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10272-07-8

10272-07-8

Identification

  • Product Name:3,5-Dimethoxyaniline

  • CAS Number: 10272-07-8

  • EINECS:233-616-5

  • Molecular Weight:153.181

  • Molecular Formula: C8H11NO2

  • HS Code:29222990

  • Mol File:10272-07-8.mol

Synonyms:3,5-Dimethoxy-phenylamine;3,5-Dimethoxybenzeneamine;Benzenamine, 3,5-dimethoxy-;3,5-dimethoxy aniline;5-Aminoresorcinol dimethylether;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn,IrritantXi

  • Hazard Codes:Xn,Xi

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:3,5-Dimethoxyaniline
  • Packaging:100 g
  • Price:$ 195
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3,5-Dimethoxyaniline >98.0%(GC)(T)
  • Packaging:25g
  • Price:$ 290
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3,5-Dimethoxyaniline >98.0%(GC)(T)
  • Packaging:5g
  • Price:$ 58
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3,5-Dimethoxyaniline
  • Packaging:25 g
  • Price:$ 95
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3,5-Dimethoxyaniline
  • Packaging:1 g
  • Price:$ 20
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3,5-Dimethoxyaniline
  • Packaging:5 g
  • Price:$ 55
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3,5-Dimethoxyaniline
  • Packaging:100 g
  • Price:$ 245
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3,5-Dimethoxyaniline 98%
  • Packaging:25g
  • Price:$ 124
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3,5-Dimethoxyaniline 98%
  • Packaging:5g
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  • Manufacture/Brand:Oakwood
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Relevant articles and documentsAll total 28 Articles be found

Self-propagated Lossen rearrangement induced by a catalytic amount of activating agents under mild conditions

Hoshino, Yujiro,Shimbo, Yuki,Ohtsuka, Naoya,Honda, Kiyoshi

, p. 710 - 712 (2015)

A mild self-propagated Lossen rearrangement induced by a catalytic amount of activating agents in medium to high polar organic solvents has been developed. The rearrangement of aromatic and aliphatic hydroxamic acids in the presence of a catalytic amount (0.01 equiv) of acetic anhydride and an equimolar amount of base such as well-dried potassium carbonate afforded the corresponding amines in high yields. This alternative to traditional Lossen rearrangement provides a simple and mild method for the synthesis of amines from free hydroxamic acids.

-

Pailer,M. et al.

, p. 1603 - 1612 (1967)

-

Porous polymeric ligand promoted copper-catalyzed C-N coupling of (hetero)aryl chlorides under visible-light irradiation

Wang, Erfei,Chen, Kaixuan,Chen, Yinan,Zhang, Jiawei,Lin, Xinrong,Chen, Mao

, p. 17 - 21 (2020/11/04)

A porous polymeric ligand (PPL) has been synthesized and complexed with copper to generate a heterogeneous catalyst (Cu@PPL) that has facilitated the efficient C-N coupling with various (hetero)aryl chlorides under mild conditions of visible-light irradiation at 80 °C (58 examples, up to 99% yields). This method could be applied to both aqueous ammonia and substituted amines, and is compatible to a variety of functional groups and heterocycles, as well as allows tandem C-N couplings with conjunctive dihalides. Furthermore, the heterogeneous characteristic of Cu@PPL has enabled a straightforward catalyst separation in multiple times of recycling with negligible catalytic efficiency loss by simple filtration, affording reaction mixtures containing less than 1 ppm of Cu residue. [Figure not available: see fulltext.]

A new ligand for copper-catalyzed amination of aryl halides to primary(hetero)aryl amines

Chen, Dong,Dong, Xinrui,Jiang, Shang,Jiang, Sheng,Qiu, Yatao,Wu, Xiaoxing

supporting information, (2020/02/11)

N,N′-Bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide was found as a new ligand for copper-catalyzed amination of aryl iodides, bromides and chlorides to afford various primary (hetero)aryl amines. These reactions proceeded efficiently under mild conditions when inexpensive aqueous ammonia (28% NH3 in H2O) was used as the amino source.

One-Pot Generation of Benzynes from Phenols: Formation of Primary Anilines by the Deoxyamination of Phenols

Akai, Shuji,Ikawa, Takashi,Masuda, Shigeaki

supporting information, (2020/03/23)

Benzynes were selectively generated in situ from phenols and trapped regioselectively with potassium hexamethyldisilazide to form primary anilines following acidic workup. The direct conversion of a phenolic hydroxyl group into a free amino group is a useful method for the preparation of primary aryl amines that are hard to synthesize by using coupling reactions involving phenol derivatives with ammonia. Whereas reactions of ortho- and meta-substituted phenols produced meta-substituted anilines exclusively, those of para-substituted phenols provided ortho-silylanilines.

Design, synthesis and biological evaluation of hypolipidemic compounds based on BRD4 inhibitor RVX-208

Yu, Ping,Liu, Wenjing,Ren, Jinghui,Wang, Yingying,Ning, Yao,Huang, Mingqi,Hu,Wei, Lili,Ji, Min,Cai, Jin

, p. 2168 - 2172 (2019/07/03)

Bromodomain-containing protein 4 (BRD4) is a new therapeutic target for the treatment of diseases including cardiovascular diseases, cancer, inflammation and central nervous system (CNS) disorders. In this study, we introduced the pharmacophore of fibrates to a BRD4 inhibitor, RVX-208, to design dual-active hypolipidemic compounds, and found that some of new analogues showed favorable hypolipidemic activities. Synthetic accessibility towards this class of compounds optimized RVX-208 as well as would supply more thoughts on hypolipidemic drugs.

Coolade. A Low-Foaming Surfactant for Organic Synthesis in Water

Lee, Nicholas R.,Cortes-Clerget, Margery,Wood, Alex B.,Lippincott, Daniel J.,Pang, Haobo,Moghadam, Farbod A.,Gallou, Fabrice,Lipshutz, Bruce H.

, p. 3159 - 3165 (2019/04/26)

Several types of reduction reactions in organic synthesis are performed under aqueous micellar-catalysis conditions (in water at ambient temperature), which produce a significant volume of foam owing to the combination of the surfactant and the presence of gas evolution. The newly engineered surfactant “Coolade” minimizes this important technical issue owing to its low-foaming properties. Coolade is the latest in a series of designer surfactants specifically tailored to enable organic synthesis in water. This study reports the synthesis of this new surfactant along with its applications to gas-involving reactions.

Process route upstream and downstream products

Process route

3,5-dihydroxyphenylamine
20734-67-2

3,5-dihydroxyphenylamine

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: aqueous dioxane
2: aqueous NaOH
3: aq.-ethanolic alkaline solution
With 1,4-dioxane; sodium hydroxide; alkaline solution;
1-bromo-3,5-dimethoxybenzene
20469-65-2

1-bromo-3,5-dimethoxybenzene

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
1-bromo-3,5-dimethoxybenzene; With magnesium; In tetrahydrofuran; Inert atmosphere;
With C10H17NO; In tetrahydrofuran; toluene; at -78 ℃; for 2h; Inert atmosphere;
With ammonium chloride; In tetrahydrofuran; water; toluene; Inert atmosphere;
78%
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate; In dimethyl sulfoxide; at 90 ℃; for 24h; Inert atmosphere; Sealed tube;
68%
With ammonia; sodium; ferric nitrate;
1-chloro-3,5-dimethoxybenzene
7051-16-3

1-chloro-3,5-dimethoxybenzene

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
With ammonium hydroxide; potassium phosphate; In dimethyl sulfoxide; at 80 ℃; UV-irradiation;
93%
With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide; In water; dimethyl sulfoxide; at 110 ℃; for 24h; Inert atmosphere;
88%
With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide; In dimethyl sulfoxide; at 120 ℃; for 24h; Inert atmosphere; Schlenk technique;
88%
3,5-dimethoxybenzoic acid
1132-21-4

3,5-dimethoxybenzoic acid

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
3,5-dimethoxybenzoic acid; With diphenylphosphoranyl azide; triethylamine; In toluene; at 80 ℃;
With sodium hydroxide; In tetrahydrofuran; toluene; at 20 ℃; for 2h;
43%
3,5-dimethoxybenzoic acid; With diphenylphosphoranyl azide; triethylamine; In toluene; at 80 ℃;
With sodium hydroxide; In tetrahydrofuran; for 2h;
43%
Multi-step reaction with 2 steps
1: triethylamine; diphenyl phosphoryl azide / 80 °C
2: sodium hydroxide; benzoic acid / tetrahydrofuran / 0.5 h / 20 °C
With diphenyl phosphoryl azide; triethylamine; benzoic acid; sodium hydroxide; In tetrahydrofuran; 1: |Curtius Rearrangement / 2: |Curtius Rearrangement;
Multi-step reaction with 2 steps
1.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 1 h / 20 °C / Inert atmosphere
1.2: 18 h / 20 °C / Inert atmosphere
2.1: potassium carbonate / dimethyl sulfoxide / 3 h / 90 °C
2.2: 0.08 h / 20 °C
With potassium carbonate; 1,1'-carbonyldiimidazole; In dimethyl sulfoxide; 2.1: |Lossen Rearrangement;
Multi-step reaction with 3 steps
1: thionyl chloride / 2 h / 90 °C
2: ammonium hydroxide / acetonitrile / 1.5 h / 20 °C / Cooling with ice
3: sodium hydroxide; sodium hypochlorite / 5 h / 80 °C
With ammonium hydroxide; sodium hypochlorite; thionyl chloride; sodium hydroxide; In acetonitrile;
1-iodo-3,5-dimethoxybenzene
25245-27-6

1-iodo-3,5-dimethoxybenzene

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate; In dimethyl sulfoxide; at 20 ℃; for 24h; Inert atmosphere; Sealed tube;
75%
1-azido-3,5-dimethoxybenzene
85862-68-6

1-azido-3,5-dimethoxybenzene

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
With sodium tetrahydroborate; palladium; In water; for 1.5h; Inert atmosphere;
99%
With sodium sulfide; water; for 0.5h; Reflux;
96%
With ammonium hydroxide; at 90 ℃; for 0.5h;
90%
With triethylamine; tris[tert-butyl]phosphonium tetrafluoroborate; In tetrahydrofuran; water; at 20 ℃; for 15h;
94 %Spectr.
N-hydroxy-3,5-dimethoxybenzamide
710311-79-8

N-hydroxy-3,5-dimethoxybenzamide

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
N-hydroxy-3,5-dimethoxybenzamide; With acetic anhydride; potassium carbonate; In dimethyl sulfoxide; at 50 ℃; for 2h;
With hydrogenchloride; In water; dimethyl sulfoxide; at 0 ℃;
3%
N-hydroxy-3,5-dimethoxybenzamide; With potassium carbonate; In dimethyl sulfoxide; at 90 ℃; for 3h;
With hydrogenchloride; In water; dimethyl sulfoxide; at 20 ℃; for 0.0833333h;
3,5-dimethoxyphenyl isocyanate
54132-76-2

3,5-dimethoxyphenyl isocyanate

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 8.7 g / sodium hydroxide (20percent) / 60 °C
With sodium hydroxide;
With benzoic acid; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.5h;
N-(3,5-dimethoxy-phenyl)-acetamide
79257-61-7

N-(3,5-dimethoxy-phenyl)-acetamide

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
N-(3,5-dimethoxy-phenyl)-acetamide; With Schwartz's reagent; In tetrahydrofuran; at 20 ℃; for 0.05h; Inert atmosphere;
With water; In tetrahydrofuran; chemoselective reaction; Inert atmosphere;
86%
With alkaline solution;
3,5-dimethoxybenzamide
17213-58-0

3,5-dimethoxybenzamide

3.5-dimethoxyaniline
10272-07-8

3.5-dimethoxyaniline

Conditions
Conditions Yield
With sodium hypobromide; at -15 ℃;
Yield given;
With sodium hypochlorite; sodium hydroxide; at 80 ℃; for 5h;
4.1 g

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