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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

868-85-9 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (L02670)  Dimethyl phosphite, 98%   

  • 868-85-9

  • 100ml

  • 144.0CNY

  • Detail
  • Alfa Aesar

  • (L02670)  Dimethyl phosphite, 98%   

  • 868-85-9

  • 500ml

  • 357.0CNY

  • Detail

868-85-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name Dimethyl phosphonate

1.2 Other means of identification

Product number -
Other names dimethyl H-phosphonate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Lubricants and lubricant additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:868-85-9 SDS

868-85-9Synthetic route

methanol
67-56-1

methanol

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With phosphorus trichloride In dichloromethane for 0.166667h;98%
With phosphorus trichloride
With phosphorus trichloride
phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; water at 25℃; Sealed tube;92%
With water In tetrahydrofuran at 20℃; Inert atmosphere;82%
With water In methanol
With [Pt(H2O)2(1,1'-bis(diphenylphosphanyl)octamethylferrocene)](trifluoromethylsulfonate)2; water In tetrahydrofuran at 20℃; for 0.0833333h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;
With trifluorormethanesulfonic acid In water at 25℃; for 0.5h; Inert atmosphere;
methanol
67-56-1

methanol

Dimethyl 2-(N-tert-butyl-N-methylamino)benzoylphosphonate
91157-34-5

Dimethyl 2-(N-tert-butyl-N-methylamino)benzoylphosphonate

A

Methyl 2-(N-tert-butyl-N-methylamino)benzoate

Methyl 2-(N-tert-butyl-N-methylamino)benzoate

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

C

Methyl N-methylanthranilate
85-91-6

Methyl N-methylanthranilate

Conditions
ConditionsYield
Heating;A 90%
B 30%
C 5%
methanol
67-56-1

methanol

A

Dimethyl phosphite
868-85-9

Dimethyl phosphite

B

Methyl phosphonochloridate

Methyl phosphonochloridate

Conditions
ConditionsYield
With phosphorus trichloride In chloroform at 0℃; for 0.5h;A 84%
B 16%
methanol
67-56-1

methanol

A

Dimethyl phosphite
868-85-9

Dimethyl phosphite

B

Methyl phosphonochloridate

Methyl phosphonochloridate

C

phosphonic acid monomethyl ester
13590-71-1

phosphonic acid monomethyl ester

Conditions
ConditionsYield
With phosphorus trichloride In chloroform at 25℃; for 0.5h;A 83%
B 3%
C 14%
dimethyl benzoylphosphonate
18106-71-3

dimethyl benzoylphosphonate

A

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 0℃; for 0.5h; Title compound not separated from byproducts;A 80%
B n/a
methanol
67-56-1

methanol

A

phosphonic Acid
13598-36-2

phosphonic Acid

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

C

phosphonic acid monomethyl ester
13590-71-1

phosphonic acid monomethyl ester

Conditions
ConditionsYield
With phosphorus trichloride at 25℃; for 1h;A 1%
B 73%
C 26%
methanol
67-56-1

methanol

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With phosphorous; 10H-phenothiazine; N,N,N,N-tetraethylammonium tetrafluoroborate In N,N-dimethyl-formamide at 53℃; electrolysis;A 9%
B 71%
methanol
67-56-1

methanol

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

C

dimethyl methane phosphonate
756-79-6

dimethyl methane phosphonate

Conditions
ConditionsYield
With phosphorous; tetraethylammonium iodide In acetonitrile at 18℃; electrolysis;A 70%
B 11%
C 3%
With phosphorous; tetraethylammonium iodide In acetonitrile at 18℃; Mechanism; Product distribution; electrolysis; var. nucleophiles; var. temperatures;A 70%
B 11%
C 3%
With phosphorous In acetonitrile at 18℃; Electrolysis;A 70%
B 11%
C 3%
dimethyl <4-(diphenylmethylene)-1,4-dihydro-1-hydroxynaphthyl>phosphonate
80094-07-1

dimethyl <4-(diphenylmethylene)-1,4-dihydro-1-hydroxynaphthyl>phosphonate

A

4-(diphenylmethylene)-1(4H)-naphthalenone
5690-41-5

4-(diphenylmethylene)-1(4H)-naphthalenone

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
under 1 Torr; Heating;A 69%
B n/a
propylamine
107-10-8

propylamine

dimethyl benzoylphosphonate
18106-71-3

dimethyl benzoylphosphonate

A

N-(n-propyl)benzamide
10546-70-0

N-(n-propyl)benzamide

B

α--α--toluol
16115-01-8

α--α--toluol

C

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
In diethyl ether for 0.05h; Ambient temperature;A 68%
B 27%
C 7%
In diethyl ether for 0.05h; Product distribution; Ambient temperature; Substituent effect of alkyl groups of Benzoyl phosphonates in Benzoylation;A 68%
B 27%
C 7%
(2-Oxo-3-phenylamino-2,3-dihydro-1H-indol-3-yl)-phosphonic acid dimethyl ester
128967-40-8

(2-Oxo-3-phenylamino-2,3-dihydro-1H-indol-3-yl)-phosphonic acid dimethyl ester

A

3-phenylimino-2-indolinone
33828-98-7, 101671-27-6

3-phenylimino-2-indolinone

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
at 230℃; under 5 Torr; for 0.5h; Product distribution;A 55%
B n/a
dimethyl phenylphosphonite
18351-42-3

dimethyl phenylphosphonite

A

methyl phenyl H-phosphonate
16390-98-0

methyl phenyl H-phosphonate

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; water at 25℃; Sealed tube;A 30 %Spectr.
B 50%
dimethyl trimethylsilyl phosphite
36198-87-5

dimethyl trimethylsilyl phosphite

acetylacetone
123-54-6

acetylacetone

A

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

B

(Z)-4-trimethylsiloxypent-3-en-2-one
25145-04-4

(Z)-4-trimethylsiloxypent-3-en-2-one

C

Dimethyl phosphite
868-85-9

Dimethyl phosphite

D

dimethyl<1-methyl-3-oxo-1-(trimethylsiloxy)butyl>phosphonate

dimethyl<1-methyl-3-oxo-1-(trimethylsiloxy)butyl>phosphonate

Conditions
ConditionsYield
at 60 - 70℃; for 4h; Further byproducts given;A 8.5%
B n/a
C 6.4%
D 20.5%
dimethyl trimethylsilyl phosphite
36198-87-5

dimethyl trimethylsilyl phosphite

acetylacetone
123-54-6

acetylacetone

A

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

C

dimethyl<1-methyl-3-oxo-1-(trimethylsiloxy)butyl>phosphonate

dimethyl<1-methyl-3-oxo-1-(trimethylsiloxy)butyl>phosphonate

Conditions
ConditionsYield
at 60 - 70℃; for 4h; Further byproducts given;A 8.5%
B 6.4%
C 20.5%
dimethyl trimethylsilyl phosphite
36198-87-5

dimethyl trimethylsilyl phosphite

acetylacetone
123-54-6

acetylacetone

A

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

C

dimethyl<1-methyl-3-oxo-1-(trimethylsiloxy)butyl>phosphonate

dimethyl<1-methyl-3-oxo-1-(trimethylsiloxy)butyl>phosphonate

D

5-(dimethoxyphosphinyl)-2-methoxy-3,5-dimethyl-3-(trimethylsiloxy)-1,2-oxaphospholane 2-oxide

5-(dimethoxyphosphinyl)-2-methoxy-3,5-dimethyl-3-(trimethylsiloxy)-1,2-oxaphospholane 2-oxide

Conditions
ConditionsYield
at 60 - 70℃; for 4h; Further byproducts given;A 8.5%
B 6.4%
C 20.5%
D 9.2%
trimethyl orthoformate
149-73-5

trimethyl orthoformate

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With hypophosphorous acid Ambient temperature;
morpholine
110-91-8

morpholine

dimethyl benzoylphosphonate
18106-71-3

dimethyl benzoylphosphonate

A

4-benzoylmorpholine
1468-28-6

4-benzoylmorpholine

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With water 1.) ether, room temperature, 24 h; 2.) THF, room temperature, 3 h; Yield given. Multistep reaction;
dimethyl (2-phenylacetyl)phosphonate
51463-66-2

dimethyl (2-phenylacetyl)phosphonate

A

Dimethyl phosphite
868-85-9

Dimethyl phosphite

B

2-phenylacetylhydrazine
937-39-3

2-phenylacetylhydrazine

Conditions
ConditionsYield
With hydrazine
methanol
67-56-1

methanol

diphenyl hydrogen phosphite
4712-55-4

diphenyl hydrogen phosphite

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
Mechanism; var. aliphatic alcohols, their relative reaction rates;
propylamine
107-10-8

propylamine

dimethyl benzoylphosphonate
18106-71-3

dimethyl benzoylphosphonate

A

N-(n-propyl)benzamide
10546-70-0

N-(n-propyl)benzamide

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With water 1.) ether, room temperature, 24 h; 2.) THF, room temperature, 3 h; Yield given. Multistep reaction;
pyrocatechol phosphorochloridite
1641-40-3

pyrocatechol phosphorochloridite

3,3-Diethoxy-butan-2-one
51933-13-2

3,3-Diethoxy-butan-2-one

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

A

2-ethoxy-1,3,2-benzodioxaphosphole
10072-02-3

2-ethoxy-1,3,2-benzodioxaphosphole

B

2-methoxy-1,3,2-benzodioxaphosphole
20570-25-6

2-methoxy-1,3,2-benzodioxaphosphole

C

[1-(Benzo[1,3,2]dioxaphosphol-2-yloxy)-2-ethoxy-1-methyl-allyl]-phosphonic acid dimethyl ester
144748-40-3

[1-(Benzo[1,3,2]dioxaphosphol-2-yloxy)-2-ethoxy-1-methyl-allyl]-phosphonic acid dimethyl ester

D

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
at 20 - 25℃; for 3h; Title compound not separated from byproducts;
thiophosgene
463-71-8

thiophosgene

triisopropyl phosphite
116-17-6

triisopropyl phosphite

A

trimethyl phosphite
512-56-1

trimethyl phosphite

B

C22H49O9P3S
101632-67-1

C22H49O9P3S

C

Dimethyl phosphite
868-85-9

Dimethyl phosphite

D

[(Diisopropoxy-phosphoryl)-(diisopropoxy-phosphorylsulfanyl)-methyl]-phosphonic acid diisopropyl ester

[(Diisopropoxy-phosphoryl)-(diisopropoxy-phosphorylsulfanyl)-methyl]-phosphonic acid diisopropyl ester

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; allowed to warm to room temperature over 16h; Title compound not separated from byproducts;
dimethyl (9-hydroxy-9H-fluoren-9-yl) phosphonate
34881-14-6

dimethyl (9-hydroxy-9H-fluoren-9-yl) phosphonate

A

9-fluorenone
486-25-9

9-fluorenone

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With triethylamine Rate constant; other reagents (n-butyl- and t-butylamine);
dimethyl benzoylphosphonate
18106-71-3

dimethyl benzoylphosphonate

isobutylamine
78-81-9

isobutylamine

A

N-isobutyl-benzamide
5705-57-7

N-isobutyl-benzamide

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With water 1.) ether, room temperature, 24 h; 2.) THF, room temperature, 3 h; Yield given. Multistep reaction;
dimethyl N,N-diisopropylphosphoramidite
122194-07-4

dimethyl N,N-diisopropylphosphoramidite

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With pyridine hydrochloride In pyridine; water for 0.0833333h;
dimethyl benzoylphosphonate
18106-71-3

dimethyl benzoylphosphonate

cyclohexylamine
108-91-8

cyclohexylamine

A

N-benzoylcyclohexylamine
1759-68-8

N-benzoylcyclohexylamine

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With water 1.) ether, room temperature, 24 h; 2.) THF, room temperature, 3 h; Yield given. Multistep reaction;
dimethyl benzoylphosphonate
18106-71-3

dimethyl benzoylphosphonate

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

A

benzoic toluene-p-sulphonic anhydride
13079-28-2

benzoic toluene-p-sulphonic anhydride

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
In benzene for 12h; Ambient temperature;
dimethyl benzoylphosphonate
18106-71-3

dimethyl benzoylphosphonate

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

A

Dimethyl phosphite
868-85-9

Dimethyl phosphite

B

phosphonic acid monomethyl ester
13590-71-1

phosphonic acid monomethyl ester

Conditions
ConditionsYield
1.) benzene, r.t., 12 h; 2.) benzene, 4 h, reflux; Yield given. Multistep reaction. Yields of byproduct given;
dimethyl (phenoxycarbonyl)phosphonate
72304-75-7

dimethyl (phenoxycarbonyl)phosphonate

A

sodium methyl hydrogen phosphite
56317-55-6

sodium methyl hydrogen phosphite

B

Dimethyl phosphite
868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
With water In acetonitrile for 0.0833333h; Mechanism; phosphate buffer pH 7.4;
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl 1-hydroxy-1-(4-chlorophenyl)methylphosphonate
6329-48-2

dimethyl 1-hydroxy-1-(4-chlorophenyl)methylphosphonate

Conditions
ConditionsYield
With triethylamine at 50℃; Pudovik Reaction; Inert atmosphere; Sealed tube;100%
Stage #1: 4-chlorobenzaldehyde With phosphotungstic acid supported on silica-coated magnetic Fe3O4 nanoparticle In neat (no solvent) at 20℃; for 0.25h; Kabachnik-Fields Reaction; Green chemistry;
Stage #2: Dimethyl phosphite In neat (no solvent) at 20℃; for 4h; Green chemistry;
96%
With potassium phosphate In neat (no solvent) at 20℃; for 0.0666667h; Green chemistry;93%
benzaldehyde
100-52-7

benzaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl 1-hydroxy-1-phenylmethylphosphonate
6329-46-0, 79296-54-1, 97995-93-2, 147731-04-2

dimethyl 1-hydroxy-1-phenylmethylphosphonate

Conditions
ConditionsYield
With potassium fluoride for 0.333333h;100%
With potassium fluoride at 20℃; for 0.416667h; Inert atmosphere;100%
Stage #1: benzaldehyde With phosphotungstic acid supported on silica-coated magnetic Fe3O4 nanoparticle In neat (no solvent) at 20℃; for 0.25h; Kabachnik-Fields Reaction; Green chemistry;
Stage #2: Dimethyl phosphite In neat (no solvent) at 20℃; for 6h; Solvent; Reagent/catalyst; Time; Green chemistry;
98%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl α-hydroxy-α-(3,4,5-trimethoxyphenyl)methanephosphonate
130190-35-1

dimethyl α-hydroxy-α-(3,4,5-trimethoxyphenyl)methanephosphonate

Conditions
ConditionsYield
With dibutylamine In diethyl ether at 20℃; for 3h;100%
With sodium methylate In methanol at 50℃;96.5%
With methanol; sodium for 0.5h; Heating;90%
Adipic acid dichloride
111-50-2

Adipic acid dichloride

Dimethyl phosphite
868-85-9

Dimethyl phosphite

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

[6-(Dimethoxy-phosphoryl)-1,6-bis-(dimethoxy-phosphoryloxy)-hexyl]-phosphonic acid dimethyl ester

[6-(Dimethoxy-phosphoryl)-1,6-bis-(dimethoxy-phosphoryloxy)-hexyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
at 130 - 135℃; for 6h;100%
suberoyl chloride
10027-07-3

suberoyl chloride

Dimethyl phosphite
868-85-9

Dimethyl phosphite

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

[1,8,8-Tris-(dimethoxy-phosphoryl)-1,8-dihydroxy-octyl]-phosphonic acid dimethyl ester

[1,8,8-Tris-(dimethoxy-phosphoryl)-1,8-dihydroxy-octyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
at 60℃; for 8h;100%
suberoyl chloride
10027-07-3

suberoyl chloride

Dimethyl phosphite
868-85-9

Dimethyl phosphite

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

[8-(Dimethoxy-phosphoryl)-1,8-bis-(dimethoxy-phosphoryloxy)-octyl]-phosphonic acid dimethyl ester

[8-(Dimethoxy-phosphoryl)-1,8-bis-(dimethoxy-phosphoryloxy)-octyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
at 130 - 135℃; for 6h;100%
triethylamine
121-44-8

triethylamine

Dimethyl phosphite
868-85-9

Dimethyl phosphite

phosphonic acid monomethyl ester methyltriethylammonium salt
122833-31-2

phosphonic acid monomethyl ester methyltriethylammonium salt

Conditions
ConditionsYield
at 70℃; for 6h;100%
In methanol for 2h; Heating;
Dimethyl phosphite
868-85-9

Dimethyl phosphite

trimethylamine
75-50-3

trimethylamine

tetramethylammonium methyl hydrogen phosphite

tetramethylammonium methyl hydrogen phosphite

Conditions
ConditionsYield
at 20℃; for 24h;100%
pimeloyl chloride
142-79-0

pimeloyl chloride

Dimethyl phosphite
868-85-9

Dimethyl phosphite

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

[1,7,7-Tris-(dimethoxy-phosphoryl)-1,7-dihydroxy-heptyl]-phosphonic acid dimethyl ester

[1,7,7-Tris-(dimethoxy-phosphoryl)-1,7-dihydroxy-heptyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
at 60℃; for 8h;100%
pimeloyl chloride
142-79-0

pimeloyl chloride

Dimethyl phosphite
868-85-9

Dimethyl phosphite

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

[7-(Dimethoxy-phosphoryl)-1,7-bis-(dimethoxy-phosphoryloxy)-heptyl]-phosphonic acid dimethyl ester

[7-(Dimethoxy-phosphoryl)-1,7-bis-(dimethoxy-phosphoryloxy)-heptyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
at 130 - 135℃; for 6h;100%
azelaoyl chloride
123-98-8

azelaoyl chloride

Dimethyl phosphite
868-85-9

Dimethyl phosphite

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

[9-(Dimethoxy-phosphoryl)-1,9-bis-(dimethoxy-phosphoryloxy)-nonyl]-phosphonic acid dimethyl ester

[9-(Dimethoxy-phosphoryl)-1,9-bis-(dimethoxy-phosphoryloxy)-nonyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
at 130 - 135℃; for 6h;100%
sebacoyl chloride
111-19-3

sebacoyl chloride

Dimethyl phosphite
868-85-9

Dimethyl phosphite

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

[10-(Dimethoxy-phosphoryl)-1,10-bis-(dimethoxy-phosphoryloxy)-decyl]-phosphonic acid dimethyl ester

[10-(Dimethoxy-phosphoryl)-1,10-bis-(dimethoxy-phosphoryloxy)-decyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
at 130 - 135℃; for 6h;100%
ethylenediamine
107-15-3

ethylenediamine

Dimethyl phosphite
868-85-9

Dimethyl phosphite

ethylenediamine monoalkylammonium salt of monomethyl phosphonate

ethylenediamine monoalkylammonium salt of monomethyl phosphonate

Conditions
ConditionsYield
In methanol at 50℃; for 2h;100%
propylamine
107-10-8

propylamine

Dimethyl phosphite
868-85-9

Dimethyl phosphite

phosphonic acid monomethyl ester methylpropylammonium salt

phosphonic acid monomethyl ester methylpropylammonium salt

Conditions
ConditionsYield
at 5℃; for 24h;100%
formaldehyd
50-00-0

formaldehyd

Dimethyl phosphite
868-85-9

Dimethyl phosphite

hydroxymethyl-phosphonic acid dimethyl ester
24630-67-9

hydroxymethyl-phosphonic acid dimethyl ester

Conditions
ConditionsYield
With potassium carbonate In methanol at 65℃;100%
With potassium carbonate In methanol at 20℃; for 1h; Pudovik reaction;98%
83%
(S)-(-)-perillaldehyde
18031-40-8

(S)-(-)-perillaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

[Hydroxy-((S)-4-isopropenyl-cyclohex-1-enyl)-methyl]-phosphonic acid dimethyl ester

[Hydroxy-((S)-4-isopropenyl-cyclohex-1-enyl)-methyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile for 24h; Ambient temperature;100%
benzaldehyde
100-52-7

benzaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

aniline
62-53-3

aniline

dimethyl (phenyl)(phenylamino)methylphosphonate
26624-91-9

dimethyl (phenyl)(phenylamino)methylphosphonate

Conditions
ConditionsYield
With tin(ll) chloride at 20℃; under 760.051 Torr; for 2.5h; Kabachnik-Fields reaction; neat (no solvent);100%
at 80℃; for 0.0333333h; Product distribution; Further Variations:; Temperatures; microwave irradiation; Kobachnik-Fields reaction; microwave irradiation;98%
With zirconium(IV) oxychloride at 20℃; for 0.0833333h;98%
Dimethyl phosphite
868-85-9

Dimethyl phosphite

(3S,4R,5S)-3,4-isopropylidenedioxy-5-methyl-1-pyrroline-N-oxide
740805-26-9

(3S,4R,5S)-3,4-isopropylidenedioxy-5-methyl-1-pyrroline-N-oxide

dimethyl (2S,3R,4R,5S)-N-hydroxy-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-phosphonate

dimethyl (2S,3R,4R,5S)-N-hydroxy-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-phosphonate

Conditions
ConditionsYield
at 40℃; for 20h;100%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

(+/-)-dimethyl hydroxy(4-fluorophenyl)methylphosphonate
183240-18-8

(+/-)-dimethyl hydroxy(4-fluorophenyl)methylphosphonate

Conditions
ConditionsYield
With dibutylamine In diethyl ether at 20℃; for 3h;100%
With triethylamine In acetone for 0.166667h; Pudovik Reaction; Reflux;96%
With guanidine supported magnetic Fe3O4 nanoparticle In neat (no solvent) at 80℃; for 3.5h;85%
bis(trifluoromethanesulfonyl)amide
82113-65-3

bis(trifluoromethanesulfonyl)amide

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethoxy(hydroxy)phosphonium bis(trifluoromethanesulfonyl)azanide

dimethoxy(hydroxy)phosphonium bis(trifluoromethanesulfonyl)azanide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 3h;100%
8-(4'-methoxyphenoxy)acetophenone
14385-49-0

8-(4'-methoxyphenoxy)acetophenone

Dimethyl phosphite
868-85-9

Dimethyl phosphite

1-phenylvinyl dimethyl phosphate
4202-12-4

1-phenylvinyl dimethyl phosphate

Conditions
ConditionsYield
With caesium carbonate In dichloromethane at 20℃; Inert atmosphere;100%
N-(p-bromophenyl)tetrahydroisoquinoline

N-(p-bromophenyl)tetrahydroisoquinoline

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl (2-(4-bromophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phosphonate
1435940-00-3

dimethyl (2-(4-bromophenyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phosphonate

Conditions
ConditionsYield
With N-hydroxyphthalimide; cobalt(II) acetate hydrate In acetonitrile at 80℃; for 16h;100%
With 10-methylacridine-3(10H)-one In methanol for 11h; Irradiation;78%
With oxygen In 1,4-dioxane at 80℃; for 30h;67%
With C44Cl8F20N4Pd; oxygen; potassium carbonate In methanol; acetonitrile for 3h; UV-irradiation;76 %Spectr.
C38H51O2P3Pd

C38H51O2P3Pd

Dimethyl phosphite
868-85-9

Dimethyl phosphite

C22H43O3P3Pd

C22H43O3P3Pd

Conditions
ConditionsYield
at 25℃; for 1h; Inert atmosphere;100%
bis(tricyclohexylphosphine)platinum(0)
55664-33-0

bis(tricyclohexylphosphine)platinum(0)

Dimethyl phosphite
868-85-9

Dimethyl phosphite

C38H73O3P3Pt

C38H73O3P3Pt

Conditions
ConditionsYield
In benzene-d6 at 20℃; for 15h; Glovebox; Inert atmosphere;100%
3-benzyl-1,3-oxazolidine
13657-16-4

3-benzyl-1,3-oxazolidine

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl <methyl>phosphonate
73215-14-2

dimethyl phosphonate

Conditions
ConditionsYield
at 30 - 40℃; for 2h;99.6%
4-Amino-2,6-dihydroxypyrimidine
873-83-6

4-Amino-2,6-dihydroxypyrimidine

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

[(2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidin-4-ylamino)-(4-fluoro-phenyl)-methyl]-phosphonic acid dimethyl ester

[(2,6-Dioxo-1,2,3,6-tetrahydro-pyrimidin-4-ylamino)-(4-fluoro-phenyl)-methyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
With dibenzo-24-crown ether In benzene for 4h; Heating;99%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

5-fluorocytosine

5-fluorocytosine

[(5-Fluoro-2-oxo-2,3-dihydro-pyrimidin-4-ylamino)-(4-fluoro-phenyl)-methyl]-phosphonic acid dimethyl ester

[(5-Fluoro-2-oxo-2,3-dihydro-pyrimidin-4-ylamino)-(4-fluoro-phenyl)-methyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
With dibenzo-24-crown ether In benzene for 4h; Heating;99%
Phenyltrichlorosilane
98-13-5

Phenyltrichlorosilane

Dimethyl phosphite
868-85-9

Dimethyl phosphite

{(CH3O)2PO}3SiC6H5
148320-91-6

{(CH3O)2PO}3SiC6H5

Conditions
ConditionsYield
With triethylamine In pentane for 72h; Ambient temperature;99%
(4-iodophenyl)phosphonate de diethyle
103697-17-2

(4-iodophenyl)phosphonate de diethyle

Dimethyl phosphite
868-85-9

Dimethyl phosphite

1-(diethoxyphosphinoyl)-4-(dimethoxyphosphinoyl)benzene

1-(diethoxyphosphinoyl)-4-(dimethoxyphosphinoyl)benzene

Conditions
ConditionsYield
With potassium tert-butylate In ammonia for 0.333333h; Irradiation;99%
benzaldehyde
100-52-7

benzaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl (S)-phenyl(hydroxy)methylphosphonate
97995-93-2

dimethyl (S)-phenyl(hydroxy)methylphosphonate

Conditions
ConditionsYield
Stage #1: benzaldehyde; Dimethyl phosphite With C41H64AlClN2O2; potassium carbonate In diethyl ether at -30℃; for 24h;
Stage #2: With hydrogenchloride; water In diethyl ether optical yield given as %ee; enantioselective reaction;
99%
With C38H48N4P(1+)*Cl(1-); potassium tert-butylate In tetrahydrofuran at -98℃; for 4h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;97%
(R)-LaLi3(binaphthoxide)3 In tetrahydrofuran at -78℃; for 8h; Yield given;

868-85-9Relevant articles and documents

Symons

, p. 785 (1974)

METHOD FOR PRODUCING ORGANOPHOSPHORUS COMPOUND

-

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.

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