N,N'-Bis(1,3-dihydroxy-2-propanyl)-2,4,6-triiodo-5-(lactoylamino)isophthalamide

Basic Information

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CAS Number

60166-93-0

Molecular Formula

C17H22I3N3O8

Molecular Weight

777.09 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Agricultural Chemicals Pesticides Herbicides

Basic Physical Properties

Melting Point

>3200C (dec)

Boiling Point

785.3°C at 760 mmHg

Density

2.0203 (estimate)

Specific Rotation

D20 -2.01° (c = 10 in water)

SMILES

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CC(C(=O)NC1=C(C(=C(C(=C1I)C(=O)NC(CO)CO)I)C(=O)NC(CO)CO)I)O

InChI

InChI=1S/C17H22I3N3O8/c1-6(28)15(29)23-14-12(19)9(16(30)21-7(2-24)3-25)11(18)10(13(14)20)17(31)22-8(4-26)5-27/h6-8,24-28H,2-5H2,1H3,(H,21,30)(H,22,31)(H,23,29)

InChIKey

XQZXYNRDCRIARQ-UHFFFAOYSA-N

LogP

-1.0143000000000004

pKa

pKa (25°) 10.70

Topological Polar Surface Area

188.45 Å²

Hydrogen Bond Donor/Acceptor

8 / 11

Complexity

583

Safety Information

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Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Toxicity

LD50 in mice, rats, rabbits, dogs (g/kg): 44.5, 28.2, 19.6, 34.7 i.v. (Felder); LD50 in mice (mg iodine/kg body wt): 21,800 i.v.; 20,000 i.p.; 1500 intracerebral (Felder, Pitre).

Synonyms & References

English

IOPAMIDOL [WHO-DD]
Iopamidol-200
SQ-13396
N,N'-bis(1,3-dihydroxypropan-2-yl)-5-(((2S)-2-hydroxypropanoyl)amino)-2,4,6-triiodobenzene-1,3-dicarboxamide
UNII-JR13W81H44
AKOS015891034
iomapidol
Isovue-250
B 15000
Iopamiron 370
Iopamiron
IOPAMIDOL [JAN]
Jopamidol
Isovue-300
(S)-N,N'-Bis(2-hydroxy-1-(hydroxymethyl)ethyl)-5-((2-hydroxy-1-oxopropyl)amino)-2,4,6-triiodoisophthaldiamide
Iopamiron 300
Prestwick0_000871
EN300-19767815
Iopamiron (TN)
HMS3714P03
L-(+)-N,N'-Bis(2-hydroxy-1-hydroxymethylethyl)-2,4,6-triiodo-5-lactamide isophthalamide
(S)-N,N inverted exclamation marka-Bis[2-hydroxy-1-(hydroxymethyl)ethyl]-2,4,6-triiodo-5-lactamidoisophthalamide
HMS2097P03
B-15000;SQ-13396
CCG-213024
N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-5-{[(2S)-2-hydroxypropanoyl]amino}-2,4,6-triiodobenzene-1,3-dicarboxamide
DTXCID203158
MFCD00867931
IOPAMIDOL [EP MONOGRAPH]
Tox21_110668
H11976

MDL Number

MFCD00867931

Customs Code

2924299090

FAQ

What are the physical and chemical properties of N,N'-Bis(1,3-dihydroxy-2-propanyl)-2,4,6-triiodo-5-(lactoylamino)isophthalamide (CAS: 60166-93-0)?

N,N'-Bis(1,3-dihydroxy-2-propanyl)-2,4,6-triiodo-5-(lactoylamino)isophthalamide is a crystalline compound with a high molecular weight due to its triiodinated structure. It has poor water solubility but good solubility in organic solvents. The compound is known for its high reactivity, particularly towards nucleophiles, and exhibits significant chemical stability in neutral to slightly acidic conditions. It crystallizes in the monoclinic system and is highly insoluble in water. This compound is also known for its low volatility and good thermal stability.

How is N,N'-Bis(1,3-dihydroxy-2-propanyl)-2,4,6-triiodo-5-(lactoylamino)isophthalamide (CAS: 60166-93-0) typically synthesized?

N,N'-Bis(1,3-dihydroxy-2-propanyl)-2,4,6-triiodo-5-(lactoylamino)isophthalamide is synthesized through a multi-step process involving the iodination of 2,4,6-triiodo-5-carboxylic acid and subsequent amidation with 1,3-dihydroxy-2-propanol and lactoyl chloride. The reaction typically requires the use of a Lewis acid catalyst, such as aluminum chloride, to facilitate the amidation step. The final product is isolated through recrystallization from an appropriate solvent, ensuring a high yield of the desired compound.

What industries use N,N'-Bis(1,3-dihydroxy-2-propanyl)-2,4,6-triiodo-5-(lactoylamino)isophthalamide (CAS: 60166-93-0)?

N,N'-Bis(1,3-dihydroxy-2-propanyl)-2,4,6-triiodo-5-(lactoylamino)isophthalamide is primarily used in the pharmaceutical industry for its potential therapeutic applications, although specific uses are limited due to its high reactivity. It is also explored in research settings for its unique chemical properties, such as its ability to form stable complexes with metal ions, making it valuable in sensor and semiconductor applications. Further, its triiodinated structure suggests potential uses in materials science for special optical and electronic properties.

What precautions should be taken when handling N,N'-Bis(1,3-dihydroxy-2-propanyl)-2,4,6-triiodo-5-(lactoylamino)isophthalamide (CAS: 60166-93-0)?

When handling N,N'-Bis(1,3-dihydroxy-2-propanyl)-2,4,6-triiodo-5-(lactoylamino)isophthalamide (CAS: 60166-93-0), it is essential to wear appropriate personal protective equipment, including gloves, goggles, and a lab coat. The compound is corrosive and can cause skin and eye irritation. Work should always be conducted in a fume hood to minimize exposure. Spills should be cleaned up immediately using appropriate absorbent materials, followed by thorough cleanup and disposal according to local regulations. Always refer to the safety data sheet (SDS) for detailed handling instructions and emergency procedures.