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868-85-9

Basic Information
CAS No.: 868-85-9
Name: Dimethyl phosphite
Article Data: 99
Molecular Structure:
Molecular Structure of 868-85-9 (Dimethyl phosphite)
Formula: C2H7O3P
Molecular Weight: 110.05
Synonyms: Dimethoxyphosphineoxide;Dimethyl acid phosphite;Dimethyl hydrogen phosphite;Dimethyl hydrogenphosphonate;Dimethyl phosphite;Dimethyl phosphonate;Hydrogen dimethylphosphite;Methyl phosphonate ((MeO)2HPO);
EINECS: 212-783-8
Density: 1.2g/mLat 25°C(lit.)
Boiling Point: 170.499 °C at 760 mmHg
Flash Point: 29.444 °C
Solubility: Soluble in water.
Appearance: colourless liquid
Hazard Symbols: HarmfulXn
Risk Codes: 21-36-10
Safety: 26-36/37
Transport Information: UN 3278
PSA: 59.00000
LogP: 0.66890
Synthetic route
67-56-1

methanol

868-85-9

Dimethyl phosphite

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

phosphorous acid trimethyl ester

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;
67-56-1

methanol

91157-34-5

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

A

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

B

868-85-9

Dimethyl phosphite

C

85-91-6

Methyl N-methylanthranilate

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

methanol

A

868-85-9

Dimethyl phosphite

B

Methyl phosphonochloridate

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

methanol

A

868-85-9

Dimethyl phosphite

B

Methyl phosphonochloridate

C

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%
18106-71-3

dimethyl benzoylphosphonate

A

613-94-5

benzoic acid hydrazide

B

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
67-56-1

methanol

A

13598-36-2

phosphonic Acid

B

868-85-9

Dimethyl phosphite

C

13590-71-1

phosphonic acid monomethyl ester

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

methanol

A

512-56-1

trimethyl phosphite

B

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%
67-56-1

methanol

A

512-56-1

trimethyl phosphite

B

868-85-9

Dimethyl phosphite

C

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%
80094-07-1

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

A

5690-41-5

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

B

868-85-9

Dimethyl phosphite

Conditions
ConditionsYield
under 1 Torr; Heating;A 69%
B n/a
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    Product Name: Dimethyl phosphite CAS: 868-85-9 MF: C2H7O3P MW: 110.05 EINECS: 212-783-8 Mol File: 868-85-9.mol Dimethyl phosphite Structure Dimethyl phosphite Chemical Properties Boiling point 170-171 °C(lit.) density

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  • Casno:

    868-85-9

    Dimethyl phosphonate

    Min.Order: 1 Metric Ton

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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 48 , 1990,p. 85.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 48 , 1990,p. 85.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NTP Carcinogenesis Studies (gavage); No Evidence: mouse NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-287 ,1985. ; Clear Evidence: rat NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-287 ,1985. . Reported in EPA TSCA Inventory.

Standards and Recommendations

DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans

Specification

The Dimethyl phosphonate, with the CAS registry number 868-85-9 and EINECS registry number 212-783-8, is also called phosphonic acid, dimethyl ester. It is a kind of colourless liquid, and belongs to the following product categories: Pharmaceutical Intermediates; Organic Building Blocks; Organic Phosphates/Phosphites; Phosphorus Compounds. And the molecular formula of this chemical is C2H7O3P. What's more, It is used  intermediate in production of insecticides or herbicides, and it is also used as organophosphorus pesticides dipterex and herbicide glyphosate.

The physical properties of Dimethyl phosphonate are as following: (1)ACD/LogP: -1.28; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 2; (6)Polar Surface Area: 59 Å2; (7)Flash Point: 29.444 °C; (8)Enthalpy of Vaporization: 39.018 kJ/mol; (9)Boiling Point: 170.499 °C at 760 mmHg; (10)Vapour Pressure: 1.945 mmHg at 25°C.

Preparation of Dimethyl phosphonate: It can be prepared by methanol and phosphorus trichloride:
3CH3OH+PCl3(CH3O)2POH+2HCl+CH3Cl

Uses of Dimethyl phosphonate: It can react with cyclohexanone to produce (1-hydroxy-cyclohexyl)-phosphonic acid dimethyl ester. This reaction will need catalyst 1,5,7-triazabicyclo[4.4.0]dec-5-ene with temperature of 0°C, and the yield is about 78%.

Dimethyl phosphonate can react with cyclohexanone to produce (1-hydroxy-cyclohexyl)-phosphonic acid dimethyl ester

You should be cautious while dealing with this chemical. It is a kind of flammable chemical, and irritates eyes, and it is also harmful in contact with skin. Therefore, you had better take the following instructions: Wear suitable protective clothing and gloves, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=P(OC)OC
(2)InChI: InChI=1/C2H7O3P/c1-4-6(3)5-2/h6H,1-2H3
(3)InChIKey: HZCDANOFLILNSA-UHFFFAOYAF

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LC inhalation > 7100mg/m3/6H (7100mg/m3) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: HEMORRHAGE
National Technical Information Service. Vol. OTS0537047,
guinea pig LD50 oral 900mg/kg (900mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 36(4), Pg. 22, 1992.
mouse LC inhalation > 7100mg/m3/6H (7100mg/m3) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0537047,
mouse LD50 oral 1831mg/kg (1831mg/kg) AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 36(4), Pg. 22, 1992.
mouse LD50 subcutaneous 2610mg/kg (2610mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 36(4), Pg. 22, 1992.
rabbit LD50 skin 681mg/kg (681mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0537044,
rat LC50 inhalation > 20gm/m3 (20000mg/m3)   Albright & Wilson Inc. Vol. #OPB-3, Pg. 1984,
rat LD50 oral 3040mg/kg (3040mg/kg)   National Toxicology Program Technical Report Series. Vol. NTP-TR-287, Pg. 1985,
rat LD50 subcutaneous 2970mg/kg (2970mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 36(4), Pg. 22, 1992.