基本情報
- 標準SMILES
Cc1cc(C2(c3cc(C)c(O)c(Br)c3)OS(=O)(=O)c3ccccc32)cc(Br)c1O- InChIKey
ABIUHPWEYMSGSR-UHFFFAOYSA-N- 分子式
- C21H16Br2O5S
- 平均分子量
- 540.2 g/mol
- 単同位体質量
- 537.90851881
概要
Bromocresol purple is a member of the class of 2,1-benzoxathioles that is 2,1-benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3-bromo-4-hydroxy-5-methylphenyl groups. A hydrophilic dye that is used as a pH indicator and to measure serum albumin concentrations. It has a role as a dye, an acid-base indicator and a two-colour indicator. It is a polyphenol, an organobromine compound, a 2,1-benzoxathiole, a sultone and an arenesulfonate ester.
名称と識別子
- 優先名称
- Bromocresol Purple
- IUPAC
- 2-bromo-4-[3-(3-bromo-4-hydroxy-5-methylphenyl)-1,1-dioxo-2,1λ6-benzoxathiol-3-yl]-6-methylphenol
- 現地名
- ブロモクレゾールパープル (0.05%, 約20%エタノール溶液) [滴定用]
- 英語名
- Bromocresol Purple
- 分子式
- C21H16Br2O5S
- 分子量
- 540.22
名称と別名
名称をさらに表示
データベース識別子
- CAS
115-40-2- PubChem CID
- 8273
- DTXSID
DTXSID3059428- ChEBI
CHEBI:86154- UNII
- 201C22C3EC
- EC Number
- 204-087-8
物性
構造計算による物性
- XLogP
- 5.1
- 極性表面積
- 92.2 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 2
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 680
実験および物理化学的性質
Melting Point
241.5 °C
241.5 °C
物理化学的性質
- 融点
- 240 °C · 240 °C (dec.) (lit.)
- 比重(密度)
- 1.6509 · 1.6509 (estimate)
- 闪点
- 36 °C · 36 °C
- 貯蔵温度
- 5 °C · Store at +5°C to +30°C.
- 溶解性
- 1 mg/mL · エタノール:可溶1mg/mL
- 酸解離定数(Pka)
- 6.21 · 6.21, 6.3, 6.4(at 25℃)
- 外見
- 個体
- 沸点
- 590.2 · 590.2±50.0 °C(Predicted)
- 色
- 紫がかった茶色
- PH
- 5.2 · pH : 5.2~6.8
- 水溶解度
- 実質的に不溶
- Merck
- 14 · 14,1387
- BRN
- 359618 · 359618
- Henry's Law Constant
- 9.9 · 9.9×1012 mol/(m3Pa) at 25℃, HSDB (2015)
- 安定性
- 安定。強力な酸化剤とは相容れない。
- 主な用途
- 導波管、燃料電池、センサー、ゾルゲル技術、表示装置、偽造防止セキュリティ用紙、塗料、洗剤、生米と古米の識別、乳酸菌の検出、歯科材料、膣感染症検査法
- InChI
- 1S/C21H16Br2O5S/c1-11-7-13(9-16(22)19(11)24)21(14-8-12(2)20(25)17(23)10-14)15-5-3-4-6-18(15)29(26,27)28-21/h3-10,24-25H,1-2H3
- InChIKey
- ABIUHPWEYMSGSR-UHFFFAOYSA-N
- SMILES
- Cc1cc(cc(Br)c1O)C2(OS(=O)(=O)c3ccccc23)c4cc(C)c(O)c(Br)c4
- CAS データベース
- 115 · 115-40-2(CAS DataBase Reference)
- EPAの化学物質情報
- Bromcresol Purple (115-40-2)
化学的性質
化学的特性Crystalline
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 6.9% (7 of 101) of reports.
Warning
H315 (93.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 101 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Phenol, 4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis[2-bromo-6-methyl-, S,S-dioxide
Hazard Traits - Bioaccumulation; Environmental Persistence
Phenol, 4,4'-(1,1-dioxido-3H-2,1-benzoxathiol-3-ylidene)bis[2-bromo-6-methyl-: Does not have an individual approval but may be used under an appropriate group standard
安全と保護具
Fire Fighting Procedures
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.
Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.
Cleanup Methods
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.
Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation.
Environmental precautions: Do not let product enter drains.
Methods for cleaning up: Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.
Observe all federal, state, and local environmental regulations.
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.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
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.
For more Preventive Measures (Complete) data for Bromocresol Purple (6 total), please visit the HSDB record page.
Protective Action Criteria (PAC)
12 [mg/m3]
130 [mg/m3]
790 [mg/m3]
Personal Protective Equipment (PPE)
Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Hand protection: For prolonged or repeated contact use protective gloves.
Eye protection: Safety glasses.
Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.
Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.
毒性情報
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.5X10+6(SRC), determined from a structure estimation method(2), indicates that bromocresol purple is expected to be immobile in soil(SRC). The pKa of bromocresol purple is 6.3(3), indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of bromocresol purple from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.0X10-18 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Bromocresol purple is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-15 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2009); however, structurally similar bromophenol blue has been shown to be biodegraded by certain fungi(7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.5X10+6(SRC), determined from a structure estimation method(2), indicates that bromocresol purple is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.0X10-18 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 4800(SRC), from an estimated log Kow of 6.08(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound it not metabolized by the organism(SRC). Bromocresol purple is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Biodegradation data were not available(SRC, 2009); however, structurally similar bromophenol blue has been shown to be biodegraded by certain fungi(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromocresol purple, which has an estimated vapor pressure of 1.1X10-15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase bromocresol purple may be removed from the air by wet or dry deposition(SRC). Bromocresol purple has a maximum absorbance wavelength of 419 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of bromocresol purple can be estimated to be 1.5X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that bromocresol purple is expected to be immobile in soil. The pKa of bromocresol purple is 6.3(3), indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
Environmental Biodegradation
PURE CULTURE: Biodegradation data for bromocresol purple were not available(SRC, 2009). However, structurally similar bromophenol blue has been shown to be biodegraded by three birds' nest fungi, Cyathus bulleri, C. stercoreus, and C. striatus(1).
Environmental Bioconcentration
An estimated BCF of 4800 was calculated in fish for bromocresol purple(SRC), using an estimated log Kow of 6.08(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC).
Volatilization from Water/Soil
The Henry's Law constant for bromocresol purple is estimated as 1.0X10-18 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that bromocresol purple is expected to be essentially nonvolatile from water surfaces(2). Bromocresol purple is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-15 mm Hg(SRC), determined from a fragment constant method(3).
Environmental Abiotic Degradation
Bromocresol purple is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Bromocresol purple has a maximum absorbance wavelength of 419 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).
Probable Routes of Human Exposure
NIOSH (NOES Survey 1981-1983) has statistically estimated that 12,042 workers (8007 of these were female) were potentially exposed to bromocresol purple in the US(1). Occupational exposure to bromocresol purple may occur through dermal contact with this compound at workplaces where bromocresol purple is produced or used(SRC).
Environmental Fate/Exposure Summary
Bromocresol purple's production and use as a pH indicator may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.1X10-15 mm Hg at 25 °C indicates bromocresol purple will exist solely in the particulate phase in the atmosphere. Particulate-phase bromocresol purple will be removed from the atmosphere by wet or dry deposition. Bromocresol purple has a maximum absorbance wavelength of 419 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, bromocresol purple is expected to have no mobility based upon an estimated Koc of 1.5X10+6. The pKa of bromocresol purple is 6.3, indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 4.0X10-18 atm-cu m/mole. Biodegradation data were not available; however, structurally similar bromophenol blue has been shown to be biodegraded by certain fungi. If released into water, bromocresol purple is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 4800 suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to bromocresol purple may occur through dermal contact with this compound at workplaces where bromocresol purple is produced or used. (SRC)
Antidote and Emergency Treatment
/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/
安全データ
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1993 3/PG 3
- hs_code
- 29349990
- risk_code
- 36/37/38-10-20/21/22
- 化審法
- (5)-533
- 安衛法
- 57,57-2
- hazard_code
- Xi,Xn
- safety_code
- 26-36-37/39-16
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 115-40-2(Hazardous Substances Data)
化学と産業
薬理情報
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
用途と製造
Uses
A sulfonphthalein dye used as a pH indicator; [CHEMINFO] Used as a pH indicator for the pH range of 5.2-6.8 and 10.2-11.8; [Ullmann]
As indicator, pH 5.2 yellow; pH 6.8 purple
応用分野
用途pH測定用、中和滴定用指示薬(弱塩基-強酸系)。
用途1. 酸塩基指示薬 2. 吸着指示薬
使用Bromocresol purple has been used as a pH indicator in the yeast culture media. It has been used as a pH indicator in the culture media of Geobacillus stearothermophilus subsp. Calidolactis.
一般的な説明Bromocresol purple is a pH indicator, which changes color from yellow (at low pH 5.2) to violet (above pH 6.8). It aids in determining the dead cell count for cells with plasma membrane damage. Bromocresol purple is widely used as a fluorescent stain in yeast cells. Cells with an intact plasma membrane are not stained, while damaged cells are seen as blue-grey ghosts.
調製方法
純化方法Dissolve the dye in aqueous 5% NaHCO3 solution and precipitate it from a hot solution by dropwise addition of aqueous HCl. Repeat this until the UV/VIS-extinction did not increase at 419nm. It can also be recrystallised from *benzene. It is an indicator: at pH 5.2 (yellow) and pH 6.8 (purple). [Beilstein 19/3 V 460.]
上流・下流製品情報
上流原料
サプライヤー50 社
補足説明
定義ChEBI: A member of the class of 2,1-benzoxathioles that is 2,1-benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 3-bromo-4-hydroxy-5-methylphenyl groups. A hydrophilic dye that is used as a pH indicator and to measure serum albumin concentrations.
関連反応
関連ノート
読み込み中…