5-(3-Bromophenyl)-1H-tetrazole
CAS3440-99-1
5-(3-Bromophenyl)-1H-tetrazole (CAS 3440-99-1) is a 5-aryl tetrazole building block that combines an acidic NH-tetrazole, a common carboxylic acid bioisostere, with a meta-bromine handle for palladium-catalyzed cross-coupling. It is used to introduce the 3-(tetrazol-5-yl)phenyl motif into drug candidates and functional molecules. KingPharm supplies research and production quantities with a batch-specific certificate of analysis.
- CAS No.
- 3440-99-1
- Formula
- C7H5BrN4
- Mol. weight
- 225.05 g/mol
Product Description
5-(3-Bromophenyl)-1H-tetrazole (C7H5BrN4, MW 225.05) is a 5-substituted tetrazole carrying a bromine atom at the meta position of the phenyl ring. It is a solid with a reported melting point of 150–152 °C and is used as a synthetic intermediate in medicinal chemistry and materials research.
The NH-tetrazole ring is acidic and largely ionized at physiological pH, so it is widely used in place of a carboxylic acid while keeping a similar hydrogen-bonding pattern. The aryl bromide can be elaborated by Suzuki–Miyaura, Buchwald–Hartwig and related couplings, and the tetrazole nitrogen can be alkylated or protected when the coupling conditions require it.
Starting from a pre-formed bromophenyl tetrazole avoids building the tetrazole from a nitrile and an azide late in a synthesis, and lets the aryl core be diversified in one coupling step. The meta substitution pattern complements the para isomer, 5-(4-bromophenyl)-1H-tetrazole, in structure–activity studies.
When sourcing, check HPLC purity, NMR identity and water content, and where relevant confirm that residual azide or tin reagents from tetrazole formation are controlled. KingPharm provides a batch-specific COA and specification; other documents are available on request.
Chemical Specifications
Identifiers
| CAS number | 3440-99-1 |
|---|---|
| Product name | 5-(3-Bromophenyl)-1H-tetrazole |
| Chinese name | 5-(3-溴苯基)-1H-四氮唑 |
| IUPAC name | 5-(3-bromophenyl)-2H-tetrazole |
| Synonyms | 5-(3-BROMOPHENYL)-1H-TETRAZOLE |
| Chinese synonyms | 5-(3-溴苯基)-1H-四氮唑; 5-(3-溴苯基)-1H-四唑; 5-(3-溴苯基)-1H-四唑,97% |
| Molecular formula | C7H5BrN4 |
| Molecular weight | 225.05 g/mol |
| MDL number | MFCD01075675 |
| PubChem CID | 4073056 |
| InChIKey | UVKPUDRFBHSFJH-UHFFFAOYSA-N |
| SMILES | C1=CC(=CC(=C1)Br)C2=NNN=N2 |
Physical and chemical properties
| Melting Point | 150-152 ( ℃ ) |
|---|---|
| Boiling Point | 190.1 ( ℃ ) |
Applications
Typical uses of 5-(3-bromophenyl)-1H-tetrazole in research and development:
Carboxylic acid bioisostere
Introduces an acidic tetrazole in place of a carboxylic acid to tune metabolic stability and lipophilicity in drug candidates.
Cross-coupling building block
The meta aryl bromide undergoes Suzuki–Miyaura and related couplings to give biaryl and heteroaryl tetrazoles.
Structure–activity studies
Serves as the meta isomer alongside the para analogue when mapping substitution effects on target binding.
Coordination chemistry
The tetrazolate anion acts as a nitrogen-donor ligand for metal complexes and coordination polymers.
Quality Documentation
The following documents can be provided for 5-(3-Bromophenyl)-1H-tetrazole to support technical evaluation and purchasing. Documents are issued for the specific grade and batch supplied.
-
Certificate of Analysis (COA) Batch-specific test results against the specification.
-
Product specification The release specification with test items, limits and methods.
Packaging, Storage & Transport
| Available pack sizes | 25 kg, 10 kg, 1 kg, 500 g, 100 g, 25 g |
|---|
Read the current safety data sheet before handling. Packaging can be adapted to the order quantity and destination.
Frequently Asked Questions
How does it differ from 5-(4-bromophenyl)-1H-tetrazole?
The two are positional isomers. The meta isomer places the tetrazole at an angle to the coupling site, giving a different geometry in the resulting biaryl; choose according to the target design.
Does the tetrazole need protection before cross-coupling?
The free NH is acidic and consumes base, and may interact with the catalyst. Many couplings proceed with additional base; otherwise protect the tetrazole nitrogen (e.g. trityl) and remove the group afterwards.
How should it be stored?
Keep tightly closed at room temperature under an inert atmosphere, protected from moisture. As with other tetrazoles, avoid strong heating.
What is the CAS number of 5-(3-Bromophenyl)-1H-tetrazole?
The CAS Registry Number of 5-(3-Bromophenyl)-1H-tetrazole is 3440-99-1. 5-(3-Bromophenyl)-1H-tetrazole is also known as 5-(3-BROMOPHENYL)-1H-TETRAZOLE.
What is the molecular formula and molecular weight of 5-(3-Bromophenyl)-1H-tetrazole?
The molecular formula of 5-(3-Bromophenyl)-1H-tetrazole is C7H5BrN4, and its molecular weight is 225.05 g/mol.
What is 5-(3-Bromophenyl)-1H-tetrazole used for?
Typical uses of 5-(3-bromophenyl)-1H-tetrazole in research and development:
Which quality documents are available for 5-(3-Bromophenyl)-1H-tetrazole?
The following documents are available for 5-(3-Bromophenyl)-1H-tetrazole: Certificate of Analysis (COA); Product specification. Contact KingPharm to request the documents for a specific batch.
How can I request a quotation for 5-(3-Bromophenyl)-1H-tetrazole?
Send an inquiry for 5-(3-Bromophenyl)-1H-tetrazole (CAS 3440-99-1) with the required quantity, target specification, destination country and any documentation requirements. KingPharm will confirm availability, packaging, lead time and price.
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