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Phenyl isothiocyanate

CAS No.
103-72-0
Chemical Name:
Phenyl isothiocyanate
Synonyms
PTC;Isothiocyanatobenzene;PITC;R1;Phenyl isothiocyanate,PITC;PHENYL ISOTHIOCYANATE SOLUTION, FOR PROT.SEQ. ANAL.;PIT;H174;JPO2;I-TAC
CBNumber:
CB5733806
Molecular Formula:
C7H5NS
Molecular Weight:
135.19
MDL Number:
MFCD00004798
MOL File:
103-72-0.mol
MSDS File:
SDS
Last updated:2024-08-21 22:41:43

Phenyl isothiocyanate Properties

Melting point −21 °C(lit.)
Boiling point 218 °C(lit.)
Density 1.132 g/mL at 20 °C(lit.)
vapor pressure 10 hPa (20 °C)
refractive index n20/D 1.6515(lit.)
Flash point 190 °F
storage temp. 2-8°C
solubility water: insoluble
form liquid
Specific Gravity 1.137 (20/4℃)
color Clear pale yellow to yellow
Water Solubility Soluble in alcohol, and ether. Insoluble in water.
Sensitive Moisture Sensitive
Merck 14,7297
BRN 471392
Dielectric constant 10.7(20℃)
Stability Stable. Combustible. Incompatible with strong oxidizing agents, strong acids.
InChIKey QKFJKGMPGYROCL-UHFFFAOYSA-N
LogP 3.280
CAS DataBase Reference 103-72-0(CAS DataBase Reference)
FDA UNII 0D58F84LSU
NIST Chemistry Reference Benzene, isothiocyanato-(103-72-0)
EPA Substance Registry System Benzene, isothiocyanato- (103-72-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS06,GHS08
Signal word  Danger
Hazard statements  H301-H314-H317-H334
Precautionary statements  P261-P270-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Hazard Codes  T,N,Xn,F
Risk 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
RIDADR  UN 1993 3/PG 2
WGK Germany  3
RTECS  NX9275000
19
TSCA  Yes
HS Code  2930 90 98
HazardClass  6.1
PackingGroup  II
Toxicity LD50 orally in Rabbit: 157 mg/kg
NFPA 704
2
3 1

Phenyl isothiocyanate price More Price(47)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich CB_99043005 R1 99043005, Reactivity: Anti-HLA-DQ 99043005-DNA-5UG $390 2024-03-01 Buy
Sigma-Aldrich CB_99043005 R1 99043005, Reactivity: Anti-HLA-DQ 1VIAL $821 2024-03-01 Buy
Sigma-Aldrich 8.07028 Phenyl isothiocyanate for synthesis 103-72-0 100mL $79.2 2024-03-01 Buy
Sigma-Aldrich 8.07028 Phenyl isothiocyanate for synthesis 103-72-0 250ML $167 2024-03-01 Buy
Sigma-Aldrich 139742 Phenyl isothiocyanate reagent grade, 98% 103-72-0 100g $74.1 2024-03-01 Buy
Product number Packaging Price Buy
CB_99043005 99043005-DNA-5UG $390 Buy
CB_99043005 1VIAL $821 Buy
8.07028 100mL $79.2 Buy
8.07028 250ML $167 Buy
139742 100g $74.1 Buy

Phenyl isothiocyanate Chemical Properties,Uses,Production

Chemical Properties

colourless to pale yellow liquid with a penetrating odour

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) .

Uses

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.

Preparation

Synthetic procedure for phenyl isothiocyanate in 1-mol scale
Into 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.

Definition

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.

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.

Synthesis Reference(s)

Tetrahedron Letters, 38, p. 1597, 1997 DOI: 10.1016/S0040-4039(97)00121-4
Synthesis, p. 300, 1989 DOI: 10.1055/s-1989-27231
Tetrahedron Letters, 23, p. 447, 1982 DOI: 10.1016/S0040-4039(00)86856-2

General Description

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.

Purification Methods

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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View Lastest Price from Phenyl isothiocyanate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Phenyl isothiocyanate pictures 2024-10-11 Phenyl isothiocyanate
103-72-0
US $5.00-2.00 / KG 1KG 99% 10000kg Hebei Chuanghai Biotechnology Co,.LTD
Phenyl isothiocyanate pictures 2023-10-09 Phenyl isothiocyanate
103-72-0
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
PHENYL ISOTHIOCYANATE pictures 2021-07-02 PHENYL ISOTHIOCYANATE
103-72-0
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
Phenyl isothiocyanate solution,PITC Phenyl isothiocyanat Phenyl isothiocyanate, 98% 100GR Benzene,isothiocyanato- Benzene-1-isothiocyanate Fenylisothiokyanat iso-Thiocyana-tobenaene isothiocyanato-benzen isothiocyanato-Benzene AKOS BBS-00004438 Phenylthiocarbonimide PHENYL ISOTHIOCYANATE, SUITABLE FOR PROT EIN SEQUENCING, 99% PHENYL ISOTHIOCYANATE SOLUTION, FOR PROT .SEQ. ANAL., 40 ML PHENYL ISOTHIOCYANATE SOLUTION FOR PROT. PHENYL ISOTHIOCYANATE, 5% SOLUTION*IN N- HEPTANE PHENYL ISOTHIOCYANATE, FOR PROTEIN SEQ. ANALYSIS, 10 X 1 ML PHENYL ISOTHIOCYANATE, FOR PROTEIN SEQUE NTIAL ANALYSIS PHENYL ISOTHIOCYANATE PROTEIN*SEQUENCING GRADE Phenyl #niso-thiocyanate PHENYL ISOTHIOCYANATE IN N-HEPTANE PROTE Phenyl isothiocyanate, sequenation grade, 99% phenyl isothiocyanate solution PHENYL MUSTARD OIL PHENYL ISOTHIOCYANATE Phenyl isothiocyanate Phenyl mustard oil PHENYL ISOTHIOCYANATE PROTEIN SEQUENCING REAGENT PIT THIOCARBANIL ISOTHIOCYANIC ACID PHENYL ESTER EDMAN'S REAGENT Phenyl isothiocyanate 99%, for protein sequencing Phenyl isothiocyanate for HPLC derivatization, the detection of alcohols and amines, >=99.0% Phenyl isothiocyanate reagent grade, 98% Platinum on activated charcoal hydrogenation catalyst Platinum on activated charcoal hydrogenation catalyst, 5% Pt basis PHENYL ISOTHIOCYANATE PROTEIN*SEQUEN PHENYL ISOTHIOCYANATE, 5% SOLUTION*I Isothiocyanatobenzene, PITC PITC (Phenylisothiocyanate) Phenyl isothiocyanate, for sequential analysis Isothiocyanate benzene ester H174 I-TAC SCYB9B Inteferon-inducible T cell α-chemoattractant Protein 9 (IP9) SCYB11 RET (658-end), active, GST tagged human CDCA7L DKFZp762L0311 JPO2 PHENYLISOTHIOCYANATE,REAGENT PHENYL ISOTHIOCYANATE(RG) Phenyl Isothiocyanate [for HPLC Labeling] PHENYL ISOTHIOCYANATE (PITC) pure PHENYL ISOTHIOCYANATE extrapure AR 1-isothiocyanatobenzene Phenyl isothiocyanate, 99%, sequenation grade