フェニルイソチオシアナート
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
識別子と物理属性
| CAS No. | 103-72-0 |
|---|---|
| 分子式 | C7H5NS |
| 平均分子量 | 135.19 g/mol |
| 単同位体質量 | 135.01427034 g/mol |
| SMILES | S=C=Nc1ccccc1 |
| InChIKey | QKFJKGMPGYROCL-UHFFFAOYSA-N |
| PubChem CID | 7673 |
| ChEMBL | CHEMBL309036 |
| ChEBI | CHEBI:85103 |
| EC No. | 203-138-1 |
| DTXSID | DTXSID0021129 |
| 現地名 | フェニルイソチオシアナート |
化学・物理的性質
| XLogP | 3.3 |
|---|---|
| 極性表面積 | 44.5 |
| 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 |
| 形式電荷 | 0 |
| 複雑度 | 121 |
| 蒸気圧 | 1.5 [mmHg]10 hPa (20 °C) |
| Physical Description | Liquid[Merck Index] Colorless liquid[Sigma-Aldrich MSDS] |
| Kovats Retention Index | 11631138 |
| 融点 | −21 °C(lit.) |
| 沸点 | 218 °C(lit.) |
| 密度 | 1.132 g/mL at 20 °C(lit.) |
| 屈折率 | n20/D 1.6515(lit.) |
| 引火点 | 190 °F |
| 貯蔵条件 | 2-8°C |
| 溶解度 | 水：不溶アルコール、エーテルに可溶。水に不溶。 |
| 外観・状態 | 液体 |
| 比重 | 1.137 (20/4℃) |
| 色 | 澄んだ淡い黄色～黄色 |
| Merck | 14,7297 |
| BRN | 471392 |
| ヘンリー定数 | 3.3×10-3 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 誘電率 | 10.7(20℃) |
| 安定性 | 安定。可燃性。強酸化剤、強酸とは相容れない。 |
| InChI | 1S/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H |
| InChIKey | QKFJKGMPGYROCL-UHFFFAOYSA-N |
| SMILES | S=C=Nc1ccccc1 |
| LogP（分配係数） | 3.280 |
| 表面張力 | 41.5mN/m at 20°C |
| CAS データベース | 103-72-0(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzene, isothiocyanato-(103-72-0) |
| EPAの化学物質情報 | Benzene, isothiocyanato- (103-72-0) |
化学的特性
colourless to pale yellow liquid with a penetrating odour
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 0.5% (1 of 214) of reports.DangerH301 (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. |
|---|---|
| 規制情報 | Chemical: Benzene, isothiocyanato-Status: Active Update: 10-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26134Phenyl isothiocyanate: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Dermal studies of guinea pigs demonstrate severe irritation, good absorption, and sensitization |
用途
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.
製法・合成法
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.]