ChemicalBook--->CAS DataBase List--->83948-54-3

83948-54-3

83948-54-3 Structure

83948-54-3 Structure
IdentificationBack Directory
[Name]

5-(T-BOC-AMINO)-1-PENTYL BROMIDE
[CAS]

83948-54-3
[Synonyms]

5-(Boc-aMino)pentyl broMide
5-(T-BOC-AMINO)-1-PENTYL BROMIDE
tert-Butyl (5-broMopentyl)carbaMate
5-(tert-Butoxycarbonylamino)pentyl bromide
1,1-DiMethylethyl (5-broMopentyl)carbaMate
N-(tert-Butoxycarbonyl)-1-bromopentan-5-ylamine
N-(5-BroMopentyl)carbaMic Acid 1,1-DiMethylethyl Ester
CarbaMic acid, N-(5-broMopentyl)-, 1,1-diMethylethyl ester
[Molecular Formula]

C10H20BrNO2
[MDL Number]

MFCD03425513
[MOL File]

83948-54-3.mol
[Molecular Weight]

266.18
Chemical PropertiesBack Directory
[Appearance]

Low melting solid
[Melting point ]

approx. 35°C
[Boiling point ]

324℃
[density ]

1.214
[Fp ]

150℃
[storage temp. ]

Refrigerator, Under Inert Atmosphere
[solubility ]

Chloroform, Ethyl Acetate, Methanol
[form ]

Solid
[pka]

12.87±0.46(Predicted)
[color ]

White Low melting
[InChI]

InChI=1S/C10H20BrNO2/c1-10(2,3)14-9(13)12-8-6-4-5-7-11/h4-8H2,1-3H3,(H,12,13)
[InChIKey]

OHUJQWJCNMMZFM-UHFFFAOYSA-N
[SMILES]

C(OC(C)(C)C)(=O)NCCCCCBr
Hazard InformationBack Directory
[Chemical Properties]

Low melting solid
[Synthesis]

5-(BOC-AMINO)-1-PENTANOL

75178-90-4

5-(T-BOC-AMINO)-1-PENTYL BROMIDE

83948-54-3

The general procedure for the synthesis of 5-Boc-amino-1-pentyl bromide from 5-(N-tert-butoxycarbonylamino)-1-pentanol was as follows: 5-(N-tert-butoxycarbonylamino)-1-pentanol (3.00 g, 14.8 mmol) was dissolved in THF (41 mL) and cooled to 0 °C. CBr4 (7.34 g, 22.1 mmol) and PPh3 (5.96 g, 22.7 mmol) were added sequentially. After stirring at 0 °C for 1 h, CBr4 (2.55 g, 7.68 mmol) and PPh3 (2.17 g, 8.27 mmol) were added. The reaction mixture was continued to be stirred at room temperature for 14 hours. After completion of the reaction, it was diluted with 30% EtOAc/hexane, filtered and washed with the same ratio of EtOAc/hexane. The filtrates were combined, concentrated in vacuum and the residue was purified by silica gel column chromatography (eluent: CHCl3/hexane, gradient from 20% to 100%) to afford the target product tert-butyl N-(5-bromopentyl)carbamate (3.2 g, 81% yield).

[References]

[1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 510 - 515
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 11, p. 1156 - 1161
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7892 - 7901
[4] Patent: WO2012/177782, 2012, A1. Location in patent: Page/Page column 87
[5] Journal of Organic Chemistry, 1983, vol. 48, p. 24
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)Corrosion (GHS05)
GHS07,GHS05
[Signal word ]

Danger
[Hazard statements ]

H318-H335-H315
[Precautionary statements ]

P280-P305+P351+P338-P310-P264-P280-P302+P352-P321-P332+P313-P362
Spectrum DetailBack Directory
[Spectrum Detail]

5-(T-BOC-AMINO)-1-PENTYL BROMIDE(83948-54-3)1HNMR
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