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2094-72-6

  • Product Name:1-Adamantanecarbonyl chloride
  • Molecular Formula:C11H15ClO
  • Appearance:white to almost white crystalline solid
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Product Details

Appearance:white to almost white crystalline solid

Purity:99%

High Purity 1-Adamantanecarbonyl chloride 2094-72-6 In Bulk Supply

2094-72-6 Name

Name

1-Adamantanecarbonyl chloride

Synonym

 1-ADAMANTANECARBONYL CHLORIDE;1-ADAMANTANECARBOXYLIC ACID CHLORIDE;1-ADAMANTANECARBOXYLIC ACID CHLOROANHYDRIDE;ADAMANTANE-1-CARBONYL CHLORIDE;AKOS BC-0659;TRICYCLO[3.3.1.1]DECANE-1-CARBOXYLIC ACID CHLORIDE;1-Adamantanecarbony chloride;38. 1-adamantanecarbonyl chloride

 

 Chemical & Physical Properties

Melting point 

49-51 °C(lit.)

Boiling point

270.6±0.0 °C at 760 mmHg

Density

1.2±0.1 g/cm3

Molecular Formula

C11H15ClO

Molecular Weight

198.689

Flash Point

 139.0±8.3 °C

PSA

17.07000

LogP

3.34

Exact Mass

198.081146

Vapour Pressure

0.0±0.5 mmHg at 25°C

Index of Refraction

1.556

Storage condition

2-8°C

Water Solubility

may decompose

1-Adamantanecarbonyl chloride 2094-72-6 Usage

1-Adamantanecarbonyl chloride was used in the preparation of efficient amine-modified oligodeoxynucleotides for fabrication of DNA microarrays. The hydroxyl groups of NDs first reacted with 1, 1-adamantanecarbonyl chloride to obtain ND-Ad, IUdR was derivatized with either 1-adamantanecarbonyl chloride or 4-(1-adamantyl-carbamoyl)butanoic acid, to prepare 5’-O-(1-adamantoyl)-5-iodo-2’-deoxyuridine 1 and 5’-O-(4-(1-adamantylcarbamoyl)butoyl)-5-iodo-2’-deoxy-uridine 4, respectively. 1-adamantanecarbonyl chloride is the most common and is available commercially in bulk quantities.

InChI:InChI=1/C11H15ClO/c12-10(13)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2

2094-72-6 Relevant articles

Quantitative Electrochemical Reduction of 1‐Adamantanecarbonyl Chloride to 1‐Adamantanecarboxaldehyde at Carbon and Mercury Cathodes in Acetonitrile

MS Mubarak, DG Peters

Journal of the Electrochemical Society, 1995

A cyclic voltammogram for reduction of 1‐adamantanecarbonyl chloride at a glassy carbon or hanging mercury drop electrode in acetonitrile containing 0.10M tetraethylammonium perchlorate displays two irreversible cathodic waves, we conclude that 1‐adamantanecarbonyl chloride undergoes one‐electron reduction to an acyl radical, which accepts a hydrogen (deuterium) atom from the solvent to afford the aldehyde.

Intermolecular interactions in crystalline 1-(adamantane-1-carbonyl)-3-substituted thioureas with Hirshfeld surface analysis

Saeed, Aamer,Bolte, Michael,Erben, Mauricio F.,Pérez, Hiram

, p. 7551 - 7563 (2015)

The relative contributions of the main intermolecular contacts as well as the enrichment ratios derived from the Hirshfeld surface analysis establish the 1-acyl thiourea synthon to be a widespread contributor.

Hyaluronic acid-based supramolecular nanomedicine with optimized ratio of oxaliplatin/chlorin e6 for combined chemotherapy and O2-economized photodynamic therapy

Yuan-Fu Ding , Xun Xu , Junyan Li , Ziyi Wang , Jingwei Luo , Greta S.P. Mok , Shengke Li , Ruibing Wang

Acta Biomaterialia Available online 31 March 2023

Chlorin e6 (Ce6) was purchased from Frontiersci. Nsingle bondHydroxysulfosuccinimide (NHS), 1-Adamantanecarbonyl chloride, N-Boc-ethylenediamine, N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide (EDC), cysteamine (Cys), dithiothreitol (DTT), and 4-dimethylaminopyridine (DMAP) were provided.

2094-72-6 Process route

adamontoyltris(trimethylsilyl)germane
104164-53-6

adamontoyltris(trimethylsilyl)germane

tris(trimethylsilyl)germyl chloride
104164-55-8

tris(trimethylsilyl)germyl chloride

{(CH<sub>3</sub>)3Si}2Ge{C(OSi(CH<sub>3</sub>)3)C<sub>10</sub>H<sub>15</sub>}

{(CH3)3Si}2Ge{C(OSi(CH3)3)C10H15}

chloroform
67-66-3,8013-54-5

chloroform

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

Conditions
Conditions Yield
In tetrachloromethane; byproducts: Me3SiCl, hexachloroethane; Irradiation (UV/VIS); NMR tubes contg. the acylgermane/CCl4 sealed under vac., irradiated (two 100W Hg lamps, λ>360 nm) for up to 3h, with cooling to -15°C), soln. remained colourless; not isolated, detected by NMR-spect.;
>65
>99
<1
0%
1-Adamantyl bromide
768-90-1

1-Adamantyl bromide

1-Adamantanecarbonyl chloride
2094-72-6

1-Adamantanecarbonyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1.) magnesium, 1,2-dibromoethane / 1.) diethyl ether, 35 deg C
2: 90 percent / SOCl2 / 1 h / Heating
With thionyl chloride; magnesium; ethylene dibromide;
 
Multi-step reaction with 2 steps
1: sulfuric acid / hexane / 5 h / Cooling with ice
2: thionyl chloride / benzene / 5 h / 80 °C / Reflux
With thionyl chloride; sulfuric acid; In hexane; benzene;
 
Multi-step reaction with 2 steps
1.1: magnesium; iodine / diethyl ether / 2 h / Inert atmosphere
1.2: 3.5 h / Inert atmosphere
2.1: thionyl chloride / 1 h / 80 °C
With thionyl chloride; iodine; magnesium; In diethyl ether;
 
Multi-step reaction with 2 steps
1: sulfuric acid / tetrahydrofuran / 3 h / 5 - 10 °C
2: thionyl chloride / 2 h / 80 °C
With thionyl chloride; sulfuric acid; In tetrahydrofuran;
 
Multi-step reaction with 2 steps
1: sulfuric acid / tetrahydrofuran / 3 h / 5 - 10 °C / Green chemistry
2: thionyl chloride / 2 h / 80 °C / Green chemistry
With thionyl chloride; sulfuric acid; In tetrahydrofuran;
 
Multi-step reaction with 2 steps
1: sulfuric acid / hexane / 4 h / 5 - 10 °C
2: thionyl chloride / 1 h / 80 °C
With thionyl chloride; sulfuric acid; In hexane;
 
Multi-step reaction with 2 steps
1: sulfuric acid / hexane / 4 h / 5 - 10 °C
2: thionyl chloride / 1 h / 80 °C
With thionyl chloride; sulfuric acid; In hexane;
 

2094-72-6 Upstream products

  • 828-51-3
    828-51-3

    1-Adamantanecarboxylic acid

  • 768-90-1
    768-90-1

    1-Adamantyl bromide

  • 104164-53-6
    104164-53-6

    adamontoyltris(trimethylsilyl)germane

  • 281-23-2
    281-23-2

    adamantane

2094-72-6 Downstream products

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    (adamant-1-yl)-acetic acid

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    ((morphonyl)tricyclo[3.3.1.13,7]dec-1-yl)methanone

  • 35871-25-1
    35871-25-1

    N-(benzo[d]thiazol-2-yl)adamantane-1-carboxamide

  • 1660-05-5
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