1-Boc-3-iodoazetidine Chemical Properties

Boiling point:

282.0±33.0 °C(Predicted)

Density 

1.63g/ml

refractive index 

1.5090 to 1.5130

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

pka

-3.39±0.40(Predicted)

color 

Colorless to Brown

Sensitive 

Light Sensitive

InChI

InChI=1S/C8H14INO2/c1-8(2,3)12-7(11)10-4-6(9)5-10/h6H,4-5H2,1-3H3

InChIKey

XPDIKRMPZNLBAC-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC(I)C1

CAS DataBase Reference

254454-54-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,T

Risk Statements 

25-36-50

Safety Statements 

26-45

RIDADR 

UN 3082 9 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

1-Boc-3-iodoazetidine Usage And Synthesis

Chemical Properties

Colorless to red-brown liquid

Uses

1-Boc-3-iodoazetidine is used as an organic chemical synthesis intermediate.

Synthesis

The general procedure for the synthesis of 1-Boc-3-iodoazetidine from N-Boc-3-hydroxyazetidine is as follows: Step B: Synthesis of tert-butyl 3-iodoazetidine-1-carboxylate. To a solution of tert-butyl 3-hydroxyazetidine-1-carboxylate (3.35 g, 19.3 mmol) in toluene (200 mL) was sequentially added imidazole (3.95 g, 58.0 mmol), triphenylphosphine (10.1 g, 38.7 mmol) and iodine (7.36 g, 29.0 mmol). The reaction mixture was heated at 100 °C for 1 h, subsequently cooled to room temperature and poured into aqueous sodium bicarbonate solution (30 mL). Iodine was added to quench the excess triphenylphosphine until the iodine color in the organic layer disappeared. The organic layer was separated, washed with saturated aqueous sodium thiosulfate and dried over anhydrous sodium sulfate. The crude product was purified by silica gel column chromatography (eluent ratio: hexane/ethyl acetate = 9:1 to 1:1) to afford 1-Boc-3-iodoazetidine (5.42 g, 99% yield) as a clear oil. MS (ESI) m/z 284 (M + 1)+.

References

[1] Patent: WO2010/84767, 2010, A1. Location in patent: Page/Page column 47
[2] Patent: WO2006/40182, 2006, A1. Location in patent: Page/Page column 132-133
[3] Patent: WO2008/116831, 2008, A1. Location in patent: Page/Page column 37
[4] Patent: WO2011/140488, 2011, A1. Location in patent: Page/Page column 287; 288
[5] Patent: EP2773638, 2015, B1. Location in patent: Paragraph 0805; 0806

1-Boc-3-iodoazetidine(254454-54-1)Related Product Information

• Boc-Beta-iodo-Ala-Ome
• 1-BOC-3-(METHOXY)AZETIDINE
• 1-BOC-3-METHYL-PIPERIDIN-4-ONE
• N-1-Boc-3-phenylpiperazine
• 3-Oxetanone
• 1-Boc-3-piperidone
• 1-Boc-3-Hydroxypyrrolidine
• 1-Boc-3-(Amino)azetidine
• 1-N-Boc-3-hydroxyazetidine
• TRIMETHYLENE OXIDE
• ISOBUTANE
• Azetidine
• n-Butane
• 1-Chloro-2-methylpropane
• tert-Butyl carbazate
• DI-TERT-BUTYL ETHER
• 1-Boc-3-iodoazetidine