イソシアン酸フェニル

Phenyl isocyanate

HCID 7672CAS 103-71-9

基本情報

標準SMILES
O=C=Nc1ccccc1
InChIKey
DGTNSSLYPYDJGL-UHFFFAOYSA-N
分子式
C7H5NO
平均分子量
119.12 g/mol
単同位体質量
119.03711378

名称と識別子

優先名称
Phenyl isocyanate
IUPAC
isocyanatobenzene
現地名
イソシアン酸フェニル
英語名
Phenyl isocyanate
分子式
C7H5NO
分子量
119.12

名称と別名

PHENYL ISOCYANATEIsocyanatobenzene103-71-9Benzene, isocyanato-PhenylcarbimideCarbanilphenylisocyanatePhenyl carbonimideFenylisokyanatIsocyanic acid, phenyl esterMondur PPhNCO
名称をさらに表示
イソシアン酸フェニルイソシアン酸フェニルエステルフェニルイソシアネ-トフェニルイソシアネートフェニルイソシアナートイソシアン酸フェニル,フェニル=イソシアナートpicAdditive tiYQSBZN-Phenylisocyanate1-Isocyanatobenzenemondurp
Karbanil196GO6BSOHDTXSID5051521CHEBI:53806NSC-74454RefChem:172961DTXCID1030070203-137-6

データベース識別子

CAS
103-71-9
PubChem CID
7672
DTXSID
DTXSID5051521
ChEBI
CHEBI:53806
UNII
196GO6BSOH
EC Number
203-137-6
Nikkaji
J5.018K

物性

構造計算による物性

XLogP
2.7
極性表面積
29.4 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
1
重原子数
9

実験および物理化学的性質

OdorAcrid odor
Density · 4 件

1.08870 at 25.9 °C/4 °C; 1.0956 at 19.6 °C/4 °C; 1.092 at 15 °C/4 °C; 1.101 at 11.6 °C/4 °C

Density: 1.0956 g/cu cm at 20 °C

Relative density (water = 1): 1.095

1.0956 @ 19.6°C

Color/FormLiquid
Solubility · 2 件

Decomposes in water, alcohol; very soluble in ether

Solubility in water: reaction

Flash Point · 3 件

132 °F (55.5 °C) (Open Cup)

51 °C c.c.

132 °F (open cup)

Boiling Point · 4 件

158-168 °C

BP: 55 °C at 13 mm Hg

158-168 °C

325.4 °F

物理化学的性質

融点
-30 °C · -30 °C (lit.)
沸点
162 · 162-163 °C (lit.)
比重(密度)
1.096 g/mL · 1.096 g/mL at 25 °C (lit.)
蒸気圧
1.4 mm · 1.4 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.535(lit.)
闪点
132 °F · 132 °F

化学的性質

化学的特性Phenyl isocyanate is a colorless liquid with an irritating odor.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H226 (85.2%): Flammable liquid and vapor [Warning Flammable liquids];H302 (90.5%): Harmful if swallowed [Warning Acute toxicity, oral];H314 (89%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H317 (93.1%): May cause an allergic skin reaction [Warning Sensitization, Skin];H318 (62.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H330 (90.5%): Fatal if inhaled [Danger Acute toxicity, inhalation];H334 (97.4%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory];H335 (67%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H400 (62.9%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (46%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard];H411 (18.2%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P333+P317, P342+P316, P362+P364, P363, P370+P378, P391, P403, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 391 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 5 件

Chemical: Benzene, isocyanato-

Benzene, isocyanato- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, isocyanato- 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: 14-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33957;Status: Active Update: 03-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/12563;Status: Active Update: 01-03-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/8140

Phenyl isocyanate: HSNO Approval: HSR004628 Approved with controls

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 LabelPoison Inhalation Hazard Flammable Liquid
Fire Hazards · 3 件

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:;HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapors may travel to source of ignition and flash back. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Corrosives in contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. (ERG, 2024)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;· Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.;· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapors may travel to source of ignition and flash back.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff.;· Corrosives in contact with metals may evolve flammable hydrogen gas.;· Containers may explode when heated or if contaminated with water.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 51 °C explosive vapour/air mixtures may be formed.

Fire Potential · 2 件

Flammable liquid when exposed to heat or flame ... .

Moderate fire risk.

Health Hazards · 2 件

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:;TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators (cause eye irritation and flow of tears). Reaction with water or moist air may release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination. (ERG, 2024)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.;· Bromoacetates and chloroacetates are extremely irritating/lachrymators (cause eye irritation and flow of tears).;· Reaction with water or moist air may release toxic, corrosive or flammable gases.;· Reaction with water may generate much heat that will increase the concentration of fumes in the air.;· Fire will produce irritating, corrosive and/or toxic gases.;· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:;Note: Most foams will react with the material and release corrosive/toxic gases. CAUTION: For Acetyl chloride (UN1717), use CO2 or dry chemical only.;SMALL FIRE: CO2, dry chemical, dry sand, alcohol-resistant foam.;LARGE FIRE: Water spray, fog or alcohol-resistant foam. FOR CHLOROSILANES, DO NOT USE WATER; use alcohol-resistant foam. If it can be done safely, move undamaged containers away from the area around the fire. Avoid aiming straight or solid streams directly onto the product.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

Use dry powder, carbon dioxide, alcohol-resistant foam. NO water. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.

First Aid Measures · 4 件

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

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

Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. 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.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.;· All equipment used when handling the product must be grounded.;· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.;· Stop leak if you can do it without risk.;· A vapor-suppressing foam may be used to reduce vapors.;· FOR CHLOROSILANES, use alcohol-resistant foam to reduce vapors.;· DO NOT GET WATER on spilled substance or inside containers.;· Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material.;· Prevent entry into waterways, sewers, basements or confined areas.;Small Spill;· Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain.;· Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal.

First Aid · 2 件

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:;Refer to the "General First Aid" section. Specific First Aid: For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required. (ERG, 2024)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.

Safe StorageFireproof. Keep in a well-ventilated room. Dry.
Exposure Control and Personal Protection · 2 件

· Wear positive pressure self-contained breathing apparatus (SCBA).;· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.;· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

毒性情報

Treatment · 1 件

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

Health Effects · 1 件

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Environmental Fate · 3 件

TERRESTRIAL FATE: Isocyanates hydrolyze rapidly in water(1); therefore, soil mobility, biodegradation, and volatilization of phenyl isocyanate in moist soil are not expected to be important environmental fate processes(SRC). Volatilization of phenyl isocyanate from dry soils is expected based on an extrapolated vapor pressure of 2.6 mm Hg at 25 °C(2).

AQUATIC FATE: Since isocyanates hydrolyze rapidly in water(1) (hydrolysis half-lives of phenyl isocyanate range from 20 seconds(2) to 75.5 minutes)(3), biodegradation, aquatic bioconcentration, volatilization, and adsorption to sediment of phenyl isocyanate are not expected to be important fate processes(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenyl isocyanate, which has an extrapolated vapor pressure of 2.6 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase phenyl isocyante 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 days(SRC), calculated from its rate constant of 2.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Adverse Effects · 1 件

Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.;Skin Sensitizer - An agent that can induce an allergic reaction in the skin.;Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

Exposure Routes · 2 件

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

Oral (L96) ; inhalation (L96) ; dermal (L96)

Toxicity Summary · 2 件

IDENTIFICATION AND USE: Phenyl isocyanate is a liquid with an acrid odor. It decomposes in water, alcohol; very soluble in ether. It is used as a chemical intermediate and as a reagent. HUMAN EXPOSURE AND TOXICITY: Workers exposed to phenyl isocyanate showed increases in asthmatic symptoms. Exposure to isocyanates is irritating to the skin, mucous membranes, eyes and respiratory tract. Contact dermatitis can result in symptoms such as rash, itching, hives and swelling of the extremities. Phenyl isocyanate is a potent chemical sensitizer. A worker suspected of having isocyanate induced asthma/sensitization will exhibit traditional symptoms of acute airway obstruction coughing, wheezing, shortness of breath, tightness of chest and nocturnal awakening. Isocyanate induced hypersensitivity pneumonitis symptoms are flu like which includes shortness of breath, nonproductive cough, fever, chills sweats and malaise and nausea. An irreversible decline in pulmonary function and interstitial fibrosis have also been observed. At high doses isocyanates affect the mucous membranes of the respiratory tract and may lead to fatal pulmonary edema or chromic catarrh. ANIMAL STUDIES: The toxic effects of repeated inhalation exposures to phenyl isocyanate vapors in male rats was conducted. Animals experienced decreased weight gain, hypoactivity, hypothermia, and signs of respiratory tract irritation. There was delayed onset of mortality, and changes in organ weights. Pulmonary function tests demonstrated decreased forced expiratory flow volume. Arterial hypoxia was also observed. Pregnant mice were given phenyl isocyanate on select days of gestation. Phenyl isocyanate did demonstrate embryotoxicity. In a micronucleus assay, male and female mice received a single administration of phenyl isocyanate ip; there was an altered ratio between polychromatic and normochromatic erythrocytes in the bone marrow, and no clastogenic effect was observed. Phenyl isocyanate did not cause significant indu

Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

法規制情報

Regulatory Information · 5 件

Chemical: Benzene, isocyanato-

Benzene, isocyanato- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, isocyanato- 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: 14-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33957;Status: Active Update: 03-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/12563;Status: Active Update: 01-03-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/8140

Phenyl isocyanate: HSNO Approval: HSR004628 Approved with controls

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.)

TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 10/29/90; Reporting date: 12/27/90.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. 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. Benzene, isocyanato- is included on this list. Effective date: 10/29/90; Sunset date: 6/30/98.

安全データ

F
21
wgk
2
tsca
TSCA listed
rtecs
DA3675000
ridadr
UN 2487
hs_code
29291000

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

用途と製造

Uses · 2 件

Used as a chemical intermediate and analytical reagent; [Hawley]

Reagent for identifying alcohols and amines, intermediate

U.S. Production · 2 件

2023: 50,000 - <250,000 lb;2022: 250,000 - <550,000 lb;2021: 250,000 - <550,000 lb;2020: 50,000 - <250,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5363]

Industry UsesAdhesion/cohesion promoter
Methods of ManufacturingPrepared by passing carbonyl chloride into a hot solution of aniline in toluene, saturated with hydrochloric acid.
Household ProductsInformation on 1 consumer products that contain Phenyl isocyanate in the following categories is provided:;• Home Maintenance
General Manufacturing Information · 3 件

Adhesive Manufacturing

Benzene, isocyanato-: ACTIVE

Nature of the binding group on the protein may be studied by reacting the protein with a series of "covering" groups. ...protein modifying reagents which have been used including ... phenyl isocyanate ...

応用分野 · 3 件

用途脱水剤,ウレタン原料,アルコール?フェノール類の確認試薬 (NITE CHRIP)

使用Phenyl Isocyanate is also used in the synthesis of cyanopyridine derivatives in the search for anticancer compounds. It is also used in the synthesis of aminobenzimidazole derivatives with phenylcyclohexyl acetic groups showing antiobesity-antidiabetic activity.

一般的な説明A colorless liquid. About the same density as water. Very toxic by ingestion, inhalation or skin absorption. Very irritating to skin, eyes and mucous membranes. Flash point 132°F.

調製方法 · 2 件

製造方法To a mixture of aniline hydrochloride (12.95 g, 0.1 mol) and dry dioxane (100 mL) was added diphosgene (6.3 mL, 10.4 g, 0.05 mol). The mixture was heated to 60 °C; after stirring for 1.5 h, it became a clear solution. Heating was stopped after 3.5 h and the solvent was removed under reduced pressure. The residue was distilled at 70–73.5 °C (36 mmHg) to give 10.6 g (89%) of phenyl isocyanate. It could be redistilled almost quantitatively, bp 75–77 °C(39 mmHg) or 55–57 °C(16 mmHg).

純化方法Distil phenylisocyanate under reduced pressure from P2O5. [Beilstein 12 IV 864.]

補足説明

定義ChEBI: An isocyanate composed of a benzene ring bearing a single isocyanato substituent.

関連反応

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