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5 protocols using dimethyl methylphosphonate

1

Synthesis and Characterization of Organophosphate Compounds

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Dimethyl methylphosphonate (DMMP, 97%), diethyl methylphophate (DEMP, 97%), diethyl cyanophosphonate (DECP, 90%), and diethyl chlorophosphate (DCP, 97%), (Scheme S1) were purchased from Sigma (St. Louis, MO, USA). Dulbecco’s modified eagle’s medium (DMEM) supplemented with antibiotics for cell culture was purchased from ATCC (Manassas, VA). Fetal bovine serum (FBS) was purchased from ATLANTA biologicals (Flowery Branch, GA). All other reagents were purchased from Sigma and Fisher Scientific unless otherwise noted.
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2

Purification of Organophosphorus Compounds

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Dimethyl methyl phosphonate (>99.6%, 114 Pa, 25°C) was purchased from Sigma-Aldrich, Switzerland and distilled before use, while dimethyl phosphoramidate (>99.5%, 6.312 Pa, 91°C) was synthesized and purified following the procedure given in the literature. [9]
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3

Synthesis of Acryloyl-Based Compounds

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2-Methyl-1,4-phenylene bis(4-(3-(acryloyloxy)propoxy)benzoate)
[RM 257] (1) and 4-methoxyphenyl 4-((6-(acryloyloxy)hexyl)oxy)benzoate
[RM 105] (2) were obtained from Merck. 4-((6-(Acryloyloxy)hexyl)oxy)benzoic
acid (3) and 4-((6-(acryloyloxy)hexyl)oxy)-2-methylbenzoic
acid (4) were purchased from Synthon. Irgacure 369 (6) was purchased from CIBA. Chiral dopant (R)-(+)-3-methyladipic acid (5) and dimethylmethylphosphonate
(7) were from Sigma-Aldrich, as well as trimethylamine
and diisopropylamine. Solvents tetrahydrofuran and toluene were purchased
from Biosolve, and acetone was purchased from Sigma-Aldrich.
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4

Synthesis of Functional Materials

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Acetic acid, acetone, chitosan, citric acid, dimethyl methylphosphonate (DMMP), graphite powder, methanol (MeOH) and 2-propanol were purchased from Sigma-Aldrich (Dorset, UK). Ammonium hydroxide and ethanol were purchased from Fisher Scientific (Loughborough, UK). All chemicals are analytical grade.
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5

Simulants and Hydrolysis Products Analysis

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The neurotoxin simulants and hydrolysis product were purchased from Alfa Aesar (Ward Hill, MA, USA) for dimethyl methylphosphonate (DMMP) (97%) and from Sigma Aldrich (St. Louis, MO, USA) for diethyl ethylphosphonate (DEEP) (>98%), and pinacolyl methylphosphonic acid (PinMPA) (97%). Reagent grade sodium hydroxide pellets, sodium aluminate, sodium silicate, silicic acid and 20% solution of tetrapropylammonium hydroxide (TPA-OH solution) were obtained from Sigma Aldrich. Sodium chloride and copper sulphate were obtained from Ajax Finechem (Sydney, Australia). All of these chemicals were used without further purification. Acupuncture needles (o.d. 0.30 mm, length 40 mm; Sensei) were purchased from Acuneeds (Melbourne, VIC, Australia). UltraLime soap was purchased from Septone (Dandenong South, VIC, Australia). Sea water (Bondi Beach, Sydney, Australia) and rain water (Kensington, NSW, Australia) matrices were collected and kept at 4 °C when not in use. Urine matrix, a synthetic urine negative control, was purchased from Cerilliant (Novachem, Collingwood, VIC, Australia) and also kept at 4 °C when not in use. Chemical warfare agent simulants and hydrolysis products were used in this study owing to safety and regulatory purposes.
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