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66108-95-0

Basic Information
CAS No.: 66108-95-0
Name: Iohexol
Article Data: 32
Molecular Structure:
Molecular Structure of 66108-95-0 (Iohexol)
Formula: C19H26I3N3O9
Molecular Weight: 821.144
Synonyms: Omnipaque R;1,3-Benzenedicarboxamide,5-[acetyl(2,3-dihydroxypropyl)amino]-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-(9CI);5-(N-2,3-Dihydroxypropylacetamido)-2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)isophthalamide.;Accudenz;Exypaque;Histodenz;Nycodenz;Omnipaque;Omnipaque 140;Omnipaque 240;Omnipaque 300;Omnipaque 350;
EINECS: 266-164-2
Density: 2.2 g/cm3
Melting Point: 254-256 °C
Boiling Point: 891.5 °C at 760 mmHg
Flash Point: 493 °C
Appearance: White solid
Safety: 22-24/25
PSA: 199.89000
LogP: -0.84570
Synthetic route
31127-80-7

N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide

106-89-8

epichlorohydrin

A

66108-95-0

iohexol

B

92339-11-2

iodixanol

Conditions
ConditionsYield
With hydrogenchloride; boric acid; potassium hydroxide In water pH=10 - 11; Product distribution / selectivity; Industry scale;A 7.5%
B 86.3%
Stage #1: N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide With sodium hydroxide In methanol at 45℃;
Stage #2: epichlorohydrin With hydrogenchloride In methanol at 20℃; for 48h; Product distribution / selectivity;
A 7.42%
B 52.1%
With hydrogenchloride; sodium hydroxide In water at 20℃; for 48h; pH=12.2 - 12.7;A 5.1%
B 43.5%
96-24-2

3-monochloro-1,2-propanediol

66108-95-0

iohexol

Conditions
ConditionsYield
Stage #1: N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide With sodium hydroxide In 2-(2-methoxyethoxy)ethyl alcohol; water at 44 - 60℃;
Stage #2: 3-monochloro-1,2-propanediol In 2-(2-methoxyethoxy)ethyl alcohol; water at 29 - 31℃; for 21h;
Stage #3: With hydrogenchloride In 2-(2-methoxyethoxy)ethyl alcohol; water pH=4 - 5; Product distribution / selectivity;
Stage #1: N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide With sodium hydroxide In 2-(2-methoxyethoxy)ethyl alcohol; water at 44 - 60℃;
Stage #2: 3-monochloro-1,2-propanediol In 2-(2-methoxyethoxy)ethyl alcohol; water at 29 - 31℃; for 21h;
Stage #3: With acetic acid In 2-(2-methoxyethoxy)ethyl alcohol; water Product distribution / selectivity;
31127-80-7

N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide

96-24-2

3-monochloro-1,2-propanediol

71-36-3

butan-1-ol

66108-95-0

iohexol

Conditions
ConditionsYield
With sodium hydroxide; Ca(OH)2 In water
With sodium hydroxide; Ca(OH)2 In water
31127-80-7

N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide

66108-95-0

iohexol

31127-80-7

N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide

556-52-5

oxiranyl-methanol

66108-95-0

iohexol

Conditions
ConditionsYield
With potassium hydroxide In methanol; dimethyl sulfoxide; isopropyl alcohol
Stage #1: N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide With boric acid; potassium hydroxide In water at 10℃; for 48h; pH=12.4;
Stage #2: oxiranyl-methanol In water at 10℃; for 24h; pH=12.6-13; Time; pH-value;
31127-80-7

N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide

96-24-2

3-monochloro-1,2-propanediol

66108-95-0

iohexol

Conditions
ConditionsYield
With sodium methylate In propylene glycol
Stage #1: N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide With sodium hydroxide In methanol; 1-methoxy-2-propanol at 25 - 45℃;
Stage #2: 3-monochloro-1,2-propanediol In methanol; 1-methoxy-2-propanol at 25℃; for 25.5h; Product distribution / selectivity;
Stage #1: N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide With sodium hydroxide In 1-methoxy-2-propanol; water at 25 - 45℃;
Stage #2: 3-monochloro-1,2-propanediol In 1-methoxy-2-propanol; water at 35℃; for 27h; Product distribution / selectivity;
31127-80-7

N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide

A

66108-95-0

iohexol

B

92339-11-2

iodixanol

Conditions
ConditionsYield
Stage #1: N,N'-bis(2,3-dihydroxypropyl)-5-acetamido-2,4,6-triiodoisophthalamide With sodium hydroxide In methanol at 45℃;
Stage #2: With hydrogenchloride In methanol; water at 15℃; for 48h; Product distribution / selectivity;
76801-93-9

5-amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide

66108-95-0

iohexol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / water / 26 h / 65 - 70 °C / Green chemistry
2: sodium methylate / methanol / 40 °C / Green chemistry
3: methanol / 72 h / 20 °C / Green chemistry
View Scheme
Multi-step reaction with 3 steps
1.1: 65 - 70 °C / Green chemistry
2.1: hydrogenchloride / methanol / 3 h / Green chemistry
3.1: sodium methylate / methanol / 40 °C / Green chemistry
3.2: 72 h / 20 °C / Green chemistry
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / water / 50 - 100 °C
2: sodium hydroxide; water / 20 °C / pH 9 - 11
3: sodium hydroxide / 1,2-dimethoxyethane / 30 - 100 °C
View Scheme
76820-35-4

5-Amino-N,N'-bis[2,3-dihydroxypropyl]-1,3-benzenedicarboxamide

66108-95-0

iohexol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Iodine monochloride / 6 h / 50 °C
2: sulfuric acid / water / 50 - 100 °C
3: sodium hydroxide; water / 20 °C / pH 9 - 11
4: sodium hydroxide / 1,2-dimethoxyethane / 30 - 100 °C
View Scheme
76820-34-3

5-nitro-N,N'-bis-(2,3-dihydroxypropyl)isophthalamide

66108-95-0

iohexol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 5%-palladium/activated carbon; hydrogen / 70 °C / 9000.9 Torr / Autoclave
2: Iodine monochloride / 6 h / 50 °C
3: sulfuric acid / water / 50 - 100 °C
4: sodium hydroxide; water / 20 °C / pH 9 - 11
5: sodium hydroxide / 1,2-dimethoxyethane / 30 - 100 °C
View Scheme
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31127-80-7
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    Product name: Iohexol CAS No.:66108-95-0 Molecule Formula:C19H26I3N3O9 Molecule Weight:821.14 Purity: 99.0% Package: 25kg/drum Description:White or off-white crystalline powder Manufacture Standards:Enterprise Standard TESTING IT

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Specification

1. Introduction of Iohexol
Iohexol is a white powder or white Solid, used as imaging agent. The IUPAC Name of this chemical is 5-[acetyl(2,3-dihydroxypropyl)amino]-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide. Besides, Iohexol belongs to Miscellaneous;Aromatics;Labeling and Diagnostics Reagents;API's. In addition, Iohexol Classification Code is Contrast media; Diagnostic aid [radiopaque medium]; Drug / Therapeutic Agent; Human Data. Its water solubility is 7.96e-01 g/l.

2. Properties of Iohexol
Physical properties about Iohexol are:
(1)H bond acceptors: 12; (2)H bond donors: 8; (3)Freely Rotating Bonds: 18; (4)Polar Surface Area: 116.31Å2; (5)Index of Refraction: 1.724; (6)Molar Refractivity: 148.07 cm3; (7)Molar Volume: 373.1 cm3; (8)Surface Tension: 86.6 dyne/cm; (9)Density: 2.2 g/cm3; (10)Flash Point: 493 °C; (11)Enthalpy of Vaporization: 135.76 kJ/mol; (12)Boiling Point: 891.5 °C at 760 mmHg; (13)Vapour Pressure: 3.95E-34 mmHg at 25°C; (14)Melting point: 254-256°C; (15)Appearance: white powder; (16)Solubility in water Freely soluble.

3. Structure Descriptors of Iohexol
(1)InChI: InChI=1/C19H26I3N3O9/c1-8(29)25(4-11(32)7-28)17-15(21)12(18(33)23-2-9(30)5-26)14(20)13(16(17)22)19(34)24-3-10(31)6-27/h9-11,26-28,30-32H,2-7H2,1H3,(H,23,33)(H,24,34)
(2)Smiles: c1(N(C[C@@H](CO)O)C(C)=O)c(c(c(I)c(c1I)C(NC[C@@H](CO)O)=O)C(NC[C@@H](CO)O)=O)I
(3)InChIKey: InChIKey=NTHXOOBQLCIOLC-UHFFFAOYSA-N

4. Toxicity of Iohexol

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 20gm/kg (20000mg/kg)   Drugs in Japan Vol. -, Pg. 105, 1990.
mouse LD50 intraperitoneal 4300mg/kg (4300mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 1030, 1987.
mouse LD50 intravenous 50gm/kg (50000mg/kg)   Acta Radiologica, Supplementum. Vol. 362, Pg. 73, 1980.
mouse LD50 oral > 20gm/kg (20000mg/kg)   Drugs in Japan Vol. -, Pg. 105, 1990.
rat LD50 intraperitoneal > 2200mg/kg (2200mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 1030, 1987.
rat LD50 intravenous 25235mg/kg (25235mg/kg)   Acta Radiologica, Supplementum. Vol. 370, Pg. 41, 1987.
rat LD50 oral > 20gm/kg (20000mg/kg)   Drugs in Japan Vol. -, Pg. 105, 1990.
women TDLo intravenous 1400mg/kg (1400mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Annals of Internal Medicine. Vol. 107, Pg. 116, 1987.

5. Safety information of Iohexol
Safety Statements: 22-24/25
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: CZ2205000

6. Uses of Iohexol
Iohexol is a imaging agent. Iohexol is used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures. Its low systemic toxicity is the combined result of low chemotoxicity and low osmolality. Besides, iohexol is also considered a low-osmolality contrast agent.