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360773-84-8

360773-84-8 Structure

360773-84-8 Structure
IdentificationBack Directory
[Name]

t-Butyl 1-(4-bromophenyl)cyclopropylcarbamate
[CAS]

360773-84-8
[Synonyms]

tert-Butyl (1-(4-bromophenyl)
2-Fluoro-32-(methylthio)pyridine
N-Boc-1-(4-bromophenyl)cyclopropanamine
1-(N-BOC-Amino)-1-(4-bromophenyl)cyclopropane
t-Butyl 1-(4-bromophenyl)cyclopropylcarbamate
tert-Butyl (1-(4-broMophenyl)cyclopropyl)carbaMate
tert-Butyl N-[1-(4-bromophenyl)cyclopropyl]carbamate
[1-(4-Bromo-phenyl)-cyclopropyl]-carbamic acid tert-butyl
[1-(4-Bromo-phenyl)-cyclopropyl]-carbamic acid tert-butyl ester
Carbamic acid, N-[1-(4-bromophenyl)cyclopropyl]-, 1,1-dimethylethyl ester
[Molecular Formula]

C14H18BrNO2
[MDL Number]

MFCD16660261
[MOL File]

360773-84-8.mol
[Molecular Weight]

312.2
Chemical PropertiesBack Directory
[Melting point ]

126-128°
[Boiling point ]

385.2±31.0 °C(Predicted)
[density ]

1.37±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[pka]

11.94±0.20(Predicted)
[Appearance]

White to off-white Solid
[InChI]

InChI=1S/C14H18BrNO2/c1-13(2,3)18-12(17)16-14(8-9-14)10-4-6-11(15)7-5-10/h4-7H,8-9H2,1-3H3,(H,16,17)
[InChIKey]

ZJEMFURAGDYBTG-UHFFFAOYSA-N
[SMILES]

C(OC(C)(C)C)(=O)NC1(C2=CC=C(Br)C=C2)CC1
Spectrum DetailBack Directory
[Spectrum Detail]

t-Butyl 1-(4-bromophenyl)cyclopropylcarbamate(360773-84-8)1HNMR
Hazard InformationBack Directory
[Synthesis]

Di-tert-butyl dicarbonate

24424-99-5

1-(4-BROMO-PHENYL)-CYCLOPROPYLAMINE

345965-54-0

t-Butyl 1-(4-bromophenyl)cyclopropylcarbamate

360773-84-8

The general procedure for the synthesis of tert-butyl [1-(4-bromophenyl)-cyclopropyl]carbamate from 1-(4-bromophenyl)cyclopropan-1-amine and di-tert-butyl dicarbonate was as follows: in a 100-mL round-bottom flask, 1-(4-bromophenyl)cyclopropan-1-amine (1 g, 4.48 mmol, 1.00 equiv) and di-tert-butyl dicarbonate (3.1 g, 13.49 mmol , 3.01 eq.) were dissolved in tetrahydrofuran (20 mL). Subsequently, an aqueous solution of sodium bicarbonate (5 g, 59.5 mmol, 13.29 eq.) was slowly added to the reaction system (10 mL) at room temperature. The reaction mixture was stirred overnight at room temperature. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (3 x 10 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using ethyl acetate/petroleum ether (10% to 50% gradient) as eluent to afford tert-butyl [1-(4-bromophenyl)-cyclopropyl]carbamate (1.47 g, 99%) as a light yellow solid. Mass spectrometry (MS) analysis showed: m/z = 255.7 [M+H-56]+.

[References]

[1] Patent: US2016/96834, 2016, A1. Location in patent: Paragraph 0390
[2] Patent: US2012/108574, 2012, A1. Location in patent: Page/Page column 113
[3] Patent: WO2016/57762, 2016, A1. Location in patent: Page/Page column 30
[4] Patent: WO2016/102672, 2016, A2. Location in patent: Page/Page column 115
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