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Iopromide

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Name

Iopromide

EINECS 277-385-9
CAS No. 73334-07-3 Density 2.173 g/cm3
PSA 168.66000 LogP 0.05740
Solubility N/A Melting Point broad (160oC transition)
Formula C18H24I3N3O8 Boiling Point 840.9 °C at 760 mmHg
Molecular Weight 791.117 Flash Point 462.4 °C
Transport Information N/A Appearance off-white to white powder
Safety 60-61 Risk Codes 50/53
Molecular Structure Molecular Structure of 73334-07-3 (Iopromide) Hazard Symbols N
Synonyms

1,3-Benzenedicarboxamide,N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(methoxyacetyl)amino]-N-methyl-(9CI);Iopromidum;SHL 414C;Ultravist;Ultravist 300;Ultravist 370;ZK 35760;1,3-Benzenedicarboxamide,N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]-N1-methyl-;N,N'-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(methoxyacetyl)amino]-N-methylisophthalamide;

Article Data 15

Iopromide Synthetic route

C26H32I3N3O12

73334-07-3

iopromide

Conditions
ConditionsYield
With sodium methylate In methanol at 75℃; for 8h;100%
Stage #1: C26H32I3N3O12 With sodium hydroxide at 50℃; for 4h;
Stage #2: With hydrogenchloride pH=2-3;
99%
40137-22-2

3-methylamino-propane-1,2-diol

3-[(2,3-dihydroxypropylaminoformyl)]-2,4,6-triiodo-5-[(methoxyacetyl)amino]benzoic acid methyl ester

73334-07-3

iopromide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine Large scale;95%
616-30-8, 13552-31-3

3-Amino-1,2-propanediol

5-[(2-methoxy)acetamido]-3-(2,3-dihydroxy-N-propyl(methyl)carbamoyl)-2,4,6-triiodobenzoyl chloride

73334-07-3

iopromide

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl acetamide at 20℃; for 2h;92%
1009809-16-8

C18H27N3O8

73334-07-3

iopromide

Conditions
ConditionsYield
In water at 70 - 90℃; for 6h;88.1%
With Iodine monochloride In water at 70 - 85℃; for 3h; Temperature; Concentration;82.3 g

C25H30I3N3O13

73334-07-3

iopromide

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 5h;86%
1193076-40-2

5-methoxyacetylamino-2,4,6-triiodoisophthalic acid [(2,3-dihydroxy-N-methylpropyl)-(2,3-diacetoxypropyl)]diamide

73334-07-3

iopromide

Conditions
ConditionsYield
With water; sodium hydroxide In N,N-dimethyl acetamide at 20 - 25℃; for 10h;85%
With water; sodium hydroxide at 20 - 25℃; for 10h; Industry scale;

5-methoxyacetamido-N-methyl-N,N'-diallyl-2,4,6-triiodoisophthalamide

73334-07-3

iopromide

Conditions
ConditionsYield
With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide In acetone at 20℃; for 13h;85%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 12h;55.8 g

5-methoxyacetamido-2,4,6-triiodoisophthalic acid {[(2-oxo-1,3-dioxolan-4-yl)methyl]-(2,3-dihydroxy-N-methylpropyl)}diamide

73334-07-3

iopromide

Conditions
ConditionsYield
With water; sodium hydroxide at 50℃; for 0.5h;85%
With sodium hydroxide In water at 20 - 50℃; for 0.5h;85%

2,4,6-triiodo-5-(2-methoxyacetamido)-N1-methyl-N1,N3-bis-((2-oxo-1,3-dioxolane-4-yl)methyl)isophthalamide

73334-07-3

iopromide

Conditions
ConditionsYield
With sodium hydroxide at 20℃; for 3h;80%

C30H40I3N3O16

73334-07-3

iopromide

Conditions
ConditionsYield
With sodium hydroxide at 0 - 50℃;80%

Iopromide Specification

The Iopromide, with the CAS registry number 73334-07-3, is also known as 1,3-Benzenedicarboxamide,N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]-N1-methyl-. It belongs to the product categories of Amines; Aromatics; Diagnostic; Intermediates & Fine Chemicals; Pharmaceuticals; Isotope Labelled Compounds. Its EINECS number is 277-385-9. This chemical's molecular formula is C18H24I3N3O8 and molecular weight is 791.11. What's more, its systematic name is N,N'-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(methoxyacetyl)amino]-N-methylisophthalamide. Its classification codes are: (1)Contrast Media; (2)Diagnostic aid [radiopaque medium]; (3)Drug / Therapeutic Agent. It is a kind of labelled Iopromide and is nonionic, injectable radio-contrast medium. 

Physical properties of Iopromide are: (1)ACD/LogP: -2.658; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -2.66; (4)ACD/LogD (pH 7.4): -2.66; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 11; (10)#H bond donors: 6; (11)#Freely Rotating Bonds: 15; (12)Polar Surface Area: 168.66 Å2; (13)Index of Refraction: 1.71; (14)Molar Refractivity: 142.217 cm3; (15)Molar Volume: 364.044 cm3; (16)Polarizability: 56.379×10-24cm3; (17)Surface Tension: 78.01 dyne/cm; (18)Density: 2.173 g/cm3; (19)Flash Point: 462.376 °C; (20)Enthalpy of Vaporization: 128.074 kJ/mol; (21)Boiling Point: 840.927 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Ic1c(c(I)c(c(I)c1NC(=O)COC)C(=O)NCC(O)CO)C(=O)N(CC(O)CO)C
(2)Std. InChI: InChI=1S/C18H24I3N3O8/c1-24(4-9(28)6-26)18(31)12-13(19)11(17(30)22-3-8(27)5-25)14(20)16(15(12)21)23-10(29)7-32-2/h8-9,25-28H,3-7H2,1-2H3,(H,22,30)(H,23,29)
(3)Std. InChIKey: DGAIEPBNLOQYER-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 21gm/kg (21000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 44, Pg. 1275, 1994.
mouse LD50 intravenous 34gm/kg (34000mg/kg)   AJNR, American Journal of Neuroradiology. Vol. 4, Pg. 350, 1983.
rat LD50 intravenous 21403mg/kg (21403mg/kg)   Acta Radiologica, Supplementum. Vol. 370, Pg. 41, 1987.

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