Specifications
- Purity
- ≥95% (GC)
- Appearance
- Colourless to yellow or viscous liquid
- Identity
- 1H-NMR
Properties
- Solvents
- DMSO
- Boiling Point
- 115 °C/0.04 mmHg (lit.)
- Refractive Index
- n20/D 1.480 (lit.)
- Density
- 1.192 g/mL at 25 °C (lit.)
Available from stock
2-Hydroxymethyl-12-crown-4
- SKU
- H0514
Category: Building Blocks, Intermediates, Reagents
- Synonyms
- (12-Crown-4)-2-methanol, 1,4,7,10-Tetraoxacyclododecan-2-methanol
- 75507-26-5
- CAS-Number
- C9H18O5
- Molecular Formula
- 206.24
- Molecular Weight
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
- Shipping
- AMBIENT
- Short Term Storage
- RT
- Long Term Storage
- +4°C
- Handling Advice
- Protect from light and moisture.
- Use / Stability
- Stable for at least 2 years after receipt when stored at +4°C.
- Hazard statements
- H315 - H319 - H335
- Precautionary statements
- P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
- GHS Symbol
- GHS07
- Signal word
- Warning
- Transportation
- Not dangerous goods
- Description
- 2-Hydroxymethyl-12-crown-4 is ionophoric and used as an efficient phase transfer catalyst and as a complexing agent with a variety of small cations. This crown ether is a cyclic chemical compound that forms stable complexes with certain cations due to its ring structure containing multiple ether groups. The core structure is a 12-membered ring with 4 oxygen atoms spaced evenly around the ring. This structure is conducive to binding monovalent cations, particularly lithium (Li⁺), sodium (Na⁺) and potassium (K⁺). A hydroxymethyl group (-CH₂OH) is attached to the second carbon in the ring. This adds an additional functional group to the crown ether, which can impact its solubility, reactivity, and binding properties. Crown ethers like 2-Hydroxymethyl-12-crown-4 are often used to facilitate the transport of cations across membranes. They can act as phase transfer catalysts, helping to move ionic reactants into organic phases where they can react more readily. These compounds are studied for their ability to form stable complexes with metal ions, which has implications in both inorganic and organic chemistry. 2-Hydroxymethyl-12-crown-4 is used as a bulding block or intermediate for synthesis of probes.
- Smiles
- OCC1COCCOCCOCCO1
- InChi Key
- NJIPEIQHUNDGPY-UHFFFAOYSA-N
- References
- (1) I. Ikeda, et al.; Tetrahedr. Lett. 22, 3615 (1981) , (2) T. Miyazaki, et al.; Bull. Chem. Soc. Japan 55, 2005 (1982) , (3) S. Kitazawa, et al.; JACS 106, 6978 (1984) , (4) M.J. Pugia, et al.; J. Org. Chem. 52, 2617 (1987) , (5) B.P.S. Chauhan & P. Boudjouk; Tetrahedr. Lett. 40, 4123 (1999) , (6) A. Varnek, et al.; J. Chem. Inf. Comput. Sci. 42, 812 (2002) , (7) R. Pankiewicz, et al.; J. Mol. Struct. 749, 128 (2005) , (8) Z. Biyikliouglu & H. Kanteking; Dyes Pigm. 80, 17 (2009) , (9) P. Bruni, et al.; J. Mol. Struct. 919, 328 (2009) , (10) S.J. Warnock, et al.; PNAS 118, e2022197118 (2021) , (11) L. Pang, et al.; Mat. Design 211, 110159 (2021)
- InChi
- InChI=1S/C9H18O5/c10-7-9-8-13-4-3-11-1-2-12-5-6-14-9/h9-10H,1-8H2
2-Hydroxymethyl-12-crown-4 is ionophoric and used as an efficient phase transfer catalyst and as a complexing agent with a variety of small cations. This crown ether is a cyclic chemical compound that forms stable complexes with certain cations due to its ring structure containing multiple ether groups. The core structure is a 12-membered ring with 4 oxygen atoms spaced evenly around the ring. This structure is conducive to binding monovalent cations, particularly lithium (Li⁺), sodium (Na⁺) and potassium (K⁺). A hydroxymethyl group (-CH₂OH) is attached to the second carbon in the ring. This adds an additional functional group to the crown ether, which can impact its solubility, reactivity, and binding properties. Crown ethers like 2-Hydroxymethyl-12-crown-4 are often used to facilitate the transport of cations across membranes. They can act as phase transfer catalysts, helping to move ionic reactants into organic phases where they can react more readily. These compounds are studied for their ability to form stable complexes with metal ions, which has implications in both inorganic and organic chemistry. 2-Hydroxymethyl-12-crown-4 is used as a bulding block or intermediate for synthesis of probes.
Additional information
| Synonyms | (12-Crown-4)-2-methanol, 1,4,7,10-Tetraoxacyclododecan-2-methanol |
|---|---|
| Purity | ≥95% (GC) |
| Appearance | Colourless to yellow or viscous liquid |
| CAS-Number | 75507-26-5 |
| Molecular Formula | C9H18O5 |
| Molecular Weight | 206.24 |
| Identity | 1H-NMR |
| Solvents | DMSO |
| Boiling Point | 115 °C/0.04 mmHg (lit.) |
| Refractive Index | n20/D 1.480 (lit.) |
| Density | 1.192 g/mL at 25 °C (lit.) |
| Smiles | OCC1COCCOCCOCCO1 |
| InChi Key | NJIPEIQHUNDGPY-UHFFFAOYSA-N |
| Shipping | AMBIENT |
| Short Term Storage | RT |
| Long Term Storage | +4°C |
| Handling Advice | Protect from light and moisture. |
| Use / Stability | Stable for at least 2 years after receipt when stored at +4°C. |
| Hazard statements | H315 – H319 – H335 |
| Precautionary statements | P261 – P264 – P271 – P280 – P302 + P352 – P305 + P351 + P338 |
| GHS Symbol | GHS07 |
| Signal word | Warning |
| Transportation | Not dangerous goods |
| References | (1) I. Ikeda, et al.; Tetrahedr. Lett. 22, 3615 (1981), (2) T. Miyazaki, et al.; Bull. Chem. Soc. Japan 55, 2005 (1982), (3) S. Kitazawa, et al.; JACS 106, 6978 (1984), (4) M.J. Pugia, et al.; J. Org. Chem. 52, 2617 (1987), (5) B.P.S. Chauhan & P. Boudjouk; Tetrahedr. Lett. 40, 4123 (1999), (6) A. Varnek, et al.; J. Chem. Inf. Comput. Sci. 42, 812 (2002), (7) R. Pankiewicz, et al.; J. Mol. Struct. 749, 128 (2005), (8) Z. Biyikliouglu & H. Kanteking; Dyes Pigm. 80, 17 (2009), (9) P. Bruni, et al.; J. Mol. Struct. 919, 328 (2009), (10) S.J. Warnock, et al.; PNAS 118, e2022197118 (2021), (11) L. Pang, et al.; Mat. Design 211, 110159 (2021) |
| InChi | InChI=1S/C9H18O5/c10-7-9-8-13-4-3-11-1-2-12-5-6-14-9/h9-10H,1-8H2 |
| Quantity | 250 mg, 1 g, Bulk |
