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Home > Encyclopedia > 4,4'-Bis(hydroxymethyl)-2,2'-bipyridine

4,4'-Bis(hydroxymethyl)-2,2'-bipyridine

4,4'-Bis(hydroxymethyl)-2,2'-bipyridine structure

4,4'-Bis(hydroxymethyl)-2,2'-bipyridine 

structure
  • CAS No:

    109073-77-0

  • Formula:

    C12H12N2O2

  • Chemical Name:

    4,4'-Bis(hydroxymethyl)-2,2'-bipyridine

  • Synonyms:

    4,4'-Bis(hydroxymethyl)-2,2'-bipyridine;2,2'-Bi(pyridine-4-methanol);2,2'-Bipyridine-4,4'-bismethanol;2,2'-Bipyridine-4,4'-dimethanol;{2-[4-(hydroxyMethyl)pyridin-2-yl]pyridin-4-yl}Methanol;2,2'-Bipyridine-4,4'-dimethanol4,4'-Bis(hydroxymethyl)-2,2'-bipyridyl;[2,2'-Bipyridine]-4,4'-diyldiMethanol;4,4'is(hydroxymethyl)-2,2'-bipyridine

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

4,4'-Bis(hydroxymethyl)-2,2'-bipyridine Basic Attributes

216.24

216.089874

DTXSID30457260

29333990

Characteristics

66.2

-0.3

1.281±0.06 g/cm3(Predicted)

170.6-171.4 °C

450.4±40.0 °C(Predicted)

226.2±27.3 °C

1.628

6.74E-09mmHg at 25°C

Safety Information

24/25

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

H315

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

4,4'-Bis(hydroxymethyl)-2,2'-bipyridine Use and Manufacturing

Sodium borohydride (1.87g, 49mmol) was added to a suspension of diethyl [2, 2'-bipyridine]-4, 4'-dicarboxylate 7 (567mg, 1.89mmol) dissolved in absolute ethanol (34mL). The solution was refluxed for 3h. After cooling to room temperature, a saturated ammonium chloride solution (24mL/g of NHto a suspension of the diester 4 ( 10.0 g, 33.3 mmol) in 300 ml of absolute ethanol was added sodium borohydride (25.19 g, 665.9 mmol) in one portion. The mixture was refluxed for 3 h and cooled to RT, and excess borohydride was decomposed by the dropwise addition saturated ammonium chloride solution (300 ml). Ethanol was removed under vacuum and the precipitated solid was filtered and the solid was dissolved in ethyl acetate (400 ml), washed with water ( 100 ml), dried over anhy. NaLigand 2(1.02 g, 3.40 mmol) was suspended in 200 proof ethanol (67 mL).Sodium borohydride (2.80 g, 74.0 mmol) was added and the suspension was refluxed at 90 C for 3 h. After cooling, saturated aqueous ammonium chloride (75 mL) was added and ethanol was removed in vacuo. Water was added until all white solid was dissolved.The aqueous layer was extracted with ethyl acetate (450 mL) and the combined organic layers were dried over anhydrous Na2SO4. The solvent was removed in vacuo to yielda white solidTo a suspension of compound 4 (6.0 g, 22.0 mmol) in 200 ml of absolute ethanol was added 16.4 g (0.434 mol) of sodium borohydride. The mixture was refluxed for 3 h and cooled to room temperature, and then 200 mL of an ammonium chloride saturated water solution was added to decompose the excess borohydride. The reaction mixture was evaporated to removed the ethanol, and a minimal amount of water was added to dissolve the precipitated solid. The resulting solution was extracted with ethyl acetate (5 × 200 mL), dried overMgSO4, and evaporated to dryness product 5 (3.56 g, 75percent yield).

Computed Properties

Molecular Weight:216.24
XLogP3:-0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:216.089877630
Monoisotopic Mass:216.089877630
Topological Polar Surface Area:66.2
Heavy Atom Count:16
Complexity:191
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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