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1-Hydroxyethylidene-1,1-diphosphonic acid

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1-Hydroxyethylidene-1,1-diphosphonic acid Basic information

Product Name:
1-Hydroxyethylidene-1,1-diphosphonic acid
Synonyms:
  • ETHANE-1-HYDROXY-1,1-DIPHOSPHONIC ACID, 95+%
  • (1-Hydroxyethylidene)biphosphonic acid
  • Hydroxyethylidene Diphosphonic acid (HEDP)
  • 1-Hydroxyethylidene-1,1-diphosphonicacid,min.95%HEDP
  • 1-Hydroxyethan-1,1-diphosphonsure
  • 1-HYDROXYETHYLIDENE-1,1-DIPHOSPHONIC ACID HEDP
  • 1-Hydroxyethylidene-1,1-bis-(phosphonic acid)
  • 1-HYDROXYETHYLIDENE-1,1-DIPHOSPHONIC ACID, 98% HEDP
CAS:
2809-21-4
MF:
C2H8O7P2
MW:
206.03
EINECS:
220-552-8
Product Categories:
  • Phosphonate antiscalant
  • Analytical Chemistry
  • Industrial/Fine Chemicals
  • INORGANIC & ORGANIC CHEMICALS
  • Ligands for Pharmaceutical Research
  • Radiopharmaceutical Chemistry (Chelating Reagents)
  • organophosphorus compound
  • Water treatment
Mol File:
2809-21-4.mol
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1-Hydroxyethylidene-1,1-diphosphonic acid Chemical Properties

Melting point:
198~199℃
Boiling point:
578.8±60.0 °C(Predicted)
Density 
1.45 (60% aq.)
form 
Powder
pka
1.35, 2.87, 7.03, 11.3(at 25℃)
color 
white
PH
pH (1.7→100, 25℃) : 1.3~1.8
Water Solubility 
Soluble in water.
Merck 
14,3863
BRN 
1789291
Stability:
Stable. Incompatible with strong oxidizing agents.
InChIKey
DBVJJBKOTRCVKF-UHFFFAOYSA-N
CAS DataBase Reference
2809-21-4(CAS DataBase Reference)
EPA Substance Registry System
Etidronic acid (2809-21-4)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
37/38-41-22
Safety Statements 
26-39
RIDADR 
UN 3265
WGK Germany 
2
RTECS 
SZ8562100
10
TSCA 
Yes
HazardClass 
8
PackingGroup 
II
HS Code 
29319090
Hazardous Substances Data
2809-21-4(Hazardous Substances Data)
Toxicity
LD50 oral in mouse: 1800mg/kg

MSDS

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1-Hydroxyethylidene-1,1-diphosphonic acid Usage And Synthesis

Chemical Properties

light beige powder

Originator

Etidron,Gentili,Italy,1977

Uses

Etidronate (Didronel) is a human protein tyrosine phosphatase inhibitor with IC50 of 0.2 μM.

Definition

ChEBI: A 1,1-bis(phosphonic acid) that is (ethane-1,1-diyl)bis(phosphonic acid) having a hydroxy substituent at the 1-position. It inhibits the formation, growth, and dissolution of hydroxyapatite crystals by chemisorption to calcium phosphate surfaces.

Manufacturing Process

Phosphorous acid was premixed with acetic acid to form a 50 wt % solution of phosphorous acid dissolved in acetic acid. The acids were mixed on a molar basis of 1.36:1, acetic acid to phosphorous acid, and this corresponded on a mol percentage basis to 57.6% acetic acid and 42.4% phosphorous acid. Acetic anhydride was continuously metered into a stream of the phosphorous acid-acetic acid mixture to form the reaction solution. The acetic anhydride was metered into the acid mixture at a mol ratio of 1.33 mols of acetic anhydride per mol of phosphorous acid. The metering rates were 18.5 lb/hr of the phosphorous acid/acetic acid premixed solution and 15.1 lb/hr acetic anhydride. The reaction solution was continuously passed through a heat exchanger where it was heated to 190°F then it was continuously fed into a two stage back-mix reaction zone where due to the heat of reaction the temperature rose to 275°F. The average residence in the reaction zone was 27 min. The reaction zone consisted of two back-mix reactors each having a capacity of 7.5 pounds of the reaction solution. A stream of reaction solution was continuously with drawn from the second reactor and continuously mixed with a stream of water which was being metered at a rate of 2 lb/hr. This amount of water corresponded to 18% excess over the theoretical amount necessary to hydrolyze all of the acetyl-containing compounds in the reaction solution to free acids. The hydrolyzed solution was continuously passed through a heat exchanger and cooled to room temperature after which the solution was continuously passed to a crystallizer where, with agitation, the ethane-1-hydroxy-1,1-diphosphonic acid crystallized. The slurry was then filtered and the crystals were recovered and dried. Analysis of the product showed a conversion rate of phosphorous acid to ethane-1-hydroxy-1,1- diphosphonic acid of 86%. Sodium hydroxide may be used to give the disodium salt.

brand name

Didronel (Millot Laboratories, France); Didronel (Procter & Gamble).

Therapeutic Function

Bone calcium regulator

1-Hydroxyethylidene-1,1-diphosphonic acid Supplier

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