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Cas Database

1000342-11-9

1000342-11-9

Identification

  • Product Name:Methyl 3-amino-5-bromo-2-methylbenzoate

  • CAS Number: 1000342-11-9

  • EINECS:811-830-5

  • Molecular Weight:244.088

  • Molecular Formula:C9H10BrNO2

  • HS Code:2922499990

  • Mol File:1000342-11-9.mol

Synonyms:3-Amino-5-bromo-2-methylbenzoic acid methyl ester; benzoic acid, 3-amino-5-bromo-2-methyl-, methyl ester

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye 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

Supplier and reference price

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  • Manufacture/Brand:AK Scientific
  • Product Description:Methyl 3-Amino-5-bromo-2-methylbenzoate
  • Packaging:1g
  • Price:$ 25
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  • Manufacture/Brand:Alichem
  • Product Description:Methyl 3-Amino-5-bromo-2-methylbenzoate
  • Packaging:100g
  • Price:$ 400
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  • Manufacture/Brand:Ambeed
  • Product Description:Methyl 3-Amino-5-bromo-2-methylbenzoate 98%
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  • Manufacture/Brand:Ambeed
  • Product Description:Methyl 3-Amino-5-bromo-2-methylbenzoate 98%
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  • Manufacture/Brand:Ambeed
  • Product Description:Methyl 3-Amino-5-bromo-2-methylbenzoate 98%
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  • Manufacture/Brand:Ambeed
  • Product Description:Methyl 3-Amino-5-bromo-2-methylbenzoate 98%
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  • Manufacture/Brand:Ambeed
  • Product Description:Methyl 3-Amino-5-bromo-2-methylbenzoate 98%
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  • Manufacture/Brand:Ambeed
  • Product Description:Methyl 3-Amino-5-bromo-2-methylbenzoate 98%
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:3-AMINO-2-METHYL-5-BROMO BENZOIC ACID METHYL ESTER 95.00%
  • Packaging:5MG
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  • Manufacture/Brand:ChemScene
  • Product Description:Methyl 3-Amino-5-bromo-2-methylbenzoate 99.46%
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Relevant articles and documentsAll total 22 Articles be found

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Ning, Xiang-Li,Li, Yu-Zhi,Huo, Cui,Deng, Ji,Gao, Cheng,Zhu, Kai-Rong,Wang, Miao,Wu, Yu-Xiang,Yu, Jun-Lin,Ren, Ya-Li,Luo, Zong-Yuan,Li, Gen,Chen, Yang,Wang, Si-Yao,Peng, Cheng,Yang, Ling-Ling,Wang, Zhou-Yu,Wu, Yong,Qian, Shan,Li, Guo-Bo

supporting information, p. 8303 - 8332 (2021/06/30)

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Small molecule compound based on EZH2 protein degradation, and application thereof

-

Paragraph 0031-0035, (2021/08/07)

The invention discloses a series of small molecule compounds capable of selectively degrading EZH2 protein, and application thereof. The compounds can be prepared into proper pharmaceutical dosage forms for EZH2-mediated related tumor treatment.

SKLB1039 Compound as well as preparation method and application thereof

-

, (2021/10/27)

The invention belongs to the technical field of preparation of new compounds, and particularly relates SKLB1039 compound as well as a preparation method and application thereof. The 2 -methyl -3 -nitrobenzoic acid is taken as an initial raw material and is brominated. Esterification, reduction, reductive amination and hydrolysis synthesis 5 - bromo -2 - methyl -3 - (N - ethyl, N - (tetrahydropyran -4 - yl)) aminobenzoic acid. The cyclohexanone serving as a raw material is subjected to catalytic hydrogenation reduction of carbonyl α, acetyl cyclohexanone and cyanopyridone to synthesize 4 - aminomethyl -1 - methyl -5, 6, 7, 8 - tetrahydroisoquinoline -3 (2H) - ketone. Coupling the two to an amide is followed by catalytic coupling with an aryl sheet to give SKLB1039 a compound. SKLB1039 Large-scale preparation technology is provided, operation is easy, the post-treatment purification process is simple, the total route yield is improved, raw materials are easy to purchase, the price is low, and the production cost is greatly reduced.

POLYSUBSTITUTED BENZENE COMPOUND AND PREPARATION METHOD AND USE THEREOF

-

Paragraph 0107-108, (2021/06/10)

The present invention provides a novel EZH2 inhibitor compound represented by formula (I) and a use of the inhibitor compound in preventing or treating a disease mediated by EZH2.

Design, Synthesis, and Evaluation of VHL-Based EZH2 Degraders to Enhance Therapeutic Activity against Lymphoma

Tu, Yalin,Sun, Yameng,Qiao, Shuang,Luo, Yao,Liu, Panpan,Jiang, Zhong-Xing,Hu, Yumin,Wang, Zifeng,Huang, Peng,Wen, Shijun

, p. 10167 - 10184 (2021/07/26)

Traditional EZH2 inhibitors are developed to suppress the enzymatic methylation activity, and they may have therapeutic limitations due to the nonenzymatic functions of EZH2 in cancer development. Here, we report proteolysis-target chimera (PROTAC)-based EZH2 degraders to target the whole EZH2 in lymphoma. Two series of EZH2 degraders were designed and synthesized to hijack E3 ligase systems containing either von Hippel-Lindau (VHL) or cereblon (CRBN), and some VHL-based compounds were able to mediate EZH2 degradation. Two best degraders, YM181 and YM281, induced robust cell viability inhibition in diffuse large B-cell lymphoma (DLBCL) and other subtypes of lymphomas, outperforming a clinically used EZH2 inhibitor EPZ6438 (tazemetostat) that was only effective against DLBCL. The EZH2 degraders displayed promising antitumor activities in lymphoma xenografts and patient-derived primary lymphoma cells. Our study demonstrates that EZH2 degraders have better therapeutic activity than EZH2 inhibitors, which may provide a potential anticancer strategy to treat lymphoma.

Process route upstream and downstream products

Process route

5-bromo-2-methyl-3-nitrobenzoic acid methyl ester
220514-28-3

5-bromo-2-methyl-3-nitrobenzoic acid methyl ester

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With iron; ammonium chloride;Inethanol; water;at 90 ℃; for 1h;
99.1%
With iron; ammonium chloride;Inethanol; water;at 90 ℃; for 1h; Product distribution / selectivity;
99.14%
With ethanol; iron; ammonium chloride;Inwater; ethyl acetate;at 80 ℃; for 5h;
99%
With water; iron; ammonium chloride;Inethanol;at 90 ℃; for 1h;
99%
With ammonium chloride; zinc;Inmethanol; water;at 20 ℃; for 1.5h;
96.2%
5-bromo-2-methyl-3-nitrobenzoic acid methyl ester;With water; ammonium chloride;Inmethanol;for 0.5h; Inert atmosphere; Reflux; Large scale;
With iron;Inmethanol;for 3.33333h; Inert atmosphere; Reflux; Large scale;
95.5%
With iron; ammonium chloride;Inmethanol; water;at 80 ℃; for 1h;
92%
With iron; ammonium chloride;Inethanol; water;at 80 ℃; for 1h;
92%
With iron; ammonium chloride;Intetrahydrofuran; water;at 80 ℃; for 3h;
90%
With iron; ammonium chloride;Inmethanol; water;at 70 ℃; for 2h;
90%
With iron; ammonium chloride;Inmethanol; water;for 0.5h; Reflux;
90.9%
With methanol; iron; ammonium chloride; at 90 ℃;
90%
5-bromo-2-methyl-3-nitrobenzoic acid methyl ester;With ammonium chloride;Inethanol; water;at 80 ℃;
With iron;Inethanol; water;at 80 ℃; for 12h;
85%
With iron; ammonium chloride;Inethanol; water;at 80 ℃; for 12h;
85%
With iron; ammonium chloride;Inethanol; water;at 80 ℃; for 12h;
85%
With iron; ammonium chloride;Inethanol; water;at 80 ℃;
83%
With iron; ammonium chloride;Inethanol;at 80 ℃;
83%
With iron; ammonium chloride;Inmethanol; water;at 100 ℃; for 12h;
49.4%
With iron; ammonium chloride;Inethanol; water;at 80 ℃; for 7h; Product distribution / selectivity;
With iron; ammonium chloride;Inethanol; water;at 70 ℃; for 15h;
With iron; ammonium chloride;Inethanol; water;at 80 ℃; Inert atmosphere;
With iron; ammonium chloride;Inmethanol;at 90 ℃;
5-bromo-2-methyl-3-nitro-benzoic acid
107650-20-4

5-bromo-2-methyl-3-nitro-benzoic acid

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; iron / ethanol; water / 1 h / 90 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; iron / ethanol; water / 7 h / 80 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 20 - 60 °C
2.1: ammonium chloride / ethanol; water / 80 °C
2.2: 12 h / 80 °C
With sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; iron / water; ethanol / 12 h / 80 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; ethanol; iron / water; ethyl acetate / 5 h / 80 °C
With ethanol; iron; sodium carbonate; ammonium chloride;Inwater; ethyl acetate; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; iron / water; ethanol / 12 h / 80 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 16 h / 60 °C
2: ammonium chloride; iron / ethanol; water / 15 h / 70 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 10 h / 20 - 55 °C
2: iron; ammonium chloride / tetrahydrofuran; water / 3 h / 80 °C
With iron; sodium carbonate; ammonium chloride;Intetrahydrofuran; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: water; ammonium chloride; iron / ethanol / 1 h / 90 °C
With water; iron; sodium carbonate; ammonium chloride;Inethanol; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: thionyl chloride / Reflux
2: ammonium chloride; iron / water; ethanol / 80 °C
With thionyl chloride; iron; ammonium chloride;Inethanol; water;
Multi-step reaction with 2 steps
1: thionyl chloride / Reflux
2: iron; ammonium chloride / ethanol / 80 °C
With thionyl chloride; iron; ammonium chloride;Inethanol;
Multi-step reaction with 2 steps
1: sulfuric acid
2: ammonium chloride; zinc / methanol; water / 1.5 h / 20 °C
With sulfuric acid; ammonium chloride; zinc;Inmethanol; water;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h
2: ammonium chloride; iron / water; methanol / 2 h / 70 °C
With iron; sodium carbonate; ammonium chloride;Inmethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere; Large scale
1.2: 19 h / 20 °C / Inert atmosphere; Large scale
2.1: water; ammonium chloride / methanol / 0.5 h / Inert atmosphere; Reflux; Large scale
2.2: 3.33 h / Inert atmosphere; Reflux; Large scale
With water; sodium carbonate; ammonium chloride;Inmethanol; N,N-dimethyl-formamide;
2-methyl-3-nitrobenzic acid
1975-50-4

2-methyl-3-nitrobenzic acid

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / ethanol; water / 1 h / 90 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / ethanol; water / 7 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid / 5 h / 20 °C
1.2: Cooling
2.1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3.1: ammonium chloride; iron / ethanol; water / 1 h / 90 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1.1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 5 h / 20 °C
2.1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 20 - 60 °C
3.1: ammonium chloride / ethanol; water / 80 °C
3.2: 12 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / water; ethanol / 12 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 5 h / 0 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; ethanol; iron / water; ethyl acetate / 5 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; ethanol; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inwater; ethyl acetate; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / sulfuric acid / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / water; ethanol / 12 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; iron; sodium carbonate; ammonium chloride;Inethanol; sulfuric acid; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: N-Bromosuccinimide; sulfuric acid / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: water; ammonium chloride; iron / ethanol / 1 h / 90 °C
With N-Bromosuccinimide; sulfuric acid; water; iron; sodium carbonate; ammonium chloride;Inethanol; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid / 5 h / 20 °C
2: thionyl chloride / Reflux
3: ammonium chloride; iron / water; ethanol / 80 °C
With thionyl chloride; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; ammonium chloride;Inethanol; water;
Multi-step reaction with 3 steps
1: sulfuric acid / 5 h / 20 °C
2: thionyl chloride / Reflux
3: iron; ammonium chloride / ethanol / 80 °C
With thionyl chloride; sulfuric acid; iron; ammonium chloride;Inethanol;
Multi-step reaction with 3 steps
1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h
3: ammonium chloride; iron / water; methanol / 2 h / 70 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inmethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: thionyl chloride / 2 h / Inert atmosphere; Heating
2: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / Inert atmosphere
3: iron; ammonium chloride / ethanol; water / 80 °C / Inert atmosphere
With thionyl chloride; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; iron; ammonium chloride;Inethanol; water;
Multi-step reaction with 3 steps
1.1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 32.5 h / 3 - 25 °C / Inert atmosphere; Large scale
2.1: sodium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere; Large scale
2.2: 19 h / 20 °C / Inert atmosphere; Large scale
3.1: water; ammonium chloride / methanol / 0.5 h / Inert atmosphere; Reflux; Large scale
3.2: 3.33 h / Inert atmosphere; Reflux; Large scale
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; water; sodium carbonate; ammonium chloride;Inmethanol; N,N-dimethyl-formamide;
5-bromo-2-methylbenzoic acid
79669-49-1

5-bromo-2-methylbenzoic acid

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: nitric acid; sulfuric acid / acetone / 2.25 h / -5 - 0 °C / Cooling with acetone-ice
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / ethanol; water / 7 h / 80 °C
With sulfuric acid; nitric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide; acetone;
Multi-step reaction with 3 steps
1.1: sulfuric acid / 0.17 h / -10 °C
1.2: 1 h / -10 °C
2.1: sulfuric acid
3.1: ammonium chloride; zinc / methanol; water / 1.5 h / 20 °C
With sulfuric acid; ammonium chloride; zinc;Inmethanol; water;
2-methyl-3-nitro-benzoic acid methyl ester
59382-59-1

2-methyl-3-nitro-benzoic acid methyl ester

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / Inert atmosphere
2: iron; ammonium chloride / ethanol; water / 80 °C / Inert atmosphere
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; iron; ammonium chloride;Inethanol; water;
5-bromo-2-methyl-3-nitrobenzoic acid methyl ester
220514-28-3

5-bromo-2-methyl-3-nitrobenzoic acid methyl ester

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With iron; ammonium chloride;Inethanol; water;at 90 ℃; for 1h;
99.1%
With iron; ammonium chloride;Inethanol; water;at 90 ℃; for 1h; Product distribution / selectivity;
99.14%
With ethanol; iron; ammonium chloride;Inwater; ethyl acetate;at 80 ℃; for 5h;
99%
With water; iron; ammonium chloride;Inethanol;at 90 ℃; for 1h;
99%
With ammonium chloride; zinc;Inmethanol; water;at 20 ℃; for 1.5h;
96.2%
5-bromo-2-methyl-3-nitrobenzoic acid methyl ester;With water; ammonium chloride;Inmethanol;for 0.5h; Inert atmosphere; Reflux; Large scale;
With iron;Inmethanol;for 3.33333h; Inert atmosphere; Reflux; Large scale;
95.5%
With iron; ammonium chloride;Inmethanol; water;at 80 ℃; for 1h;
92%
With iron; ammonium chloride;Inethanol; water;at 80 ℃; for 1h;
92%
With iron; ammonium chloride;Intetrahydrofuran; water;at 80 ℃; for 3h;
90%
With iron; ammonium chloride;Inmethanol; water;at 70 ℃; for 2h;
90%
With iron; ammonium chloride;Inmethanol; water;for 0.5h; Reflux;
90.9%
With methanol; iron; ammonium chloride; at 90 ℃;
90%
5-bromo-2-methyl-3-nitrobenzoic acid methyl ester;With ammonium chloride;Inethanol; water;at 80 ℃;
With iron;Inethanol; water;at 80 ℃; for 12h;
85%
With iron; ammonium chloride;Inethanol; water;at 80 ℃; for 12h;
85%
With iron; ammonium chloride;Inethanol; water;at 80 ℃; for 12h;
85%
With iron; ammonium chloride;Inethanol; water;at 80 ℃;
83%
With iron; ammonium chloride;Inethanol;at 80 ℃;
83%
With iron; ammonium chloride;Inmethanol; water;at 100 ℃; for 12h;
49.4%
With iron; ammonium chloride;Inethanol; water;at 80 ℃; for 7h; Product distribution / selectivity;
With iron; ammonium chloride;Inethanol; water;at 70 ℃; for 15h;
With iron; ammonium chloride;Inethanol; water;at 80 ℃; Inert atmosphere;
With iron; ammonium chloride;Inmethanol;at 90 ℃;
5-bromo-2-methyl-3-nitro-benzoic acid
107650-20-4

5-bromo-2-methyl-3-nitro-benzoic acid

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; iron / ethanol; water / 1 h / 90 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; iron / ethanol; water / 7 h / 80 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 20 - 60 °C
2.1: ammonium chloride / ethanol; water / 80 °C
2.2: 12 h / 80 °C
With sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; iron / water; ethanol / 12 h / 80 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; ethanol; iron / water; ethyl acetate / 5 h / 80 °C
With ethanol; iron; sodium carbonate; ammonium chloride;Inwater; ethyl acetate; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: ammonium chloride; iron / water; ethanol / 12 h / 80 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 16 h / 60 °C
2: ammonium chloride; iron / ethanol; water / 15 h / 70 °C
With iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 10 h / 20 - 55 °C
2: iron; ammonium chloride / tetrahydrofuran; water / 3 h / 80 °C
With iron; sodium carbonate; ammonium chloride;Intetrahydrofuran; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
2: water; ammonium chloride; iron / ethanol / 1 h / 90 °C
With water; iron; sodium carbonate; ammonium chloride;Inethanol; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: thionyl chloride / Reflux
2: ammonium chloride; iron / water; ethanol / 80 °C
With thionyl chloride; iron; ammonium chloride;Inethanol; water;
Multi-step reaction with 2 steps
1: thionyl chloride / Reflux
2: iron; ammonium chloride / ethanol / 80 °C
With thionyl chloride; iron; ammonium chloride;Inethanol;
Multi-step reaction with 2 steps
1: sulfuric acid
2: ammonium chloride; zinc / methanol; water / 1.5 h / 20 °C
With sulfuric acid; ammonium chloride; zinc;Inmethanol; water;
Multi-step reaction with 2 steps
1: sodium carbonate / N,N-dimethyl-formamide / 8 h
2: ammonium chloride; iron / water; methanol / 2 h / 70 °C
With iron; sodium carbonate; ammonium chloride;Inmethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1.1: sodium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere; Large scale
1.2: 19 h / 20 °C / Inert atmosphere; Large scale
2.1: water; ammonium chloride / methanol / 0.5 h / Inert atmosphere; Reflux; Large scale
2.2: 3.33 h / Inert atmosphere; Reflux; Large scale
With water; sodium carbonate; ammonium chloride;Inmethanol; N,N-dimethyl-formamide;
2-methyl-3-nitrobenzic acid
1975-50-4

2-methyl-3-nitrobenzic acid

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / ethanol; water / 1 h / 90 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / ethanol; water / 7 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid / 5 h / 20 °C
1.2: Cooling
2.1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3.1: ammonium chloride; iron / ethanol; water / 1 h / 90 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1.1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 5 h / 20 °C
2.1: sodium carbonate / N,N-dimethyl-formamide / 8 h / 20 - 60 °C
3.1: ammonium chloride / ethanol; water / 80 °C
3.2: 12 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / water; ethanol / 12 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 5 h / 0 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; ethanol; iron / water; ethyl acetate / 5 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; ethanol; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inwater; ethyl acetate; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / sulfuric acid / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / water; ethanol / 12 h / 80 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; iron; sodium carbonate; ammonium chloride;Inethanol; sulfuric acid; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: N-Bromosuccinimide; sulfuric acid / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: water; ammonium chloride; iron / ethanol / 1 h / 90 °C
With N-Bromosuccinimide; sulfuric acid; water; iron; sodium carbonate; ammonium chloride;Inethanol; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid / 5 h / 20 °C
2: thionyl chloride / Reflux
3: ammonium chloride; iron / water; ethanol / 80 °C
With thionyl chloride; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; ammonium chloride;Inethanol; water;
Multi-step reaction with 3 steps
1: sulfuric acid / 5 h / 20 °C
2: thionyl chloride / Reflux
3: iron; ammonium chloride / ethanol / 80 °C
With thionyl chloride; sulfuric acid; iron; ammonium chloride;Inethanol;
Multi-step reaction with 3 steps
1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 5 h / 20 °C
2: sodium carbonate / N,N-dimethyl-formamide / 8 h
3: ammonium chloride; iron / water; methanol / 2 h / 70 °C
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; iron; sodium carbonate; ammonium chloride;Inmethanol; water; N,N-dimethyl-formamide;
Multi-step reaction with 3 steps
1: thionyl chloride / 2 h / Inert atmosphere; Heating
2: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / Inert atmosphere
3: iron; ammonium chloride / ethanol; water / 80 °C / Inert atmosphere
With thionyl chloride; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; iron; ammonium chloride;Inethanol; water;
Multi-step reaction with 3 steps
1.1: sulfuric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 32.5 h / 3 - 25 °C / Inert atmosphere; Large scale
2.1: sodium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere; Large scale
2.2: 19 h / 20 °C / Inert atmosphere; Large scale
3.1: water; ammonium chloride / methanol / 0.5 h / Inert atmosphere; Reflux; Large scale
3.2: 3.33 h / Inert atmosphere; Reflux; Large scale
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; water; sodium carbonate; ammonium chloride;Inmethanol; N,N-dimethyl-formamide;
5-bromo-2-methylbenzoic acid
79669-49-1

5-bromo-2-methylbenzoic acid

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: nitric acid; sulfuric acid / acetone / 2.25 h / -5 - 0 °C / Cooling with acetone-ice
2: sodium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C
3: ammonium chloride; iron / ethanol; water / 7 h / 80 °C
With sulfuric acid; nitric acid; iron; sodium carbonate; ammonium chloride;Inethanol; water; N,N-dimethyl-formamide; acetone;
Multi-step reaction with 3 steps
1.1: sulfuric acid / 0.17 h / -10 °C
1.2: 1 h / -10 °C
2.1: sulfuric acid
3.1: ammonium chloride; zinc / methanol; water / 1.5 h / 20 °C
With sulfuric acid; ammonium chloride; zinc;Inmethanol; water;
2-methyl-3-nitro-benzoic acid methyl ester
59382-59-1

2-methyl-3-nitro-benzoic acid methyl ester

2-methyl-3-amino-5-bromobenzoic acid methyl ester
1000342-11-9

2-methyl-3-amino-5-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / Inert atmosphere
2: iron; ammonium chloride / ethanol; water / 80 °C / Inert atmosphere
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; iron; ammonium chloride;Inethanol; water;

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