Phenyl isocyanate
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Hodoodo CAT#: H558097

CAS#: 103-71-9

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

Chemical Structure

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Phenyl isocyanate
CAS# 103-71-9
Instruction

Theoretical Analysis

Hodoodo Cat#: H558097
Name: Phenyl isocyanate
CAS#: 103-71-9
Chemical Formula: C7H5NO
Exact Mass: 119.04
Molecular Weight: 119.123
Elemental Analysis: C, 70.58; H, 4.23; N, 11.76; O, 13.43

Price and Availability

Size Price Availability Quantity
5g USD 200 2 Weeks
100g USD 380 2 Weeks
250g USD 630 2 Weeks
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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:

Biological target:
In vitro activity:
In vivo activity:

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:
In vitro protocol:
In vivo protocol:

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Reconstitution Calculator

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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.