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78-00-2

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78-00-2 Usage

Toxicity

Tetraethyl lead is a highly toxic compound manifesting both acute and chronic effects. These effects are insomnia, hypotension, hypothermia, tremor,weight loss, hallucination, nausea, convulsion and coma. LD50 oral (rats): 12 mg/kg.

Chemical Properties

Tetraethyl lead is a colorless oily liquid. Sweet, slight musty odor. In commerce it is usually dyed red, orange or blue. Tetraethyl lead will decompose in bright sunlight yielding needlelike crystals of tri-, di-, and mono-ethyl lead compounds, which have a garlic odor.

Physical properties

Colorless liquid; burns with orange flame with green margin; refractive index 1.5198; density 1.653 g/mL at 20°C; insoluble in water; slightly soluble in ethanol; soluble in benzene, toluene, gasoline, and petroleum ether.

Uses

Different sources of media describe the Uses of 78-00-2 differently. You can refer to the following data:
1. Tetraethyllead is used as an additive to gasolineto prevent knocking in motors. However,because of its high toxicity and the pollutionproblem, its use in gasoline has been drasticallycurtailed.
2. As a gasoline additive to prevent "knocking" in motors.Its use, however, is reduced drastically because of environmental pollution.

Production Methods

These compounds were, at one time, the major industrial use of lead and source of environmental pollution of inorganic lead combustion products. However, the addition of these compounds to gasoline in the major industrialized countries of the world has been discontinued because of the use of catalysts for the control of the amount of nitrogen oxides in automobile exhaust. Organolead additives are still being phased out in many underdeveloped countries, although the United Nations has called for a global phaseout of lead in gasoline.

Definition

Different sources of media describe the Definition of 78-00-2 differently. You can refer to the following data:
1. A poisonous liquid that is insoluble in water but soluble in organic solvents. It is manufactured by the reaction of an alloy of sodium and lead with 1-chloroethane. The product is obtained by steam distillation. Lead tetraethyl is used as an additive in internal-combustion engine fuel to increase its octane number and thus prevent preignition (knocking).
2. ChEBI: An organolead compound consisting of four ethyl groups joined to a central lead atom.

Preparation

Lead tetraethyl is prepared by heating ethyl chloride in the presence of a catalyst in an autoclave at 40 to 60°C with an alloy of lead and sodium: Pb + 4Na + 4C2H5Cl → Pb(C2H5)4 + 4NaCl Also, it can be prepared by the reaction of lead with ethylene and hydrogen in the presence of Ziegler catalyst, triethylaluminum: Pb + 4C2H4 + 2H2 → Pb(C2H5)4

General Description

A colorless liquid with a characteristic odor. Flash point 200°F. Density 14 lb / gal. Insoluble in water. Toxic by inhalation and by skin absorption.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

TETRAETHYL LEAD decomposes under UV light. Reacts with fats; reacts violently with oxidizing agents, causing fire and explosion hazards. Attacks rubber [Handling Chemicals Safely 1980. p. 890].

Hazard

Toxic by ingestion, inhalation, and skin absorption. Central nervous system impairment. Questionable carcinogen.

Health Hazard

Different sources of media describe the Health Hazard of 78-00-2 differently. You can refer to the following data:
1. Extremely poisonous; may be fatal if inhaled, swallowed, or absorbed from the skin. Contact may cause burns to skin and eyes. Most symptoms of poisoning are due to the effects of tetraethyllead on the nervous system.
2. Tetraethyllead is highly toxic by oral route.The LD50 values for rats, mice, andrabbits were all found to be <15 mg/kgwhen administered by the oral, intravenous,subcutaneous, intraperitoneal, and parenteralroutes. It may be absorbed through theskin causing lead poisoning. It is toxic tothe central nervous system. The toxicity,however, is low to moderate by dermal route.It is an acute as well as chronic toxicant.The toxic effects are insomnia, hypotension,tremor, hypothermia, pallor, weight loss,hallucination, nausea, convulsion, and coma.The toxicity of this compound by inhalationroute is also low to moderate. Because of itslow vapor pressure, 0.2 torr at 20°C (68°F),inhalation hazard is relatively low.LD50 oral (rat): 12 mg/kgOral lethal dose (rabbit): 30 mg/kgLC50 inhalation (rat): 850 mg/m3/1h.

Fire Hazard

May explode in fires. Decomposes slowly at room temperature and more rapidly at elevated temperatures.

Safety Profile

Human poison by an unspecified route. Experimental poison by ingestion, intraperitoneal, intravenous, subcutaneous, and parented routes. Moderately toxic by inhalation and skin contact. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. Lead compounds are particularly toxic to the central nervous system. It is a solvent for fatty materials and has some solvent action on rubber as well. The fact that it is a lipoid solvent makes it an industrial hazard because it can cause intoxication not only by inhalation but also by absorption through the skin. Decomposes when exposed to sunlight or allowed to evaporate; forms triethyl lead, which is also a poisonous compound, as one of its decomposition products. May cause elemental lead intoxication by coming in contact with the skin. A combustible liquid when exposed to heat, flame, or oxidizers. Can react vigorously with oxidzing materials. Exposure to air for several days may cause explosive decomposition. To fight fire, use dry chemical, CO2, mist, foam. When heated to decomposition it emits toxic fumes of Pb. See also LEAD COMPOUNDS.

Potential Exposure

Tetraethyl lead is used as a component of antiknock mixes for gas and as an intermediate in making fungicides; Tetraethyl lead (used as an antiknock compound in gasoline) can also contains impurities, such as ethylene dibromide and ethylene dichloride.

Carcinogenicity

A case-control study of former workers in a TEL-producing plant found a strong association between exposure to the TEL manufacturing process and rectal cancer (the odds ratio was 3.7 with 90% confidence limits of 1.3–10.2 for the analysis of ever/never exposed to TEL). An exposure–response relationship was noted with a fourfold elevation in the odds ratio at the high–very high cumulative exposure level. Similar results were obtained for cancers of the sigmoid colon. These results suggest to the authors that exposure to the TEL manufacturing process may have played a causal role in the colorectal cancer findings in this plant. However, IARC in 2006 has included organolead compounds (TEL and TML), with Lead and its Compounds in Group 3, not classifiable as to its carcinogenicity to humans.

Purification Methods

Its more volatile contaminants can be removed by exposure to a low pressure (by continuous pumping) for 1hour at 0o. Purify it by stirring with an equal volume of H2SO4 (d 1.40), keeping the temperature below 30o, repeating this process until the acid layer is colourless. It is then washed with dilute Na2CO3 and distilled water, dried with CaCl2 and fractionally distilled at low pressure under H2 or N2 [Calingaert Chem Rev 2 43 1926]. It prevents “knocking” in petrol combustion engines. [Milde & Beatty Adv Chem Res 23 306-318 1959, Beilstein 4 H 639.] VERY POISONOUS.

Incompatibilities

Vapors may form explosive mixture with air. A strong reducing agent. Violent reaction with strong oxidizers, sulfuryl chloride; halogens, oils and fats; rust, potassium permanganate. Decomposes slowly in light and at room temperature, and more rapidly at temperatures above 110C. Attacks rubber and some plastics and coatings.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥ 100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Controlled incineration with scrubbing for collection of lead oxides which may be recycled or land filled. It is also possible to recover alkyl lead compound from wastewaters as an alternative to disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 78-00-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 8 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 78-00:
(4*7)+(3*8)+(2*0)+(1*0)=52
52 % 10 = 2
So 78-00-2 is a valid CAS Registry Number.
InChI:InChI=1/4C2H5.Pb/c4*1-2;/h4*1H2,2H3;/rC8H20Pb/c1-5-9(6-2,7-3)8-4/h5-8H2,1-4H3

78-00-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name tetraethyllead

1.2 Other means of identification

Product number -
Other names TETRAETHYL LEAD

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:78-00-2 SDS

78-00-2Synthetic route

(η5-cyclopentadienyl)W(CO)3PbEt3
79110-50-2

(η5-cyclopentadienyl)W(CO)3PbEt3

A

{(η5-cyclopentadienyl)W(CO)3}2PbEt2
79123-28-7

{(η5-cyclopentadienyl)W(CO)3}2PbEt2

B

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
heated in vac. to 60°C for 8 h, under nitrogen, yellow-orange liquid became solid and darker orange in colour; dissolved in CH2Cl2/hexane solution, placed upon alumina column, elutedwith hexane, then hexane/CH2Cl2 solution, concentrated and placed refrigerator;A 58%
B n/a
(η5-cyclopentadienyl)Mo(CO)3PbEt3
79110-53-5

(η5-cyclopentadienyl)Mo(CO)3PbEt3

A

[(η5-C5H5)Mo(CO)3]2Pb(C2H5)2

[(η5-C5H5)Mo(CO)3]2Pb(C2H5)2

B

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
Irradiation (UV/VIS); 12 h;A 50%
B n/a
ethyl bromide
74-96-4

ethyl bromide

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With pyridine; lead sodium
With pyridine; tetrasodium-monoplumbide; water at 38℃;
With lead; sodium at 70℃; im geschlossenen Gefaess;
diethyl sulfate
64-67-5

diethyl sulfate

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With lead sodium; water; toluene; potassium iodide
ethene
74-85-1

ethene

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With lead sodium; hydrogen at 100℃; under 7355.08 Torr;
chloroethane
75-00-3

chloroethane

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With lead; lead(II) iodide at 100 - 130℃;
With lead sodium
With hydrogenchloride; lead sodium
ethyllithium
811-49-4

ethyllithium

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With lead(IV) chloride; Petroleum ether anfangs unter Kuehlung;
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With PbS
With lead(II) chloride
With lead(II) oxide
diethylzinc
557-20-0

diethylzinc

ethyl sodium
676-54-0

ethyl sodium

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
Electrolysis.an einer Bleianode;
diethylzinc
557-20-0

diethylzinc

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With lead(II) chloride
With lead(II) chloride
triethylaluminum
97-93-8

triethylaluminum

lead acetate
301-04-2

lead acetate

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With benzene
triethylaluminum
97-93-8

triethylaluminum

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With sodium fluoride Electrolysis.an Blei-Anoden;
ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With lead(II) chloride
With diethyl ether; lead(II) chloride
With lead(II) chloride
ethylmagnesium chloride
2386-64-3

ethylmagnesium chloride

A

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

B

triethyllead chloride
1067-14-7

triethyllead chloride

Conditions
ConditionsYield
With diethyl ether; lead(II) chloride anschliessend Einleiten Luft oder Sauerstoff nach Zusatz von verd.Salzsaeure;
hexaethyl diplumbane
2388-00-3

hexaethyl diplumbane

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With ethyl iodide
With silicatene
triethyllead chloride
1067-14-7

triethyllead chloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
at 170℃;
With hydrogenchloride; oxygen In neat (no solvent)
With hydrogenchloride; air In neat (no solvent)
With air; HCl In neat (no solvent)
With O2; HCl In neat (no solvent)
triethylaluminum
97-93-8

triethylaluminum

ethyl iodide
75-03-6

ethyl iodide

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With lead(II) chloride
ethyl iodide
75-03-6

ethyl iodide

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With tetrasodium-monoplumbide at 72℃;
With lead sodium
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

triethyllead bromide
41141-89-3

triethyllead bromide

ethyl acetate
141-78-6

ethyl acetate

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

diethyl sulfate
64-67-5

diethyl sulfate

water
7732-18-5

water

toluene
108-88-3

toluene

sodium-lead

sodium-lead

KI

KI

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

chloroethane
75-00-3

chloroethane

lead-sodium-alloy

lead-sodium-alloy

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
at 35 - 70℃; Kinetics;
at 35 - 70℃;
chloroethane
75-00-3

chloroethane

lead-sodium-magnesium alloy

lead-sodium-magnesium alloy

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
at 75℃; Kinetics;
at 75℃;
chloroethane
75-00-3

chloroethane

lead-sodium-potassium-alloy

lead-sodium-potassium-alloy

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
at 30℃; Kinetics;
at 30℃;
ethyl metal-compound

ethyl metal-compound

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With lead(II) oxide
With PbS
diethylzinc
557-20-0

diethylzinc

lead chloride

lead chloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

ethyl magnesium (1+); iodide

ethyl magnesium (1+); iodide

lead chloride

lead chloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

methanol
67-56-1

methanol

triethyllead chloride
1067-14-7

triethyllead chloride

sodium-compound of nitromethane

sodium-compound of nitromethane

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

triethyllead chloride
1067-14-7

triethyllead chloride

benzene
71-43-2

benzene

sodium-compound of nitromethane

sodium-compound of nitromethane

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Diazoethan
1117-96-0

Diazoethan

triethyl lead-chloride

triethyl lead-chloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Conditions
ConditionsYield
With diethyl ether; copper
tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

benzaldehyde
100-52-7

benzaldehyde

1-Phenyl-1-propanol
93-54-9

1-Phenyl-1-propanol

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -78 - -30℃; Product distribution; further aldehydes and tetraalkylleads; reaction with mixed tetraalkylleads; other conditions;98%
With titanium tetrachloride In dichloromethane at -78 - -30℃;98%
With titanium tetrachloride In dichloromethane at -78 - -30℃;96%
tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

cyclohexylpropyl alcohol
17264-02-7

cyclohexylpropyl alcohol

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -78 - -30℃;98%
bis(trifluoromethyl)chlorophosphine
650-52-2

bis(trifluoromethyl)chlorophosphine

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Ethylbis-trifluormethyl-phosphin
25196-23-0

Ethylbis-trifluormethyl-phosphin

Conditions
ConditionsYield
110°C (24 h);95%
110°C (24 h);95%
Octanal
124-13-0

Octanal

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

decan-3-ol
1565-81-7

decan-3-ol

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -78 - -30℃;94%
N-(ethoxycarbonyl)-N-methyl-1-ethoxybenzylamine
40848-81-5

N-(ethoxycarbonyl)-N-methyl-1-ethoxybenzylamine

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

Methyl-(1-phenyl-propyl)-carbamic acid ethyl ester
127202-36-2

Methyl-(1-phenyl-propyl)-carbamic acid ethyl ester

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -78 - 25℃;88%
tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

benzoyl chloride
98-88-4

benzoyl chloride

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 65℃; for 3h;84%
tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

(1-Ethoxy-octyl)-methyl-carbamic acid ethyl ester
127202-34-0

(1-Ethoxy-octyl)-methyl-carbamic acid ethyl ester

(1-Ethyl-octyl)-methyl-carbamic acid ethyl ester
127202-43-1

(1-Ethyl-octyl)-methyl-carbamic acid ethyl ester

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -78 - 25℃;82%
(p-chlorophenyl)arsonous dichloride
20738-34-5

(p-chlorophenyl)arsonous dichloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

(p-chlorophenyl)ethylarsinous chloride
83627-00-3

(p-chlorophenyl)ethylarsinous chloride

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 82%
C n/a
(S)-2-(benzyloxy)propanal
81445-44-5

(S)-2-(benzyloxy)propanal

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

(2S,3S)-2-benzyloxy-3-pentanol
114418-33-6

(2S,3S)-2-benzyloxy-3-pentanol

Conditions
ConditionsYield
With titanium tetrachloride at -78 - -60℃;81%
C5H5Ni(P(C2H5)3)GeCl3

C5H5Ni(P(C2H5)3)GeCl3

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

C5H5Ni(P(C2H5)3)Ge(C2H5)Cl2

C5H5Ni(P(C2H5)3)Ge(C2H5)Cl2

Conditions
ConditionsYield
In further solvent(s) in boiling solvent, 2 h; crystn. from C6H6/hexane, CS2/hexane or CH2Cl2;77%
In benzene in boiling benzene, 2 h; crystn. from C6H6/hexane, CS2/hexane or CH2Cl2;77%
2-(dichloroamino)-2-methylpropionitrile
16248-71-8

2-(dichloroamino)-2-methylpropionitrile

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

triethyl lead (1+); hydroxide
1529-35-7

triethyl lead (1+); hydroxide

Conditions
ConditionsYield
With NaOH; HCl In tetrachloromethane byproducts: azobisbutyronitrile; stirring (25-30°C), heating (50°C, 1 h), solvent removal (vac.), addn. of aq. NaOH, stirring (pptn. of org. byproduct), neutrlization (aq. HCl); collection of ppt. (filtration);75%
Dichlor(o-methoxyphenyl)arsin
63294-40-6

Dichlor(o-methoxyphenyl)arsin

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

ethyl-o-anisylarsine chloride
61130-93-6

ethyl-o-anisylarsine chloride

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 74%
C n/a
(p-chlorophenyl)arsonous dichloride
20738-32-3

(p-chlorophenyl)arsonous dichloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

(o-chlorophenyl)ethylarsinous chloride
83627-06-9

(o-chlorophenyl)ethylarsinous chloride

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 73%
C n/a
at 80 - 90℃; for 1h;A n/a
B 73%
C n/a
tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

diethyllead dichloride
13231-90-8

diethyllead dichloride

B

ethylmercury(II) chloride
107-27-7

ethylmercury(II) chloride

Conditions
ConditionsYield
With mercury dichloride In ethanol 4h heated at 65°C;; precipitation at cooling;;A n/a
B 72%
With HgCl2 In ethanol 4h heated at 65°C;; precipitation at cooling;;A n/a
B 72%
dichloro(4-methylphenyl)arsine
698-64-6

dichloro(4-methylphenyl)arsine

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

ethyl-p-tolylarsine chloride
51525-20-3

ethyl-p-tolylarsine chloride

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 71%
C n/a
(m-chlorophenyl)arsonous dichloride
20738-33-4

(m-chlorophenyl)arsonous dichloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

(m-chlorophenyl)ethylarsinous chloride

(m-chlorophenyl)ethylarsinous chloride

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 71%
C n/a
antimony(III) chloride
10025-91-9

antimony(III) chloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

ethyldichlorostibine
68781-06-6

ethyldichlorostibine

Conditions
ConditionsYield
In benzene refluxing in ratio of SbCl3:Pb(C2H5)4=3:1 for 8-10 h; distn.;71%
In benzene refluxing in ratio of SbCl3:Pb(C2H5)4=3:1 for 8-10 h; distn.;71%
in ratio of SbCl3:Pb(C2H5)4=3:1 in bulk at 100°C in N2 atmosphere for 7 h; distn.;
in ratio of SbCl3:Pb(C2H5)4=3:1 in bulk at 100°C in N2 atmosphere for 7 h; distn.;
(ferrocenyl)dibromoborane

(ferrocenyl)dibromoborane

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

diethylborylferrocene
181149-05-3

diethylborylferrocene

Conditions
ConditionsYield
In toluene byproducts: PbEt3Br; (argon); -60°C to room temp., stirring 2 h; solvent removal (vac.), dissoln. (hexane), filtration;71%
dichloro-(4-nitro-phenyl)-arsine
51956-43-5

dichloro-(4-nitro-phenyl)-arsine

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

ethyl(p-nitrophenyl)arsinous chloride

ethyl(p-nitrophenyl)arsinous chloride

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 70%
C n/a
p-anisylarsine dichloride
65452-83-7

p-anisylarsine dichloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

chloroethyl(p-methoxyphenyl)arsine
61130-95-8

chloroethyl(p-methoxyphenyl)arsine

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 69%
C n/a
o-Bromphenylarsindichlorid
57170-65-7

o-Bromphenylarsindichlorid

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

C8H9AsBrCl
83627-07-0

C8H9AsBrCl

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 68%
C n/a
(o-nitrophenyl)arsonous dichloride
64048-88-0

(o-nitrophenyl)arsonous dichloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

ethyl(o-nitrophenyl)arsinous chloride

ethyl(o-nitrophenyl)arsinous chloride

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 68%
C n/a
m-nitrophenylarsonous dichloride
6306-96-3

m-nitrophenylarsonous dichloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

ethyl(m-nitrophenyl)arsinous chloride

ethyl(m-nitrophenyl)arsinous chloride

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 67%
C n/a
p-bromophenylarsine dichloride
73013-32-8

p-bromophenylarsine dichloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

C8H9AsBrCl
83627-01-4

C8H9AsBrCl

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 64%
C n/a
(3-bromo-phenyl)-dichloro-arsine
58284-54-1

(3-bromo-phenyl)-dichloro-arsine

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

C8H9AsBrCl

C8H9AsBrCl

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 64%
C n/a
tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

m-biphenylyldichloroarsine
109832-49-7

m-biphenylyldichloroarsine

m-biphenylyldiethylarsine

m-biphenylyldiethylarsine

Conditions
ConditionsYield
In xylene for 20h; Heating;63.8%
dichlorophenylarsine
696-28-6

dichlorophenylarsine

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

ethylphenylarsine chloride
698-13-5

ethylphenylarsine chloride

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 63%
C n/a
o-tolylarsonous dichloride
697-97-2

o-tolylarsonous dichloride

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

A

chloroethane
75-00-3

chloroethane

B

Aethyl-o-tolylarsinchlorid
53980-31-7

Aethyl-o-tolylarsinchlorid

C

PbCl2

PbCl2

Conditions
ConditionsYield
at 90 - 110℃;A n/a
B 62%
C n/a
tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

C11H19N3O3
135441-05-3

C11H19N3O3

A

N'-(Piperidine-1-carbonyl)-hydrazinecarboxylic acid tert-butyl ester
135441-06-4

N'-(Piperidine-1-carbonyl)-hydrazinecarboxylic acid tert-butyl ester

B

N'-Ethyl-N'-(piperidine-1-carbonyl)-hydrazinecarboxylic acid tert-butyl ester
135441-08-6

N'-Ethyl-N'-(piperidine-1-carbonyl)-hydrazinecarboxylic acid tert-butyl ester

Conditions
ConditionsYield
With titanium tetrachloride In hexane; dichloromethane at -78℃; for 0.7h;A 6%
B 61%
WOCl2 (O-2,6-C6 H3 -Br2)2

WOCl2 (O-2,6-C6 H3 -Br2)2

(S)-(+)-dihydromyrcene
2436-90-0

(S)-(+)-dihydromyrcene

tetraethyllead(IV)
78-00-2

tetraethyllead(IV)

1,2,4-Trichlorobenzene
120-82-1

1,2,4-Trichlorobenzene

(-)-(S)-3-methylcyclopentene

(-)-(S)-3-methylcyclopentene

Conditions
ConditionsYield
In chlorobenzene61%

78-00-2Relevant articles and documents

On the nature and incidence of β-agostic interactions in ethyl derivatives of early transition metals: Ethyltitanium trichloride and related compounds

Haaland, Arne,Scherer, Wolfgang,Ruud, Kenneth,McGrady, G. Sean,Downs, Anthony J.,Swang, Ole

, p. 3762 - 3772 (1998)

In light of the structures and spectroscopic properties of the ethyltitanium compounds EtTiCl3 (1), and EtTiCl3(dmpe) (dmpe = Me2PCH2CH2PMe2) (2), extensive DFT calculations have been carried out to explore the structures, energetics, potential energy surfaces, and spectroscopic properties not only of these but also of related ethyl derivatives of early transition metals, M. The analysis has sought to assess the true nature of so-called β-agostic interactions in these systems and how such interactions depend on the atomic number, coordination number, valence electron (VE) count, and net charge of M. The calculations reproduce well the experimentally determined properties of 1 and 2. Analysis of wave functions indicates that, where significant β-interactions occur, the M-C bonding electrons are delocalized over the entire ethyl group, the marked reduction of the MCC valence angle allowing the metal atom to establish covalent bonding interactions with the β-C atom and, perhaps to a lesser extent, with its appended proximal H atom. A β-agostic alkyl group may be considered a two-electron ligand, and the main contribution to the stabilization arises from Ti···C(β) bonding. Barriers to conformational change of the M-Et unit depend inter alia on the space available in the coordination sphere of the central M atom, with rearrangement of the ethyl group to accommodate significant β-interaction being opposed by interligand repulsion. Such interaction is found not in 1, but in its dmpe adduct 2 because the increase in coordination number is offset by elongation of the Ti-C and Ti-Cl bonds and by the extra pliability of the EtTiCl3 moiety resulting from complexation by the dmpe ligand.

Frankland,Lawrence

, p. 244 (1879)

Frey et al.

, p. 530,532 (1960)

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