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

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

Uses

Used in Chemical Synthesis:
IODOACETIC ANHYDRIDE is used as a reactant for the synthesis of N-iodoacetyl glycosylamine derivatives and converting amino precursors to IA derivatives. It plays a crucial role in the development of reagents used for differential protein quantitation via ion scanning.
Used in Pharmaceutical Industry:
IODOACETIC ANHYDRIDE is used as a linker for linking lysine residues to N-terminal α-amino groups of peptides. This application is significant in the development of new drugs and therapeutic agents.
Used in Biochemical Research:
IODOACETIC ANHYDRIDE is used for capping amines and yielding a thiol reactive iodo-derivative. This property makes it a valuable tool in biochemical research, particularly in the study of protein structure and function.
Used in Protein Modification:
IODOACETIC ANHYDRIDE is employed in the process of iodoacetylation, which involves the modification of proteins by introducing an iodoacetyl group. This modification can be used to study protein interactions, stability, and function.

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

• 111047-29-1 2-iodo-N-1,10-phenanthrolin-5-ylacetamide 
• 1003884-98-7 C₂₃H₂₂INOS 
• 1003885-10-6 2-iodo-N-[4-[(triphenylmethyl)thio]phenyl]-acetamide 
• 1341157-26-3 N-iodoacetyl-β-alanine 2-(hydroxyphenyl)diphenylphosphino ester 
• 1085399-11-6 C₂₀H₁₇IN₂O₃ 
• 144-48-9 iodacetamide 

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.

Synthesis and Characterisation of a New DNA-binding Bifunctional Ruthenium(II) Complex

A new DNA-binding molecule, Ru(tap)2POQ(2+), in which a polypyridylruthenium(II) complex is linked to an aminochloroquinoline by a flexible chain, has been prepared and characterised (tap = 1,4,5,8-tetraazaphenanthrene and POQ corresponds to a 1,10-phenanthroline linked to an aminochloroquinoline by an aliphatic chain).This complex is regarded as bifunctional because it contains two moieties of different binding modes and photoreactivities vs.DNA.The (1)H NMR data of this compound indicate the presence of an equilibrium between two molecular species.The spectroscopic properties of Ru(tap)2POQ(2+) in absorption and luminescence are examined and compared with those of the corresponding ruthenium(II) complex which does not contain the aminochloroquinoline moiety: Ru(tap)2phen(2+).Luminescence relative quantum yields and lifetimes show that the MLCT excited-state behaviour is influenced by the presence of the linked quinoline.An intramolecular photoinduced electron transfer in one of the two species in equilibrium, is considered to be responsible for a quenching of the ruthenium(II) complex luminescence.Preliminary results on the binding characteristics of Ru(tap)2POQ(2+) to DNA and )>2 from luminescence and thermal denaturation studies are reported.The intramolecular quenching of luminescence in Ru(tap)2POQ(2+) is inhibited when it interacts with nucleic acids.Consequently, the resulting emission is more substantially enhanced in the presence of the polynucleotide relative to the luminescence increase observed with the reference complex, Ru(tap)2phen(2+).