10184-66-4

Basic information

• Product Name: dimethyl (1-hydroxyethyl)phosphonate
• Synonyms: 1-Hydroxyethylphosphonic acid dimethyl ester
• CAS NO: 10184-66-4
• Molecular Formula: C₄H₁₁O₄P
• Molecular Weight: 154.1
• EINECS: 233-456-6
• Mol File: 10184-66-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 213.6°Cat760mmHg
• Flash Point: 83°C
• Appearance: /
• Density: 1.191g/cm³
• Vapor Pressure: 0.0361mmHg at 25°C
• Refractive Index: 1.415
• CAS DataBase Reference: dimethyl (1-hydroxyethyl)phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl (1-hydroxyethyl)phosphonate(10184-66-4)
• EPA Substance Registry System: dimethyl (1-hydroxyethyl)phosphonate(10184-66-4)

Safety Data

• Hazardous Substances Data: 10184-66-4(Hazardous Substances Data)

Usage

General Description

Dimethyl (1-hydroxyethyl)phosphonate is a chemical compound that is commonly used as a flame retardant and plasticizer in various industries. It is a phosphonate ester, which means it is derived from phosphonic acid. dimethyl (1-hydroxyethyl)phosphonate is known for its ability to reduce the flammability of materials by suppressing combustion and reducing the spread of flames. Additionally, it is used as a plasticizer to improve the flexibility and durability of plastics. Dimethyl (1-hydroxyethyl)phosphonate is also used in some agricultural applications as a herbicide, and it has potential applications in pharmaceuticals and research. However, it is important to note that this chemical should be handled with care due to its potential toxicity and environmental impact.

InChI:InChI=1/C4H11O4P/c1-4(5)9(6,7-2)8-3/h4-5H,1-3H3

Upstream product

• 67-56-1 methanol 
• 72740-17-1 [1-(1-chloro-ethoxy)-ethyl]-phosphonic acid dichloride 
• 75-07-0 acetaldehyde 
• 868-85-9 Dimethyl phosphite 
• 813-78-5 dimethylphosphoric acid 
• 96-36-6 methyl phosphite 

Downstream Products

• 904702-83-6 C₁₃H₁₇ClFO₆P 
• 904702-80-3 C₁₃H₁₈FO₆P 
• 1013938-34-5 C₁₂H₁₆ClO₆P 
• 119295-29-3 (R,S)-1-hydroxyethylphosphonate cyclohexylamine 
• 1352612-18-0 1-(dimethoxyphosphoryl)ethyl cinnamate 
• 866145-41-7 O,O-dimethyl α-(3-chloro-4-fluorophenoxyacetoxy)ethylphosphonate 
• 1299293-53-0 O,O-dimethyl α-(2,4-dibromophenoxyacetoxy)ethylphosphonate 
• 1299293-51-8 O,O-dimethyl α-(2,3-dimethylphenoxyacetoxy)ethylphosphonate 
• 1299293-52-9 O,O-dimethyl α-(4-bromophenoxyacetoxy)ethylphosphonate 
• 866146-00-1 O,O-dimethyl α-(2-fluorophenoxyacetoxy)ethylphosphonate 
• 1299293-54-1 O,O-dimethyl α-(4-chloro-2-nitrophenoxyacetoxy)ethylphosphonate 
• 1246091-45-1 O,O-dimethyl-1-(4-isopropylphenoxyacetoxy)ethylphosphonate 

Relevant articles and documents

The synthesis and herbicidal evaluation of fluorine-containing phenoxyacetoxyalkylphosphonate derivatives

To investigate the influence of a fluorine moiety on the biological activity of phenoxyacetoxyalkylphosphonates, a series of fluorine-containing phenoxyacetoxyalkylphosphonates were synthesized and screened for herbicidal activity in a greenhouse. The majority of the title compounds showed better preemergence activity than postemergence activity against the test plants, especially on monocotyledon. Compound 5l exhibited notable activity. Results showed that by introducing a fluorine moiety to the parent structure of phenoxyacetoxyalkylphosphonates, a series of new compounds with satisfactory herbicidal activity could be synthesized. A reasonable combination of a fluorine moiety and other substituents on the benzene ring had a great influence on the herbicidal activity. Copyright Taylor & Francis Group, LLC.

Enzymes in Organic Chemistry, Part 1: Enantioselective Hydrolysis of α-(Acyloxy)phosphonates by Esterolytic Enzymes

α-Hydroxyphosphonates (+/-)-3 were prepared and transformed into esters (+/-)-5.Eight lipases as well as pig liver esterase were tested as catalysts for enantioselective hydrolyses of α-(acyloxy)phosphonates in a biphasic system.Two of them proved to be useful.The highest enantioselectivity was obtained with lipase F-AP 15 and α-(acetyloxy)phenylmethylphosphonates (+/-)-5a and (+/-)-5b as substrates.The (S)-enantiomers were exclusively hydrolyzed to give optically pure alcohols (S)-(-)-3a and (S)-(-)-3b.Lipases AP 6 and F-AP 15 were used to prepare phosphonates(S)-(-)-3b, (S)-(+)-3d and (S)-(-)-3e on a preparative scale with an enantiomeric excess of 81percent, 87percent, and 89percent, respectively.The absolute configurations of the α-hydroxyphosphonates were assigned by Horeau's method and 1H NMR spectroscopy of Mosher's derivatives.

Synthesis and Herbicidal Activity of α-(Substituted Phenoxybutyryloxy or Valeryloxy)alkylphosphonates and 2-(Substituted Phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one

On the basis of our work on the modification of alkylphosphonates 1, a series of α-(substituted phenoxybutyryloxy or valeryloxy)alkylphosphonates (4-5) and 2-(substituted phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one (6) were designed and synthesized. The bioassay results indicated that 14 of title compounds 4 exhibited significant postemergence herbicidal activity against velvetleaf, common amaranth, and false daisy at 150 g ai/ha. Compounds 5 were inactive against all tested weeds. Compounds 6 exhibited moderate to good inhibitory effect against the tested dicotyledonous weeds. Structure-activity relationship (SAR) analyses showed that the length of the carbon chain as linking bridge had a great effect on the herbicidal activity. Broad-spectrum tests of compounds 4-1, 4-2, 4-9, 4-30, and 4-36 were carried out at 75 g ai/ha. Especially, 4-1 exhibited 100% inhibition activity against the tested dicotyledonous weeds, which was higher than that of glyphosate.

Synthesis and biological activities of O, O-dialkyl 1-((4,6- Dichloropyrimidin-2-yl)carbamyloxy) alkylphosphonates

(Equation present) A series of new 1-((4,6-dichloropyrimidin-2-yl) carbamyloxy) alkylphosphonates were designed and synthesized. The structures of all the title compounds were confirmed by IR, 1H-NMR, 31P-NMR and elemental analysis. The results of the bioassay showed that all of title compounds exhibited weak herbicidal activities against monocotyledons and dicotyledons; however, some of them showed potential plant growth regulatory activities. 2014 Copyright Taylor & Francis Group, LLC.