페닐이소티오시아네이트

페닐이소티오시안산 · 페닐이소티오시아네이트 · 페닐 아이소티오사이아네이트 · PTC · PITC · Isothiocyanatobenzene · R1 · PIT

식별자 및 물리적 특성

CAS No.	103-72-0
분자식	C7H5NS
평균 분자량	135.19 g/mol
단동위원소 질량	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
현지명	페닐이소티오시아네이트

화학 및 물리적 성질

XLogP	3.3
극성 표면적	44.5
수소 결합 공여자 수	0
수소 결합 수용자 수	2
회전 가능 결합 수	1
무거운 원자 수	9
형식 전하	0
복잡도	121
증기압	1.5 [mmHg]10 hPa (20 °C)
Physical Description	Liquid[Merck Index] Colorless liquid[Sigma-Aldrich MSDS]
Kovats Retention Index	11631138
녹는점	−21 °C(lit.)
끓는 점	218 °C(lit.)
밀도	1.132 g/mL at 20 °C(lit.)
굴절률	n20/D 1.6515(lit.)
인화점	190 °F
저장 조건	2-8°C
용해도	물: 불용성
물리적 상태	액체
비중	1.137 (20/4℃)
색상	맑은 연한 노란색에서 노란색까지
용해도	알코올과 에테르에 용해됩니다. 물에 불용성.
Merck	14,7297
BRN	471392
헨리 상수	3.3×10-3 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
유전율	10.7(20℃)
안정성	안정적인. 타기 쉬운. 강한 산화제, 강산과 호환되지 않습니다.
InChI	1S/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H
InChIKey	QKFJKGMPGYROCL-UHFFFAOYSA-N
SMILES	S=C=Nc1ccccc1
LogP(분배 계수)	3.280
표면장력	41.5mN/m at 20°C
NIST	Benzene, isothiocyanato-(103-72-0)
EPA	Benzene, isothiocyanato- (103-72-0)

화학적 성질

colourless to pale yellow liquid with a penetrating odour

안전 및 규제

GHS 분류	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.
규제 정보	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
유해성 요약	Dermal studies of guinea pigs demonstrate severe irritation, good absorption, and sensitization

용도

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) .

일반 설명

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.

제조 및 합성 방법

제조 방법

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.