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Iodobenzene

Iodobenzene structure

Iodobenzene 

structure
  • CAS No:

    591-50-4

  • Formula:

    C6H5I

  • Chemical Name:

    Iodobenzene

  • Synonyms:

    Benzene,iodo-;Iodobenzene;Phenyl iodide;Benzene iodide;NSC 9244;1-Iodobenzene;4-Iodobenzene;172484-65-0;2222572-06-5

  • Categories:

    Pharmaceutical Intermediates  >  Respiratory Tract

Description

Colorless liquid, melting point-31.27℃, boiling point 188.3℃, 63-64℃(1.07kPa), Flash point 74 ℃,density 1.8308(20/4℃), refractive index1.6200(18.5℃) CLEAR YELLOW LIQUID


Iodobenzene is an organoiodine compound consisting of a benzene ring substituted with one iodine atom. It is useful as a synthetic intermediate in organic chemistry. It is a volatile colorless liquid, although aged samples appear yellowish.

Iodobenzene Basic Attributes

204.01

204.01

1446140

209-719-6

9HK5L7YBBR

9244

DTXSID8060452

Liquid

2827600000

Characteristics

0

3.2

Clear yellow Liquid

1.86059 g/cm3 @ Temp: 40 °C

-31.3 °C

188.4 °C

74 °C

1.620

H2O: insoluble

Store below +30°C.

1.06 mm Hg at 25 deg C (extrapolated)

Explodes when heated about 200 deg C.

1.10e-12 cm3/molecule*sec

Henry's Law constant = 8.37X10-4 atm-cu m/mol at 25 °C (est)

Specific gravity: 1.86 at 0 °C/4 °C|Explodes when heated above 200 °C. When heated it emits very toxic fumes of I(-)|Hydroxyl radical reaction rate constant = 1.10X10-12 cu cm/molec-sec at 25 °C

Safety Information

NA 1993 / PGIII

3

22-36-20/22

26-36-23

DA3390000

Xn,Xi

Irritant

Stable under normal temperatures and pressures.

P305 + P351 + P338

H302-H319

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P304+P312, P304+P340, P305+P351+P338, P312, P330, P337+P313, and P501|Aggregated GHS information provided by 54 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Eye protection: Safety glasses

Explodes when heated about 200 °C.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.

Accidental Release Measures. Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains. Methods for cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Handle with gloves. Choose body protection according to the amount and concentration of the dangerous substance at the work place.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|If inhaled, move person into fresh air. If not breathing give artificial respiration. Consult a physician. In case of skin contact, wash off with soap and plenty of water. Consult a physician. In case of eye contact, rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed, never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Causes respiratory tract irritation. ... Causes skin irritation. Causes eye irritation.

Toxicity

Hypothyroidism was produced in weanling albino rats by the oral administration of 2-thiouracil (TU) for 110 days. These animals recorded nearly 50% reduction in mitochondrial oxidation of succinate, protein content and the activity of inner mitochondrial membrane-bound beta-hydroxybutyrate dehydrogenase. Administration of iodobenzene (IB; 0.1 ug/rat/day) and L-thyroxine (T4; 0.6 ug/rat/day) to two sets of hypothyroid rats restored the reduced oxidation rate, enzyme activity and protein content to near normal values. IB was comparable to T4 and may act as a thyroid stimulant.

LD50 Rat oral 1799 mg/kg

Iodobenzene's production and use as a chemical reagent(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), a log Koc value of 3.10(2) indicates that iodobenzene is expected to have low mobility in soil(SRC). Volatilization of iodobenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.4X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 1.06 mm Hg(3), and water solubility, 340 mg/L(4). Iodobenzene is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Iodobenzene has been shown to biodegrade anaerobically in sediment/water slurries with reported half-lives of 13 to 87 days(5-6).|AQUATIC FATE: Based on a classification scheme(1), a log Koc value of 3.10(2) indicates that iodobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.4X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 1.06 mm Hg(4), and water solubility, 340 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 hours and 6 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 65(SRC), from its log Kow of 3.25(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Iodobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Iodobenzene has been shown to biodegrade anaerobically in sediment/water slurries with reported half-lives of 13 to 87 days(9-10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), iodobenzene, which has a vapor pressure of 1.06 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase iodobenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 15 days(SRC), calculated from its rate constant of 1.1X10-12 cu cm/molecule-sec at 25 °C(3). Iodobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Iodobenzene does absorb light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of iodobenzene with photochemically-produced hydroxyl radicals has been measured as 1.1X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 15 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Iodobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Iodobenzene does absorb light at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 65 was calculated in fish for iodobenzene(SRC), using a log Kow of 3.25(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

1.26e+03 L/kg|The log Koc of iodobenzene has been reported as 3.10(1). According to a classification scheme(2), this Koc value suggests that iodobenzene is expected to have low mobility in soil.

The Henry's Law constant for iodobenzene is estimated as 8.4X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 1.06 mm Hg(1), and water solubility, 340 mg/L(2). This Henry's Law constant indicates that iodobenzene is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 6 days(SRC). Iodobenzene's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of iodobenzene from dry soil surfaces may exist(SRC) based upon its vapor pressure(1).

Occupational exposure to iodobenzene may occur through inhalation and dermal contact with this compound at workplaces where iodobenzene is produced or used. (SRC)

Name Type of Test Exposure Route Species Observed Dose/Duration Toxic Effects Reference
ACUTE TOXICITY DATA LD50 - Lethal dose, 50 percent kill Oral Rodent - rat 1749 mg/kg Details of toxic effects not reported other than lethal dose value-- Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 35(12),45,1991
ACUTE TOXICITY DATA LC50 - Lethal concentration, 50 percent kill Inhalation Rodent - rat 16320 mg/m3 Details of toxic effects not reported other than lethal dose value-- Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 19(9),36,1975
ACUTE TOXICITY DATA LD50 - Lethal dose, 50 percent kill Oral Mammal - species unspecified 2 gm/kg Details of toxic effects not reported other than lethal dose value-- Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 32(10),25,1988

Drug Information

The monohydroxylation of halobenzenes by phenobarbital-induced rat liver microsomes was studied. p-Halophenol was the major metabolite from all 4 halobenzenes; o-halophenol formation decreased as the halogen atom size increased. Vmax for total hydroxylation (ortho and para products) correlated well with the sigma + Hammett constant with a negative rho value. This implied a positively charged intermediate in the rate-determining step. Vmax for either ortho or para hydroxylation alone did not correlate with a Hammett constant, implying that the product-determining step occurred after the rate-determining step. Rate-determining formation of a radical cation intermediate probably explained this data. /Halobenzenes/|Detoxification of halogenobenzenes by sulfate, glucuronic-acid, and mercapturic-acid conjugation was studied. Chinchilla-rabbits received oral doses of chlorobenzene, bromobenzene, and iodobenzene equivalent to 150, 210, and 272 mg/kg, respectively ... Ethereal sulfates (E), glucuronides (G), and mercapturic-acids (M) were quantitated in rabbit urine. For chlorobenzene, the percentages of the dose excreted as conjugates were: G, 25.2; E, 26.6; and M, 20.4. For bromobenzene percentages were: G, 40.2; E, 36.8; M, 20.9. For iodobenzene, percentages were: G, 31.3; E, 29.6; M, 22.6 ...

Iodobenzene has a bimodal effect on the receptor cell tuned to benzoic acid (BA) of the female silk moth Bombyx mori. Exposure to iodobenzene causes an inhibition of the response to BA. With stimulation by iodobenzene alone, a reduction of basic nerve impulse firing during exposure is followed by a transient post-stimulus excitation (rebound). /It was suggested/ that inhibition suppresses excitation during exposure but fades afterwards more rapidly than excitation. Due to the spatial equivalence of the iodine and the acid residue, these effects might indicate opposing interactions of iodobenzene with the specific site for the key compound BA. This is supported by the fact that substitutions by smaller halogens are less effective in both inhibition and rebound ...

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/SIGNS AND SYMPTOMS/ Causes respiratory tract irritation. May be harmful if absorbed through skin. Causes skin irritation. Causes eye irritation. Harmful if swallowed.

iodobenzene

Iodobenzene Use and Manufacturing

Methods of Manufacturing

From aniline through diazotization and substitution. Add 30% hydrochloric acid and aniline to water, stir and cool to 2℃, slowly add sodium nitrite solution dropwise, and control the temperature not to exceed 12℃. When the last part of sodium nitrite solution was added dropwise, it was tested with potassium iodide starch test paper, showing blue as the end point of the reaction, and the diazotized solution was obtained. The potassium iodide solution was added to the diazotization solution several times, and at this time, nitrogen gas was released and left for 2 hours until no nitrogen gas escaped. After cooling, the upper aqueous solution was separated. Add 10% sodium hydroxide solution to bring the reaction solution to pH14. Steam distillation is carried out, the distillate is separated into the water layer, and after drying, it is fractionated at atmospheric pressure, and the fraction of 184-188°C is collected, which is iodobenzene, and the yield is 77%.

Uses

suzuki reaction

Benzene, iodo-: ACTIVE|... The aim of this work was the isolation and identification of organic compounds evolved from four commercial resin-modified glass-ionomer cements (resin-based dental materials applied in dentistry) by using an alternative method of volatile compounds analysis-HS-SPME (headspace-solid phase microextraction). Dental materials were heated in closed vial at various temperatures and volatile substances released into the headspace phase above the sample were isolated on a thin polymeric fibre placed in SPME syringe. Identification was performed by using the GC-MS (gas chromatography-mass spectrometry) technique. Almost 50 RMGIC (resin-modified glass-ionomer cement) components (monomers and additives) were identified. The main identified leachables were: iodobenzene (DPICls-diphenyliodonium chloride degradation product), camphorquinone (photo-initiator), tert-butyl-p-hydroxyanisole (inhibitor), 4-(dimethylamino)ethyl benzoate (co-initiator), ethylene glycol dimethacrylate (monomer).

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Kovats' RI, non-polar column, isothermal Packed C78, Branched paraffin 1079.6 130. isothermal He; Column length: 3.3 m Dallos, A.Sisak, A.Kulcsár, Z.Kováts, E.Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groupsJ. Chromatogr. A2000, 904, 2, 211-242.
Kovats' RI, non-polar column, isothermal Packed Apolane 1088. 150. isothermal He, Chromosorb G AW DCMS; Column length: 3.7 m Evans, M.B.Haken, J.K.Dispersion and selectivity indices of the halogenated derivatives of cyclohexane, benzene and anisoleJ. Chromatogr.1987, 389, 240-244.
Kovats' RI, non-polar column, isothermal Packed Apolane 1088. 150. isothermal Chromosorb G AW DCMS; Column length: 3.7 m Haken, J.K.Vernon, F.Gas chromatography of halogenated derivatives of cyclohexane, benzene and anisoleJ. Chromatogr.1986, 361, 57-61.
Kovats' RI, non-polar column, isothermal Packed SE-30 1075. 180. isothermal N2, Chromosorb W AW; Column length: 3. m Oszczapowicz, J.Osek, J.Dolecka, E.Retention indices of dimethylformamidines, dimethylacetamidines and tetramethylguanidines on a non-polar columnJ. Chromatogr.1984, 315, 95-100.
Kovats' RI, non-polar column, isothermal Packed SE-30 1050. 150. isothermal Ar, Gas Chrom Q (80-100 mesh); Column length: 3. m Tiess, D.Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe1984, 33, 6-9.

Computed Properties

Molecular Weight:204.01
XLogP3:3.2
Exact Mass:203.94360
Monoisotopic Mass:203.94360
Heavy Atom Count:7
Complexity:46.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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