N-[6-(hydroxymethyl)-3-pyridinyl]-carbamic acid 1,1-dimethylethyl ester
![N-[6-(hydroxymethyl)-3-pyridinyl]-carbamic acid 1,1-dimethylethyl ester Structure](CAS/GIF/323578-38-7.gif)
- CAS No.
- 323578-38-7
- Chemical Name:
- N-[6-(hydroxymethyl)-3-pyridinyl]-carbamic acid 1,1-dimethylethyl ester
- Synonyms
- 5-(Boc-amino)-2-pyridyl]methanol;tert-butyl 6-(hydroxymethyl)pyridin-3-ylcarbamate;5-[(tert-Butoxycarbonyl)amino]-2-hydroxymethylpyridine;(6-Hydroxymethyl-pyridin-3-yl)-carbamic acid tert-butyl ester;N-[6-(hydroxymethyl)-3-pyridinyl]carbamic acid tert-butyl ester;N-[6-(hydroxymethyl)-3-pyridinyl]-carbamic acid 1,1-dimethylethyl ester;Carbamic acid, N-[6-(hydroxymethyl)-3-pyridinyl]-, 1,1-dimethylethyl ester
- CBNumber:
- CB13053376
- Molecular Formula:
- C11H16N2O3
- Molecular Weight:
- 224.26
- MDL Number:
- MFCD12031249
- MOL File:
- 323578-38-7.mol
- MSDS File:
- SDS
| Melting point | 139-140 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6)) |
|---|---|
| Boiling point | 317.6±32.0 °C(Predicted) |
| Density | 1.209±0.06 g/cm3(Predicted) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| pka | 12.73±0.70(Predicted) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302 |
| Precautionary statements | P280-P305+P351+P338 |
N-[6-(hydroxymethyl)-3-pyridinyl]-carbamic acid 1,1-dimethylethyl ester price More Price(51)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Biosynth | YMA57838 | tert-Butyl 6-(Hydroxymethyl)pyridin-3-ylcarbamate | 323578-38-7 | 250mg | $357.5 | 2026-06-05 | Buy |
| Biosynth | YMA57838 | tert-Butyl 6-(Hydroxymethyl)pyridin-3-ylcarbamate | 323578-38-7 | 2.5g | $1563.5 | 2026-06-05 | Buy |
| Matrix Scientific | 161230 | (6-Hydroxymethyl-pyridin-3-yl)-carbamic acid tert-butyl ester | 323578-38-7 | 100.00mg | $92 | 2026-05-18 | Buy |
| Matrix Scientific | 161230 | (6-Hydroxymethyl-pyridin-3-yl)-carbamic acid tert-butyl ester | 323578-38-7 | 250.00mg | $113 | 2026-05-18 | Buy |
| Matrix Scientific | 161230 | (6-Hydroxymethyl-pyridin-3-yl)-carbamic acid tert-butyl ester | 323578-38-7 | 1.00g | $291 | 2026-05-18 | Buy |
N-[6-(hydroxymethyl)-3-pyridinyl]-carbamic acid 1,1-dimethylethyl ester Chemical Properties, Uses, Production
Uses
tert-Butyl 6-(Hydroxymethyl)pyridin-3-ylcarbamate, is a reagent in the monitoring of dynamic glycosylation in vivo using supersensitive click chemistry in mammalian cells and in early zebra fish embryogenesis.
Synthesis
131052-40-9
![N-[6-(hydroxymethyl)-3-pyridinyl]-carbamic acid 1,1-dimethylethyl ester](/CAS/GIF/323578-38-7.gif)
323578-38-7
Step 3. Synthesis of tert-butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate. Lithium aluminum hydride (LAH) powder (36 g, 0.96 mol) was suspended in anhydrous tetrahydrofuran (THF, 1000 mL) under nitrogen protection and the mixture was cooled to 0 °C. To this suspension was slowly added a solution of methyl 5-((tert-butoxycarbonyl)amino)pyridine-2-carboxylate (150 g, 0.60 mol) in anhydrous THF (1000 mL). The reaction mixture was gradually warmed up to room temperature at 0 °C and stirred continuously for 12 hours. Completion of the reaction was monitored by thin layer chromatography (TLC, petroleum ether/ethyl acetate = 1:1). Upon completion of the reaction, the reaction was quenched by dropwise addition of THF-water (9:1, 400 mL) followed by addition of 15% aqueous NaOH (90 mL) and water (50 mL) at 90 °C. The mixture was stirred for 0.5 h at room temperature. The mixture was stirred at 0 °C for 0.5 h, then filtered through a Celite pad and the filter cake was washed with THF (4 x 1000 mL). The filtrate was concentrated under reduced pressure to give the crude product, which was purified by silica gel column chromatography with petroleum ether/ethyl acetate (2:1 to 1:2) as eluent. The grades containing the target product were collected and concentrated to afford tert-butyl (6-(hydroxymethyl)pyridin-3-yl)carbamate (450 g, 67% yield) as a white solid.1H NMR (400 MHz, DMSO-d6) δ 9.58-9.40 (m, 1H), 8.59-8.45 (m, 1H), 7.95-7.78 (m, 1H), 7.42-7.22 (m, 1H), 7.95-7.78 (m, 1H). 7.42-7.22 (m, 1H), 5.42-5.21 (m, 1H), 4.58-4.40 (m, 2H), 1.48 (s, 9H).
References
[1] European Journal of Inorganic Chemistry, 2010, # 13, p. 1913 - 1928
[2] Patent: US2015/158864, 2015, A1. Location in patent: Paragraph 0295
[3] Patent: WO2017/100594, 2017, A1. Location in patent: Paragraph 00304
[4] Patent: WO2006/51270, 2006, A1. Location in patent: Page/Page column 146
N-[6-(hydroxymethyl)-3-pyridinyl]-carbamic acid 1,1-dimethylethyl ester Preparation Products And Raw materials
Raw materials
Preparation Products
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