Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > 2,6-Dibromophenol

2,6-Dibromophenol

2,6-Dibromophenol structure

2,6-Dibromophenol 

structure
  • CAS No:

    608-33-3

  • Formula:

    C6H4Br2O

  • Chemical Name:

    2,6-Dibromophenol

  • Synonyms:

    Phenol,2,6-dibromo-;2,6-Dibromophenol;NSC 6214

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

2,6-Dibromophenol is an endogenous metabolite.


Solid


2,6-dibromophenol is a dibromophenol that is phenol in which both of the hydrogens that are ortho to the phenolic hydroxy group have been replaced by bromines. It has a role as a marine metabolite. It is a bromohydrocarbon and a dibromophenol. It derives from a 1,3-dibromobenzene.

2,6-Dibromophenol Basic Attributes

251.9

251.90

2043614

210-161-0

27MIP05EAV

6214

DTXSID0060561

Needles from water

29081000

Characteristics

20.2

3.4

White Crystals or Needles

2.1±0.1 g/cm3

56.5 °C

255 °C

255-256°C

1.644

soluble in ethanol and ether. Slightly soluble in water.

Room temperature.

1.34X10-3 mm Hg at 25 deg C (est)

Henry's Law constant = 8.9X10-8 atm-cu m/mol at 25 °C (est)

pKa = 6.67

Hydroxyl radical reaction rate constant = 2.88X10-12 cu cm/molec-sec at 25 °C (est)

Safety Information

III

6.1(b)

UN 2811 6.1/PG 3

3

20/21/22-36/37/38-22

28-36/37-37/39-26-36

Xn,Xi

Irritant

P280

H302 + H312 + H332

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.|Contact a licensed professional waste disposal service to dispose of this material. Observe all federal, state, and local environmental regulations.

|Warning|H302 (95.83%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Wear appropriate government approved respirator, chemical-resistant gloves, safety goggles, other protective clothing.|ENGINEERING CONTROLS: Use only in a chemical fume hood. Safety shower and eye bath.

Protective Equipment: Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes.|Suitable: Carbon dioxide, dry chemical powder, or appropriate foam.

Emits toxic fumes under fire conditions.

Cover with dry lime or soda ash, pick up, keep in a closed container, and hold for waste disposal.

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: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|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.|Do not breathe dust. Avoid contact with eyes, skin, and clothing.|For more Preventive Measures (Complete) data for 2,6-DIBROMOPHENOL (6 total), please visit the HSDB record page.

Irritating to eyes, respiratory system and skin.

2,6-Dibromophenol was identified in automotive emissions in the range of 1 to 5 ug/cu m(1). Fire residues sampled from private residences following accidental fires contained 2,6-dibromophenol, though the concentrations were reported as the sum of the various brominated flame retardants(2).

SEDIMENT: Surficial sediments from the Rhone estuary, collected in 1987/1988, contained 2,6-dibromophenol at concentrations of <0.5 to 4 ng/g, dry weight basis, from 5 sampling sites(1). Upper river and marine sediment layers in Osaka Prefecture, Japan, collected in 1981 through 1983 at 12 different locations, contained 2,6-dibromophenol at concentrations <0.2 ppb (dry weight basis)(2).

Concentrations of 2,6-dibromophenol were measured in brown algae (0.36 to 1.5 ug/kg wet weight), red algae (0.29 to 5.6 ug/kg), bryozoa (54 and 96 ug/kg), a hydroid (41 ug/kg), and sponges (0.74 to 9.6 ug/kg) collected from Exmouth Gulf, Australia, in October 1990(1).

Toxicity

/AQUATIC SPECIES/ Bromophenols are present in polychaetes as well as in algae in marine environments including the North Sea. They are thought to cause the typical sea-like taste and flavor. The ecological function of brominated phenols is not clear yet, but they may play a role in chemical defense and deterrence ... In this study 2-bromophenol (2-BP), 4-bromophenol (4-BP), 2,4-dibromophenol (2,4-DBP), 2,6-dibromophenol (2,6-DBP) and 2,4,6-tribromophenol (2,4,6-TBP), all of which are present in marine organisms, were tested. Especially 2,4-DBP and 2,4,6-TBP showed a significant effect on the Ca2+ homeostasis in endocrine cells (PC 12). The reduction of depolarization induced Ca2+ elevations by 2,4-DBP and 2,4,6-TBP and the increase of intracellular Ca2+ by both substances, partly released from intracellular stores, may suggest a link to the disrupting effect of endocrine systems by brominated phenols. 2,4-DBP was the most potent substance ... tested in respect to inhibition of voltage dependent Ca2+ currents as revealed in whole cell patch clamp experiments. Brominated phenols disturb cellular Ca2+ signaling with differential efficacy, depending on the number and position of bromine.|/OTHER TERRESTRIAL SPECIES/ 2,6-Dichlorophenol is the only active sex attractant component detected in the extracts of the Rocky Mountain wood tick, Dermacentor andersoni Stiles and the American dog tick, Dermacentor variabilis (Say). It elicits from the male of each species a hierarchy of responses culminating in copulation. This compound probably occurs generally throughout the metastriate Ixodidae. 2,6-Dibromophenol, an artifact, also elicits the same sexual responses from the wood tick, but phenol and p-cresol do not.

There is a wide occurrence of bromophenols in marine algae and provides a possible source of such compounds in fish that feed predominantly on ocean plants.

2,6-Dibromophenol's production may result in its release to the environment through various waste streams. (SRC)

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,600(SRC), determined from a log Kow of 3.36(2) and a regression-derived equation(3), indicates that 2,6-dibromophenol is expected to have low mobility in soil(SRC). The pKa of 2,6-dibromophenol is 6.67(4), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of 2,6-dibromophenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.9X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(6). 2,6-Dibromophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-3 mm Hg(SRC), determined from a fragment constant method(7). 2,6-Dibromophenol degraded in a soil-water system under anaerobic conditions with a half life of 7 days(8), suggesting that biodegradation may be an important environmental fate process under defined conditions(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,600(SRC), determined from a log Kow of 3.36(2) and a regression-derived equation(3), indicates that 2,6-dibromophenol 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 8.9X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 31(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). 2,6-Dibromophenol degraded in a soil-water system under anaerobic conditions with a half life of 7 days(7), suggesting that biodegradation may be an important environmental fate process under defined consditions(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,6-dibromophenol, which has an estimated vapor pressure of 1.3X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,6-dibromophenol 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 5.6 days(SRC), calculated from its rate constant of 2.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2,6-Dibromophenol does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 2,6-dibromophenol with photochemically-produced hydroxyl radicals has been estimated as 2.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,6-Dibromophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2,6-Dibromophenol does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 31 was calculated in fish for 2,6-dibromophenol(SRC), using a log Kow of 3.36(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).

The Koc of 2,6-dibromophenol is estimated as 1,600(SRC), using a log Kow of 3.36(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,6-dibromophenol is expected to have low mobility in soil. The pKa of 2,6-dibromophenol is 6.67(4), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

The Henry's Law constant for 2,6-dibromophenol is estimated as 8.9X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,6-dibromophenol is expected to be essentially nonvolatile from water surfaces(2). 2,6-Dibromophenol's Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). 2,6-Dibromophenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.3X10-3 mm Hg(SRC), determined from a fragment constant method(3).

DRINKING WATER: Raw water from water treatment plants in 6 Canadian cities and treated water from water treatment plants in 5 of 6 Canadian cities, collected in February 1985, contained 2,6-dibromophenol at concentrations below the quantitation limit; one sample of treated water contained 2,6-dibromophenol at 60 ng/L(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 452 workers (355 of these were female) were potentially exposed to 2,6-dibromophenol in the US(1). Occupational exposure to 2,6-dibromophenol may occur through inhalation and dermal contact with this compound at workplaces where 2,6-dibromophenol is produced or used. The most likely pathway by which the general public is exposed to 2,6-dibromophenol is by inhalation due to the release of this substance from automotive emmission, dermal contact with fire residues containing brominated flame retardants, and by ingestion of food and drinking water containing 2,6-dibromophenol(SRC).

Drug Information

/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/

2,6-DBP

2,6-Dibromophenol Use and Manufacturing

Methods of Manufacturing

It is derived from phenol through sulfonation, bromination and hydrolysis. First, 98% sulfuric acid was added dropwise to phenol at 44-50°C. After the addition, the temperature was raised to 100°C, kept for 3h, and ice water was added to dissolve the solids. Then bromine was added dropwise at 20°C, and chlorine gas was added. After reacting with sodium bisulfate for 30 minutes, filter, the filter cake is tribromide, and the filtrate is distilled through superheated steam. The first distillate (containing tribromide and monobromide) is discarded, and the distillate is collected when the internal temperature reaches 155℃. , Cooling and precipitation of crystals to obtain finished products. The yield was 80%.

Uses

Organic synthesis, preparation of 3,4,5-trimethoxybenzaldehyde, etc.

Phenol, 2,6-dibromo-: ACTIVE

Computed Properties

Molecular Weight:251.90
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:251.86084
Monoisotopic Mass:249.86289
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:87.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of 2,6-Dibromophenol

Latest News on 2,6-Dibromophenol

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.