2,6-DIIODO-4-NITROPHENOL supplier

Name
2,6-Diiodo-4-nitrophenol
EINECS 206-170-4
CAS No. 305-85-1
Article Data39
CAS DataBase
Density 2.717 g/cm³
Solubility very sparingly soluble in water
Melting Point 152-154 °C(lit.)
Formula C₆H₃I₂NO₃
Boiling Point 310.6 °C at 760 mmHg
Molecular Weight 390.904
Flash Point 141.6 °C
Transport Information UN 2811 6.1/PG 3
Appearance yellow crystalline solid
Safety 26-28-36/37/39-45-28A
Risk Codes 20/21/22-36/37/38-25
Molecular Structure
Hazard Symbols Xn, T
Synonyms 4-Nitro-2,6-diiodophenol;Ancylol;Disofen;Disophenol;Iodofen;Iodophen;Syngamix;
PSA 66.05000
LogP 3.03280

Synthetic route

: 100-02-7
4-nitro-phenol

: 305-85-1
2,6-diiodo-4-nitrophenol

Conditions

Conditions	Yield
With hydrogenchloride; potassium iodate; potassium iodide In methanol; water at 20℃;	99%
With sodium periodate; sulfuric acid; iodine; potassium iodide; sodium sulfite In water; acetic acid at 25℃; for 4h;	98%
With N-iodo-S-methyl-S-phenyl sulfoximine; acetic acid at 22℃; for 3h; Sealed tube;	98%

: 100-02-7
4-nitro-phenol

A: 305-85-1
2,6-diiodo-4-nitrophenol

B: 89487-91-2
2-iodo-4-nitrophenol

Conditions

Conditions	Yield
With iodine; silver sulfate In ethanol at 20℃; for 0.5h;	A 22% B 50%
With sulfuric acid; dihydrogen peroxide; potassium iodide In methanol at 60℃; for 2h;	A 18% B 42%
With iodine; silver nitrate In acetonitrile for 2h; Ambient temperature;	A 5% B 12%

: 636-98-6
p-nitrobenzene iodide

A: 100-25-4
para-dinitrobenzene

B: 305-85-1
2,6-diiodo-4-nitrophenol

Conditions

Conditions	Yield
With sodium nitrite

: 609-23-4
2,4,6-Triiodophenol

A: 305-85-1
2,6-diiodo-4-nitrophenol

B: 20294-48-8
diiodo-4,6 nitro-2 phenol

Conditions

Conditions	Yield
With acetic acid; sodium nitrite; benzene Trennung durch fraktionierte Krystallisation der Kaliumsalze;
With acetic acid; sodium nitrite; benzene

: 616-59-1
2-hydroxyl-5-nitrobenzenesulfonic acid

A: 305-85-1
2,6-diiodo-4-nitrophenol

B: 2-hydroxy-3-iodo-5-nitro-benzenesulfonic acid

Conditions

Conditions	Yield
With ethanol; iodine; mercury(II) oxide

: 96-97-9
5-nitrosalicylic acid

: 305-85-1
2,6-diiodo-4-nitrophenol

Conditions

Conditions	Yield
With iodine; mercury(II) oxide

: 96-97-9
5-nitrosalicylic acid

A: 305-85-1
2,6-diiodo-4-nitrophenol

B: 861565-06-2
2-hydroxy-3-iodo-5-nitro-benzoic acid

Conditions

Conditions	Yield
With ethanol; iodine; mercury(II) oxide

: 28177-54-0
2,6-diiodo-phenol

: 305-85-1
2,6-diiodo-4-nitrophenol

Conditions

Conditions	Yield
durch Nitrierung;

: 28177-54-0
2,6-diiodo-phenol

A: 305-85-1
2,6-diiodo-4-nitrophenol

B: 13073-26-2
2-iodo-6-nitro-phenol

Conditions

Conditions	Yield
With nitric acid

: 16825-79-9
1-iodyl-4-nitrobenzene

: 305-85-1
2,6-diiodo-4-nitrophenol

Conditions

Conditions	Yield
With sodium nitrite
With sodium azide

: 100-02-7
4-nitro-phenol

: 7553-56-2
iodine

: 7782-68-5
iodic acid

alkali: alkali

: 305-85-1
2,6-diiodo-4-nitrophenol

...Expand

: 100-02-7
4-nitro-phenol

: 7664-41-7
ammonia

iodine-potassium iodide solution: iodine-potassium iodide solution

: 305-85-1
2,6-diiodo-4-nitrophenol

...Expand

: 100-02-7
4-nitro-phenol

mercury oxide: mercury oxide

: 305-85-1
2,6-diiodo-4-nitrophenol

Conditions

Conditions	Yield
durch Jodierung;

: 861565-06-2
2-hydroxy-3-iodo-5-nitro-benzoic acid

alkali: alkali

: 305-85-1
2,6-diiodo-4-nitrophenol

Conditions

Conditions	Yield
bei der Jodierung;

: 64-17-5
ethanol

: 96-97-9
5-nitrosalicylic acid

: 7553-56-2
iodine

mercury oxide: mercury oxide

A: 305-85-1
2,6-diiodo-4-nitrophenol

B: 861565-06-2
2-hydroxy-3-iodo-5-nitro-benzoic acid

...Expand

: 609-23-4
2,4,6-Triiodophenol

: 64-19-7
acetic acid

: 71-43-2
benzene

NaNO2: NaNO2

A: 305-85-1
2,6-diiodo-4-nitrophenol

B: 20294-48-8
diiodo-4,6 nitro-2 phenol

Conditions

Conditions	Yield
at 12 - 15℃;

...Expand

: 616-59-1
2-hydroxyl-5-nitrobenzenesulfonic acid

A: 305-85-1
2,6-diiodo-4-nitrophenol

B 6-iodo-4-nitro-phenol-sulfonic acid-(2): 6-iodo-4-nitro-phenol-sulfonic acid-(2)

Conditions

Conditions	Yield
With ethanol; iodine; mercury

: 616-59-1
2-hydroxyl-5-nitrobenzenesulfonic acid

: 7553-56-2
iodine

mercury oxide: mercury oxide

A: 305-85-1
2,6-diiodo-4-nitrophenol

B 6-iodo-4-nitro-phenol-sulfonic acid-(2): 6-iodo-4-nitro-phenol-sulfonic acid-(2)

...Expand

: 96-97-9
5-nitrosalicylic acid

A: 305-85-1
2,6-diiodo-4-nitrophenol

B x-iodo-5-nitro-2-oxy-benzoic acid: x-iodo-5-nitro-2-oxy-benzoic acid

Conditions

Conditions	Yield
With iodine; mercury(II) oxide

: 16825-79-9
1-iodyl-4-nitrobenzene

sodium nitrite: sodium nitrite

A: 100-25-4
para-dinitrobenzene

B: 305-85-1
2,6-diiodo-4-nitrophenol

...Expand

: 16825-79-9
1-iodyl-4-nitrobenzene

aqueous NaNO2-solution: aqueous NaNO2-solution

A: 636-98-6
p-nitrobenzene iodide

B: 100-25-4
para-dinitrobenzene

C: 305-85-1
2,6-diiodo-4-nitrophenol

...Expand

: 16825-79-9
1-iodyl-4-nitrobenzene

aqueous NaN3-solution: aqueous NaN3-solution

A: 1516-60-5
4-nitrophenyl azide

B: 305-85-1
2,6-diiodo-4-nitrophenol

...Expand

: 28177-54-0
2,6-diiodo-phenol

: 7697-37-2
nitric acid

: 64-19-7
acetic acid

A: 305-85-1
2,6-diiodo-4-nitrophenol

B: 13073-26-2
2-iodo-6-nitro-phenol

Conditions

Conditions	Yield
at -5℃;

...Expand

: 108-95-2
phenol

phosphorous oxychloride: phosphorous oxychloride

: 305-85-1
2,6-diiodo-4-nitrophenol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 25 percent / AgNO3, Br2 / acetonitrile / 2 h / Ambient temperature 2: 5 percent / AgNO3, I2 / acetonitrile / 2 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 29 percent / AgNO3, I2 / acetonitrile / 2 h / Ambient temperature 2: 5 percent / AgNO3, I2 / acetonitrile / 2 h / Ambient temperature View Scheme

: 139-02-6
sodium phenoxide

: 305-85-1
2,6-diiodo-4-nitrophenol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CS2; iodine 2: durch Nitrierung View Scheme
Multi-step reaction with 2 steps 1: CS2; iodine 2: nitric acid View Scheme

: 305-85-1
2,6-diiodo-4-nitrophenol

: 75-03-6
ethyl iodide

: 31199-98-1
3,5-diiodo-4-ethoxy-nitrobenzene

Conditions

Conditions	Yield
With potassium carbonate In acetone at 60℃;	95%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 77-78-1
dimethyl sulfate

: 31106-75-9
1-methoxy-2,6-diiodido-4-nitrobenzene

Conditions

Conditions	Yield
With potassium carbonate In acetone at 0℃; for 18h; Reflux; Schlenk technique;	92%
With potassium carbonate In acetone at 65℃; for 18h; Inert atmosphere;	87%
With potassium carbonate In acetone at 0 - 65℃; for 18h; Inert atmosphere;	87%
With alkali

: 305-85-1
2,6-diiodo-4-nitrophenol

: 98-59-9
p-toluenesulfonyl chloride

: 851077-63-9
2,6-diiodo-4-nitrophenyl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
With pyridine at 0 - 20℃;	90%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 18880-00-7
1-(bromomethyl)-4-(1,1-dimethylethyl)benzene

: 1423135-83-4
4-(t-butyl)benzyl 2,6-diiodo-4-nitrophenyl ether

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	80%

: 6746-94-7
Cyclopropylacetylene

: 305-85-1
2,6-diiodo-4-nitrophenol

: 2-cyclopropyl-7-iodo-5-nitro-1-benzofuran

Conditions

Conditions	Yield
With pyridine; copper(I) oxide for 2h; Reflux;	78%
With pyridine; copper(I) oxide for 2h; Reflux;	78%

: 4187-86-4
pent-1-yn-3-ol

: 305-85-1
2,6-diiodo-4-nitrophenol

: 1-[2-(1-hydroxy-propyl)-5-nitro-benzofuran-7-yl]-pent-1-yn-3-ol

Conditions

Conditions	Yield
Stage #1: 2,6-diiodo-4-nitrophenol With copper(l) iodide; triphenylphosphine; (S)-1-Pyrrolidin-2-yl-methanol; palladium on activated charcoal In water at 25℃; for 1h; Sonogashira coupling; Stage #2: pent-1-yn-3-ol In water at 80℃; for 3h;	75%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 115-19-5
2-methyl-but-3-yn-2-ol

: 4-[2-(1-hydroxy-1-methyl-ethyl)-5-nitro-benzofuran-7-yl]-2-methyl-but-3-yn-2-ol

Conditions

Conditions	Yield
Stage #1: 2,6-diiodo-4-nitrophenol With copper(l) iodide; triphenylphosphine; (S)-1-Pyrrolidin-2-yl-methanol; palladium on activated charcoal In water at 25℃; for 1h; Sonogashira coupling; Stage #2: 2-methyl-but-3-yn-2-ol In water at 80℃; for 3h;	75%

: 305-85-1
2,6-diiodo-4-nitrophenol

: (R)-(4-(2,5-dimethyl-1H-pyrrol-1-yl)cyclopent-1-en-1-yl)methanol

: (R)-1-(3-((2,6-diiodo-4-nitrophenoxy)methyl)cyclopent-3-en-1-yl)-2,5-dimethyl-1H-pyrrole

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h;	71%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 106-89-8
epichlorohydrin

: 95646-27-8
1-<2',6'-diiodo-4'-nitrophenoxy->-2,3-epoxy propane

Conditions

Conditions	Yield
With pyridine at 90 - 95℃; for 1h;	70%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 2028-63-9
but-3-yn-2-ol

: 4-[2-(1-hydroxy-ethyl)-5-nitro-benzofuran-7-yl]-but-3-yn-2-ol

Conditions

Conditions	Yield
Stage #1: 2,6-diiodo-4-nitrophenol With copper(l) iodide; triphenylphosphine; (S)-1-Pyrrolidin-2-yl-methanol; palladium on activated charcoal In water at 25℃; for 1h; Sonogashira coupling; Stage #2: but-3-yn-2-ol In water at 80℃; for 3h;	70%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 88284-48-4
2-(trimethylsilyl)phenyl trifluoromethanesulfonate

: 1,3-diiodo-5-nitro-2-phenoxybenzene

Conditions

Conditions	Yield
With cesium fluoride In acetonitrile at 20℃; for 24h;	65%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 536-74-3
phenylacetylene

: 7-iodo-5-nitro-2-phenyl-1-benzofuran

Conditions

Conditions	Yield
With pyridine; copper(I) oxide Inert atmosphere; Reflux;	63%

: 4549-31-9
1,7-dibromoheptane

: 305-85-1
2,6-diiodo-4-nitrophenol

: 1374327-23-7
1,3-dibromo-2-(7-bromoheptyloxy)-5-nitrobenzene

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile	52%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 106-95-6
allyl bromide

: 95646-25-6
2,6-diiodo-4-nitro-(2-allyl)-oxybenzene

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;	50%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 74-88-4
methyl iodide

: 31106-75-9
1-methoxy-2,6-diiodido-4-nitrobenzene

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 60h;	42%
With potassium carbonate In acetone for 6h; Heating;

: 305-85-1
2,6-diiodo-4-nitrophenol

: 1066-54-2
trimethylsilylacetylene

: 4-nitro-2,6-bis-trimethylsilanylethynyl-phenol

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper diacetate; diisopropylamine at 20℃; for 1h;	40%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 89640-51-7
4-amino-2-iodophenol

Conditions

Conditions	Yield
With sodium hydroxide; sodium dithionite at 75℃;	30%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 2-(3,4,5-trimethoxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole

: 2,6-bis[5-(3,4,5-trimethoxyphenyl)pyrrol-2-yl]-4-nitrophenol

Conditions

Conditions	Yield
With palladium diacetate; sodium carbonate; XPhos In 1,2-dimethoxyethane; water Suzuki Coupling; Inert atmosphere; Reflux;	24%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 2-(3,4,5-trihexadecyloxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole

: 2,6-bis(5-(3,4,5-trihexadecyloxyphenyl)pyrrol-2-yl)-4-nitrophenol

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium carbonate In 1,2-dimethoxyethane; water for 5h; Suzuki Coupling; Inert atmosphere; Reflux;	22%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 39546-47-9
p-chlorobenzylisocyanide

: 107-11-9
1-amino-2-propene

: 590-86-3
isovaleraldehyde

: 1007383-12-1
C22H24ClI2N3O3

Conditions

Conditions	Yield
With ammonium chloride In water; toluene at 100℃; for 20h; Ugi-Smiles reaction; Inert atmosphere;	18%

...Expand

: 305-85-1
2,6-diiodo-4-nitrophenol

: 5-ethoxycarbonyl-3,4-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)pyrrole

: 2,6-bis(5-ethoxycarbonyl-3,4-dimethylpyrrol-2-yl)-4-nitrophenol

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 14h; Suzuki Coupling; Inert atmosphere;	18%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-phenylpyrrole

: 4-nitro-2,6-di(5-phenylpyrrol-2-yl)phenol

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium carbonate In 1,2-dimethoxyethane; water Suzuki Coupling; Inert atmosphere; Reflux;	8.7%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 2-(3,4,5-tridodecyloxyphenyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole

: 2,6-bis(5-(3,4,5-tridodecyloxyphenyl)pyrrol-2-yl)-4-nitrophenol

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium carbonate In 1,2-dimethoxyethane; water for 7h; Suzuki Coupling; Inert atmosphere; Reflux;	5.5%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(3,4,5-trioctyloxyphenyl)pyrrole

: 4-nitro-2,6-bis(5-(3,4,5-trioctyloxyphenyl)pyrrol-2-yl)phenol

Conditions

Conditions	Yield
With tri-tert-butyl phosphine; palladium diacetate; sodium carbonate In 1,2-dimethoxyethane; water Suzuki Coupling; Inert atmosphere; Reflux;	1.6%

: 305-85-1
2,6-diiodo-4-nitrophenol

: 20389-01-9
2,6-diiodo-p-benzoquinone

Conditions

Conditions	Yield
With tin; acetic acid anschliessendes Behandeln mit CrO3 in wss. H2SO4;
Multi-step reaction with 3 steps 1: sodium dithionite; aqueous sodium carbonate 2: ethanolic H2SO4 / Diazotization.anschliessendes Kochen 3: aqueous KOH; CrO3; water View Scheme

: 305-85-1
2,6-diiodo-4-nitrophenol

: 2297-82-7
2,6-diiodo-4-aminophenol

Conditions

Conditions	Yield
With hydrogenchloride; tin(ll) chloride
With sodium dithionite; sodium carbonate
With tin; acetic acid
With hydrochloride of tin dichloride
With tin(II) chloride dihdyrate In ethanol at 78℃; for 5h;	4 g

2,6-DIIODO-4-NITROPHENOL Chemical Properties

Empirical Formula: C₆H₃I₂NO₃
Molecular Weight: 390.9019
IUPAC Name: 2,6-Diiodo-4-nitrophenol
Synonyms: Phenol, 2,6-diiodo-4-nitro- ; Disofen ; Diisophenol ; Ancylol
Melting Point: 152-154 ^°C(lit.)
Flash Point: 141.6^°C
Boiling Point: 310.6 ^°C at 760 mmHg
Density of 2,6-Diiodo-4-nitrophenol (305-85-1): 2.717 g/cm³
Vapour Pressure: 0.000325 mmHg at 25^°C
Index of Refraction: 1.782
Water Solubility: 2,6-Diiodo-4-nitrophenol (305-85-1) is very sparingly soluble
Sensitive: Light Sensitive
Stability: 2,6-Diiodo-4-nitrophenol (305-85-1) is stable.
Appearance: 2,6-Diiodo-4-nitrophenol (305-85-1) is a yellow crystalline solid

2,6-DIIODO-4-NITROPHENOL Uses

2,6-Diiodo-4-nitrophenol (305-85-1) is used against hookworm.

2,6-DIIODO-4-NITROPHENOL Toxicity Data With Reference

1.	orl-rat LD50:170 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),232.
2.	ipr-rat LD50:105 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),232.
3.	scu-rat LD50:122 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),232.
4.	ivn-rat LD50:105 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),232.
5.	orl-mus LD50:212 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),232.
6.	ipr-mus LD50:107 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),232.
7.	scu-mus LD50:110 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),232.
8.	ivn-mus LD50:88 mg/kg	TXAPA9 Toxicology and Applied Pharmacology. 6 (1964),232.
9.	par-uns LDLo:36 mg/kg	FAZMAE Fortschritte der Arzneimittelforschung. 17 (1973),108.

2,6-DIIODO-4-NITROPHENOL Consensus Reports

Reported in EPA TSCA Inventory.

2,6-DIIODO-4-NITROPHENOL Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, intravenous, and parenteral routes. An anthelmintic. When heated to decomposition it emits very toxic fumes of I⁻ and NO_x. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS.
Safety: DANGER: POISON, causes cyanosis; skin, eye, lung irritation. Safety glasses, good ventilation.
Hazard Codes: Xn: Harmful ,
T: Toxic
Risk Statements: 20/21/22: Harmful by inhalation, in contact with skin and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
25: Toxic if swallowed
Safety Statements: 26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: SL0750000
HazardClass: 6.1
PackingGroup: III

2,6-DIIODO-4-NITROPHENOL Specification

2,6-Diiodo-4-nitrophenol (305-85-1) is a yellow crystalline solid used against hookworm. It is a halogenated and nitrated phenol. Reacts as a weak acid. It is stable and very sparingly soluble in water.

Product Name

2,6-Diiodo-4-nitrophenol

Synthetic route

2,6-DIIODO-4-NITROPHENOL Chemical Properties

2,6-DIIODO-4-NITROPHENOL Uses

2,6-DIIODO-4-NITROPHENOL Toxicity Data With Reference

2,6-DIIODO-4-NITROPHENOL Consensus Reports

2,6-DIIODO-4-NITROPHENOL Safety Profile

2,6-DIIODO-4-NITROPHENOL Specification

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