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597-63-7

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597-63-7 Usage

Description

Tetraethylgermanium is a kind of organic germanium compounds. Germanium shares the group 14 with silicon, tin and lead in the periodic table. Though having limited synthetic value due to the cost of organic germanium compounds, germanium is considered as a non-toxic alternative of many toxic organotin reagents. Compounds such as d tetraethylgermanium are used as precursors for germanium dioxide chemical vapor deposition in the microelectronics industry, being useful in the manufacturing of semiconductor films.

Sources

www.newworldencyclopedia.org/entry/Germanium https://en.wikipedia.org/wiki/Tetraethylgermane https://www.google.com/patents/US3211583

Chemical Properties

clear colorless liquid

Check Digit Verification of cas no

The CAS Registry Mumber 597-63-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 7 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 597-63:
(5*5)+(4*9)+(3*7)+(2*6)+(1*3)=97
97 % 10 = 7
So 597-63-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H20Ge/c1-5-9(6-2,7-3)8-4/h5-8H2,1-4H3

597-63-7 Well-known Company Product Price

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  • Alfa Aesar

  • (H27625)  Tetraethylgermanium, 99%   

  • 597-63-7

  • 1g

  • 343.0CNY

  • Detail
  • Alfa Aesar

  • (H27625)  Tetraethylgermanium, 99%   

  • 597-63-7

  • 5g

  • 1141.0CNY

  • Detail

597-63-7SDS

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 Tetraethylgermane

1.2 Other means of identification

Product number -
Other names TETRAETHYLGERMANE

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:597-63-7 SDS

597-63-7Synthetic route

ethyl bromide
74-96-4

ethyl bromide

triethylgermyl ytterbium bromide*2THF

triethylgermyl ytterbium bromide*2THF

A

YbBr2*2(C4H8O)
113173-30-1

YbBr2*2(C4H8O)

B

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
In tetrahydrofuran addn. of soln. of C2H5Br in THF to soln. of Yb complex in THF at 20°C; YbBr2*2THF as ppt., detection of (C2H5)4Ge by gas-liquid chromatography as volatile product;A 91%
B 95%
tris(1,2-benzenediolato-O,O′)germanate
112712-64-8

tris(1,2-benzenediolato-O,O′)germanate

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
In diethyl ether (N2); added dropwise a soln. of C2H5MgBr to a suspn. of Ge-compound at room temp.; stirred for 30 min; hydrolyzed; extracted with ether; washed with water; dried over MgSO4; evapd.;83%
In diethyl ether potassium tris(1,2-benzenediolato)germanate and 4 equiv EtMgBr in Et2O at 20°C for 0.5 h;83%
Coppinger's Radikal
22719-43-3, 2370-18-5

Coppinger's Radikal

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

germanium hydride trichloride
1184-65-2

germanium hydride trichloride

A

tetraethylgermane
597-63-7

tetraethylgermane

B

hexaethyldigermane
993-62-4

hexaethyldigermane

C

octaethyltrigermane
13937-05-8

octaethyltrigermane

Conditions
ConditionsYield
With water In tetrahydrofuran treatment od reaction mixt. in THF with excess EtMgBr, hydrolysis; extn. (ether), drying over Na2SO4; identification of individual compds.;A 80%
B 20%
C <1
ethyl bromide
74-96-4

ethyl bromide

GeCl2*C2H5NC2H4

GeCl2*C2H5NC2H4

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
germylene heated with EtBr at 130°C for 15 h in a sealed tube was treated with EtMgBr, Ar atm.; hydrolyse, distn.;79%
ethyl bromide
74-96-4

ethyl bromide

tris(1,2-benzenediolato-O,O′)germanate
112712-64-8

tris(1,2-benzenediolato-O,O′)germanate

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
With magnesium In tetrahydrofuran (N2); heated a suspn. of Mg and Ge-compound under stirring to 50-55°C; added dropwise a soln. of ethyl bromide; refluxed under stirring for 2 h; cooled; added ether; evapd.; distd.;78%
germanium(II) bis(3,5-di-tert-butyl-1,2-semiquinonate)
110577-18-9

germanium(II) bis(3,5-di-tert-butyl-1,2-semiquinonate)

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

germanium hydride trichloride
1184-65-2

germanium hydride trichloride

A

tetraethylgermane
597-63-7

tetraethylgermane

B

hexaethyldigermane
993-62-4

hexaethyldigermane

C

octaethyltrigermane
13937-05-8

octaethyltrigermane

Conditions
ConditionsYield
With water In benzene heating reaction mixt. in C6H6 (tube fused, 48 h, 80°C), treatment with EtMgBr soln. (ether), hydrolysis; drying (Na2SO4), mixt. chromy.;A 70%
B 25%
C 5%
ethyl bromide
74-96-4

ethyl bromide

dilithiodiethylgermane
119494-29-0

dilithiodiethylgermane

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
69%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

triethylgermyllithium
6727-87-3

triethylgermyllithium

trimethylsilyldiethylgermyllithium
104585-84-4

trimethylsilyldiethylgermyllithium

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
With water In N,N,N,N,N,N-hexamethylphosphoric triamide Equimolar mixt. of Et3GeLi and Me3SiGeEt2Li in HMPA is stirred for 94 h at 25°C, then Me3SiCl and water are added.; extn. with ether;69%
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

tetraethoxygermanium
14165-55-0

tetraethoxygermanium

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
Inert atmosphere;63%
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

tetramethoxygermanium

tetramethoxygermanium

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
Inert atmosphere;52%
ethyl bromide
74-96-4

ethyl bromide

triethylgermyllithium
6727-87-3

triethylgermyllithium

diethylgermane
1631-46-5

diethylgermane

A

Triethylgerman
1188-14-3

Triethylgerman

B

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide Mixt. of Et3GeLi and Et2Ge(H)2 in HMPA is stirred for 10 h at 25°C, then EtBr is added and stirred for 30 min.; Addn. of water and hexane, organic layer is analyzed by GLC.;A 49%
B 51%
difluorogermylene

difluorogermylene

diethylmercury
627-44-1

diethylmercury

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
In benzene Et2Hg was added to GeF2 in C6H6 at 0°C with stirring, then ambient temp., C2H4Br2 was added, then EtMgBr; hydrolysis, product was not sepd.; mixt. was analyzed by cpv;49%
ethyl bromide
74-96-4

ethyl bromide

triethylgermyl samarium bromide*99THF

triethylgermyl samarium bromide*99THF

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
In tetrahydrofuran byproducts: SmBr2; addn. of soln. of C2H5Br in THF to soln. of Sm complex in THF at 20°C; SmBr2 as ppt., detection of (C2H5)4Ge by gas-liquid chromatography as volatile product;45%
ethyl bromide
74-96-4

ethyl bromide

diethylgermane
1631-46-5

diethylgermane

A

Triethylgerman
1188-14-3

Triethylgerman

B

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
With potassium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide byproducts: Et2Ge(H)2; Small pieces of K are placed in an ampoule containing HMPA and THF, after stirring for 30 min dissolved Et2Ge(H)2 in THF is gradually added, the react. mixt. is stirred for 24 h, then EtBr is added.; Addn. of water and hexane, organic layer is examined.;A 42%
B 12%
With sodium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide byproducts: Et2GeH2; Small pieces of Na are placed in an ampoule containing HMPA and THF, after stirring for 30 min dissolved Et2Ge(H)2 in THF is gradually added, the react. mixt. is stirred for 24 h, then EtBr is added.; Addn. of water and hexane, organic layer is examined.;A 35%
B 8%
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
With germanium tetrabromide
diethylzinc
557-20-0

diethylzinc

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
With germaniumtetrachloride
triethylaluminum
97-93-8

triethylaluminum

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
With hexane; germaniumtetrachloride; sodium chloride
ethyl bromide
74-96-4

ethyl bromide

ammonia
7664-41-7

ammonia

Triethylgerman
1188-14-3

Triethylgerman

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
Reaktion der Kalium-Verbindung;
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

germanium tetrachloride

germanium tetrachloride

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
With diethyl ether; benzene Zersetzung des Reaktionsgemisches mit Eis und Eisessig;
diethylzinc
557-20-0

diethylzinc

germanium tetrachloride

germanium tetrachloride

tetraethylgermane
597-63-7

tetraethylgermane

C6H15Al*C9H21N

C6H15Al*C9H21N

germaniumtetrachloride
10038-98-9

germaniumtetrachloride

A

C2H5AlCl2*C9H21N

C2H5AlCl2*C9H21N

B

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
at 40℃; for 3h;
germanium tetrabromide
13450-92-5

germanium tetrabromide

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
In not given Grignard reaction;;
In not given Grignard reaction;;
diethylzinc
557-20-0

diethylzinc

germaniumtetrachloride
10038-98-9

germaniumtetrachloride

tetraethylgermane
597-63-7

tetraethylgermane

Conditions
ConditionsYield
In not given byproducts: ZnCl2;
In not given byproducts: ZnCl2;
germanium tetrabromide
13450-92-5

germanium tetrabromide

tetraethylgermane
597-63-7

tetraethylgermane

A

Bromotriethylgermanium
1067-10-3

Bromotriethylgermanium

B

diethylgermanium dibromide
13314-53-9

diethylgermanium dibromide

Conditions
ConditionsYield
aluminium bromide other Radiation; a mixt. of GeBr4 and tetraethylgermane in presence of AlBr3 as catalystin a Pyrex tube is irradiated with a light stream of argon for 12 min at atmospheric pressure (microwave irradiation: 300 W) (Ar); identification by (1)H-NMR, gas chromy.;A 95%
B n/a

597-63-7Relevant articles and documents

Massol et al.

, p. 895 (1971)

Direct electrochemical synthesis of germanium alkoxides

Vereshchagin,Elinson,Krylova,Novikov,Egorov

, p. 464 - 465 (2015/10/29)

Anodic galvanostatic dissolution of germanium in alcohols in an undivided cell in the presence of trace amounts of NaOAc as an electrolyte afforded germanium alkoxides with a current efficiency of 88-95%.

ETUDE DE REACTIONS PAR TRANSFERT MONOELECTRONIQUE ENTRE DIVERS HYDROGERMANES A CARACTERE ACIDE ET DES SYSTEMES QUINONIQUES DIA- ET PARA-MAGNETIQUES

Riviere, P.,Castel, A.,Abdennadher, C.

, p. 181 - 194 (2007/10/02)

The chlorogermanes PhnCl3-nGe-H (n = 0, 1, 2) were treated with diamagnetic (3,5-di-t-butylorthoquinone) 1 and the paramagnetic galvinoxyl 2.These reactions occur mainly by monoelectron transfer giving the corresponding adducts.In the case of 3,5-di-t-butylorthoquinone, the resulting 1-4 adducts decompose by two simultaneous processes (HCl elimination and redistribution) yielding germadioxolanes.The chlorogermadioxolanes prepared in this way easily cause halogenic redistribution leading to chlorogermanes and germylcatecholates having branched or spiranestructure.In the case of the galvinoxyl radical, the same chlorogermanes lead by monoelectron transfer to the corresponding quinophenol and an intermediate germanium-centered radical.The latter by recombination outside the solvent cage, gives digermane.However, its primary reaction, which occurs within the solvent cage, is with quinophenol to form two isomeric O- and C-germylated catechols.The C-isomer is by far predominant as it also formed in the secondary hydrogermylation of quinophenol produced in the initial stage of the reaction.We have been able to confirm these mechanisms by a comparative study of the reaction of germanium hydrides R3Ge?+-H?-, acidic germanes X3Ge?--H?+, and germanates X3Ge(-)N-H(+) with galvinoxyl and the corresponding quinophenol.Key words: SET reactions; germylations; quinones; chlorohydrogermanes; chlorogermanes; chlorogermanates.

The effect of substituents on the structure and reactivity of organogermanium anions

Pigarev, S. D.,Bravo-Zhivotovskii, D. A.,Kalikhman, I. D.,Vyazankin, N. S.,Voronkov, M. G.

, p. 29 - 42 (2007/10/02)

The replacement of the ethyl group in Et3GeH by a phenyl group was shown by equilibrium metallation to halve the pKa value compared with analogous CH acids.NMR showed that the decreased acceptor effect of the phenyl group in the PhEt2Ge- anion is caused by a considerably reduced contribution of the mesomeric effect to anion stabilization compared with what happens in the corresponding carbanions.At the same time, the stabilization of the organogermanium anion increases the role of ?-polarization of the aromatic substituent and this contribution is comparable with the mesomeric effect value.A stabilizing effect of organosilicon and organogermanium substituents due to a high degree of polarizability has been shown by concurrent methanolysis of Et3GeLi and REt2GeLi (R=Me3Si, Et3Si, Me3Ge, Et3Ge, t-Bu, Ph).An unexpected reaction of the trimethylsilyl anion with the Me3SiGeEt2- anion leading to diethylgermane dianion, Et2Ge2- has been revealed.The existence of this process supports the suggested absence of (d-p)? interaction in germanium anions with organo-silicon and -germanium substituents.

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