Standard Article

Di-p-tolylcarbodiimide

  1. Eric J. Stoner1,
  2. Alessandro Volonterio2,
  3. Maria C. Bellucci3

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rd474.pub2

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Stoner, E. J., Volonterio, A. and Bellucci, M. C. 2013. Di-p-tolylcarbodiimide. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    Abbott Laboratories, Chicago, IL, USA

  2. 2

    Politecnico di Milano, Milano, Italy

  3. 3

    Università degli Studi di Milano, Milano, Italy

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

original image

[726-42-1] C15H14N2 (MW 222.31)

(synthesis of nitrogen heterocycles)

Physical Data: bp 221–223 °C/20 mmHg, 114 °C/0.02 mmHg; mp 56–58 °C.

Solubility: sol diethyl ether, benzene, pyridine, t-butanol.

Form Supplied in: off-white crystalline solid.

Preparative Methods: although di-p-tolylcarbodiimide is commercially available, it is quite expensive. It can be conveniently prepared from di-p-tolylthiourea by oxidation with Mercury(II) Oxide,1 Triphenylphosphine in the presence of Diethyl Azodicarboxylate,2 or with mercury(II) benzamide.3 A synthetic method dimerizing p-tolyl isocyanate has been reported.4

Purification: recrystallizations from diethyl ether and other solvents have been reported.1

Handling, Storage, and Precautions: harmful by inhalation, ingestion, or skin absorption and exposure causes strong eye and lung irritation. The solid is light- and moisture-sensitive and should be stored refrigerated in dark, well-sealed containers under an inert atmosphere. It should be used in a fume hood.

Featured Compounds

VIEW

  1. 1 - 89
Compound Information
Molecular Weight:222.2851
Molecular Formula:C15H14N2
InChIKey:BOSWPVRACYJBSJ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:132.1179
Molecular Formula:C4H8N2O3
InChIKey:PIHPSKJRLDSJPX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:265.3098
Molecular Formula:C16H15N3O
InChIKey:ONMCZCMJIOHMBZ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:195.054
Molecular Formula:C6H11BrO2
InChIKey:IOLQWGVDEFWYNP-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:292.3749
Molecular Formula:C19H20N2O
InChIKey:YWAIMUOMBIPPKV-JZJYNLBNSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:65.409
Molecular Formula:Zn
InChIKey:HCHKCACWOHOZIP-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:157.233
Molecular Formula:C7H11NOS
InChIKey:TZRRRVKQTCVBCL-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:290.381
Molecular Formula:C15H18N2O2S
InChIKey:YEOSGDBWXAIAAX-PEZBUJJGSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:105.9884
Molecular Formula:CNa2O3
InChIKey:CDBYLPFSWZWCQE-UHFFFAOYSA-L
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:207.252
Molecular Formula:C9H9N3OS
InChIKey:FIZUKOHLDKQUAP-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:429.537
Molecular Formula:C24H23N5OS
InChIKey:PRBXQZKMACSLSL-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:268.3535
Molecular Formula:C17H20N2O
InChIKey:LIXHITRLZULOLO-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:96.1034
Molecular Formula:C4H9NaO
InChIKey:SYXYWTXQFUUWLP-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:174.0911
Molecular Formula:C6H7O4P
InChIKey:CMPQUABWPXYYSH-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:230.1975
Molecular Formula:C10H15O4P
InChIKey:DHTQKXHLXVUBCF-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:252.2647
Molecular Formula:C16H12O3
InChIKey:PMFIDDGZLNNMMQ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:474.5497
Molecular Formula:C31H26N2O3
InChIKey:CRJFLIYJMUIQFN-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:212.1233
Molecular Formula:C7H7F3O4
InChIKey:XPIULNOMJUSCIK-ARJAWSKDSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:434.4083
Molecular Formula:C22H21F3N2O4
InChIKey:AYXWYTKREKCRRQ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:216.188
Molecular Formula:C9H12O6
InChIKey:OYSKSRMOBBDAHA-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:438.473
Molecular Formula:C24H26N2O6
InChIKey:IVAVGBWCGDJXGP-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:144.1253
Molecular Formula:C6H8O4
InChIKey:XLYMOEINVGRTEX-ONEGZZNKSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:366.4104
Molecular Formula:C21H22N2O4
InChIKey:XTCGRVLAQOOGNC-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:208.0586
Molecular Formula:C5H2F6O2
InChIKey:ZSBJCNVMTCMOBW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:430.3437
Molecular Formula:C20H16F6N2O2
InChIKey:IQLXGFDYRTXXLH-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:71.121
Molecular Formula:C4H9N
InChIKey:RWRDLPDLKQPQOW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:293.406
Molecular Formula:C19H23N3
InChIKey:HDWDDOCDGJOYFM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:85.1475
Molecular Formula:C5H11N
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:307.4326
Molecular Formula:C20H25N3
InChIKey:BMNHTCIHGALIDG-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:23.99771
Molecular Formula:HNa
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:160.198
Molecular Formula:C4H8N4OS
InChIKey:NUVXXYVLEGQSEF-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:382.483
Molecular Formula:C19H22N6OS
InChIKey:PGVPMYYVBZGVNN-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:334.3751
Molecular Formula:C18H18N6O
InChIKey:ZDMZSUALDMDVHM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:112.212
Molecular Formula:C4H9KO
InChIKey:LPNYRYFBWFDTMA-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:DKGAVHZHDRPRBM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:167.1851
Molecular Formula:C8H11N2O2
InChIKey:VXNPTRVCHKEMMV-UHFFFAOYSA-O
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:344.4097
Molecular Formula:C21H20N4O
InChIKey:MPDACILQPHQWCI-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:138.2055
Molecular Formula:CK2O3
InChIKey:BWHMMNNQKKPAPP-UHFFFAOYSA-L
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:217.2438
Molecular Formula:C12H13N2O2
InChIKey:WMWUJZFDHUUYJX-UHFFFAOYSA-O
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:394.4684
Molecular Formula:C25H22N4O
InChIKey:XQGUYSBQQNLNCX-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:217.2438
Molecular Formula:C12H13N2O2
InChIKey:FXXFJLCMVLKASS-UHFFFAOYSA-O
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:394.4684
Molecular Formula:C25H22N4O
InChIKey:UKAFWJJHEGBUKM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:181.634
Molecular Formula:C4H6CuO4
InChIKey:OPQARKPSCNTWTJ-UHFFFAOYSA-L
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:342.1722
Molecular Formula:C14H15IO2
InChIKey:IERLOSGMYPXIOS-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:360.4489
Molecular Formula:C23H24N2O2
InChIKey:VCUFYIXEOXJBLU-ZNTNEXAZSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:146.1098
Molecular Formula:C7H5F3
InChIKey:GETTZEONDQJALK-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:134.1751
Molecular Formula:C9H10O
InChIKey:KRIOVPPHQSLHCZ-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:211.2591
Molecular Formula:C14H13NO
InChIKey:YUIHXKGKVSVIEL-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:RYHBNJHYFVUHQT-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:190.45
Molecular Formula:CuI
InChIKey:LSXDOTMGLUJQCM-UHFFFAOYSA-M
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:325.8198
Molecular Formula:CCs2O3
InChIKey:FJDQFPXHSGXQBY-UHFFFAOYSA-L
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:28.0101
Molecular Formula:CO
InChIKey:UGFAIRIUMAVXCW-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:98.959
Molecular Formula:C2H4Cl2
InChIKey:WSLDOOZREJYCGB-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:175.1442
Molecular Formula:C8H5N3O2
InChIKey:ISULLEUFOQSBGY-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound
Compound Information
Molecular Weight:397.4293
Molecular Formula:C23H19N5O2
InChIKey:IBHMRJXYXCYANM-UHFFFAOYSA-N
View compound in article | Full details | Search for this compound

VIEW

  1. 1 - 89