13314-52-8

Basic information

• Product Name: DIETHYLGERMANIUM DICHLORIDE
• Synonyms: DIETHYLGERMANIUM DICHLORIDE;DIETHYLDICHLOROGERMANE;DICHLORODIETHYLGERMANE;Diethyldichlorogermanium;Diethylgermaniumdichloride,min.97%;Diethylgermanium dichloride, min. 97%;Dichlorodiethylgermane,97%;Diethylgermanium dichloride 97%
• CAS NO: 13314-52-8
• Molecular Formula: C₄H₁₀Cl₂Ge
• Molecular Weight: 201.67
• EINECS: 236-344-5
• Product Categories: Organogermanium;Organometallic Reagents;Others;organogermanium compound
• Mol File: 13314-52-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: -39°C
• Boiling Point: 175 °C
• Flash Point: 145 °F
• Appearance: Colorless/Liquid
• Density: 1.372 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.471(lit.)
• Water Solubility: Decomposes in water and NH₃. Soluble in organic solvents
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: DIETHYLGERMANIUM DICHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYLGERMANIUM DICHLORIDE(13314-52-8)
• EPA Substance Registry System: DIETHYLGERMANIUM DICHLORIDE(13314-52-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-20/21/22-36/37
• Safety Statements: 16-26-36
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• TSCA: No
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 13314-52-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

As an intermediate

InChI:InChI=1/C4H10Ge.2ClH/c1-3-5-4-2;;/h3-4H2,1-2H3;2*1H/q+2;;/p-2

Synthetic route

germanium(II) chloride dioxane + 2,2-diethyl(6,8-di-tert-butyl)-4,5-benzo-2-germa-1,3-dioxolane (78100-52-4) → 2-germylene(6,8-di-t-butyl)-4,5-benzo-1,3-dioxolane (110577-20-3) + diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In tetrahydrofuran (high vacuum system), heated at 40°C for 6h; solvent removed under vacuum, agitated with pentane, elem. anal.;	A 57% B 95%

2,2-diethyl(6,8-di-tert-butyl)-4,5-benzo-2-germa-1,3-dioxolane (78100-52-4) + germaniumtetrachloride (10038-98-9) → germanium(II) bis(3,5-di-tert-butyl-1,2-semiquinonate) (110577-18-9) + diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In benzene (high vacuum system), heated at 80°C for 2h; pptd., filtered off, washed with benzene, then with pentane, dried under vacuum, elem. anal.;	A 91% B >99

diethylgermane (1631-46-5) + copper dichloride → diethyl germanium dichloride (13314-52-8)

Conditions	Yield
copper(l) iodide In diethyl ether hydrogermane mixed with 4 equiv. of CuCl2 and CuI in ether under room temp. for 8 h; solvent evapd., distilled under reduced pressure;	85%

thionyl chloride (7719-09-7) + (C2H5)2GeCl(CH2CH(OH)CH3) (77013-74-2) → (C2H5)2GeCl(CH2CHClCH3) (77013-76-4) + diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In chloroform byproducts: SO2; under N2 or Ar; soln. of SOCl2 in CHCl3 added in portions to soln. of Ge-compd. kept at 0°C, warmed to room temp., evapn. of solvent under vac.; identified by NMR;	A 78% B 22%

Dichlorophenylphosphine (644-97-3) + benzil (134-81-6) + diethyl-2,2 germa-2 phenyl-3 oxazolidone (64548-93-2) → diethyl germanium dichloride (13314-52-8) + tetraphenyl-2,3,5,9 oxo-7 trioxa-1,4,6 aza-9 phospha(V)-5 spiro<4,4>nonene-2 (64548-99-8)

Conditions	Yield
In benzene dropwise addn. of phosphine to soln. of benzile and Ge compd. with stirring, 0°C; heating to room temp.; stirring, 12h; pptn.; filtration under Ar; detn. by NMR;	A n/a B 63%

tetrachloromethane (56-23-5) + poly(diethylgermane) (22694-80-0) → diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In cyclohexane Kinetics; byproducts: CCl3CCl3; Irradiation (UV/VIS); photolysis of Ge-compd. in cyclohexane in the presence of CCl4 at 245 nm at room temp. for 30 min with a 110 W low pressure Hg arc lamp;	63%

Dichlorophenylphosphine (644-97-3) + diethyl-2,2 germa-2 phenyl-3 oxazolidone (64548-93-2) → diethyl germanium dichloride (13314-52-8) + diphenyl-2,3 oxo-5 phospha(III)-2 oxazolidine-1,3 (64548-98-7)

Conditions	Yield
In benzene dropwise addn. of phosphine to Ge compd. soln. with stirring, 0°C; heating to room temp.; stirring, 12h; pptn.; filtration under Ar;	A n/a B 59%

germaniumtetrachloride (10038-98-9) + dimethyl-4,4 diethyl-2,2 germa-2 oxo-5 dioxa-1,3 olane (64548-96-5) → Ge(OC(CH3)2C(O)O)2 (130942-71-1) + diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In dichloromethane dropwise addn. of freshly distd. GeCl4 to Ge compd. soln.; evapn.; pptn.; recrystn. (CH2Cl2,pentane);	A 53% B n/a

dichlorophenylarsine (696-28-6) + methyl-4 diethyl-2,2 germa-2 phenyl-3 oxazolidone (84973-36-4) → diethyl germanium dichloride (13314-52-8) + 2,3-diphenyl-4-methyl-5-oxo-2-arsa-1,3-oxazolidine (130942-70-0)

Conditions	Yield
In benzene dropwise addn. of PhAsCl to Ge compd. soln. with stirring, 0°C; heating to room temp.; pptn.; filtration under Ar; detn. by NMR;	A n/a B 49%

3,5-di-tert-butyl-o-benzoquinone (3383-21-9) + chlorodiethylgermane (10177-53-4) → 3,5-Di-tert-butylcatechol (1020-31-1) + 2,2-diethyl(6,8-di-tert-butyl)-4,5-benzo-2-germa-1,3-dioxolane (78100-52-4) + diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In benzene byproducts: HCl; heating in a sealed tube at 80 ° C for 12 h,; concn. (reduced pressure), anal. (IR, H-NMR, MS); 13% starting germane;	A 38% B 42% C 40%

dichlorophenylarsine (696-28-6) + dimethyl-4,4 diethyl-2,2 germa-2 oxo-5 dioxa-1,3 olane (64548-96-5) → dimethyl-4,4 phenyl-2 oxo-5 arsa-2 dioxolonne-1,3 (64548-97-6) + diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In benzene dropise addn. of PhAsCl2 soln. to Ge compd. soln. with stirring under inert gas, 5°C; heating to room temp.; evapn.;; recrystn. (CCl4);	A 42% B n/a

methyl-4 diethyl-2,2 germa-2 phenyl-3 oxazolidone (84973-36-4) → 4-methyl-3-phenyl-2,5-dioxo-1,2,3-oxathiazolidine + diethyl germanium dichloride (13314-52-8)

Conditions	Yield
With thionyl chloride In benzene slow addn. of SOCl2 soln. to Ge compd. with stirring, 3°C; pptn.; filtration under Ar; detn. by NMR;	A 35% B n/a

C6H15Al*C9H21N + germaniumtetrachloride (10038-98-9) → C2H5AlCl2*C9H21N + diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In hexane at 0 - 20℃; for 2h;

thiophosgene (463-71-8) + 2,2-diethyl-4,5-diphenyl 1,3,2-dioxagermole (104284-23-3) → diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In not given byproducts: SC(OC(C6H5)C(C6H5)O);

aluminium trichloride (7446-70-0) + tetraethylgermane (597-63-7) → diethyl germanium dichloride (13314-52-8)

Conditions	Yield
With acetyl chloride In not given

dimethyl-4,4 diethyl-2,2 germa-2 oxo-5 dioxa-1,3 olane (64548-96-5) → diethyl germanium dichloride (13314-52-8)

Conditions	Yield
In dichloromethane byproducts: CO2, acetone; at 200°C;

diethyl germanium dichloride (13314-52-8) + magnesium (7439-95-4) + bromopentene (1119-51-3) → bis(4-pentenyl)-diethylgermanium (259187-11-6)

Conditions

Yield

In tetrahydrofuran flask purged with N2; charged with Mg (0.11 mol) and dry THF; 5-bromo-1-pentene (0.08 mol) in dry THF added in portions; stirred and refluxed (0.5 h); cooled to room temp.; soln. of Et2GeCl2 (0.024 mol) added dropwise; refluxed (15 h); cooled to room temp.; poured over ice-cold 1 M NH4Cl; org. layer sepd.; washed with deionized H2O; dried over MgSO4; filtered; concd. (vac.); liq. dried over CaH2 under Schlenk vac.;

93%

diethyl germanium dichloride (13314-52-8) + Benzilic acid (76-93-7) → (C2H5)2GeCO2C(C6H5)2O (139415-85-3)

Conditions	Yield
With triethylamine In benzene byproducts: Et3NHCl; elem. anal.;	92%
With triethylamine In benzene (inert atm.); room temp. 2h; filtn., evapn., sublimation (195°C/760 mm Hg);	67%

5-mercapto-3-phenyl-Δ(4)-{1,3,4}thiadiazoline-2-thione, potassium salt (6336-51-2) + diethyl germanium dichloride (13314-52-8) → bis(2,5-dimercapto-4-phenyl-1,3,4-thiodiazolate)diethylgermanium(IV)

Conditions	Yield
In benzene N2, stoich., stirred for 12 h at 40°C; filtered, evapd. (vac.), recrystd. (ether/dichloromethane); elem. anal.;	92%

silver oxalate (15843-43-3, 31038-77-4) + diethyl germanium dichloride (13314-52-8) → C6H10GeO4 (164019-28-7)

Conditions	Yield
In tetrahydrofuran (inert atm.), stirring, (12 h, room temp.); filtn., evapn., recrystn. (THF/hexane);	91%

diethyl germanium dichloride (13314-52-8) → diethylmethoxychlorogermane (137321-07-4)

Conditions	Yield
With methanol; triethylamine In benzene byproducts: NEt3*HCl; (dry Ar or N2), dry solvents; addn. of NEt3 to soln. of Et2GeCl2 and MeOH in benzene;; filtration, conc. (reduced pressure);;	90%

diethyl germanium dichloride (13314-52-8) + bromopentene (1119-51-3) → bis(4-pentenyl)-diethylgermanium (259187-11-6)

Conditions	Yield
With magnesium In diethyl ether inert atmosphere; addn. of bromoalkene to Mg powder, refluxing for 1 h, addn. of Ge-compd. (room temp.), refluxing for 24-30 h; cooling to room temp., pouring into ice-cold aq. NH4Cl, extn. into ether, drying (MgSO4), solvent removal (vac.), fractional vac. distn. from CaH2; elem. anal.;	89%

sodium picolinate (57665-05-1) + diethyl germanium dichloride (13314-52-8) → diethylgermanium bis(2-picolinate) (1207645-37-1)

Conditions	Yield
In benzene byproducts: NaCl; under Ar atm., in unhyd. conditions; soln. of Et2GeCl2 in C6H6 added to suspn. of sodium salt in C6H6 with vigorous stirring, refluxed for 5 h; cooled to room temp., pptd. NaCl filtered off, filtrate dried under vac.: elem. anal.;	89%

2-methylallylmagnesium chloride (5674-01-1) + diethyl germanium dichloride (13314-52-8) → di(2-methylallyl)diethylgermane

Conditions	Yield
In tetrahydrofuran for 3h; Inert atmosphere;	87.5%

2-pyridinealdoxime (873-69-8) + diethyl germanium dichloride (13314-52-8) → C16H20GeN4O2

Conditions	Yield
Stage #1: 2-pyridinealdoxime With methanol; sodium Reflux; Inert atmosphere; Stage #2: diethyl germanium dichloride In benzene for 4h; Reflux; Inert atmosphere;	87%

allylmagnesium bromide (2622-05-1) + diethyl germanium dichloride (13314-52-8) → diallyldiethylgermane (1793-89-1)

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h;	87%

2-methyllactic acid (594-61-6) + diethyl germanium dichloride (13314-52-8) → dimethyl-4,4 diethyl-2,2 germa-2 oxo-5 dioxa-1,3 olane (64548-96-5)

Conditions	Yield
With triethylamine In benzene (inert atm.); room temp. 2h; filtn., evapn., recrystn.(MeCOOEt);	86%

diethyl germanium dichloride (13314-52-8) + disodium maleonitriledithiolato → (C2H5)2GeS(C(CN))2S (104284-16-4)

Conditions	Yield
In tetrahydrofuran byproducts: NaCl; to soln. of Na dithiolate in dry THF added dropwise at 0°C with stirring Ge compd., after 1 h stirring at this temp. mixt. was allowed to warm up to room temp. and filtered, then MeOH removed.; residue washed with pentane;	85%

diethyl germanium dichloride (13314-52-8) + disodium cis-1,2-dicyano-1,2-ethylenedithiolate (5466-54-6) → (C2H5)2GeS(C(CN))2S (104284-16-4)

Conditions	Yield
In tetrahydrofuran byproducts: NaCl;	85%

Methyl 3-aminothiophene-2-carboxylate (22288-78-4) + diethyl germanium dichloride (13314-52-8) + 1,8-diazabicyclo[5.4.0]undec-7-ene (6674-22-2) → 3-diethylamino 2-methylthiophoate (137321-02-9)

Conditions	Yield
In benzene byproducts: DBU*HCl; (dry Ar or N2), dry solvents; react. at 20°C;;	85%

Methyl 3-aminothiophene-2-carboxylate (22288-78-4) + diethyl germanium dichloride (13314-52-8) → diethylgermyl bis(aminothiophoate) (137321-03-0) + 3-diethylamino 2-methylthiophoate (137321-02-9)

Conditions	Yield
With triethylamine In benzene byproducts: N(C2H5)3HCl; (dry Ar or N2), dry solvents; addn. of a mixt. of thiophoate and Et3N in benzene to Ge-compd. in benzene at 0°C, stirring at 20°C (4 h);; filtration;;	A 10-15 B 85%

vinyl magnesium bromide (1826-67-1) + diethyl germanium dichloride (13314-52-8) → diethyldivinylgermane (22773-67-7)

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h;	85%
In tetrahydrofuran Sonication; germane was sonicated with a commercial 1 M soln. of CH2CHMgBr in THF;	80%
In tetrahydrofuran Inert atmosphere; Schlenk technique; Sonication;	80%

diethyl germanium dichloride (13314-52-8) + allyl bromide (106-95-6) → diallyldiethylgermane (1793-89-1)

Conditions	Yield
With magnesium In tetrahydrofuran byproducts: MgClBr; Sonication; the mixt. of magnesium, germane and halogen-compound in THF was sonicated for 2 h (inert atm.); the mixt. was washed with satd. soln. of NaCl, extd. with diethyl ether,the organic layer was dried over MgSO4, the solvent was removed under r educed pressure, column chromy. (petroleum ether-diethyl ether 95/5);	85%
With magnesium In tetrahydrofuran for 2h; Inert atmosphere; Schlenk technique; Sonication;	85%

2-pyridinealdoxime (873-69-8) + diethyl germanium dichloride (13314-52-8) → C24H20GeN4O2

Conditions	Yield
Stage #1: 2-pyridinealdoxime With methanol; sodium Reflux; Inert atmosphere; Stage #2: diethyl germanium dichloride In benzene for 4h; Reflux; Inert atmosphere;	84%

diethyl germanium dichloride (13314-52-8) + 3-Hydroxy-2-naphthoic acid (92-70-6) → (C2H5)2Ge(OC10H6CO2) (164019-31-2)

Conditions	Yield
With triethylamine In benzene (inert atm.); stiring (room temp. 2h); filtn., evapn., recrystn. (benzene/hexane);	83%

benzyl bromide (100-39-0) + diethyl germanium dichloride (13314-52-8) → dibenzyldiethylgermane (109021-78-5)

Conditions	Yield
With magnesium In tetrahydrofuran byproducts: MgClBr; Sonication; the mixt. of magnesium, germane and halogen-compound in THF was sonicated for 2 h (inert atm.); the mixt. was washed with satd. soln. of NaCl, extd. with diethyl ether,the organic layer was dried over MgSO4, the solvent was removed under r educed pressure, column chromy. (petroleum ether-diethyl ether 95/5);	82%
With magnesium In tetrahydrofuran for 2h; Inert atmosphere; Schlenk technique; Sonication;	82%

1-bromo-4-butene (5162-44-7) + diethyl germanium dichloride (13314-52-8) + magnesium (7439-95-4) → bis(3-butenyl)-diethylgermanium (259187-12-7)

Conditions

Yield

In tetrahydrofuran flask purged with N2; charged with Mg (0.11 mol) and dry THF; 4-bromo-1-butene (0.08 mol) in dry THF added in portions; stirred and refluxed (0.5 h); cooled to room temp.; soln. of Et2GeCl2 (0.024 mol) added dropwise; refluxed (15 h); cooled to room temp.; poured over ice-cold 1 M NH4Cl; org. layer sepd.; washed with deionized H2O; dried over MgSO4; filtered; concd. (vac.); liq. dried over CaH2 under Schlenk vac.;

82%

1,2-bis(dimethylgermyl)ethane-iron tetracarbonyl (120926-69-4) + diethyl germanium dichloride (13314-52-8) → (C2H5)2GeFe(CO)4Ge(C2H5)2Fe(CO)4 (15708-59-5) + 1,2-bis(chlorodimethylgermyl)ethane (63746-65-6)

Conditions	Yield
In neat (no solvent) mixt. of (CH3)2Ge(CH2)2Ge(CH3)2Fe(CO)4 and Et2GeCl2 heated at 140°C for 8h in a sealed tube under argon; determination: GC,1H-NMR;	A 12% B 81%

2K(1+)*((CH3)3CP)4(2-)*C4H8O=K2((CH3)3CP)4*C4H8O + diethyl germanium dichloride (13314-52-8) → (C2H5)2Ge((CH3)3CP)4

Conditions	Yield
In pentane byproducts: KCl; dry Ar atm.; equimolar amts., cooling (-78°C), heating (20°C), stirring (15 h); filtn., washing (pentane), evapn., drying (vac.); elem. anal.;	80.6%

diethyl germanium dichloride (13314-52-8) + 1,2-phenylenebis(methylphosphine) (96283-99-7) → C6H4(P(CH3)Ge(CH2CH3)2P(CH3)) (96338-94-2, 96284-08-1)

Conditions	Yield
With n-butyllithium In not given byproducts: LiCl; (under Ar); metallation of the phosphine with Li-n-Bu in THF (at - 30°C) or ether, dropwise addn. of Cl2GeEt2 in ether at -20°C with stirring, stirring for 2 h at room temp.; filtn. from LiCl, vac. distn., cis/trans 40/60, elem. anal.;	80%

diethyl germanium dichloride (13314-52-8) + 2-mercapto-2-methylpropanoic acid (4695-31-2) → C7H14GeO2S (164019-26-5)

Conditions	Yield
With triethylamine In benzene (inert atm.); room temp. 2h; filtn., evapn., destilation;	80%

diethyl germanium dichloride (13314-52-8) + N-phthaloyl-DL-leucine (19506-89-9) → bis-(1,3-dihydro-1,3-dioxo-α-isobutyl-2H-isoindole-2-acetato)diethylgermanium(IV)

Conditions	Yield
Stage #1: N-phthaloyl-DL-leucine With sodium In methanol; benzene for 5h; Reflux; Stage #2: diethyl germanium dichloride In methanol; benzene for 8h; Reflux;	79%

Upstream product

• 463-71-8 thiophosgene 
• 104284-23-3 2,2-diethyl-4,5-diphenyl 1,3,2-dioxagermole 
• 1631-46-5 diethylgermane 
• 10038-98-9 germaniumtetrachloride 
• 64548-96-5 dimethyl-4,4 diethyl-2,2 germa-2 oxo-5 dioxa-1,3 olane 
• 7719-09-7 thionyl chloride 
• 77013-74-2 (C₂H₅)2GeCl(CH₂CH(OH)CH₃) 
• 78100-52-4 2,2-diethyl(6,8-di-tert-butyl)-4,5-benzo-2-germa-1,3-dioxolane 
• 56-23-5 tetrachloromethane 
• 22694-80-0 poly(diethylgermane) 
• 84973-36-4 methyl-4 diethyl-2,2 germa-2 phenyl-3 oxazolidone 
• 644-97-3 Dichlorophenylphosphine 
• 134-81-6 benzil 
• 64548-93-2 diethyl-2,2 germa-2 phenyl-3 oxazolidone 

Downstream Products

• 104284-23-3 2,2-diethyl-4,5-diphenyl 1,3,2-dioxagermole 
• 862060-51-3 bis(phenylthiomethyl)diethylgermane 
• 164019-27-6 C₁₀H₁₂GeO₂S 
• 164019-28-7 C₆H₁₀GeO₄ 
• 164019-26-5 C₇H₁₄GeO₂S 
• 86691-52-3 (C₆H₅)3Ge(Ge(C₂H₅)2)Ge(C₆H₅)3 
• 109021-78-5 dibenzyldiethylgermane 
• 92682-67-2 tetraphenylcyclopentadienyldiethylgermane chloride 
• 139415-85-3 (C₂H₅)2GeCO₂C(C₆H₅)2O 
• 84973-27-3 diethylbis(phenylamino)germanium 
• 64548-96-5 dimethyl-4,4 diethyl-2,2 germa-2 oxo-5 dioxa-1,3 olane 
• 64548-94-3 2,2-Diethyl-3,4-diphenyl-[1,3,2]oxazagermolidin-5-one 
• 84973-36-4 methyl-4 diethyl-2,2 germa-2 phenyl-3 oxazolidone 

Relevant articles and documents

Process for the preparation of group IVA and group VIA compounds

Methods of preparing Group IVA and Group VIA organometallic compounds, particularly Group IVA organometallic compounds, are provided. Such manufacturing methods employ an amine and/or phosphine catalyst in a transalkylation step and may be performed in a batch, semi-continuous or continuous manner.

Laser flash photolysis of polygermanes. Generation of germylenes and polygermyl radicals

Laser flash photolysis of polygermanes involves both Ge-Ge bond homolysis to give polygermyl radicals and extrusion of germylenes.

Addition 1,4 de divers organo- et organohalogeno-hydrogermanes sur la di-t-butyl-3,5 orthoquinone

The thermal 1,4-addition of triorganohydrogermanes R3GeH(R=Et, Ph) with 3,5-di-t-butylorthoquinone leads to their corresponding mono-O-germylated catechols in good yields.Similarly, the organohalohydrogermanes give the 2,2-di-organo- (or 2,2-organohalo)(6,8-di-t-butyl)-4,5-benzo-2-germa-1,3-dioxolanes after dehydrochlorination of transient mono-O-chlorogermylated catechols.Since these reactions are only slightly dependent on solvent and radical initiators, the mechanism probably involves monoelectronic transfer with the formation of a radical anion pair in the first step.The ESR measurements show the transient formation of a paramagnetico-semiquinonic species which supports the proposed mechanism.