1-N-BOC-4-BROMOPIPERIDINE Chemical Properties

Melting point:

42 °C

Boiling point:

100-118 °C/0.5 mmHg

Density 

1.3403 g/mL at 25 °C

refractive index 

n20/D 1.4905

Flash point:

110 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to lump

pka

-2.77±0.40(Predicted)

color 

White to Light yellow

InChI

InChI=1S/C10H18BrNO2/c1-10(2,3)14-9(13)12-6-4-8(11)5-7-12/h8H,4-7H2,1-3H3

InChIKey

KZBWIYHDNQHMET-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CCC(Br)CC1

CAS DataBase Reference

180695-79-8

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-50

Safety Statements 

61

RIDADR 

UN 3082 9/PG 3

WGK Germany 

3

HS Code 

2933399990

1-N-BOC-4-BROMOPIPERIDINE Usage And Synthesis

Uses

N-Boc-4-Bromopiperidine is a biochemical reagent that can be used as a biological material or organic compound for life science related research.

Synthesis

Step 1: Synthesis of tert-butyl 4-bromopiperidine-1-carboxylate To a 35 mL dichloromethane suspension containing 5 g (0.02 mol) of 4-bromopiperidine hydrobromide, 7.09 mL (0.04 mol) of N,N-diisopropylethylamine was added slowly and dropwise at 0 °C. The reaction mixture was stirred for 30 minutes and then continued with the dropwise addition of 6.67 g (0.031 mol) of di-tert-butyl dicarbonate to a 35 mL dichloromethane solution. The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the reaction mixture was washed sequentially with 1 M aqueous hydrochloric acid (2 x 30 mL) and brine (30 mL). The organic layer was separated, dried with anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to give 6.9 g of 4-bromopiperidine-1-carboxylic acid tert-butyl ester as a yellow oil in quantitative yield. The product was characterized by 1H NMR (250 MHz, chloroform-d): δ 1.46 (9H, s), 1.79-2.00 (2H, m), 2.00-2.16 (2H, m), 3.31 (2H, ddd, J = 13.67,7.73,3.73 Hz), 3.68 (2H, ddd, J = 13.55,6.85,3.65 Hz), 4.34 (1H, tt, J = 7.69,3.81 Hz).

References

[1] Patent: US2010/76029, 2010, A1. Location in patent: Page/Page column 42
[2] Patent: US2011/71196, 2011, A1. Location in patent: Page/Page column 22; 23
[3] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 311 - 321
[4] Journal of the American Chemical Society, 2016, vol. 138, # 24, p. 7520 - 7523
[5] Organic Letters, 2000, vol. 2, # 1, p. 6 - 10

1-N-BOC-4-BROMOPIPERIDINE(180695-79-8)Related Product Information

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• 4-Acetyl-piperidine-1-carboxylic acid tert-butyl ester
• 4-Bromomethypiperidine-1-carboxylic acid tert-butyl ester
• 1-Boc-4-methanesulfonyloxypiperidine
• 1-Boc-4-methylpiperidine-4-carboxylic acid
• tert-Butyl 4-iodopyrazole-1-carboxylate
• 1-Boc-pyrazole-4-boronic acid pinacol ester
• N-BOC-piperidine-4-carboxylic acid
• N-Boc-piperidine-4-aldehyde
• tert-Butyl 3-bromopropylcarbamate
• 1-N-BOC-4-BROMOPIPERIDINE
• 1-N-BOC-3-BROMOPIPERIDINE,1-Boc-3-bromopiperidine
• 4-BROMO-N-METHYL PIPERIDINE
• N-Boc-trans-4-bromo-3-hydroxypipiridine