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Chemical Structure| 6638-79-5 Chemical Structure| 6638-79-5
Chemical Structure| 6638-79-5

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CAS No.: 6638-79-5

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Synonyms: N,O-Dimethylhydroxylamine hydrochloride

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Product Citations

Hirozumi, Ryosuke ; Kudo, Yuta ; Cho, Yuko ; Konoki, Keiichi ; Yotsu-Yamashita, Mari ;

Abstract: Mauritamide B (1a) is a taurine-connected cyclic guanidino-bromopyrrole alkaloid originally isolated from the marine sponge Agelas linnaei. To date, the total synthesis of taurine-connected guanidino-bromopyrrole alkaloids, including this compound, has not yet been reported. Herein, a total synthesis of (±)-mauritamide B (1b) was achieved by oxidation of 2-aminoimidazole of dihydro-sventrin (10) using activated carbon and air in the presence of taurine. The synthetic precursor of 10, 4-(3-aminopropyl)-2-aminoimidazole (22), was synthesized via our original route. The NMR data of the obtained product agreed with that reported for mauritamide B (1a). However, a detailed analysis of the NMR data of synthetic (±)-mauritamide B (1b) including 11H?15N HSQC spectrum revealed the need for a structural revision of the reported structure for mauritamide B (1b).

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Product Details of N,O-Dimethylhydroxylamine HCl

CAS No. :6638-79-5
Formula : C2H8ClNO
M.W : 97.54
SMILES Code : CONC.[H]Cl
Synonyms :
N,O-Dimethylhydroxylamine hydrochloride
MDL No. :MFCD00012485
InChI Key :USZLCYNVCCDPLQ-UHFFFAOYSA-N
Pubchem ID :81138

Safety of N,O-Dimethylhydroxylamine HCl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338

Application In Synthesis of N,O-Dimethylhydroxylamine HCl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 6638-79-5 ]
  • Downstream synthetic route of [ 6638-79-5 ]

[ 6638-79-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 6638-79-5 ]
  • [ 1711-07-5 ]
  • [ 226260-01-1 ]
YieldReaction ConditionsOperation in experiment
86.5% With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere To a solution of Ν,Ο-dimethylhydroxylamine hydrochloride (138 g, 1.42 mol) in DCM (1.5 L) was added Et3N (383 g, 3.78 mol) at room temperature (RT). To the stirred mixture, 1-1 (150 g, 946 mmol) was added dropwise at 0 °C under N2 atmosphere. The solution was stirred at the same temperature for 1 h, and then slowly warmed to RT for 10 h. The mixture was added to water (~1L) and extracted with EtOAc (2 x 500 mL). The combined organic phases were dried with Na2S04, filtered and concentrated. The residue was purified by flash column chromatography (eluent: PE) to give 1-2 as a white solid (150 g, yield: 86.5percent). 1H NMR (400 MHz, CDC13): δ 7.49-7.43 (1 H, m), 7.41-7.32 (2 H, m), 7.18- 7.10 (1 H, m), 3.54 (3 H, s), 3.34 (3 H, s).
References: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1415 - 1419.
[2] Patent: WO2016/145103, 2016, A1, . Location in patent: Paragraph 0165.
[3] Patent: US6174874, 2001, B1, .
[4] Patent: US2008/249095, 2008, A1, . Location in patent: Page/Page column 44.
  • 2
  • [ 455-38-9 ]
  • [ 6638-79-5 ]
  • [ 226260-01-1 ]
YieldReaction ConditionsOperation in experiment
71% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 75 h; EXAMPLE 4 3-Fluoro-N-methoxy-N-methylbenzamide To a suspension of 3-fluorobenzoic acid (140 mg, 1 mmol) and N dimethylhydroxylamine hydrochloride (107 mg, 1.1 mmol) in dichloromethane (2.5 mL) was added 1- [3- (dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (EDC) (211 mg, 1.1 mmol) and the mixture stirred at room temperature for 75 h. The solvents were removed under reduced pressure and the residue chromatographed using ethyl acetate- hexane (4: 6) to separate the pure product (130 mg, 71percent). H-n. m. r. (CDC13) 8 3.36 (s, 3H, N-Me), 3.55 (s, 3H, N-OMe), 7. 1. -7.2 (m, 1H, ArH), 7.3-7. 5 (m, 3H, Ar)
71% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 75 h; Example 4 3-Fluoro-N-methoxy-N-methylbenzamide To a suspension of 3-fluorobenzoic acid (140 mg, 1 mmol) and AC (7 dimethylhydroxylamine hydrochloride (107 mg, 1.1 mmol) in dichloromethane (2.5 mL) was added 1- [3- (DIMETHYLAMINO) PROPYL]-3-ETHYLCARBODIIMIDE hydrochloride (EDC) (211 mg, 1.1 mmol) and the mixture stirred at room temperature for 75 h. The solvents were removed under reduced pressure and the residue chromatographed using ethyl acetate- hexane (4: 6) to separate the pure product (130 mg, 71percent). APOS;H-N. m. r. (CDCL3) 8 3.36 (s, 3H, N-Me), 3.55 (s, 3H, N-OMe), 7.1.-7. 2 (m, 1H, Ar), 7.3-7. 5 (m, 3H, Ar)
61% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 3 h; Inert atmosphere 3-fluoro-N-methoxy-N-methylbenzamide
To a solution of 3-fluorobenzoic acid (30 g, 214.1 mmol) in DCM (300 mL) were added EDC.HCl (45 g, 235 mmol) and N,O-dimethylhydroxylamine.HCl (23 g, 235 mmol) at 0° C. under N2.
The reaction mixture was stirred at rt for 3 h, then diluted with water (1000 mL) and extracted with DCM (3*200 mL).
The organics were washed with brine, dried over Na2SO4, and concentrated to obtain the 3-fluoro-N-methoxy-N-methylbenzamide (24 g, 61percent).
(183.91 [M+H]) 1H NMR: (400 MHz, CDCl3) δ: 3.38 (s, 3H), 3.57 (s, 3H), 7.14-7.19 (m, 1H), 7.37-7.43 (m, 2H), 7.48-7.50 (d, J=7.6, 1H).
References: [1] Patent: WO2005/54199, 2005, A1, . Location in patent: Page/Page column 39-40.
[2] Patent: WO2004/52868, 2004, A1, . Location in patent: Page 29.
[3] Patent: US2014/274933, 2014, A1, . Location in patent: Paragraph 0091; 0092.
 

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