2-Chlorotoluene

HCID 7238CAS 95-49-8

基本情報

標準SMILES
Cc1ccccc1Cl
InChIKey
IBSQPLPBRSHTTG-UHFFFAOYSA-N
分子式
C7H7Cl
平均分子量
126.58 g/mol
単同位体質量
126.0236279

概要

O-chlorotoluene is a colorless liquid with an aromatic odor. Denser than water and poorly soluble in water. Hence sinks in water. (USCG, 1999)

名称と識別子

優先名称
2-Chlorotoluene
IUPAC
1-chloro-2-methylbenzene
現地名
2-クロロトルエン
英語名
2-Chlorotoluene
分子式
C7H7Cl
分子量
126.58

名称と別名

2-Chlorotoluene1-Chloro-2-methylbenzene95-49-8o-Chlorotolueneo-Tolyl chlorideBenzene, 1-chloro-2-methyl-ortho-ChlorotolueneToluene, o-chloro-2-Methylchlorobenzene2-Chloro-1-methylbenzeneHalso 991-METHYL-2-CHLOROBENZENE
名称をさらに表示
2-クロロトルエン2-クロロトルエン (1mg/mlメタノール溶液) [水質分析用]o-クロロトルエン1-メチル-2-クロロベンゼンo-トリルクロリド塩化o-トリルオルト-クロロトルエン1-クロロ-2-メチルベンゼン2-メチルフェニルクロリド2-メチル-1-クロロベンゼンoクロロトルエン2-クロロトルエン標準品2‐クロロトルエン標準品O‐クロロトルエン2-クロロトルエン STANDARD2-クロロトルエン Standard, 5.0 mg/mL in MeOH2-クロロトルエン, 0.2 mg/mL in MeOH2-クロロトルエン, 2.0 mg/mL in MeOHOTFOCT2-Chlortoluolo-Chlortoluol1-chloro-2-methyl-benzen2,4-Dicyano-3-methylpentanediamide
DTXSID8023977UN22382G7D0YDV9HNSC-8766O-METHYLCHLOROBENZENEDTXCID003977UN-2238RefChem:86544

データベース識別子

CAS
95-49-8
PubChem CID
7238
DTXSID
DTXSID8023977
ChEMBL
CHEMBL1797265
UNII
2G7D0YDV9H
EC Number
202-424-3
Nikkaji
J3.564E

物性

構造計算による物性

XLogP
3.4
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
0
重原子数
8

実験および物理化学的性質

Chemical Classes · 3 件

Flammable agents - 2nd degree

Industrial compound

Volatile Organic Compound (VOC)

SolventsSolvents -> Chlorinated Aromatics
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
PesticidesPesticide -> EPA IRIS
LogP · 3 件

Log Kow= 3.42

3.4

3.42

OdorAromatic odor.

物理化学的性質

融点
-36 °C · -36 °C (lit.)
沸点
157 · 157-159 °C (lit.)
比重(密度)
1.083 g/mL · 1.083 g/mL at 25 °C (lit.)
蒸気密度
4.38 · 4.38 (vs air)
蒸気圧
10 mm · 10 mm Hg ( 43 °C)
屈折率
20 · n20/D 1.525(lit.)

化学的性質

化学的特性o-Chlorotoluene is a flammable, colorless liquid with an aromatic odor.

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

P261, P271, P273, P304+P340, P317, P391, and P501 (click each P-code to see the statement)

Warning

H226 (66.4%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P340, P317, P318, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: Benzene, 1-chloro-2-methyl-

Hazard Traits - Other Toxicological Hazard Traits

Benzene, 1-chloro-2-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1-chloro-2-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13832

o-Chlorotoluene: 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.)

DOT LabelFlammable Liquid
Fire Hazards · 2 件

Special Hazards of Combustion Products: May contain toxic chloride fumes.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 43 °C explosive vapour/air mixtures may be formed.

Fire PotentialSLIGHT, WHEN EXPOSED TO HEAT OR FLAME. /4-CHLOROTOLUENE/
Health HazardsInhalation of vapor may cause respiratory irrtation. Prolonged and repeated vapor exposures may produce systemic toxic effects. (USCG, 1999)
Hazards Summary · 2 件

A respiratory irritant; Exposure to high concentrations may produce systemic toxic effects; [CAMEO] May cause skin irritation; [CHEMINFO]

The major hazards encountered in the use and handling of 2-chlorotoluene stem from its toxicologic properties and flammability. Exposure may occur at sites where 2-chlorotoluene is manufactured or used as a pesticide, solvent, or intermediate in the synthesis of dyes, pharmaceuticals, or synthetic rubber chemicals. This colorless liquid may exert its strong irritant properties upon dermal contact or inhalation. To assure protection against 2-chlorotoluene exposure a full-face mask self-contained breathing apparatus and protective clothing should be worn. The ACGIH recommends maintaining an 8-hr TLV of 50 ppm. While this substance must be moderately heated before ignition occurs, 2-chlorotoluene is nevertheless considered a combustion hazard. For fires involving 2-chlorotoluene, extinguish with "alcohol foam", CO2, dry chemical, or water in flooding quantities as fog (solid streams may be ineffective). Flooding quantities of water should be applied from as far a distance as possible, to cool affected containers. This substance should be stored away from heat or flames. Shipping regulations and other DOT regulatory requirements should be consulted before transport. For small spills of 2-chlorotoluene, take up with sand or other noncombustible absorbent and place into containers for later disposal. For large spills, dike to prevent 2-chlorotoluene from entering water sources and sewers. Prior to implementing land disposal of waste residue (including waste sludge) consult with environmental regulatory agencies for guidance.

安全と保護具

Fire Fighting · 2 件

Fire Extinguishing Agents: Small fires: dry chemical, CO2, water spray or foam; large fires: water spray, fog or foam. (USCG, 1999)

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

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again.

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

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

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 procedures)

Safe StorageFireproof. Separated from strong oxidants.
Fire Fighting Procedures · 1 件

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Chlorotoluenes/

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong 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.

毒性情報

Target OrgansEyes, skin, respiratory system, central nervous system, liver, kidneys
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a recommended classification scheme(1), measured Koc values from 170-880(2) indicate that 2-chlorotoluene will have low to moderate mobility in soil(SRC). Volatilization of 2-chlorotoluene may be important from moist soil surfaces(SRC) given a measured Henry's Law constant of 3.57X10-3 atm-cu m/mole(3) and from dry soil surfaces(SRC) based on an experimental vapor pressure of 3.43 mm Hg(SRC), determined from experimentally-derived coefficients(4). Based on limited data, 2-chlorotoluene may be resistant to biodegradation(SRC). At 100 ppm, 2-chlorotoluene showed only 0(5)-<30%(6) biodegradation in 14 days using an activated sludge inoculum. However, a microbial blend of 10 different bacteria and 2 fungi was able to degrade 2-chlorotoluene at a concentration of 200 mg/l; complete biodegradation occurred in 3 days(7).

AQUATIC FATE: Based on a recommended classification scheme(1), measured Koc values from 170-880(2) indicates that 2-chlorotoluene may adsorb to suspended solids and sediment in water(SRC). Based on limited data, 2-chlorotoluene may be resistant to aerobic biodegradation(SRC). A second order rate constant for the microbial degradation of 2-chlorotoluene in natural water was experimentally determined to be 2.7X10-11 L/organism-hr(8). At 100 ppm, 2-chlorotoluene showed only 0(3)-<30%(4) biodegradation in 14 days using an activated sludge inoculum. However, a microbial blend of 10 different bacteria and 2 fungi was able to degrade 2-chlorotoluene at a concentration of 200 mg/l; complete biodegradation occurred in 3 days(5). 2-Chlorotoluene should volatilize from water surfaces based on a measured Henry's Law constant of 3.57X10-3 atm-cu m/mole(6). Estimated half-lives for a model river and model lake are 4 hours and 5 days, respectively(1,SRC). BCF values from 20-112(3), measured in carp, indicate that 2-chlorotoluene may moderately bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-chlorotoluene, which has a measured vapor pressure of 3.43 mm Hg at 25 °C(2), determined from experimentally-derived coefficients, will exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-chlorotoluene 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 about 9 days(3,SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 件

The substance can be absorbed into the body by inhalation.

inhalation, skin absorption, ingestion, skin and/or eye contact

Signs and Symptoms · 4 件

Cough. Shortness of breath. Dizziness.

Dry skin. Redness. Pain.

Redness. Pain.

irritation eyes, skin, mucous membrane; dermatitis; drowsiness, incoordination, anesthesia; cough; liver, kidney injury

Effluent Concentrations · 1 件

Advances waste treatment concentrates from publicly owned treatment works: Jan-Feb 1976, Orange County, CA - 0.2 ng/l; July 1975, Escondido, CA - 0.2 ng/l(1). Detected in the raw influent to a textile finishing plant waste treatment system, but not found in the final effluent(2). Identified in effluent from an organics and plastic industry and an organic chemical industry(3). Detected in chlorinated leachate from a simulated landfill lysimeter used to study codisposal of metal plating sludge with municipal solid waste(4). Identified as a principal organic hazardous constituent (POHC) in the emissions from an incinerator test burn(5).

法規制情報

TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule (40 CFR Part 716). The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. o-Chlorotoluene is included on this list.

State Drinking Water Guidelines · 2 件

(ME) MAINE 140 ug/l

(CA) CALIFORNIA 140 ug/l

Federal Drinking Water GuidelinesEPA 100 ug/l

安全データ

OEB
A
OEL
TWA: 50 ppm (250 mg/m3), STEL: 75 ppm (375 mg/m3)
wgk
2
tsca
TSCA listed
rtecs
XS9000000
ridadr
UN 2238 (CHLOROTOLUENES)

化学と産業

薬理情報

Absorption, Distribution and Excretion... APPLIED UNDER OCCLUSIVE DRESSING TO 2 GUINEA PIGS ... THERE WAS ... EVIDENCE OF SKIN ABSORPTION ...

用途と製造

Uses · 6 件

Used as a solvent and chemical intermediate; [ACGIH]

Painting (Solvents) [Category: Paint]

SOLVENT; DYESTUFF INTERMEDIATE; IN ORG SYNTHESES

INSECTICIDE & BACTERICIDE

DISINFECTANT FOR COCCIDIOSIS CONTROL

2-Chlorotoluene is a starting material in the production of 2-chlorobenzyl chloride, 2-chlorobenzaldehyde, 2-chlorobenzotrichloride, 2-chlorobenzoyl chloride and 2-chlorobenzoic acid, which are precursors for dyes, pharmaceuticals, optical brighteners, fungicides, and products of other types. 2-Chlorotoluene is also used in the production of dichlorotoluenes, 3-chlorotoluene, and o-chlorobenzonitrile.

ImpuritiesA typical analysis for 2-chlorotoluene gives >99% 2-chlorotoluene, <0.1% toluene, <0.9% 4-chlorotoluene, <0.01% 3-chlorotoluene.
U.S. Production2023: 400,000 - <550,000 lb
Industry UsesIntermediate
Methods of Manufacturing · 1 件

The batch chlorination of toluene at 50 °C in the presence of ferric chloride (or of ferric chloride-sulfur monochloride at 40 °C the values for which are given in parentheses for comparison) gives at most 83%(98%) monochlorotoluene, with 52% (52%) of the product being o-chlorotoluene, 2%(0.3%) m-chlorotoluene, and 28%(46%) p-chlorotoluene, in addition to 7%(1%) unreacted toluene and 11%(1%) dichlorotoluene. 2-Chlorotoluene and 4-chlorotoluene are separated by fractional distillation.

General Manufacturing Information · 3 件

All Other Basic Organic Chemical Manufacturing

Benzene, 1-chloro-2-methyl-: ACTIVE

MONOCHLOROTOLUENE, 60% ORTHO & 40% PARA ISOMERS, IS PRODUCED COMMERCIALLY. /MONOCHLOROTOLUENE/

応用分野 · 5 件

用途塗料?農薬?医薬中間体、中沸点溶剤

用途有機合成原料、溶剤。

説明2-Chlorotoluene can be mineralized completely by Rhodococcus, strain OCT 10 DSM 45596(T). It is used in the preparation of 3-chloro-4-methylcatechol and 4-chloro-3-methylcatechol. The oxidation of 2-chlorotoluene is very well catalyzed by the enzymes: toluene dioxygenase of P. putida F1 and chlorobenzene dioxygenase from Burkholderia, strain PS12.

使用Solvent and intermediate for organic chemicals and dyes.2-Chlorotoluene is used for permanganate oxidation to give o-chlorobenzoic acid. It is used in the preparation of 3-chloro-4-methylcatechol and 4-chloro-3-methylcatechol.2-Chlorotoluene can be used as a precursor to synthesize aryl coupling products via palladium-catalyzed Negishi cross-coupling. It can also be used in the Buchwald-Hartwig amination to synthesize arylamines.

一般的な説明Colorless liquid with an aromatic odor. Denser than water and poorly soluble in water. Hence sinks in water .

調製方法 · 2 件

製造方法The solution of cuprous chloride is cooled in an ice bath 0-5° C temperature. In this cold solution, the 2-methylbenzenediazonium is poured with constant shaking and allowing the mixture to come to room temperature. After about 10 minutes, the mixture gradually warmed with a good shaking.As the temperature rises the brown addition product begins to decompose with the evolution of nitrogen and with the formation of an oily layer of 2-chlorotoluene. When the decomposition reaction is at an end, the mixture is steam distilled, continuing the process only as long as oily droplets are present in the distillate, for the product is not appreciably soluble in water. The layer of 2-chlorotoluene is carefully separated and washed twice with an equal volume of concentrated sulfuric acid, which removes both the 2-cresol and the azo compound. Then 2-chlorotoluene is washed with water in order to remove the inorganic acid. Finally, 2-chlorotoluene is dried over calcium chloride, distilled, using an air condenser and collecting the product boiling at 153-158° C. Pure 2-chlorotoluene boils at 157° C. The yield is 25-30 g.Experiments in Organic Chemistry, L. F. Fieser, 216, 1941Highly Selective Oxidative Monochlorination To Synthesize Organic Intermediates: 2-Chlorotoluene, 2-Chloroaniline, 2-Chlorophenol, and 2-Chloro-4-methylphenol

純化方法Dry 2-chlorotoluene for several days with CaCl2, then distil it from Na using a glass helices-packed column. [Beilstein 5 IV 805.]

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]

関連反応

66 件

関連ノート

読み込み中…