| Identification | More | [Name]
PHENYL ISOTHIOCYANATE | [CAS]
103-72-0 | [Synonyms]
AKOS BBS-00004438
EDMAN'S REAGENT
ISOTHIOCYANIC ACID PHENYL ESTER
PHENYL ISOTHIOCYANATE
Phenyl isothiocyanate Phenyl mustard oil
PHENYL ISOTHIOCYANATE PROTEIN SEQUENCING REAGENT
PHENYL MUSTARD OIL
PIT
PITC
PTC
R1
THIOCARBANIL
Benzene,isothiocyanato-
Benzene-1-isothiocyanate
Fenylisothiokyanat
iso-Thiocyana-tobenaene
isothiocyanato-benzen
Isothiocyanatobenzene
isothiocyanato-Benzene
Phenyl thiocyanate | [EINECS(EC#)]
203-138-1 | [Molecular Formula]
C7H5NS | [MDL Number]
MFCD00004798 | [Molecular Weight]
135.19 | [MOL File]
103-72-0.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless to pale yellow liquid with a penetrating odour | [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.)
| [Fp ]
190 °F
| [storage temp. ]
2-8°C
| [solubility ]
water: insoluble | [form ]
liquid
| [color ]
Clear pale yellow to yellow | [Specific Gravity]
1.137 (20/4℃) | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, strong acids. | [Water Solubility ]
Soluble in alcohol, and ether. Insoluble in water. | [Sensitive ]
Moisture Sensitive | [Merck ]
14,7297 | [BRN ]
471392 | [Dielectric constant]
10.7（20℃） | [InChIKey]
QKFJKGMPGYROCL-UHFFFAOYSA-N | [LogP]
3.280 | [CAS DataBase Reference]
103-72-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzene, isothiocyanato-(103-72-0) | [EPA Substance Registry System]
103-72-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,Xn,F | [Risk Statements ]
R25:Toxic if swallowed.
R34:Causes burns.
R42/43:May cause sensitization by inhalation and skin contact .
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed.
R11:Highly Flammable.
R38:Irritating to the skin.
R63:Possible risk of harm to the unborn child.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S29:Do not empty into drains .
S33:Take precautionary measures against static discharges .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S38:In case of insufficient ventilation, wear suitable respiratory equipment . | [RIDADR ]
UN 1993 3/PG 2
| [WGK Germany ]
3
| [RTECS ]
NX9275000
| [F ]
19 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29309090 | [Toxicity]
LD50 orally in Rabbit: 157 mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
colourless to pale yellow liquid with a penetrating odour | [Uses]
As Derivatizing reagent for primary and secondary amines, Phenyl isothiocyanate can be used in sequencing peptides by Edman degradation and in amino acid analyses by HPLC.
| [Uses]
Derivatizing agent for primary, secondary amines. In sequencing of peptides by Edman degradation. In amino acid analyses by HPLC (Pico-Tag). | [Definition]
ChEBI: An isothiocyanate having a phenyl group attached to the nitrogen. | [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. | [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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