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542-92-7

Basic Information
CAS No.: 542-92-7
Name: 1,3-Cyclopentadiene
Article Data: 461
Molecular Structure:
Molecular Structure of 542-92-7 (1,3-Cyclopentadiene)
Formula: C5H6
Molecular Weight: 66.1026
Synonyms: Cyclopentadiene;Pentole;Pyropentylene;R-Pentine;
EINECS: 208-835-4
Density: 0.878 g/cm3
Melting Point: - 97.2 C
Boiling Point: 41.499 °C at 760 mmHg
Solubility: 10.3 mM at 25 °C (shake flask-UV spectrophotometry, Streitwieser and Nebenzahl, 1976)
Appearance: colourless liquid
PSA: 0.00000
LogP: 1.50250
Synthetic route
142-29-0

cyclopentene

542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With n-butyllithium; potassium 2-methylbutan-2-olate In hexane 1) r.t., 14 h, 2) reflux, 5 h;100%
at 850℃; Erhitzen unter vermindertem Druck;
With chromium (III)-oxide-aluminium oxide contacts at 450 - 500℃;
With palladium at 180 - 200℃;
3559-74-8

trimethylsilylcyclopentadiene

542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With trifluoroacetic acid at 60℃; for 3h; Heating;100%
With potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 3h;100%
73138-26-8

manganocene

124-38-9

carbon dioxide

109-89-7

diethylamine

A

Mn(O2CN(C2H5)2)2

B

542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In toluene under N2 or Ar;suspn. of Mn(cp)2 in toluene treated with stoicheiometric amt. of amine, clear soln, addn. of CO2, after 2 h no gas was uptaken; evapn.,;A 99%
B n/a
16326-97-9, 16326-98-0, 59719-74-3

1,3-dihydroxycyclopentane

542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With Nafion In water at 140℃; Temperature; Solvent; Reagent/catalyst;99%
With H-USY zeolite In tetrahydrofuran at 249.84℃; Inert atmosphere;93.8%
84651-76-3

(η-cyclopentadienyl)(η-cyclopentadiene)nickel tetrafluoroborate

603-36-1

triphenylantimony

A

85836-36-8

[Ni(C5H5)(Sb(C6H5)3)2](1+)*BF4(1-)=[Ni(C5H5)(Sb(C6H5)3)2]BF4

B

542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In diethyl ether under Ar, Ni complex in ether mixed with stibane ligand (molar ratio 1:2), stirred for 5 h at room temp.; filtered, washed with ether, dried in vac., elem. anal.;A 98%
B n/a

vanadocene

546-67-8

lead(IV) tetraacetate

A

{(η5-cyclopentadienyl)vanadium diacetate}2

B

301-04-2

lead acetate

C

542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
In toluene molar ratio Cp2V/Pb-compound 1/1, sealed ampoule, 20°C, 48 h;A 97%
B n/a
C 36.6%
Conditions
ConditionsYield
Heating;96%
at 180℃;
In decalin at 180℃; Diels-Alder Cycloaddition; Inert atmosphere;
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
at 160℃;95%
at 350 - 400℃;91%
at 210℃;84.5%
79756-02-8, 79813-47-1

endo-4a-acetyl-2,3-dichloro-4a,5,8,8a-tetrahydro-5,8-methano-1,4-naphthoquinone

A

542-92-7

cyclopenta-1,3-diene

79756-04-0

4-acetyl-6,7,7',8'-tetrachloro-3'aR*,9'bR*-dihydro-5,6',9'-trihydroxy-spiro<3H-benzofuran-2S*,5'(1'H)-cyclopenta<2>benzopyran>

Conditions
ConditionsYield
In benzene-d6 at 80℃; for 6h; sealed n.m.r. sample tube;A n/a
B 95%
3048-65-5

bicyclo[4.3.0]nona-3,7-diene

542-92-7

cyclopenta-1,3-diene

Conditions
ConditionsYield
With tert-butylhydroquinone In diphenylether at 215℃; for 2.58333h; Product distribution / selectivity;94.19%
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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

OSHA PEL: TWA 75 ppm
ACGIH TLV: TWA 75 ppm
DFG MAK: 75 ppm (210 mg/m3)

Analytical Methods

For occupational chemical analysis use NIOSH: 1,3-Cyclopentadiene, 2523.

Specification

 The Cyclopentadiene, with the CAS registry number 542-92-7,is also known as 1,3-Cyclopentadiene. It belongs to the product categories of Organic matters. This chemical's molecular formula is C5H6 and molecular weight is 66.10.Its EINECS number is 542-92-7. What's more,Its systematic name is Cyclopentadiene.It is a colourless liquid which is stable at room temperature and incompatible with oxidizing agents, acids and a wide variety of other compounds.It may form peroxides in storage.And it may undergo spontaneous polymerisation. It Decomposes on heating,mixtures with air are explosive.It is used for organic synthetic intermediates, and manufacturing pesticides.In addition, it is mainly used for resin industry, synthetic rubber, etc.

Physical properties about Cyclopentadiene are:
(1)ACD/LogP:  2.087; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  2.09; (4)ACD/LogD (pH 7.4):  2.09; (5)ACD/BCF (pH 5.5):  22.72; (6)ACD/BCF (pH 7.4):  22.72; (7)ACD/KOC (pH 5.5):  325.50; (8)ACD/KOC (pH 7.4):  325.50; (9)#H bond acceptors:  0; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  0; (12)Index of Refraction:  1.503; (13)Molar Refractivity:  22.266 cm3; (14)Molar Volume:  75.303 cm3; (15)Surface Tension:  34.859001159668 dyne/cm; (16)Density:  0.878 g/cm3; (17)Flash Point:  -32.166 °C; (18)Enthalpy of Vaporization:  27.4 kJ/mol; (19)Boiling Point:  41.499 °C at 760 mmHg; (20)Vapour Pressure:  418.459991455078 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:C1C=CC=C1;
(2)Std. InChI:InChI=1S/C5H6/c1-2-4-5-3-1/h1-4H,5H2 ;
(3)Std. InChIKey:ZSWFCLXCOIISFI-UHFFFAOYSA-N.

The toxicity data of Cyclopentadiene as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 14gm/m3 (14000mg/m3) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: AGGRESSION

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 9(12), Pg. 13, 1965.
mouse LD50 oral 800mg/kg (800mg/kg)   Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 9, Pg. 27, 1967.
rabbit LD50 skin 430mg/kg (430mg/kg)   National Technical Information Service. Vol. OTS0535718,
rat LC50 inhalation 39gm/m3 (39000mg/m3) BEHAVIORAL: AGGRESSION

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 9(12), Pg. 13, 1965.
rat LD50 oral 113mg/kg (113mg/kg)   National Technical Information Service. Vol. OTS0535718,