1-(tert-Butylamino)-3-chloropropan-2-ol hydrochloride
[CAS# 41052-94-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 1-(tert-Butylamino)-3-chloropropan-2-ol hydrochloride
• Molecular Formula: C₇H₁₇Cl₂NO
• Molecular Weight: 202.12
• CAS Registry Number: 41052-94-2
• EC Number: 811-399-3
• SMILES: CC(C)(C)NCC(CCl)O.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302+H332-H302-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P270-P271-P272-P273-P280-P301+P317-P302+P352-P304+P340-P317-P321-P330-P333+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

1-(tert-Butylamino)-3-chloropropan-2-ol hydrochloride is a synthetic compound known for its pharmacological significance, particularly in the development of beta-blocker medications. This molecule's structure consists of a tert-butylamino group attached to a chloropropanol backbone, which allows it to interact effectively with beta-adrenergic receptors. The hydrochloride salt form enhances its solubility and stability, making it suitable for pharmaceutical applications.

The discovery of 1-(tert-butylamino)-3-chloropropan-2-ol hydrochloride is closely linked to research aimed at improving the efficacy and specificity of beta-adrenergic antagonists. In the mid-20th century, scientists were exploring ways to modify the basic structure of beta-blockers to optimize their therapeutic properties. This compound emerged as a key intermediate in the synthesis of selective beta-blockers, which are used to treat cardiovascular conditions such as hypertension, angina, and arrhythmias. The introduction of the tert-butyl group was crucial for enhancing receptor selectivity and reducing unwanted side effects.

The synthesis of 1-(tert-butylamino)-3-chloropropan-2-ol hydrochloride typically involves the reaction of epichlorohydrin with tert-butylamine. The reaction proceeds through nucleophilic substitution, where the amino group attacks the epoxide ring, forming the chloropropanol structure. The final step involves converting the free base to its hydrochloride salt to improve the compound's stability and ease of handling. This method is widely used due to its simplicity and efficiency.

This compound plays an important role as an intermediate in the production of beta-blockers such as propranolol and other related drugs. Beta-blockers derived from this compound are used extensively in clinical practice to manage heart-related conditions by blocking the effects of adrenaline on the heart, thereby reducing heart rate and blood pressure. These medications are also used for migraine prevention and managing symptoms of anxiety.

Research continues to explore modifications of this compound to develop new beta-blockers with improved selectivity, reduced side effects, and broader therapeutic applications. The versatility of 1-(tert-butylamino)-3-chloropropan-2-ol hydrochloride in pharmaceutical synthesis highlights its importance in medicinal chemistry and its ongoing relevance in cardiovascular drug development.