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CAS RN: 152120-54-2 | Product Number: B3619
N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine
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Purity: >98.0%(T)(HPLC)
Synonyms:
- N,N'-Di-Boc-1H-pyrazole-1-carboxamidine
- 1-[N,N'-Bis(tert-butoxycarbonyl)amidino]pyrazole
- 1-[N,N'-(Di-Boc)amidino]pyrazole
- N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboximidamide
- N,N'-Di-Boc-1H-pyrazole-1-carboximidamide
- 1-[N,N'-Bis(tert-butoxycarbonyl)carbamimidoyl]pyrazole
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Product Documents:
| Size | Unit Price | Philadelphia, PA | Portland, OR | Japan* | Quantity |
|---|---|---|---|---|---|
| 1G |
$36.00
|
2 | 1 | 21 |
|
| 5G |
$98.00
|
4 | Contact Us | ≥100 |
|
* Items in stock locally ship in 1-2 business days. Items from Japan stock are able to ship from a US warehouse within 2 weeks. Please contact TCI for lead times on items not in stock. Excludes regulated items and items that ship on ice.
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*TCI frequently reviews storage conditions to optimize them. Please note that the latest information on the storage temperature for the products is described on our website.
| Product Number | B3619 |
| Purity / Analysis Method | >98.0%(T)(HPLC) |
| Molecular Formula / Molecular Weight | C__1__4H__2__2N__4O__4 = 310.35 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| Packaging and Container | 1G-Glass Bottle with Plastic Insert (View image) |
| CAS RN | 152120-54-2 |
| Reaxys Registry Number | 8117152 |
| PubChem Substance ID | 125307236 |
| SDBS (AIST Spectral DB) | 52872 |
| MDL Number | MFCD01075122 |
Specifications
| Appearance | White to Almost white powder to crystal |
| Purity(HPLC) | min. 98.0 area% |
| Purity(Neutralization titration) | min. 98.0 % |
| Melting point | 88.0 to 92.0 °C |
Properties (reference)
| Melting Point | 90 °C |
| Solubility (soluble in) | Methanol |
GHS
| Pictogram |
|
| Signal Word | Warning |
| Hazard Statements | H315 : Causes skin irritation. H319 : Causes serious eye irritation. |
| Precautionary Statements | P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P302 + P352 : IF ON SKIN: Wash with plenty of soap and water. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. P362 : Take off contaminated clothing and wash before reuse. |
Related Laws:
Transport Information:
| HS Number | 2933.19.9000 |
Application
TCI Practical Example: Di-Boc Guanidinylation of Amine Using the Pyrazole Derivative
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Used Chemicals
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Procedure
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A solution of 4-bromophenethylamine (200 mg, 1.00 mmol) and 1-[N,N'-(di-Boc)amidino]pyrazole (341 mg, 1.10 mmol) in THF (1.7 mL) was stirred at room temperature for one day. The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography (on silica gel, ethyl acetate:hexane = 0:100 - 10:90) to give the guanidinylated compound 1 as a pale yellow solid (319 mg, 72% yield.).
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Experimenter’s Comments
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The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:3, Rf = 0.55).
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Analytical Data
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Guanidinylated Compound 1
1H NMR (270 MHz, DMSO-d6); δ 11.48 (s, 1H), 8.32 (t, J = 6.4 Hz, 1H), 7.48 (d, J = 8.1 Hz, 2H), 7.15 (d, J = 8.1 Hz, 2H), 3.51 (q, J = 6.4 Hz, 2H), 2.78 (t, J = 6.4 Hz, 2H), 1.47 (s, 9H), 1.40 (s, 9H).
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Lead Reference
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- Urethane protected derivatives of 1-guanylpyrazole for the mild and efficient preparation of guanidines
Application
A Guanidinylating Reagent
Experimental procedure: to 1.0 mmol of N,N'-bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (1) is added 1.1 mmol of amine followed by 0.4 mL dry THF and the resulting mixture is stirred for 5 – 22 h at room temperature. The reaction mixture is diluted with hexane and directly applied to a short silica gel (15 g silica) column and the product separates from unreacted 1 by a stepwise gradient elution from 0 to 30% ethyl acetate in hexane. Drying of the product fractions in vacuo generally directly produces the desired compounds.
References
- 1)Urethane protected derivatives of 1-guanylpyrazole for the mild and efficient preparation of guanidines
- 2)A Convenient Preparation of Monosubstituted N,N’-di(Boc)-Protected Guanidines
- 3)Synthesis and Anti-Influenza Virus Activity of 4-Guanidino-7-substituted Neu5Ac2en Derivatives
- 4)Emergent Molecular Recognition through Self-Assembly: Unexpected Selectivity for Hyaluronic Acid among Glycosaminoglycans
PubMed Literature
Articles/Brochures
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Safety Data Sheet (SDS)
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