4-(Hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid

Base Information

• Chemical Name: 4-(Hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid
• CAS No.: 828-52-4
• Molecular Formula: C10H16 O3
• Molecular Weight: 184.235
• Hs Code.: 2920909090
• European Community (EC) Number: 871-783-1
• NSC Number: 177415
• DSSTox Substance ID: DTXSID00306539
• Wikidata: Q82053682
• Mol file: 828-52-4.mol

Synonyms:4-(Hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid;828-52-4;4-(Hydroxymethyl)bicyclo(2.2.2)octane-1-carboxylic acid;NSC177415;4-(Hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylicacid;SCHEMBL20944070;DTXSID00306539;MFCD20640208;ZB1475;AKOS006329185;AKOS016005512;DS-3928;NSC 177415;NSC-177415;FT-0745217;EN300-198571;O11092;A864331;A1-01558;4-Hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid;4-HYDROXYMETHYL-BICYCLO[2.2.2]OCTANE-1-CARBOXYLIC ACID

Chemical Property of 4-(Hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.03E-05mmHg at 25°C
• Melting Point: 187-188 °C
• Boiling Point: 332.7°Cat760mmHg
• PKA: 4.97±0.10(Predicted)
• Flash Point: 169.2°C
• PSA: 57.53000
• Density: 1.285g/cm³
• LogP: 1.40390
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 210

Purity/Quality:

99% ^*data from raw suppliers

4-(Hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2(CCC1(CC2)CO)C(=O)O

Technology Process of 4-(Hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid

There total 5 articles about 4-(Hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid 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: 100.0%

bicyclo[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (18720-35-9) → 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid (828-52-4)

Guidance literature:

With sodium tetrahydroborate; In water; at 20 ℃;

Reference yield:

4-hydroxymethyl-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester (94994-15-7) → 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid (828-52-4)

Guidance literature:

4-hydroxymethyl-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester; With lithium hydroxide; In tetrahydrofuran; methanol; water; at 20 - 25 ℃; for 16h;

With hydrogenchloride; In water; pH=0;

Reference yield:

Aethylen-diketal von 1,4-Dihydroxymethyl-2,5-dioxo-bicyclo-<2,2,2>-octan (843-52-7) → 4-(hydroxymethyl)bicyclo[2.2.2]octane-1-carboxylic acid (828-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. HCl

2: N₂H₄*H₂O, KOH / bis-(2-hydroxy-ethyl) ether

3: aq. KOH, KMnO₄

With hydrogenchloride; potassium hydroxide; potassium permanganate; hydrazine hydrate; In diethylene glycol;

DOI:10.1021/ja01077a030

upstream raw materials:

Bicyclo<2.2.2>octane-1,4-dimethanol

Aethylen-diketal von 1,4-Dihydroxymethyl-2,5-dioxo-bicyclo-<2,2,2>-octan

1,4-bis(hydroxymethyl)bicyclo[2.2.2]octane-1,4-dione

4-hydroxymethyl-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester

Downstream raw materials:

1-Tosyloxymethyl-4-carboxy-bicyclo<2.2.2>octan

1-Tosyloxymethyl-4-brom-bicyclo<2.2.2>octan

4-hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid benzyl ester

Refernces

• 1、 -. "Adenosine receptor antagonists and methods of making and using the same". Page/Page column 58. . Retrieved 2008/06/13.