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C99205

Sigma-Aldrich

Cycloheptatriene

95%

Synonym(s):

Tropiliden, Tropilidene

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About This Item

Empirical Formula (Hill Notation):
C7H8
CAS Number:
544-25-2
Molecular Weight:
92.14
Beilstein/REAXYS Number:
506066
EC Number:
208-866-3
MDL number:
MFCD00004146
UNSPSC Code:
12352100
PubChem Substance ID:
24893206
NACRES:
NA.22

Quality Level

100

assay

95%

form

liquid

refractive index

n20/D 1.519 (lit.)

bp

116-117 °C (lit.)

density

0.888 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C1C=CC=CC=C1

InChI

1S/C7H8/c1-2-4-6-7-5-3-1/h1-6H,7H2

InChI key

CHVJITGCYZJHLR-UHFFFAOYSA-N

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General description

Contains 0.02%-0.15% BHT

Application

Cycloheptatriene can be used as a reactant to synthesize:      
  • 2-Hydroxyazulene via [2+2] cycloaddition reaction with dichloroketene, and subsequent ring expansion reaction with diazomethane.      
  • 7-Alkyl-bicyclo[4.2.1]nona-2,4,7-trienes by cobalt catalyzed [6+2] cycloaddition with terminal alkynes.     
  • (3,5-Cycloheptadienyl)diphenylphosphine ligand by reacting with diphenylphosphine.

pictograms

FlameSkull and crossbones
GHS02,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

41.0 °F

flash_point_c

5 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0012
MKCS0720
MKCP1186
MKCK2617
MKCH4917

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Molybdenumhexacarbonyl ≥99.9% trace metals basis

Sigma-Aldrich

577766

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Michael H Palmer et al.
The Journal of chemical physics, 153(5), 054301-054301 (2020-08-11)
The vacuum ultraviolet (VUV) spectrum for cyclohepta-1,3,5-triene up to 10.8 eV shows several broad bands, which are compared with electron impact spectra. Local curve fitting exposed groups of sharp vibrational peaks, which are assigned to Rydberg states. The vertical excitation
(Cycloheptadienyl) diphenylphosphine: A Versatile Hybrid Ligand
Massard A, et al.
Organometallics, 31(3), 947-958 (2012)
[2+ 2] Cycloaddition reaction of cycloheptatriene with dichloroketene. A novel and efficient synthetic strategy for the synthesis of 2-hydroxyazulene
Yokoyama R, et al.
Journal of the Chemical Society. Perkin Transactions 1, (18), 2257-2261 (2001)
Mathieu Achard et al.
Organic letters, 7(12), 2353-2356 (2005-06-04)
[reaction: see text] The CoI2(dppe)/Zn/ZnI2 system effectively catalyzes the [6 + 2] cycloaddition of cycloheptatriene with terminal alkynes to afford 7-alkyl-bicyclo[4.2.1]nona-2,4,7-trienes in fair to excellent yields. The catalyst proved to be tolerant toward functional groups such as ketone, sulfone, ester
Katharina Thum et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 27(7), 2513-2522 (2020-11-17)
The first intermolecular early main group metal-alkene complexes were isolated. This was enabled by using highly Lewis acidic Mg centers in the Lewis base-free cations (Me BDI)Mg+ and (tBu BDI)Mg+ with B(C6 F5 )4 - counterions (Me BDI=CH[C(CH3 )N(DIPP)]2

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