to Pt-complexes, was measured by a RP-HPLC method. It was found that the second-order rate constant for the reaction of 4a with GSH was similar to that that reported for CDDP, indicating that reactivity towards GSH does not explain the different levels of cross resistance.

Piperazine derivatives and process for the preparation thereof

-

, (2008/06/13)

PCT No. PCT/KR97/00128 Sec. 371 Date Feb. 27, 1998 Sec. 102(e) Date Feb. 27, 1998 PCT Filed Jun. 28, 1997 PCT Pub. No. WO98/00402 PCT Pub. Date Jan. 8, 1998The present invention relates to novel compound having strong antimumor activities of the general formula(I) wherein R1 and R2 are independently hydrogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C2-C8 unsaturated alkyl, ketone, substituted or unsubstituted aryl, substituted or unsubstituted C1-C4 alkoxy, substituted or unsubstituted arylhydroxy, substituted or unsubstituted amino, C1-C4 lower ester, C1-C4 lower thioester, thiol, substituted or unsubstituted carboxyl, epoxy, substituted or unsubstituted C1-C4 lower thioalkoxy; or R1 and R2 are fused to form C3-C4 saturated or unsaturated chain; R3, R4, R5, R6 and R7 are independently hydrogen, halogen, hydroxy, nitro, C1-C4 lower ester, C1-C4 lower alkyl, C1-C4 lower thioalkyl, substituted or unsubstituted C3-C6 cycloalkyl, C1-C4 lower alkoxy, C1-C4 lower thioalkoxy, substituted or unsubstituted aryl, substituted or unsubstituted lower arylalkoxy, substituted or unsubstituted lower alkylamino, or lower alkyl substituted or unsubstituted carbamate; or among R3, R4, R5, R6 and R7, two adjacent groups are bonded with each other to form 1,2-phenylene or 2,3-naphthylene; X is oxygen, sulfur, or substituted or unsubstituted imino; Y is bonded at the 3-position or 4-position of the aromatic ring part wherein Y is oxygen or -NR8- (wherein, R8 is the same with the above-mentioned R3.); Z is hydroxy, C1-C4 lower alkoxy, C1-C4 lower thioalkoxy, substituted or unsubstituted aryloxy, C1-C4 lower alkylamino, substituted or unsubstituted cycloamino containing 1-5 nitrogen atoms; A is nitrogen or -CH=; its pharmaceutically acceptable acid addition salts and process for the preparation thereof.

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