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)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

37/38-41-22

Safety Statements 

26-39

RIDADR 

UN 3265

WGK Germany 

2

RTECS 

SZ8562100

F 

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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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 (2809-21-4)Related Product Information

• MINODRONATE
• 4-(4-(bis(2-chloroethyl)amino)phenyl)-1-hydroxybutane-1,1-bisphosphonic acid
• 1-Hydroxyethylidene-1,1-Diphosphonic Acid Sodium Salt
• 1-HYDROXYETHYLIDENE-1,1-DIPHOSPHONIC ACID TRISODIUM SALT
• NERIDRONATE SODIUM HYDRATE
• [1-Hydroxy-3-(methylpentylamino)-propylidene]bisphosphonic acid sodium salt
• 1-HYDROXYETHANE-1,1-DIPHOSPHONIC ACID [1-14C]
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• CLODRONIC ACID
• phosphoric acid
• Ascoric Acid
• Citric acid
• Glycine
• 2-HYDROXYACETAMIDE
• Amino tris(methylene phosphonic acid)
• Ethyl 2-(Chlorosulfonyl)acetate
• Disodium pamidronate
• 4'-Hydroxyacetophenone