5-Amino-2,4,6-triiodoisophthalic acid supplier

Name
5-Amino-2,4,6-triiodoisophthalic acid
EINECS 252-575-4
CAS No. 35453-19-1
Article Data12
CAS DataBase
Density 3.053 g/cm³
Solubility
Melting Point 265-270 °C
Formula C₈H₄I₃NO₄
Boiling Point 539.4 °C at 760 mmHg
Molecular Weight 558.838
Flash Point 280 °C
Transport Information
Appearance slightly yellow powder
Safety 26-36/37/39
Risk Codes 42/43
Molecular Structure
Hazard Symbols Xn
Synonyms 5-amino-2,4,6-triiodo-benzene-1,3-dicarboxylate;Isophthalic acid, 5-amino-2,4,6-triiodo-;5-Amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid;1,3-Benzenedicarboxylic acid, 5-amino-2,4,6-triiodo-;5-Amino-2,4,6-Triiodoisophthalic Acid(ATIPA);2,4,6-Triodo Isophthalic Acid (ATIPA);5-Amino-2,4,6-Iodoisophthalic Acid;
PSA 100.62000
LogP 3.06020

Synthetic route

: 99-31-0
5-aminoisophthalic acid

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

Conditions

Conditions	Yield
With potassium iodate; sulfuric acid; potassium iodide In water at 30 - 75℃; for 5h; pH=< 0.5; Reagent/catalyst; Temperature; pH-value;	95.3%
With sulfuric acid; iodine; iodic acid In water at 72℃; for 6.2h; pH=1; Product distribution / selectivity;	82.6%
With K(1+)*Cl2I(1-) In water at 60 - 90℃; for 25h;	75%

: 5-amino-1,3-benzenedicarboxylic acid sodium salt

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

Conditions

Conditions	Yield
With sulfuric acid; iodine; Iodine monochloride; sodium hydrogensulfite In hydrogenchloride; water
With sulfuric acid; iodine; Iodine monochloride; sodium hydrogensulfite In hydrogenchloride; water

: sodium metabisulfite

: 99-31-0
5-aminoisophthalic acid

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

Conditions

Conditions	Yield
With Iodine monochloride In water

: 618-88-2
5-nitrobenzene-1,3-dicarboxylic acid

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

Conditions

Conditions	Yield
With Iodine monochloride at 70℃; for 5h; Inert atmosphere;

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 37441-29-5
5-amino-2,4,6-triiodoisophthalic acid dichloride

Conditions

Conditions	Yield
With pyridine; thionyl chloride In 1,2-dichloro-ethane at 70 - 85℃; for 8.5h;	100%
With pyridine; thionyl chloride In 1,2-dichloro-ethane at 70 - 85℃; for 7.5 - 8h;	100%
With pyridine; thionyl chloride In 1,2-dichloro-ethane at 70 - 85℃; for 7.5 - 8h;	100%

: 186581-53-3, 908094-01-9
diazomethane

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 154921-11-6
dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate

Conditions

Conditions	Yield
In methanol; diethyl ether 1.) O deg C, 2 h, 2.) r.t., overnight;	98%

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 108-24-7
acetic anhydride

: 90947-02-7
5-acetylamino-2,4,6-triiodo-isophthalic acid

Conditions

Conditions	Yield
sulfuric acid In acetonitrile Product distribution / selectivity;	97%
sulfuric acid for 0.5h; Product distribution / selectivity;	83%

: 34557-54-5
methane

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 5-amino-2,4,6-triiodoisodecanoyl chloride

Conditions

Conditions	Yield
With hydrogenchloride; oxygen; triphenylphosphine at 100℃; for 10h; Temperature;	97%

: 116193-72-7
2-(2-propyl)-1,3-dioxane-5-carboxylic acid

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: C16H16I3NO7

Conditions

Conditions	Yield
Stage #1: 2-(2-propyl)-1,3-dioxane-5-carboxylic acid With N,N-dimethyl acetamide; bis(trichloromethyl) carbonate In dichloromethane at 0℃; for 0.5h; Stage #2: 2,4,6-triiodo-5-aminoisophthalic acid In dichloromethane at 0 - 50℃; for 16h;	95.7%

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 37091-73-9
2-chloro-1,3-dimethylimidazolinium chloride

A 5-amino-2,4,6-triodoisophthaloyl dichloride: 5-amino-2,4,6-triodoisophthaloyl dichloride

B: 37441-29-5
5-amino-2,4,6-triiodoisophthalic acid dichloride

Conditions

Conditions	Yield
In hexane; toluene	A 95% B n/a

...Expand

: 67-56-1
methanol

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 154921-11-6
dimethyl 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylate

Conditions

Conditions	Yield
With sulfuric acid for 4h; Reagent/catalyst; Reflux; Large scale;	95%

: 2051-76-5
acrylic acid anhydride

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 783279-02-7
2,4,6-triiodo-5-(prop-2-enamido)benzene-1,3-dicarboxylic acid

Conditions

Conditions	Yield
With sulfuric acid In acetonitrile at 80℃;	95%

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 677-30-5
glycinium trifluoroacetate

: 2,4,6-triiodo-5-{methyl-[2-(2,2,2-trifluoroacetyl-amino)-acetyl]-amino}isophthalic acid dichloride

Conditions

Conditions	Yield
Stage #1: glycinium trifluoroacetate With thionyl chloride In ISOPROPYLAMIDE at 0℃; for 1h; Stage #2: 2,4,6-triiodo-5-aminoisophthalic acid In ISOPROPYLAMIDE at 0 - 20℃; for 96h;	94%

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 37091-73-9
2-chloro-1,3-dimethylimidazolinium chloride

: 37441-29-5
5-amino-2,4,6-triiodoisophthalic acid dichloride

Conditions

Conditions	Yield
	93%

: 50-00-0
formaldehyd

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 40976-89-4
2,4,6-triiodo-5-(methylamino)isophthalic acid

Conditions

Conditions	Yield
With sulfuric acid at 5 - 55℃; for 3.25h;	91.6%
With sulfuric acid In methanol at 45 - 50℃; for 3h; Concentration;	83.7%
With sulfuric acid In water at 40 - 50℃; for 2h;
Stage #1: 2,4,6-triiodo-5-aminoisophthalic acid With sulfuric acid at 50℃; Stage #2: formaldehyd at 40 - 50℃; for 2h;

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 36394-75-9
(S)-2-acetoxypropanoyl chloride

: (S)-5-(2-acetoxypropanamido)-2,4,6-triiodoisophthalic acid

Conditions

Conditions	Yield
In ISOPROPYLAMIDE at 20 - 50℃; for 22h;	81%
In N,N-dimethyl acetamide at 20 - 50℃; for 22h; Time; Temperature;	81%

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 5-amino-2,4-diiodo-1,3-phthalic acid

Conditions

Conditions	Yield
With sodium tetrahydroborate; palladium 10% on activated carbon; sodium hydroxide In water at 1 - 25℃; for 5h; Reagent/catalyst;	81%

: 52550-63-7
1,4-bis(2-methyl-1H-imidazol-1-yl)butane

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 6147-53-1
cobalt(II) diacetate tetrahydrate

: [Co(1,4-bis(2-methyl-imidazol-1-yl)butane)(5-amino-2,4,6-triiodoisophthalate)]

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide at 80℃; for 72h; Autoclave;	80.56%

...Expand

: 52550-63-7
1,4-bis(2-methyl-1H-imidazol-1-yl)butane

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 6147-53-1
cobalt(II) diacetate tetrahydrate

: [Co(1,4-bis(2-methyl-imidazol-1-yl)butane)(5-aminoisophthalate)]

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide at 150℃; for 72h; Autoclave;	79.6%

...Expand

: zinc(II) nitrate hexahydrate

: 17252-51-6
1,3-di(4-pyridyl)propane

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 7732-18-5
water

: [Zn8(5-amino-2,4,6-triiodoisophthalate)8(1,3-di(4-pyridyl)propane)8]*4H2O

Conditions

Conditions	Yield
In ethanol; water; N,N-dimethyl-formamide Zn compd. (0.0277 mmol), H2atip (0.0179 mmol), dpp (0.05 mmol) in DMF/EtOH/H2O=5/2/1, mixt. stirred at room temp. for 10 min; filtered, crystd. on storage for 3 d at 90°C, elem. anal.;	75%

...Expand

: 4422-95-1
1,3,5-benzene tris(carbonyl chloride)

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: C33H12I9N3O15

Conditions

Conditions	Yield
With dmap In N,N-dimethyl acetamide at 25℃; for 12h; Inert atmosphere;	71%

: 52550-63-7
1,4-bis(2-methyl-1H-imidazol-1-yl)butane

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 6147-53-1
cobalt(II) diacetate tetrahydrate

: [Co(1,4-bis(2-methyl-imidazol-1-yl)butane)(5-amino-2,4,6-triiodoisophthalate)]·2H2O

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide at 130℃; for 72h; Autoclave;	70.21%

...Expand

: 52550-63-7
1,4-bis(2-methyl-1H-imidazol-1-yl)butane

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 7732-18-5
water

: 5970-45-6
zinc(II) acetate dihydrate

: {[Zn(1,4-bis(2-methyl-imidazol-1-yl)butane)(5-amino-2,4,6-triiodoisophthalate)]·2water}n

Conditions

Conditions	Yield
In ethanol at 150℃; for 36h; High pressure;	70.2%

...Expand

: 1004-38-2
2,4,6-triaminopyrimidine

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: C4H7N5*C8H4I3NO4

Conditions

Conditions	Yield
In ethanol; water for 0.5h;	70%

: 69506-86-1
1,1'-(1,4-butanediyl)bis(imidazole)

: aqueous cadmium chloride

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: C8H2I3NO4(2-)*Cd(2+)*C10H14N4

Conditions

Conditions	Yield
Stage #1: 2,4,6-triiodo-5-aminoisophthalic acid With sodium hydroxide In water at 20℃; Stage #2: 1,1'-(1,4-butanediyl)bis(imidazole); aqueous cadmium chloride In water at 20℃;	70%

...Expand

: 492-98-8
2,2'-biimidazole

: aqueous cadmium chloride

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: C8H2I3NO4(2-)*Cd(2+)*2H2O*C6H6N4

Conditions

Conditions	Yield
Stage #1: 2,4,6-triiodo-5-aminoisophthalic acid With sodium hydroxide In water at 20℃; Stage #2: 2,2'-biimidazole; aqueous cadmium chloride In methanol; water at 20℃;	68%

...Expand

: 366-18-7
[2,2]bipyridinyl

: aqueous cadmium chloride

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: [Cd(5-amino-2,4,6-triiodoisophthalato)(2,2'-bipyridine)(H2O)]*3H2O

Conditions

Conditions	Yield
With NaOH In water addn. of aq. soln. of CdCl2*2.5H2O to mixt. of 5-amino-2,4,6-triiodoisophthalic acid in H2O and NaOH whilst stirring at molar ratio NH2C6I3(COOH)2:NaOH=1:2, addn. of soln. of 2,2'-bipy in water; crystn., filtration; elem. anal.;	67%

...Expand

: 553-26-4
4,4'-bipyridine

: zinc(II) nitrate hexahydrate

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 7732-18-5
water

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: [Zn2(5-amino-2,4,6-triiodoisophthalate)2(4,4'-bipyridine)2]*2DMF*3H2O

Conditions

Conditions	Yield
In ethanol; water; N,N-dimethyl-formamide Zn compd. (0.0277 mmol), H2atip (0.0179 mmol), 4,4'-bpy (0.064 mmol) in DMF/EtOH/H2O=5/2/1, mixt. stirred at room temp. for 10 min; filtered, crystd. on storage for 1 wk at room temp., elem. anal.;	65%

...Expand

: 855766-92-6
4,4'-bis-(1H-imidazol-1-yl)biphenyl

: cobalt(II) nitrate hexahydrate

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: Co(2+)*C18H14N4*2C8H3I3NO4(1-)*2H2O

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water; N,N-dimethyl-formamide at 134.84℃; for 72h; pH=6; Autoclave;	63%

...Expand

: 492-98-8
2,2'-biimidazole

: zinc(II) nitrate hexahydrate

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: C8H2I3NO4(2-)*Zn(2+)*C6H6N4*3H2O

Conditions

Conditions	Yield
Stage #1: 2,4,6-triiodo-5-aminoisophthalic acid With sodium hydroxide In water at 20℃; Stage #2: 2,2'-biimidazole; zinc(II) nitrate hexahydrate In methanol; water at 20℃;	62%

...Expand

: aqueous cadmium chloride

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: 7732-18-5
water

: 345952-55-8
1,4-bis(1,2,4-triazol-1-yl)butane

: [Cd(5-amino-2,4,6-triiodo-2,4,6-triiodoisophthalate)(1,4-bis(1,2,4-triazsol-1-yl)butane)(H2O)2]*3H2O

Conditions

Conditions	Yield
With NaOH In water NaOH and isophthalic acid deriv. dissolved in water, then aq. CdCl2*2.5H2O added while stirring, bis(triazolyl)butane in water added; filtered; elem. anal.;	61%

...Expand

: 67-56-1
methanol

: 366-18-7
[2,2]bipyridinyl

: copper(II) nitrate trihydrate

: 35453-19-1
2,4,6-triiodo-5-aminoisophthalic acid

: [Cu(5-amino-2,4,6-triiodoisophthalato)(2,2'-bipyridine)]*3H2O*CH3OH

Conditions

Conditions	Yield
With NaOH In methanol; water addn. of aq. soln. of Cu(NO3)2*3H2O to mixt. of 5-amino-2,4,6-triiodoisophthalic acid in H2O and NaOH whilst stirring at molar ratio NH2C6I3(COOH)2:NaOH=1:2, addn. of soln. of 2,2'-bipy in MeOH; crystn., filtration; elem. anal.;	61%

...Expand

5-Amino-2,4,6-triiodoisophthalic acid Specification

The IUPAC name of 5-Amino-2,4,6-triiodoisophthalic acid is 5-amino-2,4,6-triiodobenzene-1,3-dicarboxylic acid. With the CAS registry number 35453-19-1, it is also named as 1,3-Benzenedicarboxylic acid, 5-amino-2,4,6-triiodo-. The product's categories are Organic Acids; (Intermediate of Iohexol); Aromatic Amino Acids; Peptide Synthesis; Unnatural Amino Acid Derivatives. Besides, it is slightly yellow powder, which should be stored in sealed, cool and dry place. In addition, its molecular formula is C₈H₄I₃NO₄ and molecular weight is 558.84.

The other characteristics of this product can be summarized as: (1)EINECS: 252-575-4; (2)ACD/LogP: 0.60; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): -3.55; (5)ACD/LogD (pH 7.4): -3.55; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 1; (9)ACD/KOC (pH 7.4): 1; (10)#H bond acceptors: 5; (11)#H bond donors: 4; (12)#Freely Rotating Bonds: 3; (13)Index of Refraction: 1.869; (14)Molar Refractivity: 83.06 cm³; (15)Molar Volume: 182.9 cm³; (16)Surface Tension: 103.8 dyne/cm; (17)Density: 3.053 g/cm³; (18)Flash Point: 280 °C; (19)Melting point: 265-270 °C; (20)Enthalpy of Vaporization: 85.96 kJ/mol; (21)Boiling Point: 539.4 °C at 760 mmHg; (22)Vapour Pressure: 1.83E-12 mmHg at 25 °C.

Preparation of 5-Amino-2,4,6-triiodoisophthalic acid: this chemical can be prepared by 5-Amino-isophthalic acid.

This reaction needs aq. potassium iododichloride and H₂O at temperature of 55-60 °C. The reaction time is 18 hours. The yield is 74 %.

Uses of 5-Amino-2,4,6-triiodoisophthalic acid: it can react with Diazomethane to get 5-Amino-2,4,6-triiodo-isophthalic acid dimethyl ester.

This reaction needs Methanol and Diethyl ether at temperature of 0 °C for 2 hours. The yield is 98 %.

When you are using this chemical, please be cautious about it as the following: it may cause sensitization by inhalation and skin contact. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
(1)SMILES: Ic1c(C(=O)O)c(I)c(c(I)c1N)C(=O)O
(2)InChI: InChI=1/C8H4I3NO4/c9-3-1(7(13)14)4(10)6(12)5(11)2(3)8(15)16/h12H2,(H,13,14)(H,15,16)
(3)InChIKey: JEZJSNULLBSYHV-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C8H4I3NO4/c9-3-1(7(13)14)4(10)6(12)5(11)2(3)8(15)16/h12H2,(H,13,14)(H,15,16)
(5)Std. InChIKey: JEZJSNULLBSYHV-UHFFFAOYSA-N

Product Name

5-Amino-2,4,6-triiodoisophthalic acid

Synthetic route

5-Amino-2,4,6-triiodoisophthalic acid Specification

Related Products

Hot Products