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Basic Information

Molecular Structure:
CAS No.:	73334-07-3
Name:	Iopromide
Article Data:	15

Formula:	C₁₈H₂₄I₃N₃O₈
Molecular Weight:	791.117
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;
EINECS:	277-385-9
Density:	2.173 g/cm³
Melting Point:	broad (160oC transition)
Boiling Point:	840.9 °C at 760 mmHg
Flash Point:	462.4 °C
Appearance:	off-white to white powder
Hazard Symbols:	N
Risk Codes:	50/53
Safety:	60-61
PSA:	168.66000
LogP:	0.05740

Synthetic route

: C26H32I3N3O12

: 73334-07-3
iopromide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium carbonate In N,N-dimethyl acetamide at 20℃; for 2h;	92%

: 1009809-16-8
C18H27N3O8

: 73334-07-3
iopromide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: C30H40I3N3O16

: 73334-07-3
iopromide

Conditions

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

Total:147 Page 1 of 4 1 2 3 4 Next>>

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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 C₁₈H₂₄I₃N₃O₈and 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)	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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