1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane
- CAS No.
- 170161-27-0
- Chemical Name:
- 1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane
- Synonyms
- TriBoc-Cyclam;Plerixafor Impurity 37;1,4,8-Tri-boc-1,4,8,12-tetraazacyclotetradecane;1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane;tri-tert-butyl 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate;1,4,8,11-Tetraazacyclotetradecane-1,4,8-tricarboxylic acid, tris(1,1-diMethylethyl) ester;1,?4,?8,?11-?Tetraazacyclotetrade?cane-?1,?4,?8-?tricarboxylic acid, 1,?4,?8-?tris(1,?1-?dimethylethyl) ester
- CBNumber:
- CB81569072
- Molecular Formula:
- C25H48N4O6
- Molecular Weight:
- 500.67
- MDL Number:
- MFCD09263315
- MOL File:
- 170161-27-0.mol
- MSDS File:
- SDS
| Melting point | 48-54°C |
|---|---|
| Boiling point | 570.3±45.0 °C(Predicted) |
| Density | 1.044±0.06 g/cm3(Predicted) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| pka | 10.01±0.20(Predicted) |
| Sensitive | Hygroscopic |
| InChI | InChI=1S/C25H48N4O6/c1-23(2,3)33-20(30)27-15-11-16-29(22(32)35-25(7,8)9)19-18-28(14-10-12-26-13-17-27)21(31)34-24(4,5)6/h26H,10-19H2,1-9H3 |
| InChIKey | FIPOUUYFPSMVMX-UHFFFAOYSA-N |
| SMILES | N1(C(OC(C)(C)C)=O)CCCNCCN(C(OC(C)(C)C)=O)CCCN(C(OC(C)(C)C)=O)CC1 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a | |||||||||
| NFPA 704 |
|
1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane price More Price(21)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Matrix Scientific | 298396 | Tri-tert-butyl 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate | 170161-27-0 | 250.00mg | $54 | 2026-05-19 | Buy |
| Matrix Scientific | 298396 | Tri-tert-butyl 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate | 170161-27-0 | 1.00g | $124 | 2026-05-19 | Buy |
| Matrix Scientific | 298396 | Tri-tert-butyl 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate | 170161-27-0 | 5.00g | $433 | 2026-05-19 | Buy |
| aablocks | AA003DJF | Tri-tert-butyl 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate 96% | 170161-27-0 | 100mg | $20 | 2026-05-28 | Buy |
| aablocks | AA003DJF | Tri-tert-butyl 1,4,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate 96% | 170161-27-0 | 250mg | $35 | 2026-05-28 | Buy |
1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane Chemical Properties, Uses, Production
Synthesis
295-37-4
24424-99-5
170161-27-0
The general procedure for the synthesis of tri-tert-butyl 1,3,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate from 1,4,8,11-tetraazacyclotetradecane (cyclam) and di-tert-butyl dicarbonate was carried out in the following manner: first, the synthesis of tri-tert-butyl 1,3,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylate was carried out according to the methodology reported by Dessolin et al. (J. Dessolin, P. Galea, P. Vlieghe, J. Chermann, J. Kraus, J. Med. Chem. 1999, 42, 229-241) was synthesized with slight modifications. The procedure was as follows: 1,4,8,11-tetraazacyclotetradecane (1.00 g, 5.00 mmol, 1 eq.) was dissolved in ice-cold dichloromethane (100 mL) under ice-bath conditions, followed by the addition of di-tert-butyl dicarbonate (2.0 g, 9.00 mmol, 1.8 eq.). The reaction mixture was stirred overnight. Upon completion of the reaction, the solvent was removed by evaporation to give the crude product as a light yellow oil. The crude product was purified by fast column chromatography (eluent ratio methanol/dichloromethane 5:95). The first fraction collected was the tri-Boc-protected cyclam (1), i.e., the target product 1,3,8,11-tetraazacyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester in the form of a thick colorless oil (0.75 g, 30% yield). Mass spectrometry (electrospray) analysis showed a molecular ion peak of 523 (M + Na)+.
References
[1] Molecular Pharmaceutics, 2017, vol. 14, # 5, p. 1395 - 1404
[2] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 21, p. 4965 - 4972
[3] Journal of the American Chemical Society, 2006, vol. 128, # 45, p. 14448 - 14449
[4] Chemical Communications, 2018, vol. 54, # 33, p. 4116 - 4119
[5] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 1, p. 65 - 73
1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane Preparation Products And Raw materials
1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane Suppliers
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