N,N'-bis(2-mercaptoethyl)-1,4-diazacycloheptane cobalt(II) dimer
monosodium iodoacetate
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; Inert atmosphere; Schlenk technique; | 98% |
1-Phenyl-3-buten-1-ol
monosodium iodoacetate
4-Phenyl-3-oxahept-6-enoic acid
Conditions | Yield |
---|---|
Stage #1: 1-Phenyl-3-buten-1-ol With sodium hydride In tetrahydrofuran for 1h; Metallation; Stage #2: monosodium iodoacetate for 2h; Alkylation; Esterification; Heating; | 95% |
1.) THF, 2.) reflux, 2 h; Yield given. Multistep reaction; |
(2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>methanol
monosodium iodoacetate
2-{[(2R,3S)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}acetic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0 - 20℃; | 95% |
With sodium hydride In tetrahydrofuran | 95% |
With sodium hydride In tetrahydrofuran |
(Z)-4-benzyloxy-but-2-en-1-ol
monosodium iodoacetate
(Z)-(4-benzyloxybut-2-enyloxy)acetic acid
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; | 95% |
monosodium iodoacetate
[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methanol
2-{[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}acetic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0 - 20℃; | 94% |
With sodium hydride In tetrahydrofuran | 94% |
monosodium iodoacetate
(3R,4R)-4-Methoxymethoxy-hexadec-1-en-3-ol
((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 0 - 20℃; | 92% |
methanol
(E)-2-Hexen-1-ol
monosodium iodoacetate
[((E)-Hex-2-enyl)oxy]-acetic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (E)-2-Hexen-1-ol; monosodium iodoacetate With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: methanol With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; | 92% |
(N,N'-bis(2-mercaptoethyl)-N,N'-diazacyclooctane)nickel(II)
monosodium iodoacetate
Conditions | Yield |
---|---|
In methanol; acetonitrile addn. of ICH2CO2Na dissolved in CH3OH to a soln. of (C6H12N2)Ni(C2H4S)2 in CH3CN at 60°C under stirring; filtration of the soln. after 4 h, slow evapn. of the solvent, elem. anal.; | 90% |
monosodium iodoacetate
2-Benzyloxybut-3-en-1-ol
5-Benzyloxy-3-oxahept-6-enoic acid
Conditions | Yield |
---|---|
Stage #1: 2-benzyloxy-3-buten-1-ol With n-butyllithium In tetrahydrofuran; hexane for 0.166667h; Metallation; Stage #2: monosodium iodoacetate In tetrahydrofuran; hexane for 2h; Alkylation; Heating; | 89% |
methanol
(Z)-2-hexen-1-ol
monosodium iodoacetate
[((Z)-Hex-2-enyl)oxy]-acetic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: (Z)-2-hexen-1-ol; monosodium iodoacetate With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: methanol With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; | 87% |
monosodium iodoacetate
Conditions | Yield |
---|---|
In methanol; acetonitrile Inert atmosphere; | 87% |
methanol
monosodium iodoacetate
3-methyl-2-buten-1-ol
(3-Methyl-but-2-enyloxy)-acetic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: monosodium iodoacetate; 3-methyl-2-buten-1-ol With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #2: methanol With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.5h; | 86% |
monosodium iodoacetate
6,9,12,15,18-penta(4-thiophenyl)-1,6,9,12,15,18-hexahydro(C60-Ih)[5,6]fullerene
Conditions | Yield |
---|---|
Stage #1: monosodium iodoacetate; 6,9,12,15,18-penta(4-thiophenyl)-1,6,9,12,15,18-hexahydro(C60-Ih)[5,6]fullerene With sodium hydroxide In tetrahydrofuran for 5.5h; Stage #2: With hydrogenchloride | 84% |
homoalylic alcohol
monosodium iodoacetate
methyl iodide
methyl (but-3-enyloxy)acetate
Conditions | Yield |
---|---|
Stage #1: homoalylic alcohol; monosodium iodoacetate With sodium hydride In N,N-dimethyl-formamide Stage #2: methyl iodide In N,N-dimethyl-formamide Further stages.; | 84% |
N,N'-bis(2-mercaptoethyl)-1,4-diazacycloheptanezinc(II) dimer
monosodium iodoacetate
Conditions | Yield |
---|---|
In methanol byproducts: NaI; under N2; MeOH added to Zn complex; stirred at room temp.; soln. of Na(ICH2CO2) in MeOH added; refluxed at 80°C (oil bath) overnight; cooled to 22°C; filtered; solvent removed from filtrate on rotary evaporator; purified by column chromy. (silica gel, MeOH); dried; recrystd. by vapor diffusionof Et2O into MeOH soln; elem. anal.; | 83.6% |
monosodium iodoacetate
2-[2-(2-azidoethoxy)ethoxy]ethanol
11-azido-3,6,9-trioxaundecanoic acid
Conditions | Yield |
---|---|
Stage #1: 2-[2-(2-azidoethoxy)ethoxy]ethanol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: monosodium iodoacetate In N,N-dimethyl-formamide at 20℃; for 32h; | 83% |
Conditions | Yield |
---|---|
Stage #1: Nerol With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: monosodium iodoacetate In tetrahydrofuran at -78 - 20℃; Stage #3: isopropyl alcohol With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; | 82% |
3-phenylsulfanyl-butan-2-one
monosodium iodoacetate
3-methyl-4-oxo-3-(phenylthio)pentanoic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran 1.) 1 h, 2.) 4 h, room temperature; | 81% |
With sodium hydride Multistep reaction; |
monosodium iodoacetate
dianion of methyl acetoacetate
5-methoxycarbonyl-4-oxopentanoic acid
Conditions | Yield |
---|---|
With acid | 81% |
[N,N′-bis(2-mercaptidoethyl)-1,4-diazacycloheptane]nickel(II)
water
monosodium iodoacetate
Conditions | Yield |
---|---|
In methanol; acetonitrile (Ar); addn. of methanolic soln. of 2.5 equiv. of iodoacetate salt to suspn. of nickel compd. in methanol and CH3CN at 22°C, stirring for 24 h; evapn., chromy. (silica, CH3CN/methanol), evapn., washing with diethyl ether, MS and IR; | 80.8% |
monosodium iodoacetate
6-monohydroxy permethylated β-cyclodextrin
Conditions | Yield |
---|---|
Stage #1: 6-monohydroxy permethylated β-cyclodextrin With sodium hydride In tetrahydrofuran for 2h; Heating; Stage #2: monosodium iodoacetate In dichloromethane Heating; | 80% |
Geraniol
monosodium iodoacetate
isopropyl alcohol
((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-acetic acid isopropyl ester
Conditions | Yield |
---|---|
Stage #1: Geraniol With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: monosodium iodoacetate In tetrahydrofuran at -78 - 20℃; Stage #3: isopropyl alcohol With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; | 78% |
Conditions | Yield |
---|---|
With potassium carbonate In water at 300℃; for 2h; | 77.91% |
monosodium iodoacetate
4a,5-dihydrocyclopentapyren-3(4H)-one
Conditions | Yield |
---|---|
With PPA In dichloromethane at 80 - 90℃; | 76% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; for 20h; Substitution; | 76% |
Conditions | Yield |
---|---|
Stage #1: 2-(3-chlorophenyl)ethanol; monosodium iodoacetate With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: methanol With thionyl chloride at -15 - 20℃; for 1.5h; | 76% |
Conditions | Yield |
---|---|
Stage #1: 2-(3-chlorophenyl)ethanol; monosodium iodoacetate With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Stage #2: With hydrogenchloride; water In hexane pH=1; Stage #3: methanol With thionyl chloride at -15 - 20℃; for 1.5h; | 76% |
1-(phenylsulfanyl)acetone
monosodium iodoacetate
4-oxo-3-(phenylthio)pentanoic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran Ambient temperature; | 74% |
With sodium hydride Multistep reaction; |
monosodium iodoacetate
2A,2B,2C,2D,2E,2F,3A,3B,3C,3D,3E,3F,3G,6A,6B,6C,6D,6E,6F,6G-eicosa-O-methylcyclomaltoheptaose
Conditions | Yield |
---|---|
Stage #1: 2A,2B,2C,2D,2E,2F,3A,3B,3C,3D,3E,3F,3G,6A,6B,6C,6D,6E,6F,6G-eicosa-O-methylcyclomaltoheptaose With sodium hydride In tetrahydrofuran for 2h; Heating; Stage #2: monosodium iodoacetate In dichloromethane Heating; | 73% |
monosodium iodoacetate
Conditions | Yield |
---|---|
In methanol; dichloromethane Ambient temperature; | 72% |
IUPAC Name: Sodium 2-iodoacetate
Synonyms: Sodium iodoacetate ; Acetic acid, 2-iodo-, sodium salt (1:1) ; Acetic acid, iodo-, sodium salt ; Iodoacetate, sodium salt ; Iodoacetic acid Sodium salt ; Sodium monoiodoacetate
Molecular Structure of Sodium monoiodoacetate (CAS NO:305-53-3) :
Molecular Formula of Sodium monoiodoacetate (CAS NO:305-53-3) : C2H2IO2.Na
Molecular Weight of Sodium monoiodoacetate (CAS NO:305-53-3) : 207.93
CAS NO: 305-53-3
EINECS : 206-165-7
Mol File: 305-53-3.mol
Flash Point: 112.3 °C
Enthalpy of Vaporization: 55.03 kJ/mol
Boiling Point: 262.1 °C at 760 mmHg
Vapour Pressure: 0.00329 mmHg at 25°C
Melting point: 208 °C (dec.)(lit.)
Storage temp: -20°C
Solubility: methanol: 0.1 M at 20 °C, clear, colorless
Appearance:light yellow to yellow-brown powder
Sodium monoiodoacetate (CAS NO:305-53-3) is used in pharmaceutical industry.
1. | dni-hmn:lyms 10 mmol/L | STBIBN Studia Biophysica. 50 (1975),97. | ||
2. | ipr-rat LDLo:30 mg/kg | JPPMAB Journal of Pharmacy and Pharmacology. 17 (1965),814. | ||
3. | orl-mus LD50:63 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 86 (1946),336. | ||
4. | ipr-mus LD50:75 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 . |
Reported in EPA TSCA Inventory.
Poison by ingestion and intraperitoneal routes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of I− and Na2O.
Hazard Codes T,Xn
Risk Statements 25-37/38-41-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R37/38:Irritating to respiratory system and skin.
R25 :Toxic if swallowed.
R41:Risk of serious damage to the eyes.
Safety Statements 26-39-45-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S39:Wear eye / face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR UN 2811 6.1/PG 1
WGK Germany 3
RTECS AI3675000
F 3-8-10
HazardClass 6.1(b)
PackingGroup III
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.
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