rel-(1R,4E,pR)-Cyclooct-4-enol

Product Name: rel-(1R,4E,pR)-Cyclooct-4-enol
CAS No.: 85081-69-2
Chemical Name: rel-(1R,4E,pR)-Cyclooct-4-enol
Synonyms: TCO-OH;(E)-Cyclooct-4-enol;4-Cycloocten-1-ol, (4E)-;(4E)-TCO-OH;trans-Cyclooctenol;(E)-Cyclooct-4-eno;TCO-OH,TCO-hydroxyl;(4E)-4-Cycloocten-1-ol;(E)-cyclooct-4-en-1-ol;(E)-Cyclooct-4-enol
CBNumber: CB12755590
Molecular Formula: C8H14O
Formula Weight: 126.2
MOL File: 85081-69-2.mol

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rel-(1R,4E,pR)-Cyclooct-4-enol Property

Boiling point:: 202.2±29.0 °C(Predicted)
Density: 0.954±0.06 g/cm3(Predicted)
storage temp.: -20°C
solubility: Soluble in DMSO
pka: 15.13±0.20(Predicted)
form: Liquid
color: Colorless to light yellow
InChI: InChI=1S/C8H14O/c9-8-6-4-2-1-3-5-7-8/h1-2,8-9H,3-7H2/b2-1+
InChIKey: UCPDHOTYYDHPEN-OWOJBTEDSA-N
SMILES: C1(O)CCCC=CCC1 |t:5|

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Safety

Hazard Codes: Xi
Risk Statements: 41-52
Safety Statements: 26-39
WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H318Causes serious eye damage

Precautionary statements

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

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

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 764396
Product name: (E)-Cyclooct-4-enol
Packaging: 10mg
Price: $115
Updated: 2025/07/31

Sigma-Aldrich

Product number: 764396
Product name: (E)-Cyclooct-4-enol
Packaging: 50mg
Price: $591.5
Updated: 2025/07/31

BroadPharm

Product number: BP-23975
Product name: TCO-OH
Purity: 95%
Packaging: 100mg
Price: $320
Updated: 2021/12/16

Ambeed

Product number: A467258
Product name: (E)-Cyclooct-4-enol
Purity: 85%
Packaging: 25mg
Price: $188
Updated: 2021/12/16

Ambeed

Product number: A467258
Product name: (E)-Cyclooct-4-enol
Purity: 85%
Packaging: 100mg
Price: $309
Updated: 2021/12/16

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rel-(1R,4E,pR)-Cyclooct-4-enol Chemical Properties,Usage,Production

Description

TCO-OH is a TCO intermediate allowed for further derivatizion

Uses

Hydroxyl modified cyclooctene derivative. Cyclooctenes are useful in strain-promoted copper-free click chemistry cycloaddition reactions with 1,2,4,5-tetrazines. This cyclooctene will react with tetrazine functionalized compounds or biomolecules without the need for a catalyst to result in a stable covalent linkage. The 4+2 inverse electron demand Diels-Alder cycloaddition between trans-cyclooctene and tetrazines is the fastest biologically compatible ligation technology reported and has had many applications in biological labeling and imaging.

reaction suitability

reaction type: click chemistry
reagent type: linker

Synthesis

4277-34-3

General procedure for the synthesis of 4-hydroxycyclooctene from 4-hydroxycyclooctene: Reagent grade ether (500 mL) was added to a Teflon-lined quartz flask containing (Z)-cyclooct-4-enol (1 g, 7.9 mmol) and methyl benzoate (1.1 g, 7.9 mmol) with a PTFE-coated magnetic stir bar. The quartz flask was placed in a Rayonet reactor and connected via Teflon PTFE tubing to a column containing 40 g of ISCO RediSep silica gel and an FMI pump. The column was filled with an 8 cm high bed of dry silica gel, silver nitrate impregnated silica gel (16.8 g, 10% w/w, 9.9 mmol AgNO3) was placed at the top of the column, and the column was rinsed with ether. The pump circulation rate was adjusted to approximately 100 mL/min for an 8 h photolysis reaction. The column was washed with 200 mL of ether and dried by a stream of compressed air. The column contents were poured into a 500 mL conical flask and the silica gel was stirred with 200 mL ammonium hydroxide and 200 mL methylene chloride for 5 minutes. The silica gel was filtered and the filtrate was transferred to a dispensing funnel. Separate the organic layer and wash the ammonium hydroxide layer with 200 mL of methylene chloride. The organic layers were combined, washed with 100 mL of water and dried with MgSO4. The solvent was evaporated by decompression to give the title product as a 2:1 mixture of diastereoisomers in a yield of 0.73 g (73%). The experiment was repeated to give 0.72 g (72%). The two diastereoisomers were separated in trace amounts by gravity silica gel column chromatography (4:1 pentane:ether): rf = 0.42 (major diastereoisomer: rf = 0.30).

IC 50

Alkyl-Chain

References

[1] Patent: US2009/23916, 2009, A1. Location in patent: Page/Page column 15
[2] Monatshefte fur Chemie, 2016, vol. 147, # 3, p. 579 - 585
[3] Angewandte Chemie - International Edition, 2014, vol. 53, # 38, p. 10242 - 10246
[4] Angew. Chem., 2014, vol. 126, # 38, p. 10407 - 10412,5
[5] Patent: US2016/115180, 2016, A1. Location in patent: Paragraph 0139

rel-(1R,4E,pR)-Cyclooct-4-enol Preparation Products And Raw materials

Raw materials

Preparation Products

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rel-(1R,4E,pR)-Cyclooct-4-enol Suppliers

China 44 United States 5 Global 49

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View Lastest Price from rel-(1R,4E,pR)-Cyclooct-4-enol manufacturers

Xian confluore Biological Technology Co., Ltd.

Product: (4E)-TCO-OH 85081-69-2
Price: US $0.00/mg
Min. Order: 25mg
Purity: >95.00%
Supply Ability: 25mg
Release date: 2024-03-21

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85081-69-2