基本信息
- 标准SMILES
IC(I)I- InChIKey
OKJPEAGHQZHRQV-UHFFFAOYSA-N- 分子式
- CHI3
- 平均分子量
- 393.732 g/mol
- 单同位素质量
- 393.72124403
概述
Iodoform appears as bright yellow or yellow powder or crystals. Penetrating odor. Unctuous feel. Odor threshold 0.4 ppb. (NTP, 1992)
名称与标识
- 首选名称
- Iodoform
- IUPAC
- iodoform
- 中文名
- 碘仿
- 英文名
- Iodoform
- 分子式
- CHI3
- 分子量
- 393.73
名称与别名
展开更多名称
数据库标识
- CAS
75-47-8- PubChem CID
- 6374
- DTXSID
DTXSID4020743- ChEMBL
CHEMBL1451116- ChEBI
CHEBI:37758- UNII
- KXI2J76489
- EC Number
- 200-874-5、685-642-5
- Nikkaji
- J1.456G
性质
结构计算性质
- XLogP
- 2.7
- 极性表面积
- 0 Ų
- 氢键供体
- 0
- 氢键受体
- 0
- 可旋转键
- 0
- 重原子
- 4
- 形式电荷
- 0
- 复杂度
- 8
实验与物化性质
Density
4.008 at 68 °F (NTP, 1992) - Denser than water; will sink
Specific Gravity: 4.008 g/cu cm @ 25 °C
4.008
4.01
Color/Form
Yellow powder or crystals
YELLOW HEXAGONAL PRISMS OR NEEDLES FROM ACETONE
Solubility
less than 1 mg/mL at 75 °F (NTP, 1992)
Slightly soluble
SOL IN ACETIC ACID
13.6 g/100 ml ether @ 25 °C
7.8 g/100 ml ethanol @ 25 °C
One gram dissolves in 60 ml cold alcohol, 16 ml boiling alcohol, 10 ml chloroform, 7.5 ml ether, 80 ml glycerol, 3 ml carbon disulfide, 34 ml olive oil; freely sol in benzene, acetone, slightly sol in petr ether.
Boiling Point
424 °F at 760 mmHg (Sublimes) (NTP, 1992)
218 °C
424 °F (sublimes)
410 °F (Decomposes)
Decomposition
DECOMPOSES VIOLENTLY @ 400 °F (204 °C)
DECOMPOSES @ HIGH TEMP WITH EVOLUTION OF IODINE.
WHEN HEATED TO DECOMPOSITION ... EMITS TOXIC FUMES OF /HYDROGEN IODIDE/.
Melting Point
248 °F (NTP, 1992)
119-122
119 °C
Enthalpy of melting @ mp: 3.9 kcal/mole; enthalpy of sublimation @ 298 K: 16.7 kcal/mole; specific heat @ 400 K: 19.60 cal/K.mole, @ 600 K: 21.52 cal/K.mole, @ 800 K: 22.64 cal/K.mole, @ 1000 K: 23.38 cal/K.mole
246 °F
246 °F
Vapor Density
4.1 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
13.6 (Air= 1)
4.1
物理化学性质
- 熔点
- 119 °C · 119 °C
- 沸点
- 218 °C · 218°C
- 密度
- 4.008 g/mL · 4.008 g/mL at 25 °C(lit.)
- 折射率
- 1.4975 · 1.4975 (estimate)
- 储存条件
- -20 °C · -20°C
- 溶解度
- 5 % · chloroform: soluble5%
- 形态
- Crystalline Powder
- 颜色
- Bright yellow to dark yellow
- 气味 (Odor)
- char. pungent odor
- 生物来源
- mouse
- 水溶解性
- 0.1 g/100 · Insoluble. <0.1 g/100 mL at 24 ºC
- 比热容
- 0.19 J/ · Cp(gas): 0.19 J/(g·K), at 25℃
- 敏感性
- Light Sensitive
- Merck
- 14 · 14,5033
- BRN
- 1697010 · 1697010
- Henry's Law Constant
- 6.2 · 6.2×10-3 mol/(m3Pa) at 25℃, Fogg and Sangster (2003)
- 暴露限值
- 10 mg/m3 · PC-TWA:10 mg/m3
- 稳定性
- Stable. Incompatible with strong oxidizing agents, reducing agents. May explode when heated.
- 化妆品成分功效
- ANTIMICROBIAL
- InChI
- 1S/CHI3/c2-1(3)4/h1H
- InChIKey
- OKJPEAGHQZHRQV-UHFFFAOYSA-N
- SMILES
- IC(I)I
- LogP
- 3.51 · 3.510 (est)
- CAS 数据库
- 75 · 75-47-8(CAS DataBase Reference)
- NIST化学物质信息
- Methane, triiodo-(75-47-8)
- EPA化学物质信息
- Iodoform (75-47-8)
化学性质
黄色有光泽片状结晶。熔点120℃,相对密度4.1(20/4℃)。易溶于苯和丙酮,溶于醇、醚、氯仿、二硫化碳和橄榄油,微溶于水、甘油和石油醚。能升华,加热温度高于熔点时分解析出碘,能随水蒸气挥发,有滑腻感,有刺激辛辣气味。
安全与法规
GHS分类
GHS Classification
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1363) of reports.
Warning
H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1363 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
危害信息
Regulatory Information
Chemical: Methane, triiodo-
Iodoform: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Cases of CNS depression, delirium, and hallucinations were reported when iodoform was used as a topical antiseptic and absorbed through the wound. It causes severe liver injury in animal experiments. 2021 TLV Basis: thyroid effects and fetal/neonatal damage; [ACGIH] See Iodine for the TLV of Iodides.
Special Reports
USEPA; Ambient Water Quality Criteria Doc: Halomethanes (1980) EPA 440/5-80-051
Bioassay of Iodoform for Possible Carcinogenicity (1978) Technical Rpt Series No. 110 DHEW Pub No. (NIH) 78-1365, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014
Reactivity Profile
IODOFORM decomposes at high temperatures. Decomposes slowly in light at room temperature. Reacts violently with lithium. Is incompatible with mercuric oxide, calomel, silver nitrate, tannin, and balsam Peru. Is also incompatible with strong bases, strong oxidizing agents and magnesium. Vigorous reactions occur with acetone in the presence of solid potassium hydroxide or calcium hydroxide, hexamethylenetetramine at 352 °F, mercury(I) fluoride and finely divided reduced silver. (NTP, 1992)
安全与防护
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
(General first aid procedures)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed or replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
Threshold Limit Values (TLV)
0.001 [ppm], as elemental iodine, inhalable fraction and vapor
8 hr Time Weighted Avg (TWA): 0.6 ppm.
Excursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded.
0.001 ppm (inhalable fraction and vapor) [2021]
Recommended Exposure Limit (REL)
0.6 ppm (10 mg/m³)
TWA 0.6 ppm (10 mg/m3)
Personal Protective Equipment (PPE)
Excerpt from NIOSH Pocket Guide for Iodoform:
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
毒理信息
Ecotoxicity Values
LC50 Pimephales promelas (fathead minnows) 2.92 mg/l/96 hr, flow-through bioassay @ 25.1 °C, pH 7.7, water hardness 44.2 mg/l CaCO3 /Purity 98%/
EC50 Pimephales promelas (fathead minnows) 2.01 mg/l/96 hr, flow-through bioassay @ 25.1 °C, pH 7.7, water hardness 44.2 ml/l CaCO3 /Purity 98%/. /EC50 was based upon loss of equlibrium as manifested by the fish's inability to maintain an upright position when swimming./
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 35(SRC), determined from a structure estimation method(2), indicates that iodoform is expected to have very high mobility in soil(SRC). Volatilization of iodoform from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Iodoform is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.040 mm Hg(SRC), determined from a fragment constant method(4). Data on the biodegradability of iodoform in soil is not available(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 35(SRC), determined from an estimation method(2), indicates that iodoform is not 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 3.1X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 40 hours and 25 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 43(SRC), from an estimated log Kow of 3.03(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Data on the biodegradability of iodoform in water is not available(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), iodoform, which has an estimated vapor pressure of 0.396 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase iodoform 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 56 days(SRC), from its rate constant of 0.289X10-12 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Iodoform absorbs radiation >290 nm(4) and therefore may be susceptible to direct photolysis(SRC). Photolysis rates for iodoform were not located.
Ongoing Test Status
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=75-47-8]
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for iodoform can be estimated to be 35(SRC). According to a classification scheme(2), this estimated Koc value suggests that iodoform is expected to have very high mobility in soil.
Human Toxicity Excerpts
SYSTEMIC INTOXICATION AND VISUAL DISTURBANCES RESULTED FROM ABSORPTION OF EXCESSIVE AMT /OF IODOFORM/ APPLIED TO WOUNDS OR ABSCESSES, OR FROM INGESTION OF LARGE QUANTITIES, BUT NOT FROM APPLICATION TO THE EYE. ... MOST CHARACTERISTICALLY VISION WAS IMPAIRED BY RETROBULBAR NEURITIS WITH ACCOMPANYING CENTRAL SCOTOMA. IN RARE INSTANCES TRANSITORY COMPLETE BLINDNESS OCCURRED. IN SOME CASES THE BULBAR PORTION OF THE OPTIC NERVE WAS INVOLVED, WITH NEURORETINITIS & OCCASIONAL RETINAL HEMORRHAGES. AS A RULE, RECOVERY WAS SLOW ... IN MOST CASES VISION WAS COMPLETELY OR PARTIALLY RECOVERED, BUT RESIDUAL PALLOR OF THE TEMPORAL PART OF THE OPTIC NERVEHEAD WAS COMMON. EXCEPTIONALLY THE WHOLE NERVEHEAD BECAME ATROPHIC AND WHITE AND LITTLE VISION WAS RECOVERED.
Both di- and tri-halogenated methane derivatives have been found to produce increased blood levels of methemoglobin; the greatest increase caused by iodo-, followed by bromo- and chloro- compounds. CNS functional disturbances are reported, including depression of rapid eyemovement sleep, as seen in carbon monoxide exposures. /Di- and tri-halogenated methane derivatives/
POISONING IS OFTEN DUE TO ABSORPTION THROUGH WOUND WHEN IODOFORM DRESSINGS ARE USED (NO MORE THAN 2 G IODOFORM SHOULD BE SO USED). MAY CAUSE DERMATITIS. SYSTEMIC EFFECTS INCL VOMITING & ALL DEGREES OF CEREBRAL DEPRESSION OR EXCITATION, INCL DELIRIUM, HALLUCINATIONS, COMA, & DEATH. VERY RAPID PULSE IS CHARACTERISTIC, WITH OR WITHOUT SLIGHT FEVER.
... Severe poisoning, which may be fatal, is characterized by headache, somnolence, delirium, and rapid feeble pulse.
Artificial Pollution Sources
Iodoform's production and use as an antiseptic and sensitizing agent in certain printing processes may result in its release to the environment through various waste streams(1,2). However its present use is rather limited. Iodoform may be formed in finished drinking water during the chlorination process(3). When iodinated trihalomethanes occur, a medicinal taste or musty odor is imparted to the water. While there are only a few reports of iodoform in treated drinking water in the literature, strong medicinal odors have long been known to occur in such water.
Carcinogen Classification
Iodoform
TR-110: Bioassay of Iodoform for Possible Carcinogenicity (CASRN 75-47-8) (1978 )
04/26/78
No Evidence
No Evidence
No Evidence
Environmental Bioconcentration
An estimated BCF of 43 was calculated for iodoform(SRC), using an estimated log Kow of 3.03(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.
法规信息
安全数据
- F
- 13
- wgk
- 3
- tsca
- TSCA listed
- 毒性
- LD50 s.c. in mice: 1.6 mmoles/kg (Kutob, Plaa)
- RTECS号
- PB7000000
- 存储类别
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 安全说明
- 26-36/37-36/37/39-22-24/25
- 海关编码
- 29033990
- 危险品标志
- Xn
- 危险性类别
- Acute Tox. 3 InhalationAcute Tox. 4 DermalAcute Tox. 4 OralAquatic Chronic 2Eye Irrit. 2Skin Irrit. 2STOT SE 3
- 危险类别码
- 20/21/22-36/37/38
- 毒害物质数据
- 75-47-8(Hazardous Substances Data)
- 职业暴露等级
- B
- 职业暴露限值
- TWA: 0.6 ppm (10 mg/m3)
- 危险品运输编号
- UN 1851
化学与工业
药理信息
ATC Code
D - Dermatologicals
QD - Dermatologicals
Pharmacodynamics
Iodoform exhibits antibacterial activities after topical application. In a comparative study of wound dressing agents, iodoform gauze exerted an antibacterial effect 3 hours after the start of bacterial growth of _E. coli_ and subsequently maintained the strong antibacterial effectiveness. A study demonstrated that direct and indirect exposure to high concentrations of iodoform induces a cytotoxic effect on cultures of macrophages and epithelial cells _in vitro_, while cell proliferation was enhanced at low concentrations of iodoform. This cytotoxic effect of iodoform in root canals may further lead to long-term local irritation to follicles of permanent successors and formation of cyst-like radiolucent defects.
Mechanism of Action
While the mechanism of action of iodoform remains unclear, it is proposed that iodoform releases iodine, which denatures bacterial proteins by oxidation of the free iodine. Iodoform may also play a role in chemical debridement for effective necrotic wound healing and tissue damage repair via collagen fibrinolysis; upon treatment in necrotic tissue, iodoform reduced the size of the macromolecules containing collagen I in wound surface proteins. In human gingival fibroblasts _in vitro_, high concentrations of iodoform was shown to decrease the viability of macrophages and epithelial cells and reduced the secretion of _P. gingivalis_-induced TNFα. P. gingivalis is an anaerobic bacteria present in anaerobic oral niches including periapical sites and periodontal pockets.
Metabolism/Metabolites
It is expected to be oxidized to iodine.
HALOFORMS ARE METABOLIZED TO CARBON MONOXIDE BY HEPATIC MICROSOMAL MIXED FUNCTION OXIDASES & THIS REACTION IS MARKEDLY STIMULATED BY SULFHYDRYL COMPOUNDS. /HALOFORMS/
TRIHALOMETHANES (HALOFORMS) WERE METABOLIZED TO CARBON MONOXIDE BY A RAT LIVER MICROSOMAL FRACTION REQUIRING BOTH NADPH AND MOLECULAR OXYGEN FOR MAXIMAL ACTIVITY. THE METABOLISM OF HALOFORMS TO CARBON MONOXIDE FOLLOWED THE HALIDE ORDER; IODOFORM YIELDED THE GREATEST AMOUNT OF CARBON MONOXIDE, WHEREAS CHLOROFORM YIELDED THE SMALLEST AMOUNT.
ADMINISTRATION OF HALOFORMS (TRIHALOMETHANES) TO RATS LED TO SUBSTANTIAL ELEVATIONS IN BLOOD CARBON MONOXIDE LEVELS. /TRIHALOMETHANES/
Absorption, Distribution and Excretion
Iodoform is reported to be absorbed through denuded skin, wounds or mucous membranes.
No pharmacokinetic data available.
No pharmacokinetic data available.
No pharmacokinetic data available.
用途与制造
Uses
Used as a disinfectant and veterinary antiseptic; [Merck Index, #5033]
Using Disinfectants or Biocides [Category: Clean]
Iodoform is used as a component of adhesives and as a polymerization control agent
Wound dressing and sensitizing agent in certain printing processes.
MEDICATION
MEDICATION: VET
U.S. Production
(1977) PROBABLY GREATER THAN 3.18X10+6 G
(1979) PROBABLY GREATER THAN 3.18X10+6 G
Methods of Manufacturing
Prepn from acetone, sodium hypochlorite, potassium iodide, and sodium hydroxide: Glass, Quart. J. Pharm. Pharmacol. 8, 351 (1935); from chloroform + methyl iodide: Soroos, Hinkamp, J. Am. Chem. Soc. 67, 1642 (1945); by electrolysis: Glasstone, Ind. Chem. 7, 315 (1931)
Electrolysis of an iodide solution in dilute alcohol or acetone.
Formulations/Preparations
GRADE: TECHNICAL, NF
Purified grades
BIPP gauze: sterile ribbon gauze impregnated with a sterile paste consisting of iodoform 40%, bismuth subnitrate 20%, and liquid paraffin 40%.
Bismuth subnitrate & iodoform paste: bismuth subnitrate 1, iodoform 2, sterilized liquid paraffin 1, by wt, prepared aseptically.
For more Formulations/Preparations (Complete) data for IODOFORM (8 total), please visit the HSDB record page.
应用领域
用途在医芭和生物化学中用作防腐剂和消毒剂。小鼠口服LD50为910mg/kg。
制备方法
生产方法由丙酮(或乙醇)经卤化、水解而得。先将水、碘化钠及丙酮加入反应锅,加冰降温至10℃。搅拌下缓缓加入次氯酸钠,直至不产生浑浊即达终点,控制温度不超过20℃。静置1h,吸去上层清液,取出碘仿层过滤。滤饼用水洗至中性,再用蒸馏水洗至无氯根为止。然后将其他35-40℃干燥,即得成品。此外,由氯仿与碘甲烷反应也可制备该品。
上下游产品信息
上游原料
下游产品
试剂价格
- A13664 · 50g
- 碘仿, 99% Iodoform, 99% — 457元
- 14912 · 100g
- 碘仿Iodoform, 99+%, Thermo Scientific Chemicals — 650元
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