54907-61-8

Basic information

• Product Name: IODOACETIC ANHYDRIDE
• Synonyms: IODOACETIC ANHYDRIDE;iodoaceticanhydride90+%;Bis(iodoacetic acid)anhydride;Di(iodoacetic)anhydride;Iodoacetic acid anhydride;Iodoacetic anhydride,97%;2-iodoacetic anhydride;Iodoacetyl anhydride
• CAS NO: 54907-61-8
• Molecular Formula: C₄H₄I₂O₃
• Molecular Weight: 353.88
• Product Categories: Carbonyl Compounds;Carboxylic Acid Anhydrides;Organic Building Blocks
• Mol File: 54907-61-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 47-49 °C(lit.)
• Boiling Point: 276.9oC at 760 mmHg
• Flash Point: >230 °F
• Appearance: Yellow/Crystalline Powder
• Density: 2.664g/cm3
• Vapor Pressure: 0.00468mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: 2-8°C
• Solubility: chloroform: soluble10%, clear to slightly hazy, yellow (pink or
• BRN: 1812140
• CAS DataBase Reference: IODOACETIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: IODOACETIC ANHYDRIDE(54907-61-8)
• EPA Substance Registry System: IODOACETIC ANHYDRIDE(54907-61-8)

Safety Data

• Hazard Codes: T,C
• Statements: 25-35
• Safety Statements: 22-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 8-10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 54907-61-8(Hazardous Substances Data)

Usage

Chemical Properties

Golden flakes

Uses

Reagent used as linker for development of reagents used for differential protein quantitation via ion scanningReactant used for:Sythesis of N-iodoacetyl glycosylamine derivatives and converting amino precursors to IA derivativesLinking lysine residues to N-terminal α-amino groups of peptidesCapping amines and yielding a thiol reactive iodo-derivativeIodoacetylation

InChI:InChI=1/C4H4I2O3/c5-1-3(7)9-4(8)2-6/h1-2H2

Synthetic route

2-iodoacetyl chloride (38020-81-4) → iodoacetic anhydride (54907-61-8)

Conditions	Yield
beim Aufbewahren in lose verschlossenen Flaschen;

Iodoacetic acid (64-69-7) → 2-iodoacetyl chloride (38020-81-4) + iodoacetic anhydride (54907-61-8)

Conditions	Yield
With thionyl chloride at 45 - 50℃;

Iodoacetic acid (64-69-7) → iodoacetic anhydride (54907-61-8)

Conditions	Yield
With dicyclohexyl-carbodiimide In acetonitrile
With dicyclohexyl-carbodiimide In ethyl acetate for 2h; Darkness;

thionyl chloride (7719-09-7) + Iodoacetic acid (64-69-7) → 2-iodoacetyl chloride (38020-81-4) + iodoacetic anhydride (54907-61-8)

iodoacetic anhydride (54907-61-8) + N1-betainylsulfanilamide dihydrochloride → N4-(iodoacetyl)-N1-betainylsulfanilamide

Conditions	Yield
In dichloromethane Ambient temperature;	100%

iodoacetic anhydride (54907-61-8) + 6-aminohexanoic acid (60-32-2) → 6-(2-iodo-acetylamino)-hexanoic acid (2018-22-6)

Conditions	Yield
In 1,4-dioxane at 20 - 50℃; for 19h;	100%

iodoacetic anhydride (54907-61-8) + 2,3,4-tri-O-acetyl-1-amino-6-azido-1,6-dideoxy-β-D-glucose → C14H19IN4O8 (1415238-64-0)

Conditions	Yield
In N,N-dimethyl-formamide at -10℃; for 4h; Inert atmosphere;	99%

iodoacetic anhydride (54907-61-8) + dansylethylenediamine (35060-08-3) → N-(2-ethyl-iodo-acetamide)-dansyl (1180491-15-9)

Conditions	Yield
In chloroform at 20℃; for 2h;	98%

1,10-phenanthroline-5-amine (54258-41-2) + iodoacetic anhydride (54907-61-8) → 2-iodo-N-1,10-phenanthrolin-5-ylacetamide (111047-29-1)

Conditions	Yield
In chloroform Heating;	96%
	57%
In acetonitrile Darkness;

iodoacetic anhydride (54907-61-8) + (5-{4-[(3-ammoniopropyl)oxy]phenyl}-10,15,20-tris(1-methylpyridinium-4-yl))porphyrin benzotriazolate iodide → (5-{4-[3-(iodoacetamido)propyloxy]phenyl}-10,15,20-tris(1-methylpyridinium-4-yl))porphyrin triiodide

Conditions	Yield
In N,N-dimethyl-formamide at 0℃; for 2h;	95%

iodoacetic anhydride (54907-61-8) + (4-aminophenylsulphonyl)nitromethane (122263-36-9) → (4-iodoacetamidophenylsulfonyl)nitromethane

Conditions	Yield
In acetonitrile at 20℃; for 18h; Acetylation;	95%

iodoacetic anhydride (54907-61-8) + (4-amino-2,6-dimethylphenylsulphonyl)nitromethane (132414-04-1) → (4-iodoacetamido-2,6-dimethylphenylsulfonyl)nitromethane

Conditions	Yield
In acetonitrile at 20℃; Acetylation;	95%

iodoacetic anhydride (54907-61-8) + 2-amino-3-(4-benzoylphenyl)-N-(prop-2-yn-1-yl)propanamide → 3-(4-benzoylphenyl)-2-(2-iodoacetamido)-N-(prop-2-yn-1-yl)propanamide

Conditions	Yield
In dichloromethane at 20℃; for 0.25h;	95%

iodoacetic anhydride (54907-61-8) + 2-Amino-4-oxo-4H-3,1-benzothiazin (131357-73-8) → 2-iodoacetylamino-4H-3,1-benzothiazin-4-one

Conditions	Yield
In toluene for 0.5h; Heating;	92%

1-Amino-1-deoxy-D-glucitol (488-43-7) + iodoacetic anhydride (54907-61-8) → 2-iodo-N-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl)acetamide (328933-07-9)

Conditions	Yield
In N,N-dimethyl-formamide at 0 - 4℃; Inert atmosphere;	86%

(6R,7R)-3-(4-Amino-phenylsulfanylmethyl)-7-(2-tert-butoxycarbonylamino-acetylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (851047-89-7) + iodoacetic anhydride (54907-61-8) → (6R,7R)-7-(2-tert-Butoxycarbonylamino-acetylamino)-3-[4-(2-iodo-acetylamino)-phenylsulfanylmethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (851047-90-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;	85%

2-[2-(2-amino-ethylsulfanyl)-vinylsulfanyl]-ethylamine hydrochloride + iodoacetic anhydride (54907-61-8) → 2-iodo-N-(2-{2-[2-(2-iodo-acetylamino)-ethylsulfanyl]vinylsulfanyl}-ethyl)-acetamide

Conditions	Yield
With sodium hydroxide In water; 1,2-dichloro-ethane for 0.0333333h;	85%

AZCO-OH + iodoacetic anhydride (54907-61-8) → iodoacetylaza-coumarin

Conditions	Yield
With pyridine In chloroform for 2.08333h;	85%

3-azidopropylamine (88192-19-2) + iodoacetic anhydride (54907-61-8) → N-(3-azidopropyl)-2-iodoacetamide (352307-52-9)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	85%

iodoacetic anhydride (54907-61-8) + 6,7,9,10,17,18,20,21-octahydro-5,8,11,16,19,22-hexaoxadibenzo[a,j]cyclooctadecen-2-yl amine (126531-26-8) → N-(dibenzo-18-crown-6-ether)-2-iodo-acetamide (1180491-16-0)

Conditions	Yield
In chloroform at 20℃; for 2h;	84%

iodoacetic anhydride (54907-61-8) + c,c,t-[Pt(NH3)2Cl2(OH)(benzoate)] → cis,cis,trans-[Pt(NH3)2Cl2(CO2C6H5)(CO2CH2I)]

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 12h;	83.1%
In N,N-dimethyl-formamide at 20℃; for 12.5h; Darkness; Cooling with ice;	71.4%

N-(pepstatinyl)cystamine (80562-36-3) + iodoacetic anhydride (54907-61-8) → N-(iodoacetyl)-N'-(pepstatinyl)cystamine

Conditions	Yield
In N,N-dimethyl-formamide for 2h;	83%

iodoacetic anhydride (54907-61-8) + 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethylamine (134179-38-7) → N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-2-iodoacetamide (1594986-04-5)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	83%

iodoacetic anhydride (54907-61-8) + 1-azido-5-aminopentane (148759-41-5) → N-(5-azidopentyl)-2-iodoacetamide (1594986-08-9)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	83%

iodoacetic anhydride (54907-61-8) + N1,N1'-(((2-aminoethyl)azanediyl)bis(ethane-2,1-diyl))bis(2-hydroxy-N3-methylisophthalamide) (1364917-04-3) → N1,N1'-(((2-(2-iodoacetamido)ethyl)azanediyl)bis(ethane-2,1-diyl))bis(2-hydroxy-N3-methylisophthalamide)

Conditions	Yield
In methanol for 1h;	81%

iodoacetic anhydride (54907-61-8) + 5-amino-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid (53497-35-1) → 5-(iodoacetamido)-1,3-dioxo-1H-benzisoquinoline-2(3H)-acetic acid

Conditions	Yield
With dmap In tetrahydrofuran at 0℃; for 1h;	80%

2-[2-(2-azidoethoxy)ethoxy]ethanamine (166388-57-4) + iodoacetic anhydride (54907-61-8) → N-(2-(2-(2-azidoethoxy)ethoxy)ethyl)-2-iodoacetamide (1407523-50-5)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h; Inert atmosphere;	80%

iodoacetic anhydride (54907-61-8) + 4-[(triphenylmethyl)thio]aniline (22948-03-4) → 2-iodo-N-[4-[(triphenylmethyl)thio]phenyl]-acetamide (1003885-10-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;	79%

3-[2-(2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid (663921-15-1) + iodoacetic anhydride (54907-61-8) → 1-iodo-2-oxo-6, 9,12,15-tetraoxa-3-azaoctadecan-18-oic acid (1430410-50-6)

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	77%
In dichloromethane at 20℃; Darkness;	42%
In dichloromethane at 20℃; Darkness;	42%

iodoacetic anhydride (54907-61-8) + N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5S,6R)-5-Amino-4-hydroxy-6-methyl-2-((2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide (197655-25-7) → N-[(2R,3S,4S,5S,6S)-5-((2S,3R,4R,5S,6R)-3-Acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-hydroxy-2-methyl-6-((2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-2-iodo-acetamide (197655-29-1)

Conditions	Yield
In methanol for 24h; Ambient temperature;	71.3%

iodoacetic anhydride (54907-61-8) + 2-amino tritylthio ethane (1095-85-8) → C23H22INOS (1003884-98-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h;	70%

iodoacetic anhydride (54907-61-8) + tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (153086-78-3) → tert-butyl-N-[2-[2-[2-[(2-iodoacetyl)amino]ethoxy]ethoxy]ethyl]carbamate

Conditions	Yield
In diethyl ether at 20℃; for 1h; Inert atmosphere; Darkness;	70%
In diethyl ether at 20℃; for 1h; Inert atmosphere; Darkness;	70%

iodoacetic anhydride (54907-61-8) + dimethyl 4-aminopyridine-2,6-dicarboxylate (150730-41-9) → 4-iodoacetamidodipicolinic acid dimethylester (150730-43-1)

Conditions	Yield
sulfuric acid at 60℃; for 1h;	67%

iodoacetic anhydride (54907-61-8) + N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5S,6R)-6-Aminomethyl-4-hydroxy-5-methoxy-2-((2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide (187173-21-3) → C31H55IN2O16 (187173-25-7)

Conditions	Yield
In methanol for 24h; Ambient temperature;	62%

Upstream product

• 7719-09-7 thionyl chloride 
• 64-69-7 Iodoacetic acid 
• 38020-81-4 2-iodoacetyl chloride 

Downstream Products

• 1085399-11-6 C₂₀H₁₇IN₂O₃ 
• 111047-29-1 2-iodo-N-1,10-phenanthrolin-5-ylacetamide 
• 118020-04-5 [4-(2-iodo-acetylamino)-phenyl]-arsonic acid 
• 1341157-26-3 N-iodoacetyl-β-alanine 2-(hydroxyphenyl)diphenylphosphino ester 
• 1003885-10-6 2-iodo-N-[4-[(triphenylmethyl)thio]phenyl]-acetamide 
• 1003884-98-7 C₂₃H₂₂INOS 
• 144-48-9 iodacetamide 
• 5434-66-2 4-iodoacetylaminobenzoic acid 
• 856289-60-6 C₄₈H₅₇IN₆O₁₅^(4-)*Dy⁽³⁺⁾ 

Relevant articles and documents

A superprotein triangle driven by nickel(II) coordination: Exploiting non-natural metal ligands in protein self-assembly

(Chemical Equation Presented) We previously devised a strategy (metal-directed protein self-assembly, MDPSA) that utilizes the simultaneous stability, lability, and directionality of metal-ligand bonds to drive protein-protein interactions. Here we show that both the structural and functional scopes of MDPSA can be broadened by incorporation of non-natural metal-chelating ligands onto protein surfaces. A cytochrome cb562 variant, MBP-Phen1, which features a covalently attached phenanthroline (Phen) group on its surface, self-assembles into an unusual triangular architecture (Ni3:MBP-Phen13) upon binding Ni as a result of specific Phen-protein interactions. The crystal structure of Ni3:MBP- Phen13 reveals that the Phen group is buried in a small pocket on the protein surface, which results in an unsaturated Ni coordination environment.