tert-butyl (4-bromobutyl)carbamate Chemical Properties

Boiling point:

308.8±25.0 °C(Predicted)

Density 

1.228

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Low-Melting Solid

pka

12.76±0.46(Predicted)

color 

White to Pale Yellow

InChI

InChI=1S/C9H18BrNO2/c1-9(2,3)13-8(12)11-7-5-4-6-10/h4-7H2,1-3H3,(H,11,12)

InChIKey

GKGFAEREWWZBKY-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NCCCCBr

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

WGK Germany 

3

tert-butyl (4-bromobutyl)carbamate Usage And Synthesis

Chemical Properties

Off-White Low Melting Solid

Uses

4-(Boc-amino)butyl bromide can be used:

• For the synthesis of N-Boc-aminoalkoxyphenyl derivatives, precursor to pharmacophore elements for the treatment of glaucoma.
• For the synthesis of various aloperine derivatives with potential application as anti-HIV agents.
• For the modification of 4,5,6,7-tetrabromobenzotriazole (TBB) derivatives to generate improved CK2 inhibitors.

reaction suitability

reagent type: cross-linking reagent

Synthesis

General procedure for the synthesis of tert-butyl N-(4-bromobutyl) carbamate from 4-(N-tert-butoxycarbonylamino)-1-butanol: 4-(N-tert-butoxycarbonylamino)-1-butanol (1.06 g, 5.788 mmol) was dissolved in anhydrous THF (54 mL), followed by the addition of triphenylphosphine (2.86 g, 10.92 mmol, 1.9 equiv) . Carbon tetrabromide (3.62 g, 10.92 mmol, 1.9 eq.) was added slowly with stirring. The reaction mixture was stirred at room temperature for 3 h. After stirring, the reaction mixture was filtered through a diatomaceous earth pad to remove by-products and the filter cake was washed with ether. The filtrate was concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel fast column chromatography (eluent: hexane/ethyl acetate, 3:1) to afford tert-butyl N-(4-bromobutyl)carbamate (1.73 g, quantitative yield) as a white solid.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1151 - 1155
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 11, p. 1156 - 1161
[3] Patent: WO2017/53360, 2017, A1. Location in patent: Paragraph 0154
[4] Patent: WO2017/96045, 2017, A1. Location in patent: Paragraph 00884
[5] Patent: WO2012/9309, 2012, A1. Location in patent: Page/Page column 58

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