フェニルイソチオシアナート

Phenyl Isothiocyanate

HCID 7673CAS 103-72-0

基本情報

標準SMILES
S=C=Nc1ccccc1
InChIKey
QKFJKGMPGYROCL-UHFFFAOYSA-N
分子式
C7H5NS
平均分子量
135.19 g/mol
単同位体質量
135.01427034

名称と識別子

優先名称
Phenyl Isothiocyanate
IUPAC
isothiocyanatobenzene
現地名
フェニルイソチオシアナート
英語名
Phenyl isothiocyanate
分子式
C7H5NS
分子量
135.19

名称と別名

IsothiocyanatobenzenePHENYL ISOTHIOCYANATE103-72-0PhenylisothiocyanatePITCThiocarbanilBenzene, isothiocyanato-PhenylsenfoelIsothiocyanic acid phenyl esterBenzene-1-isothiocyanatePhenyl thioisocyanateIsothiocyanic acid, phenyl ester
名称をさらに表示
イソチオシアン酸フェニル(フェニルイミノ)メタンチオンフェニルチオイソシアナートチオカルバニルN-(チオキソメチレン)アニリンフェニルからし油フェニルマスタードオイルフェニルイソチオシアネートフェニルゼンフオイルイソチオシアナトベンゼンフェニルイソチオシアネ-トイソチオシアン酸フェニル(PITC)イソチオシアン酸フェニル 溶液フェニル=イソチオシアナートフェニル=チオシアナートフェニルイソチオシアナート(イソシアナトスルファニル)ベンゼン(2S,3R,4S,5S,6R)-2-{[(2S)-2-[(1S,3aR,3bR,5S,5aR,9aR,9bR,11aR)-5-{[(2R,3R,4S,5S,6R)-4,5-ジヒドロキシ-6-(ヒドロキシメチル)-3-{[(2S,3R,4S,5S,6R)-3,4,5-トリヒドロキシ-6-(ヒドロキシメチル)オキサン-2-イル]オキシ}オキサン-2-イル]オキシ}-7,11-ジヒドロキシ-3a,3b,6,6,9a-ペンタメチル-ヘキサデカヒドロ-1H-シクロペンタ[a]フェナントレン-1-イル]-6-メチルヘプタ-5-エン-2-イル]オキシ}-6-(ヒドロキシメチル)オキサン-3,4,5-トリオール3,12-ジヒドロキシ-6α-(2-O-β-D-グルコピラノシル-β-D-グルコピラノシルオキシ)-20-β-D-グルコピラノシルオキシダンマラ-24-エンスルホカルバニルPTCR1PITPhenyl thiocyanatePhenyl isothiocyanate,PITCPHENYL ISOTHIOCYANATE SOLUTION, FOR PROT.SEQ. ANAL.RR1H174
FenylisothiokyanatDTXSID0021129CHEBI:851030D58F84LSUNSC-5583DTXCID501129RefChem:57537Phenylisothiocyanate 1533

データベース識別子

CAS
103-72-0
PubChem CID
7673
DTXSID
DTXSID0021129
ChEMBL
CHEMBL309036
ChEBI
CHEBI:85103
UNII
0D58F84LSU
EC Number
203-138-1
Nikkaji
J5.019I

物性

構造計算による物性

XLogP
3.3
極性表面積
44.5 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

Vapor Pressure1.5 [mmHg]
Physical DescriptionLiquid; [Merck Index] Colorless liquid; [Sigma-Aldrich MSDS]
Kovats Retention Index · 2 件

1163

1138

物理化学的性質

融点
21 °C · −21 °C(lit.)
沸点
218 °C · 218 °C(lit.)
比重(密度)
1.132 g/mL · 1.132 g/mL at 20 °C(lit.)
蒸気圧
10 hPa · 10 hPa (20 °C)
屈折率
20 · n20/D 1.6515(lit.)
闪点
190 °F · 190 °F

化学的性質

化学的特性colourless to pale yellow liquid with a penetrating odour

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 0.5% (1 of 214) of reports.

Danger

H301 (82.2%): Toxic if swallowed [Danger Acute toxicity, oral];H314 (79.4%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation];H317 (79%): May cause an allergic skin reaction [Warning Sensitization, Skin];H318 (54.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H334 (76.2%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory];H341 (54.2%): Suspected of causing genetic defects [Warning Germ cell mutagenicity];H361 (54.2%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];H400 (21.5%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (24.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P203, P233, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P333+P317, P342+P316, P362+P364, P363, P391, P403, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 214 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 214 reports by companies.;There are 10 notifications provided by 213 of 214 reports by companies with hazard statement code(s).;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

Regulatory Information · 3 件

Chemical: Benzene, isothiocyanato-

Status: Active Update: 10-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26134

Phenyl isothiocyanate: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 件

Dermal studies of guinea pigs demonstrate severe irritation, good absorption, and sensitization; Effects on thyroid function (decreased serum T4 levels) observed in 4-week oral study of rats; [EPA - PPRTV] Causes burns and lachrymation; May cause skin and respiratory sensitization; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion; Targets the kidney and bladder; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesAcute Tox. 3 (82.2%);Skin Corr. 1B (79.4%);Skin Sens. 1 (79%);Eye Dam. 1 (54.7%);Resp. Sens. 1 (76.2%);Muta. 2 (54.2%);Repr. 2 (54.2%);Aquatic Acute 1 (21.5%);Aquatic Chronic 1 (24.3%)

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

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)

Adverse Effects · 1 件

Dermatotoxin - Skin burns.;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.;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

Exposure RoutesInhalation (L96) ; oral (L96) ; dermal (L96)
Toxicity Summary · 1 件

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)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

法規制情報

Regulatory Information · 3 件

Chemical: Benzene, isothiocyanato-

Status: Active Update: 10-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26134

Phenyl isothiocyanate: Does not have an individual approval but may be used under an appropriate group standard

安全データ

F
19
wgk
3
tsca
TSCA listed
rtecs
NX9275000
ridadr
UN 1993 3/PG 2
毒性
LD50 orally in Rabbit: 157 mg/kg

毒性と防護

毒性LD50 87 mg/kg(マウス,経口).

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 to derive primary and secondary amines, in sequencing of peptides by Edman degradation, and in amino acid analysis by HPLC; [Merck Index]

Phenyl isothiocyanate is a reagent used in reversed phase high-performance liquid chromatography (HPLC). (L197)

General Manufacturing InformationBenzene, isothiocyanato-: ACTIVE
応用分野 · 4 件

解説フェニルイソチオシアナート,可燃性の無色の液体(着火温度38 ℃).融点-21 ℃,沸点221 ℃,95 ℃(1.6 kPa).d425"1.13.nD23"1.649.水に不溶,有機溶媒に可溶.アミノ酸と反応してフェニルチオヒダントインを生成する.アミノ酸の自動分析試薬(エドマン分解)に用いられる.催奇形性がある.森北出版「化学辞典(第2版)

用途フェニルイソチオシアネート (PITC、イソチオシアン酸フェニル)は、逆相高速液体クロマトグラフィーに利用される試薬である。PITCはオルトフタルアルデヒド(OPA)以下の感度で、自動化出来ない。OPAと異なり、第二級アミンを分析する事が可能である。 エドマン分解に使用されるエドマン試薬としても知られる。 リノグリリドの合成にも利用される。

使用Phenyl isothiocyanate is the reagent of choice in automated Edman degradation systems. However, this reagent is highly toxic and for manual modification other reagents are preferred such as dimethy laminoazobenzene isothiocyanate (Chang, 1983; Wang et al, 2000) or trifluoroethyl isothiocyanate (Bartlet-Jones et al, 1994). This last reagent has the advantage of being volatile, so that the excess of reagent is easily removed by vacuum before MS analysis (Spengler, 1997). This compound was used successfully during seven successive cycles of manual cleavage coupled with MS analysis. Nevertheless, the high reactivity of such compounds seems to shows artefactual modification such as“acetylation' of the hydroxyl groups of the Ser and Thr. Allyl isothiocyanate shows better selectivity, but again this reagent is toxic and difficult to use in manual approaches (Gu & Preswich, 1997) .

一般的な説明Phenyl isothiocyanate is an aromatic isothiocyanate. It participates in dehydration reactions of alcohols. It is widely used for synthesis of various biologically important heterocyclic compounds.

調製方法 · 2 件

製造方法Synthetic procedure for phenyl isothiocyanate in 1-mol scaleInto a 2-L jacketed flask, 91.2 g of CS2 (1.2 mol) was dropwise added to a mixture of aniline (93.0 g, 1.0 mol) and K2CO3 (276.0 g, 2.0 mol) in 700 mL of water at room temperature within a period of 2.5 h. After the addition was complete, the mixture was stirred another 2 h. Then, the mixture was cooled to 0 °C, and a solution of 92.3 g of TCT (0.5 mol) in 450 mL of CH2Cl2 was dropwise added within 4 h. After the addition was complete, the mixture was stirred another 1 h to complete the conversion. The resulting mixture was basified to pH >11 with 250 mL of 6 N NaOH and yielded a clear solution. The organic layer was separated and the aqueous layer was extracted with 150 mL of CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent of filtrate was removed via distillation under atmospheric pressure with a 25-cm Vigreux column. The residue was vacuum distilled and the desired product fraction was collected at 72–74 °C/1 mmHg. Finally, 127.0 g of colorless liquid (94%) was obtained.

純化方法It is insoluble in H2O, but soluble in Et2O and EtOH. If impure (due to formation of thiourea), then steam distil it into a receiver containing 5-10mL of N H2SO4. Separate the oil, dry over CaCl2 and distil it under vacuum. [Dains et al. Org Synth Coll Vol I 447 1941, Beilstein 12 IV 867.]

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補足説明

定義ChEBI: Phenyl isothiocyanate is an isothiocyanate having a phenyl group attached to the nitrogen; used for amino acid sequencing in the Edman degradation. It has a role as an allergen and a reagent.

関連反応

334 件

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