868-85-9 Usage
Chemical Properties
colourless liquid
Uses
Different sources of media describe the Uses of 868-85-9 differently. You can refer to the following data:
1. Dimethyl Phosphite(DMP)is used as a reagent in the synthesis of 4-(thiophen-2-ylmethyl)-2H-phthalazin-1-ones as potent PARP-1 inhibitors.
It is also used as a reagent in the synthesis of estafiatin phosphonate derivatives which exhibit antibacterial and antifungal activity.
Dimethyl Phosphite is a degradation product of the pesticides trichlorphon and malathion and may be released into the envionment following their application. It is a contaminant (approxiately 2%) in the chemical intermediate triethyl phosphite, which hydrolyses readily to dimethyl hydrogen phosphite in the presence of moist air or water.
Dimethyl Phosphite is used as a flame retardant on Nylon 6 fibres and, in combination with guanidine and formaldehyde, to impart flame and crease resistance to cotton textiles. The compound is also used to increase fire resistance to cellulosic textiles, acrolein-grafted polyamide fibres and y-irdiated polyethylene.
lt is used as a lubricant additive, as a chemical intermediate in the production of organophosphorous pesticides and as an adhesive.
Dimethyl Phosphite has also been used as a stabilizer in oil and plaster and, in combination with pyroctechol, as a corrosion inhibitor on steel.
2. As a flame retardant on Nylon 6 fibers;
intermediate in the production of pesticides
and herbicides; as a stabilizer in oil and plaster;
an additive to lubricants
Application
DMP is a basic chemical which is used industrially as an intermediate. Because of its reactivity
DMP participates in a large number of chemical reactions:
Addition to oxo compounds
Addition to oxo compounds with subsequent condensation e.g. with amines
Oxidation with oxygen or chlorine
Addition to alkenes
Due to these properties DMP is used as an intermediate for the manufacturing of
water treatment chemicals e.g. corrosion inhibitors for cooling-water circuits (about 50 %)
pesticides and pharmaceuticals (about 20 %)
flame retardants and other specialities (about 15 %)
textile finishing products (about 15 %)
Health Hazard
Dimethyl Phosphite (DMP) is rapidly absorbed via the oral and dermal routes. The main metabolic pathway in rodents is demethylation to monomethyl hydrogen phosphite (MMP) and further oxidation to CO2. DMP was mainly eliminated via urine and expired air. Over the studied dose range between 10 and 200 mg/kg bw and 5 x 200 mg/kg bw, respectively, only little evidence of bioaccumulation or saturation of absorption and elimination was observed. The only difference in studied toxicokinetics between rats and mice was the more rapid metabolism and elimination in mice.
An inhalation LC50 value is not available, but an exposure of 7100 mg/m3 (concentration estimated based on air flow and net loss of material) over 6 hours was not lethal for rats, mice and guinea pigs. Clinical signs were observed in mice only, and included occasionally laboured respiration after approximately 2 hours of exposure and ptosis after 5 hours. The acute dermal LD50 was 681 mg/kg bw (rabbits). Signs of intoxication were depression, ptosis, labored respiration, ataxia and placidity. The acute oral LD50 values were: 3283 mg/kg bw for male rats, 3040 mg/kg bw for female rats, 2815 mg/kg bw for male mice, and between 2150 and 3160 mg/kg bw for female mice. Clinical signs were inactivity, weakness, prostration and shallow breathing at doses near to or exceeding the LD50 values. White opaque eyes were seen in male mice.
Dimethyl Phosphite is irritating to the skin and eyes of rabbits. After prolonged or repeated exposures moderate to severe irritation of skin and mucosa was observed in rats. No sensitisation studies are available.
Proposed metabolic pathways of DMP in rats and mice (Nomeir and Matthews, 1997).
Safety Profile
Suspected carcinogen
with experimental carcinogenic data.
Moderately toxic by ingestion and skin
contact. A skin and eye irritant. Mutation
data reported. When heated to
decomposition it emits toxic fumes of POx
Carcinogenicity
Dimethyl hydrogen phosphite was not
mutagenic to several strains of Salmonella
typhimurium, but it did cause sister chromatid
exchanges and chromosomal aberrations in the
Chinese hamster CHO line.
An ACGIH threshold limit value (TLV)
has not been established for dimethyl hydrogen
phosphite.
Check Digit Verification of cas no
The CAS Registry Mumber 868-85-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,6 and 8 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 868-85:
(5*8)+(4*6)+(3*8)+(2*8)+(1*5)=109
109 % 10 = 9
So 868-85-9 is a valid CAS Registry Number.
InChI:InChI=1/C2H7O3P/c3-1-6(5)2-4/h3-4,6H,1-2H2
868-85-9Relevant articles and documents
METHOD FOR PRODUCING ORGANOPHOSPHORUS COMPOUND
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Paragraph 0083; 0094, (2020/05/02)
PROBLEM TO BE SOLVED: To provide a method for producing an organophosphorus compound which has excellent energy efficiency without containing a halogenated alkyl or a by-product derived from a halogenated alkyl. SOLUTION: There is provided a method for producing an organophosphorus compound by reacting a trivalent organophosphorus compound represented by the following general formula (1) in the presence of a super strong acid and/or at least one acid catalyst containing a solid superstrong acid catalyst to generate a pentavalent organophosphorus compound represented by the following general formula. (where Z1 represents OR2 or R2; Z2 represents OR3 or R3; R1, R2 and R3 represent an alkyl group, an alkenyl group or the like; when R2 and R3 are an alkyl group or the like, R2 and R3 may be bonded to each other to form a cyclic structure; and R1 may be a hydrogen atom.) SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds
Li, Chunya,Wang, Qi,Zhang, Jian-Qiu,Ye, Jingjing,Xie, Ju,Xu, Qing,Han, Li-Biao
supporting information, p. 2916 - 2922 (2019/06/18)
Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.
Synthesis and herbicidal activity of α-[(substituted phenoxybutyryloxy or valeryoxy)]alkylphosphonates and 2-(substituted phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one containing fluorine
Wang, Wei,Zhou, Yuan,Peng, Hao,He, Hong-Wu,Lu, Xing-Tao
, p. 8 - 16 (2016/11/25)
Based on our previous work on the structural modification of the lead compound I, three series of novel fluorine-containing phosphonates derivatives (II, III and IV) were designed and synthesized. Their post-emergence herbicidal activities against some species of weeds were evaluated in a green house. The compounds II were synthesized by introducing of two methylene into the structure I. Compared with the commercial herbicidal clacyfos, compounds II showed moderate herbicidal activity with 60–85% inhibition effect against chingma abutilon (Abutilon theophrasti), common amaranth (Amaranthus retroflexus) and white eclipta (Eclipta prostrate) at a rate of 150 g ai/ha. The compounds III were designed by introducing open-chain phosphonates, which displayed notable herbicidal activity. Especially, the compounds III-1–III-4, III-6, III-8, III-11 and III-12 exhibited significant herbicidal activity (80–100%) comparing to the clacyfos against all tested broadleaf weeds, while compounds IV with five carbon atoms in the carboxylic acid chain were inactive against all of the tested weeds. Structure-activity relationship analyses indicated that the length of the carbon chain had a great effect on the herbicidal activity. Furthermore, a broad spectrum test confirmed that compounds III-4 and III-8 were comparable with glyphosate against all of the tested weeds at a rate of 75 g ai/ha.