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ベンジルブロミド

Benzyl Bromide

HCID 7498
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
100-39-0
標準SMILES
BrCc1ccccc1
InChIKey
AGEZXYOZHKGVCM-UHFFFAOYSA-N
分子式
C7H7Br
平均分子量
171.03 g/mol
単同位体質量
169.97311232

概要

Benzyl bromide appears as a colorless liquid with an agreeable odor. Toxic by inhalation and by skin absorption. It is slightly soluble in water and denser than water (density 1.44 g / cm3 (Aldrich)). A lachrymator. Corrosive to metals and tissue.

名称と識別子

優先名称
Benzyl Bromide
IUPAC
bromomethylbenzene
現地名
ベンジルブロミド
英語名
Benzyl bromide
分子式
C7H7Br
分子量
171.03

名称と別名

BENZYL BROMIDE100-39-0(Bromomethyl)benzenealpha-BromotolueneBromophenylmethaneBenzene, (bromomethyl)-Phenylmethyl bromide1-BromotolueneCycliteToluene, alpha-bromo-DTXSID8024658NSC-8041
名称をさらに表示
ベンジルブロミドα-ブロモトルエンブロモメチルベンゼンブロモ(フェニル)メタン(ブロモメチル)ベンゼン臭化ベンジルフェニルブロモメタンω-ブロモトルエンブロモフェニルメタン1-(ブロモメチル)ベンゼンベンジルブロマイドベンジルブロマイド 臭化物Α‐ブロモトルエンベンジル=ブロミドベンジル=ブロミド, 99%BnBrBenzybromideBenzylBromide,98%1-(Bromomethyl)benzeneBromo Thluene
XR75BS721DAI3-15300DTXCID304658CHEBI:59858omega-BromotolueneRefChem:5595202-847-3bromomethylbenzene

データベース識別子

CAS
100-39-0、28807-97-8
PubChem CID
7498
DTXSID
DTXSID8024658
ChEMBL
CHEMBL1085946
ChEBI
CHEBI:59858
UNII
XR75BS721D
EC Number
202-847-3
Nikkaji
J3.230A

物性

構造計算による物性補完中

XLogP
2.9
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
1
重原子数
8
形式電荷
0
複雑度
55.4

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Halogenated Monoaromatics

Corrosives

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 2 件

log Kow = 2.92

2.92

OdorVery sharp; pungent; like tear gas
Density · 4 件

1.441 at 71.6 °F (USCG, 1999) - Denser than water; will sink

1.4380 at 20 °C

Relative density (water = 1): 1.438

1.738 @25 °C

Color/Form · 3 件

Clear, refractive liquid

Colorless to yellow liquid

Lacrimatory liquid

Solubility · 4 件

Reaction (NTP, 1992)

Miscible in ethanol and ether; soluble in carbon tetrachloride

Sol in benzene

Solubility in water: reaction

Corrosivity · 2 件

Corrosive to metal ... .

Corrosive

Flash Point · 5 件

188 °F (NTP, 1992)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H315: 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)

Warning

H315 (99.2%): 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)

危険有害性情報

Regulatory Information · 4 件

Chemical: Benzene, (bromomethyl)-

Status: Active Update: 07-08-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23901

Benzyl bromide: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Benzene, (bromomethyl)-: Human health tier I assessment
DOT LabelPoison Corrosive
Fire Hazards · 3 件

Special Hazards of Combustion Products: Irritating hydrogen bromide gas may be formed.

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 79 °C explosive vapour/air mixtures may be formed.

Fire PotentialCombustible. Gives off irritating or toxic fumes (or gases) in a fire.
Health Hazards · 2 件

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

Absorption, Distribution and ExcretionThe substance can be absorbed into the body by inhalation and by ingestion.

用途と製造

Uses · 3 件

Used to make foaming agents and other organic chemicals; [Hawley]

Making foaming and frothing agents, organic synthesis

It is used in organic synthesis for the introduction of the benzyl protecting group for alcohols and carboxylic acids. Because of these properties, it has been used as a war gas. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.

ImpuritiesMixt of benzyl bromide (technical prod contained o- and p-bromotoluene contaminants).
U.S. Production · 3 件

(1972) GREATER THAN 9.08X10+5 GRAMS

(1975) GREATER THAN 9.08X10+5 GRAMS

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#1124]

Methods of Manufacturing · 3 件

Bromination of toluene; interaction of benzyl alcohol and hydrobromic acid.

... By action of bromine on toluene in UV light.

... By action of bromine on dibenzyl ether.

Formulations/Preparations · 3 件

Grade: commercial

Grades: Purified grades.

Grade: 98% purity

General Manufacturing Information · 3 件

Benzene, (bromomethyl)-: ACTIVE

関連反応

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化合物ノート

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79 °C

86 °C (187 °F) - closed cup

79 °C (closed cup)

79 °C c.c.

Boiling Point · 4 件

388 to 390 °F at 760 mmHg (NTP, 1992)

191 °C

198-199 °C

201 °C @760 [mm Hg]

Decomposition · 3 件

The substance decomposes slowly on contact with water producing hydrogen bromide.

When strongly heated, they emit highly toxic fumes of /hydrogen bromide/. /bromides/

On combustion, forms toxic fumes including hydrogen bromide.

Melting Point · 3 件

27 to 30 °F (NTP, 1992)

-1.5 °C

-4.0 °C

物理化学的性質

融点
3.9 °C · −3.9 °C (25.0 °F; 269.2 K)
沸点
201 °C · 201 °C (394 °F; 474 K)
比重(密度)
1.438 g/cm3 · 1.438 g/cm3
蒸気密度
5.8 · 5.8 (vs air)
蒸気圧
0.5 hPa · 0.5 hPa (20 °C)
屈折率
1.5752 · 1.5752
闪点
70 °C · 70 °C (158 °F; 343 K)
貯蔵温度
30 °C · Store below +30°C.
溶解性
ベンゼン、四塩化炭素、エタノール、エーテルと混和します。
外見
liquid
色
Colorless
臭い (Odor)
催涙ガスのように非常に鋭く刺激的です。
Merck
14 · 14,1128
BRN
385801 · 385801
Henry's Law Constant
1.4 · 1.4×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
Dielectric constant
5.1 · 5.1(20℃)
安定性
安定。可燃性。強力な酸化剤とは相容れない。
InChI
1S/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
InChIKey
AGEZXYOZHKGVCM-UHFFFAOYSA-N
SMILES
BrCc1ccccc1
CAS データベース
100 · 100-39-0(CAS DataBase Reference)
NISTの化学物質情報
Benzene, (bromomethyl)-(100-39-0)
EPAの化学物質情報
Benzyl bromide (100-39-0)
化学的性質 · 1 件

化学的特性Benzyl bromide is an aromatic compound in which the benzene ring substituted with a bromomethyl group, and is produced by the reaction of toluene with bromine in the presence of an oxidizing agent. It is a combustible, colorless to yellow liquid with a pleasant odor. insoluble in water and easily soluble in most organic solvents. Has a strong tearing effect and unpleasant pungent odor, minimum irritant concentration of 4 mg/m3, intolerable concentration of 50-60 mg/m3.

Inhalation causes irritation of nose and throat; severe exposure may cause pulmonary edema. Vapors cause severe eye irritation; liquid can burn eyes. Skin contact causes irritation. Ingestion causes irritation of mouth and stomach. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards Summary · 2 件

A severe skin, eye, and respiratory tract irritant; Skin contact can cause redness and pain; A lachrymator; [ICSC] May cause pulmonary edema; [HSDB] Causes lacrimation; High concentrations can cause CNS depression; [Merck Index] Causes skin and eye burns; May be harmful if ingested, absorbed through skin, or inhaled; [MSDSonline]

The major hazards encountered in the use and handling of benzyl bromide stem from both its toxicologic and physical/chemical properties. Toxic by all routes (ie, oral, dermal, inhalation), exposure to benzyl bromide may occur environmentally from inhaling air contaminated by exhaust from automobiles using leaded gasoline, or occupationally from its use in research. This colorless to slightly yellow liquid is an intense irritant to skin, eyes, and mucous membranes; and, in large doses, can cause CNS depression. Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of the pungent smelling, benzyl bromide. If contact is anticipated (eg, if handling broken benzyl bromide containers), wear a self-contained breathing apparatus, goggles, rubber gloves, and full protective clothing. Any material which contacts the body must be washed away with copious amounts of water. Benzyl bromide does not ignite readily, and burns only with great difficulty. However, when strongly heated, it emits highly toxic fumes and gases. Fire fighters should wear a positive-pressure breathing apparatus and protective clothing, and extinguish benzyl bromide fires with alcohol foam, CO2, or dry chemical agents. Water also may be used particularly in flooding quantities as a spray or fog (solid streams may be ineffective), to reduce vapor and to cool containers. However, care must be taken because benzyl bromide may react with water to form hydrogen bromide gas. Because runoff from fire control water may be toxic or corrosive, it should be diked or otherwise contained. Store benzyl bromide in cool, well-ventilated areas, out of the sun, and away from potential fire hazard and combustibles (wood, paper, oil, etc). It is also important that the location be dry, because benzyl bromide will react slowly with water to generate hydrogen bromide. Packaging materials are limited by the fact benzyl bromide is corrosive to metal (it decomposes rapidly in the presence of all common metals except nickel and lead; liberating heat and hydrogen bromide). Containers of benzyl bromide may be shipped by air, rail, road, or water, and should be affixed with labels stating, "Poison and Corrosive". Regulatory requirements of the DOT should be consulted before transport. For all benzyl bromide spills, water spray may be needed to knock down vapor. Small spills of benzyl bromide should be taken up with sand or other noncombustible absorbent and placed in containers for later disposal. Large land spills should be deposited in excavated pits, ponds, or other holding areas (fitted with impermeable flexible membrane liners, if possible) for later disposal. Any surface flow should be diked with soil or sand bags, and a "universal" gelling agent applied to immobilize the spill. For water spills, trap the substance at the bottom with sand bag barriers and remove with suction hoses, or apply activated carbon and remove immobilized masses of pollutants and precipitates with mechanical dredges of lifts. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance.

DOT ID and Guide1737 156
Reactive GroupHalogenated Organic Compounds
EC ClassificationSymbol: Xi; R: 36/37/38; S: (2)-39
UN ClassificationUN Hazard Class: 6.1; UN Subsidiary Risks: 8; UN Pack Group: II
Reactivity AlertsPolymerizable

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 件

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:

Safe StorageSeparated from strong oxidants, strong bases and food and feedstuffs. Dry. Well closed.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 5 件

Water spray, dry chemical, foam or carbon dioxide is effective. Water is effective not only for dispersing of leaked chemicals prior to its ignition, but also for cooling fire-exposed containers.

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical or carbon dioxide.

Powder, water spray, foam, carbon dioxide.

In case of fire: keep drums, etc., cool by spraying with water.

For more Fire Fighting Procedures (Complete) data for BENZYL BROMIDE (9 total), please visit the HSDB record page.

Storage Conditions · 4 件

In general, materials which are toxic as stored or which can decomposition into toxic components due to heat, moisture, acids, or acid fumes, should be stored in cool, well ventilated place, out of sun, away from area of high fire hazard and should be periodically inspected and monitored. Incompatible materials should be isolated.

... Store in dry, cool place preferably in segregated store.

Separated from strong oxidants, strong bases, food and feedstuffs. Dry. Well closed.

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Light sensitive. Moisture sensitive.

Cleanup Methods · 5 件

Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Chemical protection suit including self-contained breathing apparatus.

Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations (see section 13). Keep in suitable, closed containers for disposal.

Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.

Nonfire Spill ResponseExcerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
Disposal Methods · 5 件

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.

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 permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. 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 be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Spillage Disposal: Wear eye protection, laboratory coat and nitrile rubber gloves. Depending on the size of the spill, breathing apparatus may be required. Cover the spill with a 1:1:1 mixture by weight of sodium carbonate or calcium carbonate. Clay cat litter (bentonite) and sand. When the benzyl bromide has been absorbed, scoop the mixture into a plastic container and package for disposal by burning /in incinerator equipped with air pollution control equipment/. Wash site of spillage with soap and water.

Waste Disposal: Package Lots. Place in a separate, labeled container for recycling or disposal by burning. Dissolve the compound in a flammable solvent and burn in a furnace /incinerator/ equipped with an afterburner and scrubber.

For more Disposal Methods (Complete) data for BENZYL BROMIDE (8 total), please visit the HSDB record page.

Spillage Disposal · 1 件

Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: chemical protection suit including self-contained breathing apparatus.

毒性情報

Treatment · 1 件

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 件

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 340(SRC), determined from a log Kow of 2.92(2) and a regression-derived equation(3), indicates that benzyl bromide is expected to have moderate mobility in soil(SRC). Volatilization of benzyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.9X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, due to a calculated half-life of 79 minutes for benzyl bromide(5), adsorption, volatilization, bioconcentration, and biodegradation are not expected to be important environmental fate processes in moist soil(SRC). Benzyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.45 mm Hg at 25 °C(6). Biodegradation data in soil were not available(SRC, 2014).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 340(SRC), determined from a log Kow of 2.92(2) and a regression-derived equation(3), indicates that benzyl bromide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 6.9X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 5 hrs and 6 days, respectively(SRC). According to a classification scheme(67), an estimated BCF of 39(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). However, due to a calculated half-life of 79 minutes for benzyl bromide(7), adsorption, volatilization, bioconcentration, and biodegradation are not expected to be important environmental fate processes in water(SRC). Biodegradation data in water were not available(SRC, 2014).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzyl bromide, which has a vapor pressure of 0.45 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase benzyl bromide 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 7 days(SRC), calculated from its rate constant of 2.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Benzyl bromide in methanol at low concentration (59.4 mg/L) does not absorb light at wavelengths >290 nm but does at high concentration (297 mg/L)(4); therefore, benzyl bromide is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation and by ingestion.

Oral (L626) ; inhalation (L626) ; dermal (L626)

Toxicity Summary · 2 件

IDENTIFICATION AND USE: Benzyl bromide is a colorless to yellow lacrimatory liquid with a very sharp pungent tear gas odor. It is miscible in ethanol and ether, and soluble in carbon tetrachloride, benzene, and water. It is used as a chemical intermediate for foaming and frothing agents and other organic chemicals. HUMAN EXPOSURE AND TOXICITY: Liquid benzyl bromide can burn the eyes; skin contact causes irritation. Inhalation causes irritation of nose and throat; severe exposure may cause pulmonary edema. It is intensely corrosive to skin, eyes, and mucous membranes. Occupational exposure to this chemical may occur through inhalation, and dermal contact with this compound at workplaces where it is produced or used. Monitoring data indicated that the general population may have been exposed to benzyl bromide by inhalation of automobile exhaust from vehicles using leaded gasoline. ANIMAL STUDIES: Benzyl bromide was inactive as a carcinogen at doses in rats. Benzyl bromide was negative for mutagenic results in Salmonella typhimurium strains TA 98 and TA 100 . This chemical was used to study chemical reactivity with 4-(p-nitrobenzyl)pyridine, and guanosine in vitro, in relation to mutagenic potency in Salmonella typhimurium and sister chromatid exchange induction in Chinese hamster cells. Benzyl bromide was found to be reactive, causing base-pair mutations in Salmonella typhimurium and also inducing sister chromatid exchange in Chinese hamster cells.

Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)

Signs and Symptoms · 5 件

Cough. Sore throat.

Redness. Pain.

Redness. Pain. Watering of the eyes.

Burning sensation. Abdominal pain. Diarrhoea. Nausea. Vomiting.

Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627)

Ongoing Test Status · 1 件

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.[Available from, as of February 18, 2014: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=100-39-0]

Effluent ConcentrationsBenzyl bromide was identified in automotive emissions from cars burning leaded gasoline containing ethylene dibromide as a lead scavenger; the concentration detected was 1.4 ug/cu m(1).
Soil Adsorption/Mobility · 1 件

The Koc of benzyl bromide is estimated as 340(SRC), using a log Kow of 2.92(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that benzyl bromide is expected to have moderate mobility in soil. However, adsorption on moist soil is expected to be attenuated by hydrolysis(SRC), with a calucalted chemical hydrolysis half-life of 79 minutes(4).

Human Toxicity Excerpts · 4 件

/SIGNS AND SYMPTOMS/ ... Liquid can burn eyes; skin contact causes irritation.

/SIGNS AND SYMPTOMS/ Inhalation causes irritation of nose and throat; severe exposure may cause pulmonary edema.

/SIGNS AND SYMPTOMS/ Redness, pain, Cough, sore throat, lacrimation, burning sensation, abdominal pain, diarrhea, nausea, vomiting.

/SIGNS AND SYMPTOMS/ Skin contact can cause severe, irritation, redness, swelling and sores. High level can cause dizziness because it attacks the nervous system.

Artificial Pollution Sources · 1 件

Benzyl bromide's production and use in the manufacture of foaming and frothing agents, and in organic synthesis(1) may result in its release to the environment through various waste streams(SRC). Its former use in leaded gasoline(2) resulted in its direct release to the environment(SRC).

安全データ

F
9-19-21
wgk
2
tsca
TSCA listed
rtecs
XS7965000
ridadr
UN 1737
毒性
dns-esc 1300 mmol/L ZKKOBW 92,177,78
hs_code
2903 99 80
risk_code
36/37/38
化審法
(3)-2689
安衛法
変異原性物質
消防法
危-4-3-III
hazard_code
Xi
safety_code
39-2
hazard_class
6.1
packing_group
II
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
有毒物質データの
100-39-0(Hazardous Substances Data)
危険度評価(NFPA 704基準/消防庁データ)
火災[赤]=2

Benzene, bromomethyl-: INACTIVE

Benzyl bromide originates in automobile exhaust from ethylene dibromide (a lead scavenger) in leaded gasoline, presumably via radical halogenation during or after combustion of fuel in the engine.

応用分野 · 5 件

解説ベンジルブロミド,刺激臭のある無色の催涙性液体.皮膚,眼,粘膜を強く刺激する.融点-4 ℃,沸点198 ℃,127 ℃(10 kPa).d022"1.4380.nD20"1.5752.λmax 224.5 nm(log ε 3.87).エタノール,エーテルに易溶,水に不溶.求電子置換反応を受けやすく,ベンジル化剤として用いられる.水によって徐々に分解されて,香料の重要な原料であるベンジルアルコールを与える.森北出版「化学辞典(第2版)

用途医薬中間体

用途有機合成原料。

使用Benzyl bromide is widely useful in organic synthesis as a benzyl protecting group for alcohols and carboxylic acids. It is used in the preparation of foaming and frothing agents, quaternary ammonium compounds, peniclins, photographic chemicals, synthetic resins, dyes and plasticizers and esters. It is also involved in the synthesis of (E)-(2-Iodovinyl)benzene by reacting it with diiodomethane.

一般的な説明Benzyl bromide appears as a colorless liquid with an agreeable odor. Toxic by inhalation and by skin absorption. It is slightly soluble in water and denser than water (density 1.44 g / cm3 (Aldrich)). A lachrymator. Corrosive to metals and tissue.

調製方法 · 2 件

製造方法Benzyl bromide is synthesized by toluene bromination. Toluene heated to 50°C, add bromine reaction, the reaction temperature of 75-80°C, reaction 6h, fractional distillation at atmospheric pressure to remove the fraction before 140°C, and then distillation under reduced pressure, collect 112-114°C(2.0kPa) fraction, to get benzyl bromide.

純化方法Wash benzyl chloride with conc H2SO4 (CARE), water, 10% Na2CO3 or NaHCO3 solution, and again with water. Dry it with CaCl2, Na2CO3 or MgSO4 and fractionally distil it in the dark, under reduced pressure. It has also been thoroughly degassed at 10-6 mm and redistilled in the dark. This gives material with max (MeCN): 226nm ( 8200) [Mohammed & Kosower J Am Chem Soc 93 2709 1971]. [Beilstein 5 IV 829.] Handle in a fume cupboard, extremely LACHRYMATORY.

上流・下流製品情報

下流製品

2-(Boc-aminomethyl)-piperidine(S)-(-)-N-ベンジル-1-フェニルエチルアミンベンジルマロン酸ジエチル1-ベンジルホモピペラジンカンデサルタン2-メチル-1-フェニル-2-プロパノール4-アミノ-1-ベンジルピペリジンO-(2-MethoxyEthoxy)BenzeneSulfonamide4-(フェニルメトキシ)ベンゼンエタノール4'-(ベンジルオキシ)ベンジリデン-4-フルオロアニリンα-シアノ-3-フェノキシベンジル=2,2-ジクロロ-1-(4-エトキシフェニル)-1-シクロプロパンカルボキシラート塩化セタルコニウム1-(4,6-ジメトキシ-1,3,5-トリアジン-2-イル)-3-[[2-(2-メトキシエトキシ)フェニル]スルホニル]尿素3,5-ジベンジルオキシベンジルアルコール3-メトキシ-4-(ベンジルオキシ)ベンズアルデヒドtrans-2,5-ジメチルピペラジンスリンダクN-(4-ピペリジニルメチル)カルバミン酸TERT-ブチルテルブタリン硫酸塩7‐ヒドロキシインドール4-ベンジルオキシフェニルボロン酸3-ベンジルオキシベンズアルデヒド3,5-ジベンジルオキシベンジルブロミド1-(ベンジル)-1H-イミダゾール-2-カルボン酸インドブフェンベンジル4-アミノフェニルエーテル1,3,5-ベンゼントリカルボアルデヒドアナグレリドブテナフィン·塩酸塩6-クロロ-7-アザインドール 塩化物ベンジルジメチルドデシルアミニウム·ブロミド5-ヒドロキシインドールN-(tert-ブトキシカルボニル)-O-ベンジル-L-セリン2-ベンジルフェノールN-(tert-ブトキシカルボニル)-3-ヨード-D-アラニンベンジル6-アミノ-3-メチル-3H-プリンベンジル(R)-(-)-グリシジルエーテルα-(2-メチルプロピル)ベンゼンエタノールクロコナゾールα-[4-[2-(ジエチルアミノ)エトキシ]フェニル]-α-フェニルベンゼンエタノール

補足説明

定義ChEBI: Benzyl bromide is a member of the class of benzyl bromides that is toluene substituted on the alpha-carbon with bromine. It has a role as a lachrymator.