Phenyl isothiocyanate

Base Information

• Chemical Name: Phenyl isothiocyanate
• CAS No.: 103-72-0
• Deprecated CAS: 2124236-45-7
• Molecular Formula: C7H5NS
• Molecular Weight: 135.189
• Hs Code.: 2930 90 98
• European Community (EC) Number: 203-138-1
• NSC Number: 5583
• UNII: 0D58F84LSU
• DSSTox Substance ID: DTXSID0021129
• Nikkaji Number: J5.019I
• Wikipedia: Phenyl_isothiocyanate
• Wikidata: Q422311
• Metabolomics Workbench ID: 130223
• ChEMBL ID: CHEMBL309036
• Mol file: 103-72-0.mol

Synonyms:phenyl isothiocyanate;phenylisothiocyanate

Chemical Property of Phenyl isothiocyanate

Chemical Property:

• Appearance/Colour: colourless to pale yellow liquid with a penetrating odour
• Vapor Pressure: 0.163mmHg at 25°C
• Melting Point: -21 °C(lit.)
• Refractive Index: n20/D 1.6515(lit.)
• Boiling Point: 221 °C at 760 mmHg
• Flash Point: 87.8 °C
• PSA: 44.45000
• Density: 1.04 g/cm³
• LogP: 2.42090
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: water: insoluble
• Water Solubility.: Soluble in alcohol, and ether. Insoluble in water.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 135.01427034
• Heavy Atom Count: 9
• Complexity: 121

Purity/Quality:

98% ^*data from raw suppliers

PIT ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N, Xn, F
• Hazard Codes: T,N,Xn,F
• Statements: 25-34-42/43-51/53-67-65-50/53-36/37/38-22-11-38-63-23/24/25-36/38
• Safety Statements: 9-16-29-33-60-61-62-36-26-23-45-36/37/39-38-28A-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Isothiocyanates
• Canonical SMILES: C1=CC=C(C=C1)N=C=S
• Uses: 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) . Phenyl isothiocyanate acts as a derivatizing reagent for primary and secondary amines. It is used in sequencing peptides by Edman degradation and in amino acid analyses by HPLC. It is used for derivatizing N-terminal amino acids of proteins for automated sequential analysis. It is a synthon for dithiadiazafulvalenes.
• Biological Functions: Phenyl isothiocyanate (PITC) is a well-established reagent in protein chemistry since its introduction in Edman degradation. PITC reacts with primary and secondary amines under alkaline conditions within 20 min. The resulting phenylthiocarbamyl (PTC) derivatives of the amino acids are stable and do not interfere with reaction by-products during chromatography. The absorption maximum is around 245 nm with a detection limit of 1 pmol.Phenyl isothiocyanate may be employed as a derivatization reagent for high-performance liquid chromatographic (HPLC) analysis of various amphetamine derivatives in body fluids for forensic purposes.

Technology Process of Phenyl isothiocyanate

There total 384 articles about Phenyl isothiocyanate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

carbon disulfide (75-15-0,12122-00-8) + C24H20AsBrN2 → bis(diphenylarsenic) sulfide (3134-95-0) + phenyl isothiocyanate (103-72-0) + N,N-diphenylthiourea (102-08-9) + 4-Bromophenyl isothiocyanate (1985-12-2)

Guidance literature:

In benzene; for 20h; Further byproducts given;

Reference yield: 80.0%

thiochromone (6005-15-8) + benzohydroximoyl chloride (698-16-8) → 1-benzopyran-4(4H)-one (491-38-3) + phenyl isothiocyanate (103-72-0)

Guidance literature:

With triethylamine; In chloroform; at 0 ℃; for 3h;

DOI:10.1016/S0040-4020(01)89803-3

Reference yield: 63.0%

C24H20AsBrN2 → bis(diphenylarsenic) sulfide (3134-95-0) + phenyl isothiocyanate (103-72-0) + N,N-diphenylthiourea (102-08-9) + 4-Bromophenyl isothiocyanate (1985-12-2)

Guidance literature:

With carbon disulfide; In benzene; for 20h; Further byproducts given;

upstream raw materials:

carbon disulfide

triisopentyl-phenylimino-phosphorane

triethyl-phenylimino-phosphorane

3-n-butyl-1-phenylthiourea

Downstream raw materials:

azetidine-1-carbothioic acid anilide

1-phenyl-3-(2-(piperidin-1-yl)ethyl)thiourea

3,3-bis-[(N'-phenyl-thioureido)-methyl]-oxetane

5-methyl-pyrrole-2-carbothioic acid anilide

Refernces

• 1、 Wong, Rince,Dolman, Sarah J.. "Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts". . p. 3969 - 3971. Retrieved 2007.
• 2、 G?tz, Kathrin H.,Hacker, Stephan M.,Mayer, Daniel,Dürig, Jan-Niklas,Stenger, Steffen,Marx, Andreas. "Inhibitors of the Diadenosine Tetraphosphate Phosphorylase Rv2613c of Mycobacterium tuberculosis". . p. 2682 - 2689. Retrieved 2017.
• 3、 Kim, Jae Nyoung,Ryu, Eung K.. "A convenient synthesis of isothiocyanates from nitrile oxides". . p. 8283 - 8284. Retrieved 1993.
• 4、 Shan,Bian,Su,Liang. "A facile one-pot preparation of isothiocyanates from N-formamides and sulfur powder with bis (Trichloromethyl) carbonate". . p. 283 - 286. Retrieved 2004.
• 5、 Fujiwara, Shin-Ichi,Shin-Ike, Tsutomu,Sonoda, Noboru,Aoki, Minoru,Okada, Kazuhiro,Miyoshi, Noritaka,Kambe, Nobuaki. "Novel selenium catalyzed synthesis of isothiocyanates from isocyanides and elemental sulfur". . p. 3503 - 3506. Retrieved 1991.
• 6、 Nath, Jayashree,Ghosh, Harisadhan,Yella, Mamesh,Patel, Bhisma K.. "Molecular iodine mediated preparation of isothiocyanates from dithiocarbamic acid salts". . p. 1849 - 1851. Retrieved 2009.
• 7、 Seelam, Mohan,Shaikh, Baji Vali,Tamminana, Ramana,Kammela, Prasada Rao. "An efficient methodology for the synthesis of thioureas from amine mediated by a cobalt source". . p. 5297 - 5300. Retrieved 2016.
• 8、 Yu, Jiao,Lin, Jin-Hong,Xiao, Ji-Chang. "Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines". . p. 16669 - 16673. Retrieved 2017.
• 9、 Scattolin, Thomas,Pu, Maoping,Schoenebeck, Franziska. "Investigation of (Me4N)SCF3 as a Stable, Solid and Safe Reservoir for S=CF2 as a Surrogate for Thiophosgene". . p. 567 - 571. Retrieved 2018.
• 10、 Kaboudin, Babak,Jafari, Ehsan. "Diethyl chlorophosphate: A mild and versatile reagent for the one-pot preparation of isothiocyanates from amines". . p. 2683 - 2685. Retrieved 2008.