25383-06-6

Basic information

• Product Name: cis-propenylphosphonic acid
• Synonyms: cis-propenylphosphonic acid;propenylphosphonic acid;(Z)-1-Propenylphosphonic acid;[(Z)-1-Propenyl]phosphonic acid;(Z)-prop-1-en-1-ylphosphonic acid;Cis-Propenylphosphoric acid
• CAS NO: 25383-06-6
• Molecular Formula: C₃H₇O₃P
• Molecular Weight: 122.059641
• EINECS: 246-928-1
• Mol File: 25383-06-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 274.1 °C at 760 mmHg
• Flash Point: 119.6 °C
• Appearance: /
• Density: 1.343 g/cm³
• Vapor Pressure: 0.00152mmHg at 25°C
• Refractive Index: 1.483
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO, Methanol (Slightly)
• PKA: 1.59±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: cis-propenylphosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cis-propenylphosphonic acid(25383-06-6)
• EPA Substance Registry System: cis-propenylphosphonic acid(25383-06-6)

Safety Data

• Hazardous Substances Data: 25383-06-6(Hazardous Substances Data)

Usage

Uses

[(Z)-Prop-1-enyl]phosphonic Acid could be useful as a pumping agent in concrete or cement.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 3510, 1970 DOI: 10.1021/jo00835a070

InChI:InChI=1/C3H7O3P/c1-2-3-7(4,5)6/h2-3H,1H3,(H2,4,5,6)/b3-2-

Synthetic route

Di-tert-butyl cis-1-propenylphosphonate (25383-05-5) → cis-1-propenylphosphonic acid (25383-06-6)

Conditions	Yield
With cis-1-propenylphosphonic acid In benzene Heating;

cis-1-propenylphosphonic acid (25383-06-6) + (R)-1-phenyl-ethyl-amine (3886-69-9) → (-)-1,2-epoxypropylphosphonic acid-(+)-α-phenylethylamine salt

Conditions	Yield
With ethylenediaminetetraacetic acid; dihydrogen peroxide In ethanol; water at 40 - 55℃; for 1h; pH=6;	99.8%

cis-1-propenylphosphonic acid (25383-06-6) + (R)-1-phenyl-ethyl-amine (3886-69-9) → (1R,2S)-(-)-cis-1,2-epoxypropyl phosphoric acid-R-(+)-α-phenethylamine salt

Conditions	Yield
Stage #1: cis-1-propenylphosphonic acid; (R)-1-phenyl-ethyl-amine In ethanol at 20 - 40℃; pH=5.5 - 6; Stage #2: With ethylenediaminetetraacetic acid; dihydrogen peroxide at 40 - 50℃;	21.05%

cis-1-propenylphosphonic acid (25383-06-6) → (1R,2S)-1-chloro-2-hydroxypropanephosphonic acid (640716-21-8)

Conditions	Yield
With sodium hypochlorite

cis-1-propenylphosphonic acid (25383-06-6) → ((1RS,2SR)-1-chloro-2-hydroxy-propyl)-phosphonic acid (25460-60-0, 26432-55-3, 29203-94-9, 29305-57-5, 44802-97-3)

Conditions	Yield
With sodium hypochlorite

cis-1-propenylphosphonic acid (25383-06-6) + 2-methoxy-1,3-dimethyl-[1,3,2]diazaphospholidine 2-oxide (31755-42-7) → C8H20N2O5P2

Conditions	Yield
In N,N-dimethyl-formamide

cis-1-propenylphosphonic acid (25383-06-6) → (1,2-Dibromopropyl)phosphonic acid (143247-73-8)

Conditions	Yield
With bromine In tetrachloromethane; chloroform at 64 - 70℃; for 1h; Irradiation;

cis-1-propenylphosphonic acid (25383-06-6) → sodium; 3-methyl-oxirane-2-phosphonate

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; sodium tungstate In water at 40℃; pH=5.5; Kinetics; Further Variations:; Solvents; Temperatures; Catalysts;

cis-1-propenylphosphonic acid (25383-06-6) + rac-methylbenzylamine (618-36-0) → 1-Phenyl-ethylamine; compound with ((2S,3R)-3-methyl-oxiranyl)-phosphonic acid + 1-Phenyl-ethylamine; compound with ((2R,3S)-3-methyl-oxiranyl)-phosphonic acid

Conditions	Yield
With (+)-camphor-based molybdenum(VI); dihydrogen peroxide In dichloromethane; water at 0℃; for 72h; Title compound not separated from byproducts;

starch-iodide + cis-1-propenylphosphonic acid (25383-06-6) → SODIUM (2-HYDROXY-1-BROMOPROPYL)PHOSPHONATE

Conditions	Yield
With sodium hydroxide; N-bromoacetamide In water

Upstream product

• 18689-36-6 diethyl (Z)-1-propenylphosphonate 
• 25383-05-5 Di-tert-butyl cis-1-propenylphosphonate 

Downstream Products

• 933443-26-6 C₃H₇O₃P*C₈H₁₁N 

Relevant articles and documents

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