tert-Butyl N-(2-bromoethyl)carbamate Chemical Properties

Melting point:

30-32 °C(lit.)

Boiling point:

262.3±23.0 °C(Predicted)

Density 

1.321±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in Chloroform, Dichloromethane and Ethyl Acetate.

pka

11.76±0.46(Predicted)

form 

Liquid

color 

Clear colorless to yellow

BRN 

2325117

InChI

InChI=1S/C7H14BrNO2/c1-7(2,3)11-6(10)9-5-4-8/h4-5H2,1-3H3,(H,9,10)

InChIKey

TZRQZPMQUXEZMC-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCBr

CAS DataBase Reference

39684-80-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

F 

10-21

HazardClass 

IRRITANT

HS Code 

29241990

MSDS

• Language:English Provider:SigmaAldrich

tert-Butyl N-(2-bromoethyl)carbamate Usage And Synthesis

Chemical Properties

White Solid

Uses

N-t-Boc-2-bromoethylamine is a building block for preparing fluorinated spacers having nucleophilic and electrophilic termini.

reaction suitability

reagent type: cross-linking reagent

Synthesis

Di-tert-butyl dicarbonate (80.0 g, 366 mmol) was slowly added to a solution of 2-bromoethylamine (75.0 g, 366 mmol) and triethylamine (100 mL, 732 mmol) in methanol (700 mL) at 0 °C. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, water (500 mL) was added for dilution and extracted with dichloromethane (2 x 500 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give N-Boc-2-bromoethylamine (78.0 g, 92% yield) as a colorless oil. NMR hydrogen spectrum (400MHz, DMSO-d6) δ 7.08 (broad single peak, 1H), 3.42 (double peak, J=6.8Hz, 2H), 3.29 (double peak, J=6.8Hz, 2H), 1.39 (single peak, 9H).

References

[1] European Journal of Organic Chemistry, 2015, vol. 2015, # 29, p. 6458 - 6465
[2] Patent: WO2016/176423, 2016, A1. Location in patent: Page/Page column 120
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3213 - 3215
[4] Organic and Biomolecular Chemistry, 2013, vol. 11, # 26, p. 4414 - 4418
[5] Patent: US2014/134110, 2014, A1. Location in patent: Paragraph 0087; 0088; 0089

tert-Butyl N-(2-bromoethyl)carbamate(39684-80-5)Related Product Information

• N-Carbobenzyloxyglycine
• Butyl acetate
• tert-Butyl carbamate
• L-1-Phenylethylamine
• Sodium bromate
• Ethyl acetate
• Ethanol
• Ethylamine
• POLYURETHANE
• tert-Butyl 4-aminobenzoate
• Triethylamine hydrochloride
• tert-Butanol
• Phosphorus oxybromide
• Diethylamine
• Buprofezin
• Clidinium bromide
• tert-Butyl carbazate
• Butyl acrylate