기본 정보
- 표준 SMILES
S=C=Nc1ccccc1- InChIKey
QKFJKGMPGYROCL-UHFFFAOYSA-N- 분자식
- C7H5NS
- 평균 분자량
- 135.19 g/mol
- 단동위원소 질량
- 135.01427034
이름 및 식별자
- 우선 이름
- Phenyl Isothiocyanate
- IUPAC
- isothiocyanatobenzene
- 현지명
- 페닐이소티오시아네이트
- 영어명
- Phenyl isothiocyanate
- 분자식
- C7H5NS
- 분자량
- 135.19
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
103-72-0- PubChem CID
- 7673
- DTXSID
DTXSID0021129- ChEMBL
CHEMBL309036- ChEBI
CHEBI:85103- UNII
- 0D58F84LSU
- EC Number
- 203-138-1
- Nikkaji
- J5.019I
물성
구조 계산 물성
- XLogP
- 3.3
- 극성 표면적
- 44.5 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 1
- 무거운 원자 수
- 9
- 형식 전하
- 0
- 복잡도
- 121
실험 및 물리화학적 성질
Kovats Retention Index
1163
1138
물리화학적 성질
- 녹는점
- 21 °C · −21 °C(lit.)
- 끓는 점
- 218 °C · 218 °C(lit.)
- 밀도
- 1.132 g/mL · 1.132 g/mL at 20 °C(lit.)
- 증기압
- 10 hPa · 10 hPa (20 °C)
- 굴절률
- 20 · n20/D 1.6515(lit.)
- 인화점
- 190 °F · 190 °F
- 저장 조건
- 2 · 2-8°C
- 용해도
- 물: 불용성
- 물리적 상태
- 액체
- Specific Gravity
- 1.137 · 1.137 (20/4℃)
- 색상
- 맑은 연한 노란색에서 노란색까지
- 수용성
- 알코올과 에테르에 용해됩니다. 물에 불용성.
- Merck
- 14 · 14,7297
- BRN
- 471392 · 471392
- Henry's Law Constant
- 3.3 · 3.3×10-3 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Dielectric constant
- 10.7 · 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
- 3.28 · 3.280
- 표면장력
- 41.5 mN/m · 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
GHS Classification
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.
유해성 정보
Regulatory Information
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
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]
독성 정보
Treatment
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
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
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.
Toxicity Summary
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)
RAIS Toxicity Values
0.0002
SCREEN Current
0.002
PPRTV Current
EPA Provisional Peer-Reviewed Toxicity Values
Phenyl Isothiocyanate
2 x 10^-3 mg/kg-day
PDF Document
Inadequate information to assess carcinogenic potential
2009
Hazard Quotient Level 0.1 or Cancer Risk Level 1E-06
1.60e+01
2.30e+02
2.60e+00
1.5E+01(G)
1.70e-03
2.00e-04
Hazard Quotient Level 3 or Cancer Risk Level 1E-04
4.70e+01
7.00e+02
7.90e+00
1.5E+01 (G)
2.00e-04
Volatile
규제 정보
Regulatory Information
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
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- NX9275000
- ridadr
- UN 1993 3/PG 2
- 독성
- LD50 orally in Rabbit: 157 mg/kg
- HS 번호
- 2930 90 98
- risk_code
- 25-34-42/43-51/53-67-65-50/53-36/37/38-22-11-38-63-23/24/25-36/38
- hazard_code
- T,N,Xn,F
- safety_code
- 9-16-29-33-60-61-62-36-26-23-45-36/37/39-38-28A-36/37
- 포장분류
- II
- 위험 등급
- 6.1
- 기존화학 물질
- KE-21760
- F 고인화성물질
- 19
- Hazard Classifications
- Acute Tox. 3 OralResp. Sens. 1Skin Corr. 1BSkin Sens. 1
- 스토리지 클래스
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
화학 및 산업
약리 정보
Metabolism/Metabolites
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)
용도 및 제조
Uses
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)
응용 분야
용도Phenyl 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 설명Phenyl 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 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.
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
정의ChEBI: 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.
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