ChemicalBook > CAS DataBase List > 1,4,8,11-TETRAAZACYCLOTETRADECANE

1,4,8,11-TETRAAZACYCLOTETRADECANE

Product Name
1,4,8,11-TETRAAZACYCLOTETRADECANE
CAS No.
295-37-4
Chemical Name
1,4,8,11-TETRAAZACYCLOTETRADECANE
Synonyms
CYCLAM;jm1498;Cyclam, 98+%;otetradecane;Compound PDK0168;Valine Impurity 134;1,4,8,11-TetraazacycL;Plerixafor Impurity 67;cyclaM, Methanol adduct;Plerixafor intermediate
CBNumber
CB3136889
Molecular Formula
C10H24N4
Formula Weight
200.32
MOL File
295-37-4.mol
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1,4,8,11-TETRAAZACYCLOTETRADECANE Property

Melting point:
184-186 °C (lit.)
Boiling point:
328.07°C (rough estimate)
Density 
1.0203 (rough estimate)
refractive index 
1.5200 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Dichloromethane, Methanol
pka
10.90±0.20(Predicted)
form 
Fluffy Needle-Like Crystalline Powder
color 
White
Water Solubility 
Soluble in water.
Sensitive 
Air Sensitive
BRN 
111811
InChI
InChI=1S/C10H24N4/c1-3-11-7-9-13-5-2-6-14-10-8-12-4-1/h11-14H,1-10H2
InChIKey
MDAXKAUIABOHTD-UHFFFAOYSA-N
SMILES
N1CCCNCCNCCCNCC1
CAS DataBase Reference
295-37-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
XA5254800
F 
3-9-34
HS Code 
29339900
Toxicity
LD50 intraperitoneal in mouse: 371mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
259160
Product name
1,4,8,11-Tetraazacyclotetradecane
Purity
98% (GC)
Packaging
1g
Price
$78.18
Updated
2025/07/31
Sigma-Aldrich
Product number
259160
Product name
1,4,8,11-Tetraazacyclotetradecane
Purity
98% (GC)
Packaging
5g
Price
$190
Updated
2025/07/31
TCI Chemical
Product number
T1597
Product name
1,4,8,11-Tetraazacyclotetradecane
Purity
>98.0%(T)
Packaging
1g
Price
$91
Updated
2025/07/31
TCI Chemical
Product number
T1597
Product name
1,4,8,11-Tetraazacyclotetradecane
Purity
>98.0%(T)
Packaging
5g
Price
$302
Updated
2025/07/31
Strem Chemicals
Product number
07-1959
Product name
1,4,8,11-Tetraazacyclotetradecane, min. 98% CYCLAM
Packaging
250mg
Price
$44
Updated
2024/03/01
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1,4,8,11-TETRAAZACYCLOTETRADECANE Chemical Properties,Usage,Production

Chemical Properties

white fluffy needle-like crystalline powder

Uses

Reagent used in the preparation of Plerixafor derivatives.

Uses

1,4,8,11-Tetraazacyclotetradecane is macrocyclic ligand that is used as an antioxidant in rubber and has been shown to suppress oxidation catalyzed by some metal ions.

Uses

1,4,8,11-Tetraazacyclotetradecane is used in the synthesis of molecules with electroactive cavities. It acts as a nitrogen crown ether analogue and as an antioxidant in rubber. It is also used in the preparation of plerixafor derivatives.

Definition

ChEBI: 1,4,8,11-tetraazacyclotetradecane is a saturated organic heteromonocyclic parent, a crown amine and an azacycloalkane. It derives from a hydride of a cyclotetradecane.

General Description

1,4,8,11-Tetraazacyclotetradecane is an azamacrocycle that forms more stable metal complexes as compared to open chain ligands.

Synthesis

71089-74-2

295-37-4

The general procedure for the synthesis of 1,4,8,11-tetrakis[(4-methylphenyl)sulfonyl]-1,4,8,11-tetraazacyclotetradecane from 1,4,8,11-tetrakis(4-methylphenyl)sulfonyl]-1,4,8,11-tetraazacyclotetradecane is as follows: 1,4,8,11-tetra-tosyl-1,4,8,11-tetraazacyclotetradecane (13 mmol) was dissolved in 90% concentrated sulfuric acid, and the reaction was carried out at 100 °C The reaction was stirred for 48 hours at 100 °C. Upon completion of the reaction, the reaction mixture was cooled to 0°C. Subsequently, anhydrous ethanol (120 mL) and anhydrous ether (100 mL) were added dropwise to the reaction mixture to precipitate the solid product. The solid was collected by filtration and the filter cake was washed with a small amount of anhydrous ethanol and anhydrous ether, followed by vacuum drying. The resulting off-white solid was dissolved in 1 mol/L aqueous NaOH (90 mL) and extracted with chloroform (3 x 100 mL). The chloroform layers were combined and dried with anhydrous sodium sulfate overnight. Afterwards, the chloroform was removed by distillation under reduced pressure and the residue was vacuum dried to give a white solid product. Finally, the product was recrystallized from toluene to give 2.2 g of 1,4,8,11-tetraazacyclotetradecane in 85% yield. Mass spectral analysis of the product showed [M]+ = 200.3 m/e, 1H-NMR (400 MHz, CDCl3) δ ppm: 1.72 (t, 4H), 2.23 (s, 4H), 2.68 (s, 8H), 2.75 (t, 8H).

Purification Methods

Purify cyclam by recrystallisation from dioxane (white needles), and it sublimes above 120o. It has been distilled, b 132-140o/4-8mm. It forms complexes with metals and gives a sparingly soluble nitrate salt, m 205o(dec), which crystallises from H2O and is dried at 150o. [UV: Bosnich et al. Inorg Chem 4 1102 1963, van Alphen Recl Trav Chim Pays-Bas 56 343 1937, Beilstein 26 III/IV 1647.]

References

[1] Patent: EP2163553, 2010, A1. Location in patent: Page/Page column 18-19
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1987, vol. 36, # 2, p. 372 - 376
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1987, # 2, p. 413 - 417
[4] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990, vol. 26, # 3, p. 346 - 349
[5] Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 3, p. 401 - 404

1,4,8,11-TETRAAZACYCLOTETRADECANE Preparation Products And Raw materials

Raw materials

Preparation Products

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1,4,8,11-TETRAAZACYCLOTETRADECANE Suppliers

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View Lastest Price from 1,4,8,11-TETRAAZACYCLOTETRADECANE manufacturers

YiZheng HaiFan Chemical CO., LTD.
Product
1,4,8,11-Tetraazacyclotetradecane 295-37-4
Price
US $0.00/kg/paper drum
Min. Order
15kg/paper drum
Purity
98%
Supply Ability
10 tons
Release date
2025-12-04
Wuhan Boye Science And Technology Development Co., Ltd.
Product
1,4,8,11-Tetraazacyclotetradecane 295-37-4
Price
US $3840.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
5 tons
Release date
2021-03-23
Zhuozhou Wenxi import and Export Co., Ltd
Product
1,4,8,11-Tetraazacyclotetradecane 98% (GC) 295-37-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27

295-37-4, 1,4,8,11-TETRAAZACYCLOTETRADECANERelated Search:

Plerixafor 8HCl (AMD3100 8HCl) 1,4,8-Tri-Boc-1,4,8,11-tetraazacyclotetradecane 1,4,8,11-Tetrakis(dimethylaminocarbonylmethyl)-1,4,8,11-tetraazacyclotetradecane 1,4,8,11-Tetrakis(aminocarbonylmethyl)-1,4,8,11-tetraazacyclotetradecane,1,4,8,11-Tetraazacyclotetradecane-N,N',N'',N'''-tetraacetamide, min. 98% 1,4,8,11-Tetrakis(diethylaminocarbonylmethyl)-1,4,8,11-tetraazacyclotetradecane 1,8-Dibenzyl-1,4,8,11-tetraazacyclotetradecane 1-Benzyl-1,4,8,11-tetraazacyclotetradecane,N-Benzyl-1,4,8,11-tetraazacyclotetradecane, min. 98% 1,4,8,11-Tetramethyl-1,4,8,11-tetraazacyclotetradecane,98%,1,4,8,11-TETRAMETHYL-1,4,8,11-TETRAAZACYCLOTETRADECANE 1,4,8,11-TETRAAZACYCLOTETRADECANE CIS-1,4,8,11-PERHYDROTETRAAZAPYRENE 1,4,8-Tris(aminocarbonylmethyl)-1,4,8,11-tetraazacyclotetradecane monohydriodide 1,4,8,11-Tetrakis(ethoxycarbonylmethyl)-1,4,8,11-tetraazacyclotetradecane Tetradecane 1,4,8,11-TETRAAZA-CYCLOTETRADECANE-5,12-DIONE 1,4,8,11-TETRAAZACYCLOTETRADECANE-5,7-DIONE 1,4,8,11-TETRAAZACYCLOTETRADECANE-1,4,8,11-TETRAACETIC ACID TETRAHYDROCHLORIDE HYDRATE 1 8-DIMETHYL-1 4 8 11-TETRAAZACYLCO- 1,1'-[1,3-PHENYLENEBIS-(METHYLENE)]-BIS-(1,4,8,11-TETRAAZACYCLOTETRADECANE) OCTAHYDROCHLORIDE

  • 1,4,8-Tris(trifluoroacetyl)-1,4,8,11-tetraazacyclotetradecane
  • 1,4,8-Tris(trifluoroacetyl)cyclaM
  • cyclaM, Methanol adduct
  • 1,4,8,11-Tetraazacyclotetradecane 98% (GC)
  • jm1498
  • CYCLAM
  • Cyclam, 98+%
  • 1,4,8,11-TETRAAZACYCLOTETRADECANE
  • Cyclam=1,4,8,11-Tetraazacyclotetradecane
  • 1,4,8,11-Tetraazacyclotetradecane, 99+%
  • 1,4,8,11-Tetraazacyclotetradecane,min.98%CYCLAM
  • 1,4,8,11-TETRAAZACYCLOTETRADECANE(CYCLAM)
  • 1,4,8,11-Tetraazacyclotetradecane 98%
  • 1,4,8,11-TETRAAZACYCLOTETRADECANE, 98+%
  • (1α,4β,8β,11α)-1,4,8,11-Tetraazacyclotetradecane
  • 1,4,8,11-tetraazacyclotetradecane Hexa(trifluoroacetate)
  • 1,1',1''-(1,4,8,11-Tetraazacyclotetradecane-1,4,8-triyl)tris[2,2,2-trifluoro-ethanone
  • 1,4,8,11-Tetraazacyclotetradecane, 99+% 1GR
  • Tetraazacyclotetradecane
  • 1,4,8,11-TetraazacycL
  • otetradecane
  • 1,4,8,11-tetrazacyclotetradecane
  • Plerixafor 1,4,8,11-Tetraazacyclotetradecane
  • Plerixafor intermediate
  • Plerixafor 1,4,8,11-Tetraazacyclotetradecane/ 1,4,8,11-Tetraazacyclotetradecane
  • 1,4,8,11-TETRAAZACYCLOTETRADECANE 295-37-4
  • 1,4,8,11-Tetraazacyclotetradecane (6CI, 7CI, 8CI, 9CI, ACI)
  • Compound PDK0168
  • Plerixafor Impurity 67
  • Valine Impurity 134
  • 295-37-4
  • C10H20N4
  • C10H24N4
  • C16H21F9N4O3
  • Synthetic Reagents
  • Macrocycles for Host-Guest Chemistry
  • Azacrown Ethers
  • Crown Ethers
  • Chelation/Complexation Compounds
  • Ring Systems
  • organic amine
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Azacrown Ethers
  • Crown Ethers
  • Functional Materials
  • Macrocycles for Host-Guest Chemistry
  • Achiral Nitrogen
  • Cy-N