2-(Bromomethyl)-3-nitrobenzoic acid

• CAS: 632340-56-8
• Catalog Number: ACM632340568
• Category: Other Products
• Molecular Weight: 260.04
• Molecular Formula: C8H6BrNO4
• Description: 2-(Bromomethyl)-3-nitrobenzoic acid is a chemical compound that is widely used in scientific research. It is a derivative of benzoic acid and contains a nitro group and a bromomethyl group. This compound has several applications in the fields of chemistry, biochemistry, and pharmacology.
• Synonyms: Benzoic acid, 2-(bromomethyl)-3-nitro-
• IUPAC Name: 2-(bromomethyl)-3-nitrobenzoic acid
• Canonical SMILES: C1=CC(=C(C(=C1)[N+](=O)[O-])CBr)C(=O)O
• InChI: InChI=1S/C8H6BrNO4/c9-4-6-5(8(11)12)2-1-3-7(6)10(13)14/h1-3H,4H2,(H,11,12)
• InChI Key: WNTCNOMUJRQWGP-UHFFFAOYSA-N
• Boiling Point: 381.088ºC at 760 mmHg
• Flash Point: 184.276ºC
• Density: 1.815 g/mL
• Application: 2-(Bromomethyl)-3-nitrobenzoic acid has several applications in scientific research. It is used as a reagent in organic synthesis reactions to introduce a bromomethyl group into various compounds. This compound is also used as a fluorescent probe to study the binding interactions of proteins and nucleic acids. Additionally, it is used as a precursor for the synthesis of various bioactive molecules.
• Storage: Store at 0-8 °C
• Exact Mass: 258.948
• HTS Code: 2916397900
• MDL Number: MFCD11042348
• PSA: 83.12
• Refractive Index: 1.652
• Shipping: Room Temp
• XLogP3: 2.7111

Case Study

Method of Synthesizing Lenalidomide from 2-(Bromomethyl)-3-Nitrobenzoic Acid

A. N. Balaev, et al. Pharmaceutical Chemistry Journal, 2013, 46,676-678.

The synthesis steps of conventional lenalidomide are shown in Scheme 1, including four steps, with a yield of approximately 51%.
An alternative preparation method (Scheme 2) greatly simplifies the synthesis of lenalidomide and enables it to be obtained in a higher yield (59.8%). The preparation procedure starting from 2-(Bromomethyl)-3-nitrobenzoic acid includes:
· Condensation of 2-(Bromomethyl)-3-nitrobenzoic acid (III) with 3-aminopiperidine-2,6-dione (VI) at room temperature in DMF in the presence of NEt3 gave V. The yield of V under the selected reaction conditions was 86%.
· Compound I was obtained by hydrogenation of V using palladium hydroxide. Use of palladium hydroxide instead of Pd on C enabled the reaction to be carried out at atmospheric pressure and the yield of the hydrogenation step to be increased to 79%. Thus, the overall yield of I for the whole scheme was 59.8%; the purity, 99.6% (by HPLC).

Custom Q&A

What is the molecular formula of 2-(bromomethyl)-3-nitrobenzoic acid?

The molecular formula of 2-(bromomethyl)-3-nitrobenzoic acid is C8H6BrNO4.

What is the IUPAC name of 2-(bromomethyl)-3-nitrobenzoic acid?

The IUPAC name of 2-(bromomethyl)-3-nitrobenzoic acid is 2-(bromomethyl)-3-nitrobenzoic acid.

What is the InChIKey of 2-(bromomethyl)-3-nitrobenzoic acid?

The InChIKey of 2-(bromomethyl)-3-nitrobenzoic acid is WNTCNOMUJRQWGP-UHFFFAOYSA-N.

What is the molecular weight of 2-(bromomethyl)-3-nitrobenzoic acid?

The molecular weight of 2-(bromomethyl)-3-nitrobenzoic acid is 260.04 g/mol.

How many hydrogen bond donor counts does 2-(bromomethyl)-3-nitrobenzoic acid have?

2-(bromomethyl)-3-nitrobenzoic acid has 1 hydrogen bond donor count.

What is the topological polar surface area of 2-(bromomethyl)-3-nitrobenzoic acid?

The topological polar surface area of 2-(bromomethyl)-3-nitrobenzoic acid is 83.1Ų.

How many heavy atoms are present in 2-(bromomethyl)-3-nitrobenzoic acid?

2-(bromomethyl)-3-nitrobenzoic acid has 14 heavy atoms.

Is 2-(bromomethyl)-3-nitrobenzoic acid considered a canonical compound?

Yes, 2-(bromomethyl)-3-nitrobenzoic acid is considered a canonical compound.

What is the XLogP3-AA value of 2-(bromomethyl)-3-nitrobenzoic acid?

The XLogP3-AA value of 2-(bromomethyl)-3-nitrobenzoic acid is 1.8.

What is the CAS number of 2-(bromomethyl)-3-nitrobenzoic acid?

The CAS number of 2-(bromomethyl)-3-nitrobenzoic acid is 632340-56-8.