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MedKoo Cat#: 558097 | Name: Phenyl isocyanate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phenyl isocyanate is a aromatic monoisocyanate and potent inducer of both cellular and humoral immune responses.

Chemical Structure

Phenyl isocyanate
Phenyl isocyanate
CAS#103-71-9

Theoretical Analysis

MedKoo Cat#: 558097

Name: Phenyl isocyanate

CAS#: 103-71-9

Chemical Formula: C7H5NO

Exact Mass: 119.0371

Molecular Weight: 119.12

Elemental Analysis: C, 70.58; H, 4.23; N, 11.76; O, 13.43

Price and Availability

Size Price Availability Quantity
5g USD 200.00
100g USD 380.00
250g USD 630.00
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Related CAS #
No Data
Synonym
Fenylisokyanat; HSDB 5356; Isocyanatobenzene; Karbanil;
IUPAC/Chemical Name
Benzene, isocyanato-
InChi Key
DGTNSSLYPYDJGL-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H
SMILES Code
O=C=NC1=CC=CC=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phenyl isocyanate is a aromatic monoisocyanate and potent inducer of both cellular and humoral immune responses.
In vitro activity:
In the current work, 3,5-Bis(trifluoromethyl)phenyl isocyanate (BTP) was successfully anchored onto Cr-MIL-101 walls via covalent incorporation to afford Cr-MIL-101-BTP as a novel adsorbent for the high-efficiency removal of ACT in aqueous solutions. Given the π-π stacking and hydrogen bond interaction, the adsorption capacity in Cr-MIL-101-BTP approached a maximum of 312.5 mg/g for ACT, which was considerably higher than the adsorption capacities of many other reported adsorbents. The excellent adsorption characteristics of Cr-MIL-101-BTP toward ACT were preserved in a wide pH range and high concentration of background electrolytes. In addition, the result showed that partition coefficient (PC) of Cr-MIL-101-BTP was 356.14 mg/g/μM at 5 mg/L of ACT concentration, which was found as the outperformer in all tested subjects. Reference: Sci Total Environ. 2020 Mar 25;710:135512. https://pubmed.ncbi.nlm.nih.gov/31785897/
In vivo activity:
The potency of PI (phenyl isocyanate) as a contact sensitizer was assessed using the mouse ear swelling test. PI was found to be the most potent isocyanate tested yielding an SD50 (dose predicted to sensitize 50% of the mice) of 0.04 mumol/kg, compared with SD50 values of 0.5, 2.1, and 30.4 mumol/kg, for the diisocyanate sensitizers hexamethylene diisocyanate, MDI, and toluene diisocyanate (TDI), respectively. When tested for ability to stimulate humoral immune responses, antibody titers to PI were more than ten-fold greater than those induced by TDI. The mean hapten-specific IgG antibody titer to PI was 1.4 x 10(4), compared with 1.3 x 10(3) for TDI. The anti-PI IgG1 anaphylactic antibody titer (1.2 x 10(4) was significantly greater than the anti-TDI IgG1 titer of 6.4 x 10(2). Reference: Toxicol Lett. 1996 Dec 16;89(2):139-46. https://pubmed.ncbi.nlm.nih.gov/8960156/

Preparing Stock Solutions

The following data is based on the product molecular weight 119.12 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
2. Wang B, Yang Y, Lu Y, Wang W, Wang Q, Dong X, Zhao J. Rapid and efficient removal of acetochlor from environmental water using Cr-MIL-101 sorbent modified with 3, 5-Bis(trifluoromethyl)phenyl isocyanate. Sci Total Environ. 2020 Mar 25;710:135512. doi: 10.1016/j.scitotenv.2019.135512. Epub 2019 Nov 16. PMID: 31785897. 3. Wang B, Yang Y, Lu Y, Wang W, Wang Q, Dong X, Zhao J. Rapid and efficient removal of acetochlor from environmental water using Cr-MIL-101 sorbent modified with 3, 5-Bis(trifluoromethyl)phenyl isocyanate. Sci Total Environ. 2020 Mar 25;710:135512. doi: 10.1016/j.scitotenv.2019.135512. Epub 2019 Nov 16. PMID: 31785897.
In vitro protocol:
1. Wang B, Yang Y, Lu Y, Wang W, Wang Q, Dong X, Zhao J. Rapid and efficient removal of acetochlor from environmental water using Cr-MIL-101 sorbent modified with 3, 5-Bis(trifluoromethyl)phenyl isocyanate. Sci Total Environ. 2020 Mar 25;710:135512. doi: 10.1016/j.scitotenv.2019.135512. Epub 2019 Nov 16. PMID: 31785897.
In vivo protocol:
1. Wang B, Yang Y, Lu Y, Wang W, Wang Q, Dong X, Zhao J. Rapid and efficient removal of acetochlor from environmental water using Cr-MIL-101 sorbent modified with 3, 5-Bis(trifluoromethyl)phenyl isocyanate. Sci Total Environ. 2020 Mar 25;710:135512. doi: 10.1016/j.scitotenv.2019.135512. Epub 2019 Nov 16. PMID: 31785897.
1: Johansson Mali'n T, Lindberg S, Åstot C. Novel glutathione conjugates of phenyl isocyanate identified by ultra-performance liquid chromatography/electrospray ionization mass spectrometry and nuclear magnetic resonance. J Mass Spectrom. 2014 Jan;49(1):68-79. doi: 10.1002/jms.3306. PubMed PMID: 24446265. 2: Servos MA, Smart NC, Kassabaum ME, Scholtens CA, Peters SJ. Phenyl isocyanate anion radicals and their cyclotrimerization to triphenyl isocyanurate anion radicals. J Org Chem. 2013 Apr 19;78(8):3908-17. doi: 10.1021/jo4003008. Epub 2013 Apr 10. PubMed PMID: 23541236. 3: Wong KT, Tanskanen JT, Bent SF. Formation of stable nitrene surface species by the reaction of adsorbed phenyl isocyanate at the Ge(100)-2 × 1 surface. Langmuir. 2013 Dec 23;29(51):15842-50. doi: 10.1021/la4036216. Epub 2013 Dec 10. PubMed PMID: 24359033. 4: Uehara K, Fukaya K, Mizuno N. Reactive N-protonated isocyanate species stabilized by bis(μ-hydroxo)divanadium(IV)-substituted polyoxometalate. Angew Chem Int Ed Engl. 2012 Jul 27;51(31):7715-8. doi: 10.1002/anie.201108205. Epub 2012 Jun 26. PubMed PMID: 22736381. 5: Lyons CE, Victor KG, Moshnikov SA, Bachmann LM, Baras AS, Dettmann KM, Cross JV, Templeton DJ. PICquant: a quantitative platform to measure differential peptide abundance using dual-isotopic labeling with 12C6- and 13C6-phenyl isocyanate. Anal Chem. 2011 Feb 1;83(3):856-65. doi: 10.1021/ac102461e. Epub 2010 Dec 30. PubMed PMID: 21192683; PubMed Central PMCID: PMC3079250. 6: Karol MH, Kramarik JA. Phenyl isocyanate is a potent chemical sensitizer. Toxicol Lett. 1996 Dec 16;89(2):139-46. PubMed PMID: 8960156. 7: Pauluhn J, Rüngeler W, Mohr U. Phenyl isocyanate-induced asthma in rats following a 2-week exposure period. Fundam Appl Toxicol. 1995 Feb;24(2):217-28. PubMed PMID: 7737433. 8: Nehéz M, Fischer GW, Nehéz I, Scheufler H, Dési I. Investigations on the acute toxic, cytogenetic, and embryotoxic activity of phenyl isocyanate and diethoxyphosphoryl isocyanate. Ecotoxicol Environ Saf. 1989 Apr;17(2):258-63. PubMed PMID: 2737118. 9: Ishido Y, Hirao I, Itoh K, Tamaki K, Araki Y. Dibutyltin oxide--phenyl isocyanate system for regioselective phenylcarbamoylation of the hydroxy-groups of ribonucleosides. Nucleic Acids Symp Ser. 1980;(8):s7-8. PubMed PMID: 7255200. 10: Ishido Y, Hirao I, Sakairi N, Araki Y. Regioselective phenylcarbamoylation of hydroxy-groups of ribonucleosides with bis(tributyltin) oxide--phenyl isocyanate system. Nucleic Acids Symp Ser. 1979;(6):s37-40. PubMed PMID: 547238. 11: Turnipseed SB, Clark SB, Karbiwnyk CM, Andersen WC, Miller KE, Madson MR. Analysis of aminoglycoside residues in bovine milk by liquid chromatography electrospray ion trap mass spectrometry after derivatization with phenyl isocyanate. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 May 15;877(14-15):1487-93. doi: 10.1016/j.jchromb.2009.03.025. Epub 2009 Mar 24. PubMed PMID: 19345161. 12: FARNWORTH AJ. The reaction between wool and phenyl isocyanate. Biochem J. 1955 Apr;59(4):529-33. PubMed PMID: 14363143; PubMed Central PMCID: PMC1215614. 13: Knapp S, Schreck RP, Carignan YP. A mechanistic study of the reaction of phenyl isocyanate with methyl 2,3,4-tri-O-acetyl-alpha-D-glucopyranoside. Carbohydr Res. 1990 Aug 15;203(2):290-5. PubMed PMID: 2276125. 14: Iarym-Agaeva NT, Putilina ON. [Photometric method of determining aniline and phenyl isocyanate in workplace air]. Gig Tr Prof Zabol. 1986 Oct;(10):56-7. Russian. PubMed PMID: 3792900. 15: Mason DE, Liebler DC. Quantitative analysis of modified proteins by LC-MS/MS of peptides labeled with phenyl isocyanate. J Proteome Res. 2003 May-Jun;2(3):265-72. PubMed PMID: 12814266. 16: Marvania B, Kakadiya R, Christian W, Chen TL, Wu MH, Suman S, Tala K, Lee TC, Shah A, Su TL. The synthesis and biological evaluation of new DNA-directed alkylating agents, phenyl N-mustard-4-anilinoquinoline conjugates containing a urea linker. Eur J Med Chem. 2014 Aug 18;83:695-708. doi: 10.1016/j.ejmech.2014.06.066. Epub 2014 Jun 28. PubMed PMID: 25014640. 17: Hopkins SJ, Wormall A. Phenyl isocyanate protein compounds and their immunological properties. Biochem J. 1933;27(3):740-53. PubMed PMID: 16745152; PubMed Central PMCID: PMC1252938. 18: Hopkins SJ, Wormall A. Phenyl isocyanate protein compounds and their immunological properties: The gelatin compounds. Biochem J. 1933;27(5):1706-15. PubMed PMID: 16745289; PubMed Central PMCID: PMC1253085. 19: Davies R, Rydberg P, Westberg E, Motwani HV, Johnstone E, Törnqvist M. A new general pathway for synthesis of reference compounds of N-terminal valine-isocyanate adducts. Chem Res Toxicol. 2010 Mar 15;23(3):540-6. doi: 10.1021/tx900278p. PubMed PMID: 20085231. 20: Germain N, Müller I, Hanauer M, Paciello RA, Baumann R, Trapp O, Schaub T. Synthesis of Industrially Relevant Carbamates towards Isocyanates using Carbon Dioxide and Organotin(IV) Alkoxides. ChemSusChem. 2016 Jul 7;9(13):1586-90. doi: 10.1002/cssc.201600580. Epub 2016 Jun 20. PubMed PMID: 27319978.

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