n-Hydroxyadamantane-1-carboxamide

Base Information

• Chemical Name: n-Hydroxyadamantane-1-carboxamide
• CAS No.: 28309-44-6
• Molecular Formula: C11H17 N O2
• Molecular Weight: 195.261
• Hs Code.: 2924299090
• European Community (EC) Number: 621-727-5
• DSSTox Substance ID: DTXSID80351547
• Nikkaji Number: J1.682.503D
• Wikidata: Q82128044
• Mol file: 28309-44-6.mol

Synonyms:n-hydroxyadamantane-1-carboxamide;28309-44-6;adamantylhydroxamic acid;1-adamantanehydroxamic acid;Oprea1_052664;IFLab1_000254;DTXSID80351547;N-hydroxy-1-adamantanecarboxamide;HMS1412L12;AKOS000206286;AKOS006238836;IDI1_008473;CS-0343740;EN300-16983;SR-01000396860;SR-01000396860-1;Z56853707;F0075-0016

Chemical Property of n-Hydroxyadamantane-1-carboxamide

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 52.82000
• Density: 1.257g/cm³
• LogP: 2.54850
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 195.125928785
• Heavy Atom Count: 14
• Complexity: 233

Purity/Quality:

97% ^*data from raw suppliers

N-HYDROXYADAMANTANE-1-CARBOXAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)(C3)C(=O)NO

Technology Process of n-Hydroxyadamantane-1-carboxamide

There total 5 articles about n-Hydroxyadamantane-1-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1-Adamantanecarboxylic acid (828-51-3) → (3r,5r,7r)-N-hydroxyadamantane-1-carboxamide (28309-44-6)

Guidance literature:

1-Adamantanecarboxylic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 1h;

With hydroxylamine hydrochloride; In tetrahydrofuran; for 16h;

DOI:10.1080/00397910903026723

Reference yield: 91.0%

methyl adamantane-1-carboxylate (711-01-3) → (3r,5r,7r)-N-hydroxyadamantane-1-carboxamide (28309-44-6)

Guidance literature:

With hydroxylamine hydrochloride; potassium hydroxide; In methanol; at 20 ℃; for 12h; pH=10;

DOI:10.1039/c6ob01178k

Reference yield: 75.0%

1-Adamantanecarbonyl chloride (2094-72-6) → (3r,5r,7r)-N-hydroxyadamantane-1-carboxamide (28309-44-6)

Guidance literature:

With hydroxylamine hydrochloride; potassium carbonate; In water; ethyl acetate; at 0 - 20 ℃; for 16h;

DOI:10.1039/c8ob00490k

upstream raw materials:

1-Adamantanecarboxylic acid

C₁₇H₂₇NO₂

1-Adamantanecarbonyl chloride

methyl adamantane-1-carboxylate

Downstream raw materials:

1-Adamantanamine

BPA

Refernces

• 1、 Chen, Qishu,Du, Bingnan,Ouyang, Yuxin,Yu, Wing-Yiu. "Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones". supporting information. p. 14962 - 14968. Retrieved 2021/09/29.
• 2、 Hoshino, Yujiro,Ohtsuka, Naoya,Okada, Takuya,Honda, Kiyoshi. "One-pot synthesis of primary amines from carboxylic acids through rearrangement of in situ generated hydroxamic acid derivatives". supporting information. p. 5304 - 5307. Retrieved 2016/11/16.