dimethyl methane phosphonate
A
methylphosphonic acid dichloroanhydride
B
methylene chloride
Conditions | Yield |
---|---|
With thionyl chloride; N-Formylpiperidine for 19h; Heating; various conditions and cactalasts investigated; | A 99.2% B n/a |
methylphosphonic acid bis(trimethylsilyl) ester
A
methylphosphonic acid dichloroanhydride
B
chloro-trimethyl-silane
Conditions | Yield |
---|---|
With phosphorus pentachloride In tetrachloromethane for 1h; Ambient temperature; | A 98% B n/a |
Conditions | Yield |
---|---|
With thionyl chloride; N,N-dimethyl-formamide for 4h; Reagent/catalyst; Reflux; | 96.4% |
With thionyl chloride | 92.8% |
With calcium fluoride; thionyl chloride for 20h; Substitution; Heating; | 92.8% |
methylphosphonic acid bis(trimethylsilyl) ester
A
methylphosphonic acid dichloroanhydride
B
chloro-trimethyl-silane
C
o-phenylene chlorophosphate
Conditions | Yield |
---|---|
With CPT | A 86.5% B n/a C n/a |
Conditions | Yield |
---|---|
With phosphorus pentachloride for 14h; Chlorination; Heating; | 81% |
With thionyl chloride | 80% |
With phosphorus pentachloride In tetrachloromethane at 45℃; for 12h; | |
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In chloroform at 50℃; for 0.0833333h; | 86 % Spectr. |
With thionyl chloride |
1,3-dichloro-2-butene
A
methylphosphonic acid dichloroanhydride
B
1,2-dichloroethyl phosphorodichloridate
C
acetyl chloride
D
chloromethylphosphonic dichloride
Conditions | Yield |
---|---|
With oxygen; phosphorus trichloride at -10 - 10℃; Product distribution; Mechanism; | A n/a B 80% C n/a D n/a E n/a |
With oxygen; phosphorus trichloride at -10 - 10℃; Title compound not separated from byproducts; | A n/a B 80% C n/a D n/a E n/a |
With oxygen; phosphorus trichloride at -10 - 10℃; | A n/a B 80% C n/a D n/a E n/a |
methylphosphonic acid dichloroanhydride
Conditions | Yield |
---|---|
With pyridine; thionyl chloride for 4h; Heating; | 75% |
Conditions | Yield |
---|---|
With pyridine; thionyl chloride for 4h; Heating; | 71% |
Conditions | Yield |
---|---|
With pyridine; thionyl chloride for 4h; Heating; | 65% |
methyl-thiophosphonic acid O,O'-dipropyl ester
methylphosphonic acid dichloroanhydride
Conditions | Yield |
---|---|
With pyridine; thionyl chloride for 4h; Heating; | 62% |
methyl dichlorophosphite
O-(methylchloroformoimino)methyldichlorophosphonium chloride
A
methylphosphonic acid dichloroanhydride
B
methylene chloride
C
acetonitrile
Conditions | Yield |
---|---|
In diethyl ether at 30℃; for 1h; | A 9.8% B n/a C n/a D n/a |
In diethyl ether at 30℃; for 1h; | A 9.8 g B n/a C n/a D n/a |
Conditions | Yield |
---|---|
With nickel(II) iodide; phosphorus trichloride at 250℃; |
Conditions | Yield |
---|---|
With thionyl chloride |
Conditions | Yield |
---|---|
With phosphorus pentachloride; chlorine |
bis(2-chloroethyl) methylphosphonate
A
methylphosphonic acid dichloroanhydride
B
methyl-phosphonic acid-(2-chloro-ethyl ester)-chloride
Conditions | Yield |
---|---|
With phosphorus pentachloride |
Conditions | Yield |
---|---|
With phosphorus pentachloride |
formaldehyd
methyldichlorophosphane
A
methylphosphonic acid dichloroanhydride
B
chloromethyl(methyl)phosphinic chloride
Conditions | Yield |
---|---|
at 200℃; for 2h; |
methyldichlorophosphane
1,1-dichloro-1-nitrosoethane
methylphosphonic acid dichloroanhydride
Conditions | Yield |
---|---|
at 100℃; Yield given; |
methyldichlorophosphane
A
methylphosphonic acid dichloroanhydride
B
chloromethyl(methyl)phosphinic chloride
Conditions | Yield |
---|---|
With formaldehyd at 200℃; for 2h; |
4,4-dimethyl-2-pentyne
A
methylphosphonic acid dichloroanhydride
B
tert-butyl phosphinyl dichloride
Conditions | Yield |
---|---|
With oxygen; phosphorus trichloride Yield given. Yields of byproduct given; |
O-(Trimethylsilyl)acetohydroxamoyl chloride
O-(methylchloroformoimino)methyldichlorophosphonium chloride
A
methylphosphonic acid dichloroanhydride
B
chloro-trimethyl-silane
C
acetonitrile
Conditions | Yield |
---|---|
A 1.5 g B n/a C n/a |
propenyl chloride
A
methylphosphonic acid dichloroanhydride
B
1,2,2-trichloroethyl phosphorodichloridate
Conditions | Yield |
---|---|
With oxygen; phosphorus trichloride at -10 - 10℃; Product distribution; Mechanism; |
methylphosphonic acid dichloroanhydride
Conditions | Yield |
---|---|
With water |
2-chloropropene
A
methylphosphonic acid dichloroanhydride
B
acetyl chloride
D
chloromethylphosphonic dichloride
Conditions | Yield |
---|---|
With oxygen; phosphorus trichloride at -10 - 10℃; Title compound not separated from byproducts; | |
With oxygen; phosphorus trichloride at -10 - 10℃; Product distribution; Mechanism; |
Conditions | Yield |
---|---|
Stage #1: methylene chloride With aluminium trichloride; phosphorus trichloride at 25℃; under 3420 Torr; for 2h; Stage #2: With water In dichloromethane at 0℃; | 10.1 g |
With phosphorus trichloride In acetonitrile at 30 - 80℃; Autoclave; |
Conditions | Yield |
---|---|
With oxygen | |
With sulfuryl dichloride at 0 - 30℃; for 2.41667h; Temperature; Sealed tube; | 130.7 g |
methyl phosphine chloride
methylphosphonic acid dichloroanhydride
Conditions | Yield |
---|---|
With phosphorus; iodine; chlorine; phosphorus trichloride at 50 - 70℃; for 5h; Temperature; Autoclave; |
methanol
A
methylphosphonic acid dichloroanhydride
B
dimethyl methane phosphonate
Conditions | Yield |
---|---|
With phosphorus trichloride at 70℃; |
methylphosphonic acid dichloroanhydride
2,2-dimethyl-3-(methylamino)propan-1-ol
Conditions | Yield |
---|---|
With triethylamine In benzene for 20h; Ambient temperature; | 100% |
1-(2-cyanoethyl)aziridine
methylphosphonic acid dichloroanhydride
N-(2-cyanoethyl)-N-(2-chloroethyl)-P-methylphosphonamidic chloride
Conditions | Yield |
---|---|
In benzene at 20℃; | 99% |
methylphosphonic acid dichloroanhydride
p-cresol
O,O-di-4-methylphenyl methylphosphonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Cooling with ice; | 99% |
With triethylamine In dichloromethane at 20℃; for 1h; | 70% |
at 160℃; for 6h; | 65% |
With triethylamine In benzene at 50 - 60℃; for 6h; | 56% |
methylphosphonic acid dichloroanhydride
propan-1-ol
methylphosphonic acid dipropyl ester
Conditions | Yield |
---|---|
With aluminum oxide at 20℃; | 98% |
methylphosphonic acid dichloroanhydride
acrylic acid
2-carboxyethyl-methyl-phosphinic acid
Conditions | Yield |
---|---|
Stage #1: methylphosphonic acid dichloroanhydride; acrylic acid at 60 - 80℃; Inert atmosphere; Stage #2: With water In acetone for 0.166667h; Solvent; Reflux; | 98% |
Conditions | Yield |
---|---|
Stage #1: 1-ethynyl-4-fluorobenzene With isopropylmagnesium bromide In tetrahydrofuran; 2-methyltetrahydrofuran at -20℃; for 4h; Inert atmosphere; Stage #2: methylphosphonic acid dichloroanhydride In tetrahydrofuran; 2-methyltetrahydrofuran at -20℃; for 4h; | 98% |
methylphosphonic acid dichloroanhydride
O-ethylethylthiophosphonic acid
bis(ethylethoxythiophosphonyl)methylphosphonate
Conditions | Yield |
---|---|
With triethylamine In diethyl ether 1.) -45 deg C, 1 h, 2.) 20 deg C, 1 h; | 97.2% |
methylphosphonic acid dichloroanhydride
isopropyl alcohol
diisopropyl methanephosphonate
Conditions | Yield |
---|---|
With aluminum oxide at 20℃; | 97% |
With N,N-diethylaniline | |
With pyridine |
methylphosphonic acid dichloroanhydride
methoxydimethylsilyl cyanide
A
methyl (cyano)methylphosphonate
B
dimethylsilicon dichloride
Conditions | Yield |
---|---|
at 40 - 45℃; for 0.0833333h; | A 87.6% B 97% |
methylphosphonic acid dichloroanhydride
4-chloro-phenol
O,O-di-4-chlorophenyl methylphosphonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Cooling with ice; | 97% |
With triethylamine In dichloromethane at 20℃; for 1h; | 77% |
With triethylamine In benzene at 50 - 60℃; for 6h; | 68% |
at 160℃; for 6h; | 64% |
Conditions | Yield |
---|---|
With aluminum oxide at 20℃; | 97% |
methylphosphonic acid dichloroanhydride
2,2,3,3,4,4,5,5-octafluoropentan-1-ol
bis(1H,1H,5H-octafluoropentyl) methylphosphonate
Conditions | Yield |
---|---|
With lithium chloride for 2.5h; bath temperature 170 - 195 deg C; | 96.8% |
methylphosphonic acid dichloroanhydride
(R,R)-TADDOL
(3aR,8aR)-tetrahydro-2,2,6-trimethyl-4,4,8,8-tetraphenyl-1,3-dioxolo[4,5-e][1,3,2]dioxaphosphepin 6-oxide
Conditions | Yield |
---|---|
Stage #1: (R,R)-TADDOL With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 1h; Stage #2: methylphosphonic acid dichloroanhydride In tetrahydrofuran at -78 - 20℃; for 3.5h; | 96% |
methylphosphonic acid dichloroanhydride
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 20℃; for 8h; Inert atmosphere; Large scale; | 96% |
With triethylamine In diethyl ether at 20℃; for 8h; Inert atmosphere; | 96% |
With caesium carbonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; |
methylphosphonic acid dichloroanhydride
methanol
dimethyl methane phosphonate
Conditions | Yield |
---|---|
With aluminum oxide at 20℃; | 95% |
With triethylamine | 80% |
methylphosphonic acid dichloroanhydride
N-allyl (L)-leucine methyl ester
C3H5NHCHC4H9CO2CH3POClCH2
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane Substitution; Heating; | 95% |
With dmap; triethylamine In dichloromethane Substitution; Heating; | |
With dmap; triethylamine In dichloromethane Heating; | |
With dmap; triethylamine In dichloromethane Heating; |
methylphosphonic acid dichloroanhydride
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Cooling with ice; | 95% |
methylphosphonic acid dichloroanhydride
2-methyl-propan-1-ol
isobutyl hydrogen methylphosphonite
Conditions | Yield |
---|---|
With ammonia In cyclohexane at -10℃; for 2h; | 95% |
methylphosphonic acid dichloroanhydride
tert-butylamine
P-methyl-N-t-butylphosphonamidic chloride
Conditions | Yield |
---|---|
In diethyl ether for 40h; Ambient temperature; | 94% |
methylphosphonic acid dichloroanhydride
phenol
diphenyl methylphosphonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Cooling with ice; | 94% |
With triethylamine In dichloromethane for 1h; Ambient temperature; | 86% |
With triethylamine In dichloromethane at 0 - 20℃; for 3h; | 86% |
Conditions | Yield |
---|---|
Stage #1: methylphosphonic acid dichloroanhydride With dmap; triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: Allylbenzylamine In dichloromethane at 40℃; for 3h; | 94% |
methylphosphonic acid dichloroanhydride
tetrafluoroethane-β-sultone
chlorosulfuric acid trifluorovinyl ester
Conditions | Yield |
---|---|
In dichloromethane at -10°C; | 94% |
In dichloromethane at -10°C; | 94% |
Conditions | Yield |
---|---|
With ammonia In cyclohexane at -10℃; for 1h; | 93.3% |
methylphosphonic acid dichloroanhydride
4-nitro-phenol
O,O-di-4-nitrophenyl methylphosphonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; Cooling with ice; | 93% |
With triethylamine In dichloromethane at 20℃; for 4h; Cooling with ice; | 91% |
With triethylamine In dichloromethane at 20℃; for 4h; Cooling with ice; | 91% |
methylphosphonic acid dichloroanhydride
2,2,2-trifluoroethanol
bis(2,2,2-trifluoroethyl)(methyl)phosphonate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 10 - 30℃; for 2.5h; Inert atmosphere; | 93% |
With triethylamine In tetrahydrofuran for 2h; Ambient temperature; | 92% |
With lithium chloride for 4h; bath temperature 160 deg C; | 85% |
methylphosphonic acid dichloroanhydride
rac-octan-2-ol
di(methylheptyl)methylphosphonate
Conditions | Yield |
---|---|
With hydrogenchloride at 30 - 85℃; for 4.25h; | 93% |
methylphosphonic acid dichloroanhydride
hexan-1-ol
n-hexyl methylphosphinate
Conditions | Yield |
---|---|
With ammonia In cyclohexane at 0℃; for 3h; | 92.8% |
IUPAC: Dichlorophosphorylmethane
Methyl phosphonic dichloride (676-97-1) is also called for 4-04-00-03509 (Beilstein Handbook Reference) ; BRN 1071305 ; EINECS 211-634-4 ; HSDB 6329 ; Methanephosphonyl chloride ; Phosphonic dichloride, methyl- ; Phosphonic dichloride, P-methyl- ; Phosphonic dichloride, methyl- ; NA9206 ; 228052_ALDRICH ; 64262_FLUKA and so on.
Molecular Formula: CH3Cl2OP
Molecular Weight: 132.91
EINECS: 211-634-4
Melting Point: 31-34°C
Density: 1.445 g/cm3
Flash Point: 44.1°C
Boiling Point: 163°C at 760 mmHg
LogP: ACD/LogP: 0.26
XLogP: 0.80
ALOGPS: 0.67
ACD/LogD (pH 5.5): 0.26
ACD/LogD (pH 7.4): 0.26
ACD/BCF (pH 5.5): 1
ACD/BCF (pH 7.4): 1
ACD/KOC (pH 5.5): 32.79
ACD/KOC (pH 7.4): 32.79
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 0
Heavy Atom Count: 5
Formal Charge: 0
Complexity: 64
Isotope Atom Count: 0
Defined Atom StereoCenter Count: 0
Undefined Atom StereoCenter Count: 0
Defined Bond StereoCenter Count: 0
Undefined Bond StereoCenter Count: 0
Covalently-Bonded Unit Count: 1
Index of Refraction: 1.419
Molar Refractivity: 23.25 cm3
Molar Volume: 91.9 cm3
Surface Tension: 33.3 dyne/cm
Vapour Pressure: 2.76 mmHg at 25°C
Enthalpy of Vaporization: 38.31 kJ/mol
The molecular structure of Methyl phosphonic dichloride (676-97-1) :
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LC50 | inhalation | 26ppm/4H (26ppm) | BEHAVIORAL: EXCITEMENT LUNGS, THORAX, OR RESPIRATION: DYSPNEA SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | American Industrial Hygiene Association Journal. Vol. 25, Pg. 470, 1964. |
EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory.
Poison by inhalation. A corrosive irritant to the eyes, skin, and mucous membranes. When heated to decomposition it emits toxic fumes of Cl− and POx. See also CHLORIDES.
Hazard Codes: T+
Risk Statements: 14-26-34
R14: Reacts violently with water
R26: Very Toxic by inhalation
R34: Causes burns
Safety Statements: 26-36/37/39-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR: UN 3390 6.1/PG 1
WGK Germany: 3
F10: Keep under argon
HazardClass: 6.1
PackingGroup: I
RTECS: TA1840000
DOT Classification: 6.1; Label: Poison, Corrosive
1.Treatment of Methyl phosphonic dichloride (676-97-1) in Wastewater,see as follows :
Total removal: 2.60 percent
Total biodegradation: 0.09 percent
Total sludge adsorption: 1.75 percent
Total to air: 0.76 percent
(using 10000 hr Bio P,A,S)
2.Reactivity Profile
Methyl phosphonic dichloride (676-97-1) is incompatible with water, strong oxidizing, agents, alcohols, bases (including amines). May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts.
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