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2-(3-bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride
  • 2-(3-bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride2-(3-bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride

2-(3-bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride

Model: 92015-18-4
The compound is 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride, a substituted phenethylamine derivative characterized by the presence of a bromine atom at the meta position relative to the ethylamine side chain, two methoxy groups at the 4- and 5-positions, and a primary amine group forming the hydrochloride salt. Structurally, the molecule comprises a 3,4,5-trisubstituted benzene ring bearing a two‑carbon ethylamine tether, creating an architecture that closely resembles the endogenous neurotransmitters dopamine and noradrenaline, yet with distinct substitutional differences. The bromine atom at the 3‑position introduces a heavy halogen with significant polarizability and electron‑withdrawing character, modulating the electronic environment of the aromatic ring and providing a versatile handle for further cross‑coupling functionalization. The 4,5‑dimethoxy substitution pattern, in contrast to the 3,4‑dihydroxy pattern found in dopamine, substantially enhances lipophilicity and metabolic stability while preserving the distance between the aromatic ring and the basic amine nitrogen. The hydrochloride salt form in 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride protonates the primary amine to produce a water‑soluble, non‑hygroscopic crystalline solid, conferring advantages in handling, storage, and formulation over the free base. This precise combination — a phenethylamine backbone, a strategically placed bromine atom for synthetic diversification, a 4,5‑dimethoxylation pattern, and stable hydrochloride salt formation — underlies the compound‘s utility as a critical building block in modern pharmaceutical synthesis and medicinal chemistry.

2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride serves as a versatile synthetic building block in the pharmaceutical industry, finding particular utility as a key intermediate and process-related impurity in the synthesis of baricitinib (Olumiant®), a selective Janus kinase (JAK)1/JAK2 inhibitor approved for the treatment of rheumatoid arthritis, atopic dermatitis, and alopecia areata. As a functionalized phenethylamine scaffold, 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride offers the bromine atom as a handle for palladium‑catalyzed cross‑coupling reactions — including Suzuki–Miyaura, Buchwald–Hartwig, and Sonogashira couplings — enabling the construction of structurally diverse compound libraries for drug discovery programs. In research settings, 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride is primarily used to investigate the pharmacology and signaling mechanisms of the serotonin receptor family, where its interaction with 5‑HT₂ receptors can provide critical insights into receptor function, G‑protein coupling, and downstream signaling pathways. As a reference standard, 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride is employed in quality control (QC) testing for baricitinib, where it appears as a process-related impurity during API manufacturing, making it an important marker for method validation, impurity profiling, and ANDA filing.


Product Parameters

Parameter

Specification

Product Name

2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride

CAS Number

92015-18-4

Molecular Formula

C₁₀H₁₄BrNO₂

Molecular Weight (Hydrochloride)

296.59 g/mol

Purity (HPLC)

≥95% – ≥98% (depending on grade)

Physical Form

Crystalline solid

Appearance

White to off-white powder

Melting Point

199.7 – 200.2 °C


Product Advantages

1.Key Intermediate in Baricitinib Synthesis

2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride is a critical building block in the synthetic route to baricitinib (Olumiant®), a selective JAK1/JAK2 inhibitor used globally for rheumatoid arthritis, atopic dermatitis, and alopecia areata. The bromine atom at the 3‑position provides the handle for the key C–C bond‑forming steps that assemble the full baricitinib molecular architecture.

2.Versatile Cross‑Coupling Handle

The bromine substituent on 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride participates in palladium‑catalyzed cross‑coupling reactions — Suzuki–Miyaura with boronic acids, Buchwald–Hartwig for C–N bond formation, and Sonogashira for alkyne incorporation — enabling rapid diversification of the phenethylamine scaffold for medicinal chemistry hit‑to‑lead optimization.

3.Hydrochloride Salt — Enhanced Water Solubility and Stability

The hydrochloride salt form offers three practical advantages over the free base: enhanced water solubility for biological assays and aqueous reaction systems, improved long‑term storage stability by protecting the primary amine from oxidation, and a non‑hygroscopic crystalline solid that is convenient to weigh and handle in the laboratory.

4.Scales for Every Stage — From Reference Standard to Commercial Batch

From 1g reference standard quantities for analytical method development to 1kg+ batches for commercial API manufacturing, Cosperpharm supplies 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride at any scale required. R&D samples are available for route scouting and reaction optimization.

5.Process Impurity Reference Standard for Baricitinib QC

As a process‑related impurity in baricitinib manufacturing, 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride serves as a certified reference standard for analytical method development, method validation (AMV), quality control (QC) testing, forced degradation studies, and Abbreviated New Drug Application (ANDA) filings. Cosperpharm provides DMF‑ready documentation packages and traceability support for regulatory submissions.


FAQ

Q1: What is the primary application of this compound in pharmaceutical manufacturing?

A: 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride has two principal applications: as a synthetic intermediate in the manufacture of baricitinib, where the bromine atom provides the handle for key C–C bond‑forming cross‑coupling reactions; and as a process impurity reference standard for analytical method development, method validation (AMV), quality control (QC) testing, forced degradation studies, and ANDA filing for generic baricitinib manufacturers.

Q2: Is this compound intended for human consumption?

A: No. 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride is supplied as a chemical intermediate for pharmaceutical synthesis and as an analytical reference standard for quality control purposes only. It is not intended for human consumption, therapeutic administration, or in vivo applications.


Contact us

Ready to source 2-(3-Bromo-4,5-dimethoxyphenyl)ethan-1-amine hydrochloride for your baricitinib intermediate program, impurity profiling, or medicinal chemistry research? Cosperpharm streamlines the procurement process.


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