Hypophosphorous acid

Base Information

• Chemical Name: Hypophosphorous acid
• CAS No.: 6303-21-5
• Deprecated CAS: 60062-19-3
• Molecular Formula: H3O2P
• Molecular Weight: 65.9964
• Hs Code.: 28111990
• DSSTox Substance ID: DTXSID90873902
• Wikidata: Q409658
• Mol file: 6303-21-5.mol

Synonyms:Dihydroxyphosphine;Hydroxyphosphine oxide;Phosphine oxide, hydroxy-;Phosphonous acid;Hypophosphorous acid (HPA);Hypophosphorous acid (HPA 50%);Hypophosphorous Acid 30% to 32% (As per NF Specs) up to 80%;Hypophosphorous acid 50%;

Chemical Property of Hypophosphorous acid

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: <17 mmHg ( 20 °C)
• Melting Point: -25 °C
• Boiling Point: 108 °C (759.8513 mmHg)
• PKA: pK1 1.1.
• PSA: 108.10000
• Density: 1.206 g/mL
• LogP: -0.50560
• Storage Temp.: no restrictions.
• Water Solubility.: SOLUBLE
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 64.97924130
• Heavy Atom Count: 3
• Complexity: 10.3

Purity/Quality:

Hypophosphorous acid solution 50 wt. % in H2O ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: O[PH+]=O
• Uses: 1. Hypophosphorous acid is used as reducing agent for electroless plating; 2. It can be used to prevent discoloration of phosphoric acid resin; 3. It is used as esterification catalyst, the refrigerant; 4. It is used to produce hypophosphite, sodium salts, manganese salts, iron salts are generally used as nourishing substances; 5. Hypophosphorous acid is used in medicine and as reducing agent, the determination of arsenic, tellurium and separation of tantalum, niobium and other reagents. 6. It is strong reducing agent, It can be used for the preparation of sodium hypophosphite, calcium phosphate and other hypophosphite. 7. It can be used for the plating bath. Pharmaceuticals. reducing agent. general reagents. 8. It is strong reducing agent, it can be used in making sodium hypophosphite, calcium phosphate and other hypophosphite. 9. This product is widely used as reducing agent, Ag, Cu, Ni, Hg and other metals are reduced to the corresponding metal, for the verification of As, Nb, Ta and other reagents, it can be used for the preparation of Na, K, Ca, Mn, Fe and other types of hypophosphite. Hypophosphorous acid is primarily used for electroless nickel plating. It is involved in the reduction of arenediazonium salts. It acts as an additive in Fischer esterification reactions. Also, it serves as a neutralizing agent, antioxidant, catalyst in polymerization and poly condensation, and wetting agent. Further, it is used in the formulation of pharmaceuticals, discoloration of polymers, water treatment and retrieval of precious or non-ferrous metals. In addition to this, it is used as bleaching agents for plastics, synthetic fibers, decolorizing agent and for color stabilization during the manufacture of chemicals and several plastics.
• Production method: Ion exchange resin method: put about 70 g water-soluble cation exchange resins to fill into a glass tube. Circulate with 5 mol/L hydrochloric acid for about 15 min and wash sufficiently with water. Have a high aqueous sodium hypophosphite solution (15 g/60 ml H2O) to flow through the resin column, followed by being washed first with 50 ml water, and then rinsing with 25 rnl distilled water. The effluent acid and the washings were combined and concentrated by evaporation on a water bath. The concentrated acid is send to the highly vacuum, P205 dryer for dehydration, followed by cooling crystallization, filtration and recrystallization to obtain the finished product of hypophosphorous acid.
• Description: Hypophosphorous acid is a powerful reducing agent with a molecular formula of H3PO2. Inorganic chemists refer to the free acid by this name although its IUPAC name is dihydridohydroxidooxidophosphorus, or the acceptable name of phosphinic acid. It is a colorless low-melting compound, which is soluble in water, dioxane, and alcohols. The formula for hypophosphorous acid is generally written H3PO2, but a more descriptive presentation is HOP(O)H2 which highlights its monoprotic character. Salts derived from this acid are called phosphinates (hypophosphites). This acid has the general formula ofH4P2O6 and differs from the other oxy-phosphorous acids. It has many peculiarities. It is formed along with phosphorous and phosphoric acids, when phosphorus is oxidized by moist air. If white phosphorus is exposed to air, and sodium acetate is addedto the liquidwhich forms, the somewhat insoluble sodium hypophosphate,Na2H2P2O6·6H2Oseparates. The sodium hypophosphate monohydrate, however, is very soluble and deliquescent at ～98.7 g/100 ml.
• Physical properties: Colorless deliquescent crystals or oily liquid; sour odor; density 1.493 g/cm3;melts at 26.5°C; boils at 130°C; very soluble in water, alcohol and ether; den-sity of a 50% aqueous solution is 1.13 g/mL.

Technology Process of Hypophosphorous acid

There total 70 articles about Hypophosphorous 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: 93.0%

hydrogenchloride (7647-01-0,15364-23-5) + phosphorus + dihydrogen peroxide (7722-84-1) + tri-n-butyl-tin hydride (688-73-3) → phosphonic Acid (13598-36-2) + tributyltin chloride (1461-22-9) + hypophosphorous acid (6303-21-5)

Guidance literature:

phosphorus; tri-n-butyl-tin hydride; In toluene; at 20 ℃; for 16h; Irradiation; Schlenk technique;

dihydrogen peroxide; In water; toluene; at 20 ℃; for 0.5h; Cooling with liquid nitrogen;

hydrogenchloride; In 1,4-dioxane; hexane; water; acetonitrile; for 1h;

DOI:10.1038/s41557-021-00657-7

Reference yield:

water (7732-18-5) + iodine (7553-56-2,12190-71-5,8031-47-8) + phosphan (7803-51-2) → hydrogen iodide (10034-85-2) + hypophosphorous acid (6303-21-5)

Guidance literature:

In water; passing PH3 (prepared from Ca-phosphide and HCl) into an aq. suspension of I2 in a bulb under CO2 or N2 (agitation) until initial brown discoloration has vanished;; removal of H2O and HI by repeated distn. at 40 °C and 40 Torr and addn. of small amounts of water to the residue before 2nd and 3rd distillation;;

Reference yield:

sodium hypophosphite monohydrate (10039-56-2) + benzyl chloride (100-44-7) → hypophosphorous acid (6303-21-5) + sodium chloride (7647-14-5) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

In ethanol; sodium hypophosphite monohydrate dissolved in ethanol, benzyl chloride added; volatile products sepd. by vac. distn.;

upstream raw materials:

water

phosphan

sulphurous acid

phosphonic Acid

Downstream raw materials:

cerium orthophosphate

ammonium hypophosphorous acid

bis(phenyl) carbonate

phenyl chloroformate

Refernces

Determination of the absolute configuration of phosphinic analogues of glutamate

10.1039/c4ob01960a

The research focuses on the determination of the absolute configuration of phosphinic analogues of glutamate, specifically LSP1-2111, which are known to be potent agonists of metabotropic glutamate (mGlu) receptors and have shown promising in vivo activity. The study aimed to separate the mixture of two diastereomers of LSP1-2111, whose absolute and relative configurations were previously unknown, using a Crownpack CR(+) column. The absolute configuration was assessed through a diastereoselective synthesis involving various reactants such as phosphinic acid, 3-nitrobenzaldehydes, and amino acids. The experiments included radical processes, condensation, acid hydrolysis, and the use of chiral HPLC for separation. The analysis involved optical rotation, 1H NMR, 31P NMR, and X-ray crystallography to characterize the diastereomers and determine their absolute configuration. The study also investigated the biological activity of the separated L-stereomers, finding that they activated the mGlu4 receptor with varying EC50 values.

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