51874-27-2

Basic information

• Product Name: 5-bromopentan-1-amine
• CAS NO: 51874-27-2
• Molecular Formula: BrH*C₅H₁₂BrN
• Molecular Weight: 166.0595
• Mol File: 51874-27-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 190.9°C at 760 mmHg
• Flash Point: 69.2°C
• Density: 1.298g/cm³
• Vapor Pressure: 0.53mmHg at 25°C
• Refractive Index: 1.482
• CAS DataBase Reference: 5-bromopentan-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromopentan-1-amine(51874-27-2)
• EPA Substance Registry System: 5-bromopentan-1-amine(51874-27-2)

Safety Data

• Hazardous Substances Data: 51874-27-2(Hazardous Substances Data)

Usage

General Description

5-Bromopentan-1-amine, also known as 1-Aminopentyl bromide, is a chemical compound with the formula C5H12BrN. It is a primary amine with a bromine substituent on the fifth carbon atom of the pentyl chain. 5-Bromopentan-1-amine is commonly used as a building block in organic synthesis, especially in the preparation of pharmaceuticals and agrochemicals. It can also be used in the production of surfactants, herbicides, and pesticides. 5-Bromopentan-1-amine is a colorless to pale yellow liquid with a strong, ammonia-like odor. It is classified as a hazardous substance and should be handled with caution due to its potential to cause skin and eye irritation, and respiratory and digestive problems if inhaled or ingested.

Synthetic route

5-hydroxypentylamine (2508-29-4) → 1-amino-5-bromopentane hydrobromide (51874-27-2)

Conditions	Yield
With hydrogen bromide In water for 3h; Inert atmosphere; Reflux;	100%
With hydrogen bromide for 3h; Reflux;	92%
Multi-step reaction with 3 steps 1: dichloromethane / 2 h / 20 °C 2: triphenylphosphine; carbon tetrabromide / dichloromethane / 0 - 20 °C 3: trifluoroacetic acid / dichloromethane / 8 h / 220 °C View Scheme

N-(tert-butyloxycarbonyl)-5-aminopentanol (75178-90-4) → 1-amino-5-bromopentane hydrobromide (51874-27-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0 - 20 °C 2: trifluoroacetic acid / dichloromethane / 8 h / 220 °C View Scheme

tert-butyl (5-bromopentyl)carbamate → 1-amino-5-bromopentane hydrobromide (51874-27-2)

Conditions	Yield
Stage #1: tert-butyl (5-bromopentyl)carbamate With trifluoroacetic acid In dichloromethane at 220℃; for 8h; Stage #2: With hydrogen bromide In diethyl ether

4-tert-butylpyridine (3978-81-2) + 1-amino-5-bromopentane hydrobromide (51874-27-2) → 1-(5-aminopentyl)-4-(tert-butyl)pyridinium bromide (1426807-47-7)

Conditions	Yield
Stage #1: 4-tert-butylpyridine; 1-amino-5-bromopentane hydrobromide at 100℃; for 3h; Stage #2: With sodium hydroxide In water pH=9.4;	95%

1-amino-5-bromopentane hydrobromide (51874-27-2) + n-octanoic acid chloride (111-64-8) → N-(5-bromopentyl)octanamide (1619235-31-2)

Conditions	Yield
Stage #1: 1-amino-5-bromopentane hydrobromide With sodium carbonate In dichloromethane; water at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: n-octanoic acid chloride In dichloromethane; water at 0 - 20℃; for 4h; Inert atmosphere;	89%

di-tert-butyl dicarbonate (24424-99-5) + 1-amino-5-bromopentane hydrobromide (51874-27-2) → tert-butyl (5-bromopentyl)carbamate (83948-54-3)

Conditions	Yield
With iodine at 20℃; for 4h;	70%

5'-d{CCCTTT[(S)-thiophosphoryldioxy]TTTCCC}-3' + 1-amino-5-bromopentane hydrobromide (51874-27-2) → 5'-d{CCCTTT[(S)-S-(5-aminopent-1-yl)thiophosphoryldioxy]TTTCCC}-3'

Conditions	Yield
In N,N-dimethyl-formamide at 45℃; for 24h; pH=6.5; aq. buffer;	53%

5'-d{CCCTTT[(R)-thiophosphoryldioxy]TTTCCC}-3' + 1-amino-5-bromopentane hydrobromide (51874-27-2) → 5'-d{CCCTTT[(R)-S-(5-aminopent-1-yl)thiophosphoryldioxy]TTTCCC}-3'

Conditions	Yield
In N,N-dimethyl-formamide at 45℃; for 24h; pH=6.5; aq. buffer;	43%

Conditions	Yield
Multi-step reaction with 2 steps 1: iodine / 4 h / 20 °C 2: sodium amide / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

Upstream product

• 83948-54-3 tert-butyl (5-bromopentyl)carbamate 
• 75178-90-4 N-(tert-butyloxycarbonyl)-5-aminopentanol 
• 2508-29-4 5-hydroxypentylamine 

Downstream Products

• 14502-42-2 7-amino-1-heptyne 
• 83948-54-3 tert-butyl (5-bromopentyl)carbamate 
• 41182-89-2 N-(5-Bromo-pentyl)-benzimidoyl bromide 
• 21679-17-4 Thioschwefelsaeure-S-(4-amino-pentylester) 
• 51874-19-2 N-(5-bromopentyl)benzamide 

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