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79722-21-7

79722-21-7 Structure

79722-21-7 Structure
IdentificationBack Directory
[Name]

TERT-BUTYL N-(BENZYLOXY)CARBAMATE
[CAS]

79722-21-7
[Synonyms]

LABOTEST-BB LT00452293
N-Boc-O-benzylhydroxylamine
TERT-BUTYL BENZYLOXYCARBAMATE
TERT-BUTYL N-(BENZYLOXY)CARBAMATE
tert-Butyl (benzyloxy)carbamate 99%
tert-Butyl N-(Benzyloxy)carbamate >
tert-Butyl N-(benzyloxy)carbamate ,98%
tert-ButylN-(benzyloxy)carbamate≥ 99%(N)
tert-Butyl N-(benzyloxy)carbamate, 98.5%
N-Boc-Bn Tert-butyl n-(benzyloxy)carbamate
N-(BENZYLOXY)CARBAMIC ACID TERT-BUTYL ESTER
TERT-BUTYL N-(BENZYLOXY)CARBAMATE ISO 9001:2015 REACH
Carbamic acid, N-(phenylmethoxy)-, 1,1-dimethylethyl ester
Carbamic acid, N-(phenylmethoxy)-, 1,1-dimethylethyl ester, 95+%
O-Benzylhydroxylamine, N-BOC protected, tert-Butyl (phenylmethoxy)carbamate
[EINECS(EC#)]

628-800-0
[Molecular Formula]

C12H17NO3
[MDL Number]

MFCD00191873
[MOL File]

79722-21-7.mol
[Molecular Weight]

223.27
Chemical PropertiesBack Directory
[Melting point ]

45-47 °C(lit.)
[density ]

1.078±0.06 g/cm3 (20 ºC 760 Torr)
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

Chloroform (Slightly), Ethyl Acetate (Slightly)
[form ]

Solid
[color ]

White
[InChI]

InChI=1S/C12H17NO3/c1-12(2,3)16-11(14)13-15-9-10-7-5-4-6-8-10/h4-8H,9H2,1-3H3,(H,13,14)
[InChIKey]

MZNBNPWFHGWAGH-UHFFFAOYSA-N
[SMILES]

C(OC(C)(C)C)(=O)NOCC1=CC=CC=C1
[CAS DataBase Reference]

79722-21-7
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36
[WGK Germany ]

3
[HS Code ]

29280000
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Dichloromethane-->N,N-Dimethylformamide-->Sodium carbonate-->Potassium carbonate-->Potassium hydroxide-->Sodium bicarbonate-->Acetonitrile-->Isopropyl alcohol-->Dimethyl sulfoxide-->Di-tert-butyl dicarbonate-->Hydrazine hydrate-->Benzyl chloride-->N,N-Diisopropylethylamine-->N-Hydroxyphthalimide
Hazard InformationBack Directory
[Chemical Properties]

White powder
[Uses]

tert-Butyl N-(benzyloxy)carbamate was used in the preparation of seven-membered cyclic hydroxamic acids. It may be used in the synthesis of 2-(N-formyl-N-hydroxyamino) ethylphosphonate (IPP).
[General Description]

tert-Butyl N-(benzyloxy)carbamate (tert-butyl benzyloxycarbamate), a protected hydroxylamine, is an N-alkyl-N-benzyloxy carbamate. Its C-N cross coupling reaction with fluorescein ditriflate has been reported. It participates in facile intramolecular cyclization with various carbon nucleophiles to afford functionalized 5- and 6-membered protected cyclic hydroxamic acids.
[Synthesis]

Di-tert-butyl dicarbonate

24424-99-5

O-Benzylhydroxylamine hydrochloride

2687-43-6

TERT-BUTYL N-(BENZYLOXY)CARBAMATE

79722-21-7

General procedure: synthesis of Intermediate 153: tert-butyl N-(benzyloxy)carbamate. To a solution of O-benzylhydroxylamine hydrochloride (225 g, 1.44 mol) in dichloromethane (300 mL) was added an aqueous sodium bicarbonate solution (261 g, 3.11 mol, 300 ml). After 1 hour of reaction, di-tert-butyl dicarbonate (375 g, 1.72 mol) was slowly added at 0°C. The reaction mixture was stirred in a water/ice bath at 0 °C for 60 min, followed by continued stirring for 16 h at room temperature. Upon completion of the reaction, the reaction was quenched by addition of 300 mL of aqueous sodium bicarbonate. The aqueous phase was separated and extracted with dichloromethane (3 x 500 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel fast column chromatography (eluent: petroleum ether/ethyl acetate=10:1) afforded 220 g (69% yield) of the target compound, tert-butyl N-(benzyloxy)carbamate, as a yellow oil.1H NMR (300 MHz, CDCl3) δ: 1.43 (9H,s), 4.85 (2H,s), 7.19-7.21 (1H brs), 7.30-7.40 (5H, m).

[References]

[1] Journal of Organic Chemistry, 1997, vol. 62, # 26, p. 9148 - 9159
[2] Archiv der Pharmazie, 2016, vol. 349, # 5, p. 373 - 382
[3] Journal of Organic Chemistry, 1983, vol. 48, p. 24
[4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 24, p. 8549 - 8555
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 19, p. 8847 - 8858
Spectrum DetailBack Directory
[Spectrum Detail]

TERT-BUTYL N-(BENZYLOXY)CARBAMATE(79722-21-7)1HNMR
TERT-BUTYL N-(BENZYLOXY)CARBAMATE(79722-21-7)IR
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