2-Bromobenzaldehyde - ≥98% , CAS No.6630-33-7

CAS: 6630-33-7 Cat. No.: B109684 Molecular Weight: 185.02 Beilstein Registry Number: 636132 EC Number: 229-622-2

GRADE & PURITY ≥98%

Synonyms

AKOS000120460 | PS-8508 | 2-Formylbromobenzene | bromo benzaldehyde | FT-0623222 | ortho-Bromobenzaldehyde | 2-brombenzaldehyde | 2-Bromobenzaldehyde, 98% | Q33859440 | B0836 | EN300-20472 | NSC60390 | NSC-60390 | S-Methyl GSH | NSC 60390 | EINECS 229-622

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Synthetic applications of 2-bromobenzaldehyde include: Synthesis of aza-fused polycyclic quinolines through copper-catalyzed cascade reaction. Preparation of 1-substituted indazoles by CuI-catalyzed coupling with N-aryl hydrazides. It is a key starting material in the total synthesis of an anticancer agent, (-)-taxol. Palladium/copper-catalyzed coupling and cyclization of terminal acetylenes derived from 2-bromobenzaldehyde and unsaturated imines can be used in the synthesis of wide range of isoquinolines, including decumbenine B. Fluoren-9-ones can be synthesized by annulation of arynes, generated in situ from 2-(trimethylsilyl)aryl triflates, with 2-bromobenzaldehyde in the presence of palladium(0) catalyst. It can also be used to build a variety of steroid frameworks, in which ring A is derived from 2-bromobenzaldehyde.

Specifications

Synonyms

AKOS000120460 | PS-8508 | 2-Formylbromobenzene | bromo benzaldehyde | FT-0623222 | ortho-Bromobenzaldehyde | 2-brombenzaldehyde | 2-Bromobenzaldehyde, 98% | Q33859440 | B0836 | EN300-20472 | NSC60390 | NSC-60390 | S-Methyl GSH | NSC 60390 | EINECS 229-622

Specifications & Purity

≥98%

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 508808394
• Canonical Smiles: C1=CC=C(C(=C1)C=O)Br
• IUPAC Name: 2-bromobenzaldehyde
• InChIKey: NDOPHXWIAZIXPR-UHFFFAOYSA-N
• INCHI: 1S/C7H5BrO/c8-7-4-2-1-3-6(7)5-9/h1-5H
• Isomeric SMILES: C1=CC=C(C(=C1)C=O)Br
• WGK Germany: 3
• Molecular Weight: 185.02
• Beilstein: 636132
• Reaxy-Rn: 636132
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=636132&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoyl derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoyl derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoyl derivatives
• Alternative Parents: Benzaldehydes Bromobenzenes Aryl bromides Vinylogous halides Organobromides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzaldehyde - Benzoyl - Aryl-aldehyde - Bromobenzene - Halobenzene - Aryl bromide - Aryl halide - Vinylogous halide - Organobromide - Organooxygen compound - Aldehyde - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SLC6A1 Tclin GABA transporter 1 (308 Activities)

Discover Target: SLC6A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Staphylococcus aureus (210822 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

B16-F10 (4610 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in alcohol and benzene. Insoluble in water.
• Sensitivity: air sensitive
• Freezing Point(°C): 16 °C
• Refractive Index: 1.595-1.597
• Flash Point(°F): 203 °F
• Flash Point(°C): 95 °C
• Boil Point(°C): 230°C
• Melt Point(°C): 16 °C
• Molecular Weight: 185.020 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 183.952 Da
• Monoisotopic Mass: 183.952 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 9
• Formal Charge: 0
• Complexity: 103.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Guichuan Xu, Huicai Zheng, Xiaoju Zhang, Wen Li, Limei Zhou, Li Qin.  (2023)  BCN materials with adjustable active sites as heterogeneous acid–base catalysts for Knoevenagel condensation reaction.  Molecular Catalysis,      [PMID:] [10.1016/j.mcat.2023.113447]

2. Xin-Yang Zhang, Ye Du, Yao Lu, Wen-Long Wang, Qian-Yuan Wu.  (2022)  Characteristics of the formation and toxicity index of nine newly identified brominated disinfection byproducts during wastewater ozonation.  SCIENCE OF THE TOTAL ENVIRONMENT,      [PMID:35182650] [10.1016/j.scitotenv.2022.153924]

3. Zhu Anlian, Li Qixing, Feng Wanlu, Fan Dongshuang, Li Lingjun.  (2020)  Biocompatible Ionic Liquid Promote One-Pot Synthesis of 2-Amino-4H-Chromenes Under Ambient Conditions.  CATALYSIS LETTERS,  151  (3): (720-733).  [PMID:] [10.1007/s10562-020-03332-7]

4. Yongjin Li, Liming Wang, Yong Gao, Weijun Yang, Yingying Li, Cancheng Guo.  (2018)  Porous metalloporphyrinic nanospheres constructed from metal 5,10,15,20-tetraksi(4′-ethynylphenyl)porphyrin for efficient catalytic degradation of organic dyes.  RSC Advances,  8  (14): (7330-7339).  [PMID:35539096] [10.1039/C7RA12701D]

5. Yongjin Li, Baoshuai Sun, Yuanrong Zhou, Weijun Yang.  (2016)  Novel conjugated nanoporous alkynyl metalloporphyrin framework as effective catalyst for oxidation of toluene with molecular oxygen.  APPLIED ORGANOMETALLIC CHEMISTRY,  31  (3): (e3578).  [PMID:] [10.1002/aoc.3578]

6. Yu Zhu, Ying Wang, Huimin Zhao, Jinli Wei, Haoyuan Chen, Maroosha Javed, Linghua Zhuang, Guowei Wang.  (2025)  Synthesis, antioxidant activity, DFT simulations, molecular docking studies of Schiff base derivatives containing 2-(2-hydrazinyl) thiazole moiety.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2025.142150]

7. Li Zhigang, Liu Xuzhuo, Wang Chunlong, Song Hanbing, Zhang Jie.  (2024)  Synthesis of novel photothermal nanomaterial ZnSe-PAM@1 and its treatment of knee osteoarthritis cells.  CHEMICAL PAPERS,  78  (14): (7943-7950).  [PMID:] [10.1007/s11696-024-03646-5]