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Cas Database

101084-39-3

101084-39-3

Identification

  • Product Name:Benzoic acid,3-bromo-2-methoxy-

  • CAS Number: 101084-39-3

  • EINECS:

  • Molecular Weight:231.046

  • Molecular Formula: C8H7BrO3

  • HS Code:2918990090

  • Mol File:101084-39-3.mol

Synonyms:o-Anisicacid, 3-bromo- (6CI);2-Methoxy-3-bromobenzoic acid;3-Bromo-2-methoxybenzoicacid;NSC 76704;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT,HarmfulXn

  • Hazard Codes:Xi,T

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowed

  • 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:TCI Chemical
  • Product Description:3-Bromo-2-methoxybenzoic Acid
  • Packaging:1G
  • Price:$ 39
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Bromo-2-methoxybenzoic Acid
  • Packaging:5G
  • Price:$ 134
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3-Bromo-2-methoxybenzoic acid 97%
  • Packaging:25 g
  • Price:$ 317
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3-Bromo-2-methoxybenzoic acid 97%
  • Packaging:5 g
  • Price:$ 133
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Bromo-2-methoxybenzoic acid 97%
  • Packaging:5g
  • Price:$ 140
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Bromo-2-methoxybenzoic acid 97%
  • Packaging:1g
  • Price:$ 43.6
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  • Manufacture/Brand:Oakwood
  • Product Description:3-Bromoanisicacid
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3-Bromo-2-methoxybenzoic acid 95+%
  • Packaging:5g
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:3-Bromo-2-methoxybenzoic acid 95+%
  • Packaging:25g
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  • Manufacture/Brand:Crysdot
  • Product Description:3-Bromo-2-methoxybenzoic Acid 98%
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Relevant articles and documentsAll total 6 Articles be found

A New Synthesis of 3-Bromo-2-methoxybenzoic Acid

Pudleiner, Heinz,Laatsch, Hartmut

, p. 286 - 287 (1989)

A convenient preparation of 3-bromo-2-methoxybenzoic acid (8) from 2-bromophenol via 3-bromo-2-methoxy-1-(1-propenyl)benzene (11) is presented.

Preparation method for intermediates of new medicine Lusutrombopag resisting to thrombopenia

-

Paragraph 0045-0046, (2017/08/15)

The invention discloses a preparation method for intermediates of a new medicine Lusutrombopag resisting to thrombopenia. According to the invention, column chromatography of each step is avoided through an effective method with regard to preparation for an intermediate I, and in addition, bromo-compounds are used for replacing chloro-compounds in the step of ring closure, thus the ring closure has a quantitative yield and is quite easy to operate. In addition, the second carbonyl group and bromine are introduced stepwise, thus the two steps achieve a yield of more than 80%, and are stable and easy to repeat. Compared with the yield of 25-30% of the last two steps of the original research document, the yield is greatly increased, and the preparation method is simple and convenient to operate, and easy to repeat. According to the invention, synthesis for an intermediate II is realized with a quite high yield (70-80%) and an extremely short route through two effective strategies with regard to the intermediate II.

Mono- and disalicylic acid derivatives: PTP1B inhibitors as potential anti-obesity drugs

Shrestha, Suja,Bhattarai, Bharat Raj,Lee, Keun-Hyeung,Cho, Hyeongjin

, p. 6535 - 6548 (2008/04/12)

A series of compounds containing one or two salicylic acid moieties were synthesized, and their efficacy to inhibit the phosphohydrolase activity of PTP1B examined. Some of the methylenedisalicylic acid derivatives were potent inhibitors of PTP1B. Of those derivatives, 3c exhibited about a 14-fold selectivity against TC-PTP, and this compound was tested in a mouse model for its efficacy to prevent diet-induced obesity. It effectively suppressed the increases in body weight and adipose mass, without any noticeable toxic effect. The compound also prevented increases in the plasma triglyceride, cholesterol, and nonesterified fatty acid concentrations; thus, expanding its therapeutic potential to other related metabolic diseases, such as hyperlipidemia and hypercholesterolemia.

First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation

Nguyen, Thi-Huu,Chau, Nguyet Trang Thanh,Castanet, Anne-Sophie,Nguyen, Kim Phi Phung,Mortier, Jacques

, p. 3419 - 3429 (2008/02/03)

(Chemical Equation Presented) New general methodology of value in aromatic chemistry based on ortho-metalation sites in o-, m-, and p-anisic acids (1-3) (Scheme 1) is described. The metalation can be selectively directed to either of the ortho positions by varying the base, metalation temperature, and exposure times. Metalation of o-anisic acid (1) with s-BuLi/TMEDA in THF at -78°C occurs exclusively in the position adjacente to the carboxylate. On the other hand, a reversal of regioselectivity is observed with n-BuLi/t-BuOK. With LTMP at 0°C, the two directors of m-anisic acid (2) function in concert to direct introduction of the metal between them while n-BuLi/t-BuOK removes preferentially the proton located ortho to the methoxy and para to the carboxylate (H-4). s-BuLi/TMEDA reacts with p-anisic acid (3) exclusively in the vicinity of the carboxylate. According to these methodologies, routes to very simple methoxybenzoic acids with a variety of functionalities that are not easily accessible by other means have been developed (Table 1).

Directed ortho-metalation of unprotected benzoic acids. Methodology and regioselective synthesis of useful contiguously 3- and 6-substituted 2-methoxybenzoic acid building blocks

Nguyen, Thi-Huu,Castanet, Anne-Sophie,Mortier, Jacques

, p. 765 - 768 (2007/10/03)

By treatment with s-BuLi/TMEDA at -78 °C, unprotected 2-methoxybenzoic acid is deprotonated exclusively in the position ortho to the carboxylate. A reversal of regioselectivity is observed when the acid is treated with n-BuLi/t-BuOK. These results are of general utility for the one-pot preparation of a variety of very simple 3- and 6-substituted 2-methoxybenzoic acids that are not easily accessible by conventional means. The potential usefulness of the method is demonstrated by the expedient synthesis of lunularic acid.

Marine Bacteria, I. - Synthesis of Pentabromopseudiline, a Cytotoxic Phenylpyrrole from Alteromonas luteo-violaceus

Laatsch, Hartmut,Pudleiner, Heinz

, p. 863 - 882 (2007/10/02)

A new synthesis of 2,3,4-tribromo-5-(3,5-dibromo-2-hydroxyphenyl)pyrrole (1a, pentabromopseudiline), an antibiotic, enzymeinhibitory and cytotoxic active constituent of the marine bacterium Alteromonas luteo-violaceus, is described.For investigation of structure-activity relationships further 2-phenylpyrroles are investigated.Key step in their synthesis is the Grignard reaction of 2-(1,3-dioxan-2-yl)ethylmagnesium bromide (9d) with benzoyl chlorides yielding γ-phenyl-γ-ketoaldehydes 24, and the Paal-Knorr cyclisation of the latter. - Key Words: Alteromonas luteo-violaceus / Bromopyrrole / Marine bacteria / Pentabromopseudiline

Process route upstream and downstream products

Process route

3-bromosalicylic acid
3883-95-2

3-bromosalicylic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

Conditions
Conditions Yield
With potassium carbonate; In acetone;
94%
With sodium hydroxide;
(E)-3-Bromo-2-methoxy-1-prop-1-enylbenzene
93292-77-4

(E)-3-Bromo-2-methoxy-1-prop-1-enylbenzene

2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

Conditions
Conditions Yield
With potassium permanganate; In acetone; at 0 ℃; for 3h;
87%
With potassium permanganate; In acetone; at 0 ℃; for 3h;
57%
2-Methoxybenzoic acid
579-75-9

2-Methoxybenzoic acid

2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

Conditions
Conditions Yield
2-Methoxybenzoic acid; With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 2h;
With 1,2-dibromo-1,1,2,2-tetrachloroethane; In tetrahydrofuran; at -78 - 20 ℃;
34%
With n-butyllithium; 1,2-dibromo-1,1,2,2-tetrachloroethane; potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 1h;
34%
methyl 3-bromo-2-methoxybenzoate
260806-90-4

methyl 3-bromo-2-methoxybenzoate

2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

Conditions
Conditions Yield
With potassium hydroxide; In methanol; water; for 4h; Heating;
87%
2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

1-(3-bromo-2-methoxyphenyl)ethan-1-one
267651-23-0

1-(3-bromo-2-methoxyphenyl)ethan-1-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: thionyl chloride / 2 h / 50 °C
1.2: 16 h / 20 °C
2.1: tetrahydrofuran; diethyl ether / 3 h / 0 °C
With thionyl chloride; In tetrahydrofuran; diethyl ether;
Multi-step reaction with 2 steps
1.1: thionyl chloride / 2 h / 50 °C
1.2: 16 h / 20 °C
2.1: tetrahydrofuran; diethyl ether / 3 h / 0 °C
With thionyl chloride; In tetrahydrofuran; diethyl ether;
Multi-step reaction with 2 steps
1.1: thionyl chloride / 2 h / 50 °C
1.2: 16 h / 20 °C
2.1: methylmagnesium bromide / tetrahydrofuran; diethyl ether / 3 h / 0 °C
With thionyl chloride; methylmagnesium bromide; In tetrahydrofuran; diethyl ether;
Multi-step reaction with 3 steps
1: thionyl chloride / toluene / 2 h / Reflux
2: triethylamine / tetrahydrofuran
3: Methyl formate / tetrahydrofuran
With thionyl chloride; Methyl formate; triethylamine; In tetrahydrofuran; toluene;
methanol
67-56-1

methanol

2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

methyl 3-bromo-2-methoxybenzoate
260806-90-4

methyl 3-bromo-2-methoxybenzoate

Conditions
Conditions Yield
With sulfuric acid; for 24h; Reflux;
99%
With hydrogenchloride;
98%
With pyridine; oxalyl dichloride; In dichloromethane; at 20 ℃;
90%
With sulfuric acid; Reflux;
60%
With sulfuric acid; Reflux;
sulfuric acid; for 14h; Heating / reflux;
2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

3-Bromo-2-methoxy-benzoyl chloride
121789-32-0

3-Bromo-2-methoxy-benzoyl chloride

Conditions
Conditions Yield
With thionyl chloride; In toluene; for 2h; Reflux;
96.8%
With thionyl chloride; for 1h; Heating;
With thionyl chloride; for 3h; Heating;
With thionyl chloride; N,N-dimethyl-formamide; for 1h; Reflux;
With thionyl chloride; at 60 ℃; for 1h;
ethyl (4-amino-3,5-dibromophenyl)acetate
5438-70-0

ethyl (4-amino-3,5-dibromophenyl)acetate

2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

ethyl 2-(4-(3-bromo-2-methoxybenzamido)phenyl)acetate

ethyl 2-(4-(3-bromo-2-methoxybenzamido)phenyl)acetate

Conditions
Conditions Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 0 - 80 ℃; Further stages; Inert atmosphere;
98%
2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

3-bromo-2,N-dimethoxy-N-methyl-benzamide

3-bromo-2,N-dimethoxy-N-methyl-benzamide

Conditions
Conditions Yield
2-methoxy-3-bromobenzoic acid; With thionyl chloride; at 50 ℃; for 2h;
N,O-dimethylhydroxylamine*hydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 16h;
57%
2-methoxy-3-bromobenzoic acid; With thionyl chloride; at 50 ℃; for 2h;
N,O-dimethylhydroxylamine*hydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 16h;
2-methoxy-3-bromobenzoic acid
101084-39-3

2-methoxy-3-bromobenzoic acid

aniline
62-53-3

aniline

3-bromo-2-methoxy-N-phenylbenzamide

3-bromo-2-methoxy-N-phenylbenzamide

Conditions
Conditions Yield
2-methoxy-3-bromobenzoic acid; With thionyl chloride; at 60 ℃; for 1h;
aniline; With pyridine; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;
79%

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