305-53-3

Basic information

• Product Name: IODOACETIC ACID SODIUM SALT
• Synonyms: IODOACETIC ACID SODIUM SALT;SODIUM MONOIODOACETATE;SODIUM IODOACETATE;SODIUM IODACETATE SODIUM SALT;Aceticacid,iodo-,sodiumsalt;Iodoacetic acid, sodium salt,99%;iodoacetate, sodium sal;Iodoacetic acid, sodiuM salt, 99% 25GR
• CAS NO: 305-53-3
• Molecular Formula: C₂H₂IO₂*Na
• Molecular Weight: 207.93
• EINECS: 206-165-7
• Mol File: 305-53-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 208 °C (dec.)(lit.)
• Boiling Point: 262.1 °C at 760 mmHg
• Flash Point: 112.3 °C
• Appearance: Light yellow to yellow-brown/Powder
• Vapor Pressure: 0.00329mmHg at 25°C
• Storage Temp.: −20°C
• Solubility: methanol: 0.1 M at 20 °C, clear, colorless
• BRN: 4009322
• CAS DataBase Reference: IODOACETIC ACID SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: IODOACETIC ACID SODIUM SALT(305-53-3)
• EPA Substance Registry System: IODOACETIC ACID SODIUM SALT(305-53-3)

Safety Data

• Hazard Codes: T,Xn
• Statements: 25-37/38-41-20/21/22-36/37/38
• Safety Statements: 26-39-45-36-36/37/39-22
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: AI3675000
• F: 3-8-10
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 305-53-3(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to yellow-brown powder

Uses

Different sources of media describe the Uses of 305-53-3 differently. You can refer to the following data:
1. Analytical reagent.
2. Reagent for the modification of cysteine residues in proteins. Used to induce animal osteoarthritis model system, which mimics both symptoms and histopathology of the human disease.

Hazard

Toxic.

Biochem/physiol Actions

Used to induce osteoarthritis-like lesions and functional impairment in rats, for testing of chondroprotective agents and diagnostic imaging techniques.

Safety Profile

Poison by ingestion and intraperitoneal routes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of Iand Na2O.

InChI:InChI=1/C2H3IO2.Na/c3-1-2(4)5;/h1H2,(H,4,5);/q;+1/p-1

Synthetic route

N,N'-bis(2-mercaptoethyl)-1,4-diazacycloheptane cobalt(II) dimer (870656-65-8) + monosodium iodoacetate (305-53-3) → 1,4-diazacycloheptane-1,4-diylbis(3-thiapentanoic)cobalt(II)

Conditions	Yield
In methanol at 20℃; for 24h; Inert atmosphere; Schlenk technique;	98%

1-Phenyl-3-buten-1-ol (80735-94-0) + monosodium iodoacetate (305-53-3) → 4-Phenyl-3-oxahept-6-enoic acid (257949-88-5)

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 (138750-71-7, 125877-82-9) + monosodium iodoacetate (305-53-3) → 2-{[(2R,3S)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}acetic acid (864719-87-9)

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 (81028-03-7) + monosodium iodoacetate (305-53-3) → (Z)-(4-benzyloxybut-2-enyloxy)acetic acid (861997-65-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;	95%

monosodium iodoacetate (305-53-3) + [(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methanol (740845-32-3) → 2-{[(2R,3R)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}acetic acid (740845-35-6)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃;	94%
With sodium hydride In tetrahydrofuran	94%

monosodium iodoacetate (305-53-3) + (3R,4R)-4-Methoxymethoxy-hexadec-1-en-3-ol (212205-68-0) → ((1R,2R)-2-Methoxymethoxy-1-vinyl-tetradecyloxy)-acetic acid (212205-62-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃;	92%

methanol (67-56-1) + (E)-2-Hexen-1-ol (928-95-0) + monosodium iodoacetate (305-53-3) → [((E)-Hex-2-enyl)oxy]-acetic acid methyl ester (256394-12-4)

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) (129964-91-6) + monosodium iodoacetate (305-53-3) → 1,5-diazaoctane-1,5-diylbis(3-thiapentanoato)nickel(II)

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 (305-53-3) + 2-Benzyloxybut-3-en-1-ol (233670-03-6) → 5-Benzyloxy-3-oxahept-6-enoic acid (257949-96-5)

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 (67-56-1) + (Z)-2-hexen-1-ol (928-94-9) + monosodium iodoacetate (305-53-3) → [((Z)-Hex-2-enyl)oxy]-acetic acid methyl ester (301659-67-6)

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%

([1-(2-mercaptoethyl)-methyl-1,4-diazacycloheptane] nickel(II)) dimer + monosodium iodoacetate (305-53-3) → C40H74I4N8Ni4O8S4

Conditions	Yield
In methanol; acetonitrile Inert atmosphere;	87%

methanol (67-56-1) + monosodium iodoacetate (305-53-3) + 3-methyl-2-buten-1-ol (556-82-1) → (3-Methyl-but-2-enyloxy)-acetic acid methyl ester (107531-92-0)

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 (305-53-3) + 6,9,12,15,18-penta(4-thiophenyl)-1,6,9,12,15,18-hexahydro(C60-Ih)[5,6]fullerene (630392-60-8) → C100H36O10S5

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 (627-27-0) + monosodium iodoacetate (305-53-3) + methyl iodide (74-88-4) → methyl (but-3-enyloxy)acetate (176238-10-1)

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 (868260-83-7) + monosodium iodoacetate (305-53-3) → [N-(3-thiabutyl)-N'-(3-thiapentanoate)-1,4-diazacycloheptane]zinc(II)

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 (305-53-3) + 2-[2-(2-azidoethoxy)ethoxy]ethanol (86520-52-7) → 11-azido-3,6,9-trioxaundecanoic acid (172531-37-2)

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%

Nerol (106-25-2) + monosodium iodoacetate (305-53-3) + isopropyl alcohol (67-63-0) → ((Z)-3,7-Dimethyl-octa-2,6-dienyloxy)-acetic acid isopropyl ester

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 (13023-53-5, 132187-18-9, 132187-19-0) + monosodium iodoacetate (305-53-3) → 3-methyl-4-oxo-3-(phenylthio)pentanoic acid (65263-91-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran 1.) 1 h, 2.) 4 h, room temperature;	81%
With sodium hydride Multistep reaction;

monosodium iodoacetate (305-53-3) + dianion of methyl acetoacetate (30568-00-4) → 5-methoxycarbonyl-4-oxopentanoic acid (191542-37-7)

Conditions	Yield
With acid	81%

[N,N′-bis(2-mercaptidoethyl)-1,4-diazacycloheptane]nickel(II) (352232-62-3) + water (7732-18-5) + monosodium iodoacetate (305-53-3) → 1,4-diazacycloheptan-1,4-diylbis(3-thiapentanoato)nickel(II) trihydrate

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 (305-53-3) + 6-monohydroxy permethylated β-cyclodextrin (94789-61-4) → 6I-O-carboxymethyl-2I-VII,3I-VII,6II-VII-eicosa-O-methyl-cyclomaltoheptaose

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 (106-24-1) + monosodium iodoacetate (305-53-3) + isopropyl alcohol (67-63-0) → ((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-acetic acid isopropyl ester (517891-54-2)

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%

C39H42N2O7 + monosodium iodoacetate (305-53-3) → C41H44N2O9

Conditions	Yield
With potassium carbonate In water at 300℃; for 2h;	77.91%

monosodium iodoacetate (305-53-3) → 4a,5-dihydrocyclopentapyren-3(4H)-one (85056-98-0)

Conditions	Yield
With PPA In dichloromethane at 80 - 90℃;	76%

monosodium iodoacetate (305-53-3) + AGN 191383 (168329-48-4) → AGN 192614

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 20h; Substitution;	76%

methanol (67-56-1) + monosodium iodoacetate (305-53-3) → [2-(3-chloro-phenyl)-ethoxy]-acetic acid methyl ester

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%

methanol (67-56-1) + 2-(3-chlorophenyl)ethanol (5182-44-5) + monosodium iodoacetate (305-53-3) → [2-(3-chloro-phenyl)-ethoxy]-acetic acid methyl ester

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 (5042-53-5) + monosodium iodoacetate (305-53-3) → 4-oxo-3-(phenylthio)pentanoic acid (65263-90-3)

Conditions	Yield
With sodium hydride In tetrahydrofuran Ambient temperature;	74%
With sodium hydride Multistep reaction;

monosodium iodoacetate (305-53-3) + 2A,2B,2C,2D,2E,2F,3A,3B,3C,3D,3E,3F,3G,6A,6B,6C,6D,6E,6F,6G-eicosa-O-methylcyclomaltoheptaose (153313-11-2) → 2I-O-carboxymethyl-2II-VII,3I-VII,6I-VII-eicosa-O-methyl-cyclomaltoheptaose

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 (305-53-3) + N,N'-Bis-L-cystinyl-bis-N'',N''-dimethylaminoethylamide → N,N'--L-cystinylbis(aminoethyl)>-N,N'-bis(carboxymethyl)-N,N'-dimethylammonium diiodide disodium salt

Conditions	Yield
In methanol; dichloromethane Ambient temperature;	72%

Downstream Products

• 613-31-0 9,10-dihydroanthracene 
• 23825-24-3 2-(9,10-dihydroanthracen-9-yl)acetic acid 
• 131581-34-5 9,10-dihydroanthracene-9,10-diacetic acid 
• 257949-95-4 5-Phenyl-3-oxahept-6-enoic acid 
• 79772-18-2 4-oxo-4-phenyl-3-(phenylthio)butanoic acid 
• 65263-91-4 3-methyl-4-oxo-3-(phenylthio)pentanoic acid 
• 104938-03-6 enterolactone 
• 257949-96-5 5-Benzyloxy-3-oxahept-6-enoic acid 
• 62723-61-9 2-[dimethyl(2-oxido-2-oxoethyl)ammonio]ethyl methacrylate 
• 108466-89-3 N-(tert-butyloxycarbonyl)-8-amino-3,6-dioxaoctanoic acid 
• 22245-55-2 pyren-4-ylacetic acid 
• 82243-05-8 4,5-dihydropyren-4-ylacetic acid 
• 60239-18-1 1,4,7,10-tetrakis(carboxymethyl)-1,4,7,10-tetraazacyclododecane 
• 1878-56-4 2-(4-cyclohexylphenoxy)acetic acid