Lot numbers can be found on the outside label of a product:
Benzoic acid, 5-amino-2-bromo-4-methyl-, methyl ester
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CAS No. 474330-54-6
- Cat. No. CS-0030486
- Purity≥95%
- MDL No.MFCD14706185
*For research and further manufacturing use only, not for direct human use.
Structure of 474330-54-6
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General Information
- CAS No. 474330-54-6
- Cat. No. CS-0030486
- Purity ≥95%
- MDL No. MFCD14706185
- Storage 4°C, protect from light
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₉H₁₀BrNO₂
- Molecular Weight 244.09
- Synonym(s) methyl 5-amino-2-bromo-4-methylbenzoate hydrochloride
- SMILES O=C(OC)C1=CC(N)=C(C)C=C1Br
Description
Methyl 5-amino-2-bromo-4-methylbenzoate features a brominated aromatic core with complementary amino and methyl substituents, enabling selective coupling in cross-coupling reactions. The electron-donating amino group enhances reactivity at the para-position, while the ester functionality offers straightforward derivatization. This compound serves as a key intermediate in the synthesis of bioactive heterocycles and functionalized pharmaceuticals under standard conditions.
Application
Methyl 5-amino-2-bromo-4-methylbenzoate serves as a versatile building block in medicinal chemistry, enabling selective functionalization at the amino and bromo sites. The ortho-bromo group facilitates palladium-catalyzed cross-coupling reactions, while the amino function supports acylation, sulfonation, or diazotization. Bench-stable and amenable to purification by recrystallization, it functions effectively in the synthesis of substituted heterocycles and bioactive scaffolds.
Synthesis
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Route1
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67-56-1 -
In-stock
745048-63-9 - ~96%
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In-stock
474330-54-6
References
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Xu, Baihua; Lv, Binhua; Feng, Yan; Xu, Ge; Du, Jiyan; Welihinda, Ajith; Sheng, Zelin; Seed, Brian; Chen, Yuanwei Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 19 p. 5632 - 5635 Title/Abstract Full Text View citing articles Show Details Lv, Binhua; Xu, Baihua; Feng, Yan; Peng, Kun; Xu, Ge; Du, Jiyan; Zhang, Lili; Zhang, Wenbin; Zhang, Ting; Zhu, Liangcheng; Ding, Haifeng; Sheng, Zelin; Welihinda, Ajith; Seed, Brian; Chen, Yuanwei Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 24 p. 6877 - 6881
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Route2
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In-stock
745048-63-9
- ~94%
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In-stock
474330-54-6
References
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Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; AKAMA, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen Patent: US2013/131017 A1, 2013 ; Location in patent: Paragraph 0380; 0582 ;
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Route3
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18595-18-1 - ~77%
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In-stock
474330-54-6
References
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Bhisetti, Govinda R.; Saunders, Jeffrey O.; Murcko, Mark A.; Lepre, Christopher A.; Britt, Shawn D.; Come, Jon H.; Deininger, David D.; Wang, Tianshang Patent: US2003/95958 A1, 2003 ; US 20030095958 A1
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 52.32
- LogP 2.12632
- H_Acceptors 3
- H_Donors 1
- Rotatable_Bonds 1
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Key Words
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