Methyl 3-amino-4-bromobenzoate

Name: Methyl 3-amino-4-bromobenzoate
Brand: ChemScene
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CAS No. 46064-79-3
Cat. No. CS-W004909
Purity≥97%
MDL No.MFCD00553090

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Methyl 3-amino-4-bromobenzoate|CS-W004909

Structure of 46064-79-3

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General Information

CAS No. 46064-79-3
Cat. No. CS-W004909
Purity ≥97%
MDL No. MFCD00553090
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₈BrNO₂
Molecular Weight 230.06
Synonym(s) Benzoicacid, 3-aMino-4-broMo-, Methyl ester
SMILES NC1=C(C=CC(=C1)C(=O)OC)Br

Description

Methyl 3-amino-4-bromobenzoate features a brominated aromatic core with complementary amino and ester functionalities, enabling direct integration into Suzuki-Miyaura couplings and amide derivatization. The para-bromo group facilitates palladium-catalyzed cross-coupling, while the ortho-amino moiety offers a handle for electrophilic modification or coordination in catalytic systems. This bifunctional scaffold supports rapid access to complex heterocycles and bioactive molecules under standard conditions.

Application

Methyl 3-amino-4-bromobenzoate serves as a versatile building block in medicinal chemistry, enabling sequential functionalization via the orthogonal reactivity of its amino and bromo groups. The amine facilitates coupling reactions or derivatization under mild conditions, while the bromo group supports palladium-catalyzed cross-coupling transformations. Bench-stable and readily purified by recrystallization, it functions efficiently in the synthesis of heterocyclic scaffolds and API intermediates.

Synthesis

Route1
- 67-56-1
- In-stock
  
  2840-29-1
- ~85%
- In-stock
  
  46064-79-3
References
- Hinsberger, Stefan; De Jong, Johannes C.; Groh, Matthias; Haupenthal, Joerg; Hartmann, Rolf W. European Journal of Medicinal Chemistry, 2014 , vol. 76, p. 343 - 351
Route2
- In-stock
  
  2363-16-8
- ~%
- In-stock
  
  46064-79-3
References
- BEIGENE, LTD.; ZHOU, Changyou; REN, Bo; WANG, Hexiang Patent: WO2013/97226 A1, 2013 ; Location in patent: Page/Page column 40; 41 ;
Route3
- In-stock
  
  4518-10-9
- ~8%
- In-stock
  
  6942-37-6
- In-stock
  
  46064-79-3
- In-stock
  
  106896-48-4
References
- Bartoli, Sandra; Cipollone, Amalia; Squarcia, Antonella; Madami, Andrea; Fattori, Daniela Synthesis, 2009 , # 8 art. no. P12608SS, p. 1305 - 1308

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 52.32
LogP 1.8179
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Methyl 3-amino-4-bromobenzoate

CAS No. 46064-79-3

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