925-93-9

Basic information

• Product Name: ETHANOL-D
• Synonyms: Ethanol-d,99 atom % D;Ethanol-d,for NMR,99.5+ atom % D;Ethanol-dEthyl alcohol-d;ETHANOL-D1 DEUTERATION DEGREE MAGNISOLV(;Ethan(ol-d) 98 atoM % D;Ethanol-d1 99atom%D;Ethanol-D1 deuteration degree min. 99.5% for NMR spectroscopy MagniSolv;MONODEUTERO ETHANOL
• CAS NO: 925-93-9
• Molecular Formula: C₂H₆O
• Molecular Weight: 47.07
• EINECS: 213-128-9
• Mol File: 925-93-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: -130 °C(lit.)
• Boiling Point: 78 °C(lit.)
• Flash Point: 55 °F
• Appearance: Clear colorless/Liquid
• Density: 0.806 g/mL at 25 °C
• Refractive Index: n20/D 1.359(lit.)
• Storage Temp.: Flammables area
• Explosive Limit: 3.5-15%(V)
• Stability: Stable. Highly flammable. Incompatible with oxidizing agents, acids, acid chlorides, alkali metals, ammonia, moisture, peroxides
• BRN: 1731246
• CAS DataBase Reference: ETHANOL-D(CAS DataBase Reference)
• NIST Chemistry Reference: ETHANOL-D(925-93-9)
• EPA Substance Registry System: ETHANOL-D(925-93-9)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16-2017/7/16
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 1
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 925-93-9(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Different sources of media describe the Uses of 925-93-9 differently. You can refer to the following data:
1. ETHANOL-D is used in alcoholic beverages in suitable dilutions. Other uses are as solvent in laboratory and industry , in the manufacture of denatured alcohol, pharmaceuticals, in perfumery , in organic synthesis.
2. Ethan(ol-d) may be used as a source of deuterium for the deuterium exchange reaction of ethyl acetoacetate.

General Description

Ethan(ol-d) (ethanol-d, ethanol-d1) is a deuterated NMR solvent useful in NMR-based research and analyses. It can be prepared by reacting tetraethylorthosilicate with deuterium oxide. The hydrogen bonding in ethanol-d1 has been investigated based on Raman spectral data. The far infrared (FIR) spectrum of ethanol-d1 has been studied using ab initio calculations.

InChI:InChI=1/C2H6O/c1-2-3/h3H,2H2,1H3/i3D

Synthetic route

ethoxy(diphenyl)-λ6-sulfanenitrile (127022-76-8) → ethyl [2]alcohol (925-93-9) + S,S-diphenylsulphoximine (22731-83-5)

Conditions	Yield
With [D3]acetonitrile; water-d2 In phosphate buffer at 20℃; for 0.75h; pH=6.1; Kinetics; Thermodynamic data; Product distribution; Further Variations:; pH-values; Reagents; Solvents; Temperatures; Hydrolysis;	A 86% B 99%

(C5(CH3)5)IrP(C6H5)3(D)(OCH2CH3) → (C5(CH3)5)Ir(P(C6H5)3)2 + ethyl [2]alcohol (925-93-9)

Conditions	Yield
With triphenyl phosphine In benzene-d6; (2)H8-toluene (N2); dissolved Ir-compound with 1 drop toluene-d-8; placed in NMR tube; added triphenyl phosphine; (2)H NMR;	A n/a B 64%

diethyl sulphide (352-93-2) → ethyl [2]alcohol (925-93-9)

Conditions	Yield
With sulfuric acid; water-d2

ethanol (64-17-5) → ethyl [2]alcohol (925-93-9)

Conditions	Yield
With (CD3COCD3)D(1+) In gas at 57.9℃; Rate constant; Mechanism; Thermodynamic data; experiment conditions: NBS pulsed ion cyclotron resonance; probability of a reactive H/D exchange encounter for the deuteronated ion as a function of the Gibbs free-energy change of the (endoergic) deuteron transfer reaction;
With (C2D5)2OD(1+) In gas at 57.9℃; Rate constant; Mechanism; experiment conditions: NBS pulsed ion cyclotron resonance; probability of a reactive H/D exchange encounter for the deuteronated ion as a function of the Gibbs free-energy change of the (endoergic) deuteron transfer reaction;
With water-d2 In water at 34.9℃; Equilibrium constant;

orthocarbonic acid tetraethyl ester (78-09-1) → ethyl [2]alcohol (925-93-9)

Conditions	Yield
With sulfuric acid; water-d2

sodium ethanolate (141-52-6) → ethyl [2]alcohol (925-93-9)

Conditions	Yield
With water-d2; decalin
With diethyl ether; water-d2
With water-d2

aluminum ethoxide (555-75-9) → ethyl [2]alcohol (925-93-9)

Conditions	Yield
With decane; water-d2
With water-d2 at 80℃;

tetraethoxy orthosilicate (78-10-4) → ethyl [2]alcohol (925-93-9)

Conditions	Yield
With thionyl chloride; water-d2 1.) 0 deg C, 1 h, 2.) ambient temp., 2 h, 3) reflux, 4 weeks;	175 g

methylene chloride (74-87-3) + diazomethane-d2 (14621-84-2) → ethanol (64-17-5) + chloromethane-d2 (4960-87-6) + ethyl [2]alcohol (925-93-9) + D3-chloromethane (1111-89-3)

Conditions	Yield
at -78℃; Product distribution; Irradiation; various alkylhalides;

chloroform-d1 (865-49-6) + diethoxyltriphenylphosphorane (86852-11-1, 18509-25-6) → chloroethane (75-00-3) + ethyl [2]alcohol (925-93-9) + ethyl deuterioformate (35976-76-2) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
at 70℃; for 72h;
at 70℃; for 72h; Product distribution;

ethanol (64-17-5) + deuteromethanol (1455-13-6) → methanol (67-56-1) + ethyl [2]alcohol (925-93-9)

Conditions	Yield
Equilibrium constant;

ethane (74-84-0) → ethylene glycol-d2 (2219-52-5) + ethyl [2]alcohol (925-93-9) + deuteroacetic acid (758-12-3) + (O-2H2)-glycolic acid (81278-02-6)

Conditions	Yield
With potassium tetrachloroplatinate; water-d2; oxygen; platinum at 108℃; under 25857.4 Torr; for 19h; Product distribution; Mechanism; var. temperatures and reaction time;	A 0.002 mmol B 0.004 mmol C 0.002 mmol D 0.0017 mmol

carbon monoxide (201230-82-2) + orthoformic acid triethyl ester (122-51-0) → diethyl ether (60-29-7) + ethyl [2]alcohol (925-93-9) + C3H6(2)H2O + [2H]-diethoxymethane + ethyl ethoxymonodeuteroacetate + di-deuteromethylcarbonate

Conditions	Yield
With deuterium; Λ(+)-tris(pentane-2,5-dionato)ruthenium; methyl iodide Product distribution; 1.) 150 deg C, 4 h, 14 MPa, CO/D2=2.5; 2.) 170 deg C, 4 h, 10 MPa, CO/D2=2.5; 3.) 200 deg C, 6 h, 8 MPa, CO/D2=1.0; product distribution after successive steps;	A n/a B n/a C 7.0 % Chromat. D 3.0 % Chromat. E 1.0 % Chromat. F 0.3 % Chromat.

C6H14(2)HO5P → ethyl [2]alcohol (925-93-9) + dimethyl acetylphosphonate (17674-28-1)

Conditions	Yield
at 18℃; Kinetics; Equilibrium constant;

d(4)-methanol (811-98-3) + acetyl propionyl peroxide (13043-82-8) → methane (34557-54-5) + Monodeuteromethan (676-49-3) + ethyl [2]alcohol (925-93-9) + C4H4(2)H4O3

Conditions	Yield
at 39.85℃; for 0.666667h; Product distribution; Further Variations:; Temperatures; reaction times;

acetyl propionyl peroxide (13043-82-8) → methane (34557-54-5) + Monodeuteromethan (676-49-3) + ethyl [2]alcohol (925-93-9) + n-butane (106-97-8)

Conditions	Yield
With d(4)-methanol at -60.15℃; for 2h; Product distribution; Further Variations:; Temperatures; reaction times;

acetic acid tert-butyl ester (540-88-5) + d(4)-methanol (811-98-3) → ethyl [2]alcohol (925-93-9) + tert-butyl alcohol-d (3972-25-6)

Conditions	Yield
With sodium methylate; lanthanum(lll) triflate at 25℃; pH=8; Kinetics;

d(4)-methanol (811-98-3) + ethyl acetate (141-78-6) → ethyl [2]alcohol (925-93-9) + methyl acetate-d3 (24704-57-2)

Conditions	Yield
With sodium methylate; lanthanum(lll) triflate at 25℃; pH=8.5; Kinetics; Further Variations:; Reagents;
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics;

ammonium 3,5-dicyano-4-ethyl-4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridin-2-olate (956541-46-1) → ethane (74-84-0) + ethyl [2]alcohol (925-93-9) + 2,6-dihydroxy-4-methyl-pyridine-3,5-dicarbonitril; ammonium salt (18519-97-6)

Conditions	Yield
With borax; diclazuril In water-d2 at 20℃; pH=8;

C2H5(2)HO2Se → ethyl [2]alcohol (925-93-9)

Conditions	Yield
With sodium periodate In water-d2; [D3]acetonitrile at 100℃; for 14h;

d(4)-methanol (811-98-3) + C8H15NO3 (912359-83-2) → ethyl [2]alcohol (925-93-9) + C7H10(2)H3NO3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;

d(4)-methanol (811-98-3) + ethyl N-isobutyryl-N-methylglycinate (1235407-80-3) → ethyl [2]alcohol (925-93-9) + C8H12(2)H3NO3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;

d(4)-methanol (811-98-3) + C10H19NO3 (1235407-81-4) → ethyl [2]alcohol (925-93-9) + C9H14(2)H3NO3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;

d(4)-methanol (811-98-3) + C9H17NO3 (1235407-82-5) → ethyl [2]alcohol (925-93-9) + C8H12(2)H3NO3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;

d(4)-methanol (811-98-3) + C10H19NO3 (1235407-83-6) → ethyl [2]alcohol (925-93-9) + C9H14(2)H3NO3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;

d(4)-methanol (811-98-3) + C11H21NO3 (1235407-84-7) → ethyl [2]alcohol (925-93-9) + C10H16(2)H3NO3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;

d(4)-methanol (811-98-3) + C12H23NO3 (1235407-85-8) → ethyl [2]alcohol (925-93-9) + C11H18(2)H3NO3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;

d(4)-methanol (811-98-3) + C13H25NO3 (1235407-86-9) → ethyl [2]alcohol (925-93-9) + C12H20(2)H3NO3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;

d(4)-methanol (811-98-3) + C8H13NO3 (3154-55-0) → ethyl [2]alcohol (925-93-9) + C7H8(2)H3NO3

Conditions	Yield
With N-ethyl-N,N-diisopropylamine at 21.5℃; Kinetics; Solvolysis;

ethyl [2]alcohol (925-93-9) + 2-(2,5-difluorophenyl)-2,2-d2-acetic acid → ethyl 2-(2,5-difluorophenyl)acetate-d2

Conditions	Yield
With sulfuric acid at 20℃;	100%

(η5-C5H4Me)(carbonyl)2manganese(η1-vinylideneiron(η5-C5Me5)(carbonyl)2) + ethyl [2]alcohol (925-93-9) → (η5-C5H4Me)(carbonyl)2manganese(η1-CCD-iron(η5-C5Me5)(carbonyl)2)

Conditions	Yield
With n-C4H9Li In tetrahydrofuran (Ar, Schlenk tube technique); n-BuLi is added to a THF soln. of the complex cooled to -78°C, the mixture is stirred for 70 min, EtOD is added, the mixture is warmed up to room temp.; the volatiles are removed under reduced pressure, the products are extd. with ether and filtered through an alumina pad, product is detected by (1)H-NMR;	99%
With NaOC2H5 In tetrahydrofuran byproducts: (Fe(C5Me5)(CO)2)2; Irradiation (UV/VIS); (Ar, Schlenk tube technique); EtONa-EtOD is added to a THF soln. of the complex, the mixture is stirred for 2 h at ambient temp.; the volatiles are removed under reduced pressure, the products are extd. with ether and filtered through an alumina pad, product is detected by (1)H-NMR;	99%
hydrogen cation In ethyl [2]alcohol

ethyl [2]alcohol (925-93-9) + phenylacetonitrile-α,α-d2 (935-66-0) → phenyldideuterioacetamidic acid ethyl ester hydrochloride

Conditions	Yield
With hydrogenchloride at 0℃;	95%

ethyl [2]alcohol (925-93-9) + (C5(CH3)5)Rh(P(CH3)3)((13)CHCH2CH2)I (104267-65-4) → (C5(CH3)5)Rh(P(CH3)3)((13)CHCH2CH2)(H) (104373-38-8)

Conditions	Yield
With tert.-butyl lithium In not given (N2); -78°C; deuteration with C2H5OD at -60°C; 55% 13C-enriched according to NMR;	93%

ethyl [2]alcohol (925-93-9) + 5-Azidocarbonyloxy-7-phenyl-2,2-dimethyl-3-heptyne (308274-37-5) → C18H24(2)HNO3 (308274-40-0)

Conditions	Yield
With chloro-trimethyl-silane; iron(II) chloride at 20℃; Cyclization; Intramolecular amination;	91%

ethyl [2]alcohol (925-93-9) + bromoacetic-2,2-d2 acid bromoanhydride (40897-88-9) → ethyl bromo-<2,2-2H2>acetate (14341-47-0)

Conditions	Yield
Ambient temperature;	90%

(Z)-3-(ferrocenyl)acrylonitrile + ethyl [2]alcohol (925-93-9) → cis-β-ferrocenyl-α-deuterio-acrylonitrile

Conditions	Yield
With potassium In tetrahydrofuran byproducts: CH3CH2OH; mixture of ferrocenyl-compd. and EtOD in THF or pure EtOD, in which metallic K was dissolved, was stirred in absence of O2 and moisture at 50°C during 4 h, stored for 12 h at 25°C; removing of the solvent in vacuum, extn. of the residue with abs. ether, filtn. and evapn., chromatographed on a thin layer of silica gel;	90%

(E)-3-(ferrocenyl)acrylonitrile + ethyl [2]alcohol (925-93-9) → trans-β-ferrocenyl-α-deuterio-acrylonitrile

Conditions	Yield
With potassium In tetrahydrofuran byproducts: CH3CH2OH; mixture of EtOD and ferrocenyl-compd. in THF or pure EtOD, in which metallic K was dissolved, was stirred in absence of O2 and moisture at 50°C during 4 h, stored for 12 h at 25°C; removing of the solvent in vacuum, extn. of the residue with abs. ether, filtn. and evapn., chromatographed on a thin layer of silica gel;	90%

pentamethylcyclopentadienyliridium(III) PMe3 dihydride (80146-01-6) + ethyl [2]alcohol (925-93-9) → (η5-methylcyclopentadienyl)(trimethylphosphine)iridium dideuteride

Conditions	Yield
With silica gel In ethyl [2]alcohol N2-atmosphere; degassed EtOD; stirring (16 h, room temp.); evapn. (vac.); EtOD addn.; stirring (16 h, room temp.); evapn. (vac.); suspended in pentane; filtration (Celite); evapn. (vac.);isotopic purity detd. by (1)H NMR spectroscopy;	90%

ethyl [2]alcohol (925-93-9) + 2-bromoacetic-d2 acid-d (14341-48-1) → ethyl bromo-<2,2-2H2>acetate (14341-47-0)

Conditions	Yield
With sulfuric acid In benzene for 4.5h; Heating;	89%

(η5-C5H4Me)(carbonyl)2manganese(η1-vinylideneiron(η5-C5Me5)(carbonyl)2) + ethyl [2]alcohol (925-93-9) + trifluoroacetic acid (76-05-1) → (η5-C5H4Me)(carbonyl)2manganese(η1-CCD-iron(η5-C5Me5)(carbonyl)2)

Conditions	Yield
In dichloromethane (Ar, Schlenk tube technique); EtOD and CF3COOH are added to a CH2Cl2 soln. of the complex, the mixture is stirred for 30 min at room temp.; the volatiles are evapd., the products are extd. with ether and filtered through an alumina pad, solvent is removed;	89%

ethyl [2]alcohol (925-93-9) + dodecamethylcyclohexasilane → dimethylethoxysilane-Si-d1

Conditions	Yield
In diethyl ether at 5℃; for 1.5h; Irradiation;	84%

3,5-dichloro-pyrazine-2-carboxylic acid methyl ester (330786-09-9) + ethyl [2]alcohol (925-93-9) → ethyl 3,5-d2-pyrazine-2-carboxylate

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate; deuterium at 20℃; under 6000.6 Torr; for 1h; Sealed tube;	83%

ethyl [2]alcohol (925-93-9) + 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoic‐2,2,4,4‐d4 acid hydrochloride → ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl‐4,6‐d2)butanoate‐2,2,4,4‐d4

Conditions	Yield
With thionyl chloride at 0 - 50℃; for 4.5h;	81.3%

ethyl [2]alcohol (925-93-9) + 6-chloro-pyrazine-2-carboxylic acid methyl ester (23611-75-8) → ethyl 6-d-pyrazine-2-carboxylate

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate; deuterium at 20℃; under 6000.6 Torr; for 1h; Sealed tube;	79%

2,5-dichloroisonicotinic acid methyl ester (623585-74-0) + ethyl [2]alcohol (925-93-9) → ethyl 2,5-d2-isonicotinate

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate; deuterium at 20℃; under 6000.6 Torr; for 4h; Sealed tube;	72%
With palladium on activated charcoal; potassium carbonate; deuterium

(CH3)3Ge(B(C4H9)2)CCH(OC2H5) (115880-58-5) + ethyl [2]alcohol (925-93-9) → (CH3)3Ge((2)H)CC(H)OC2H5 (115880-67-6)

Conditions	Yield
In tetrahydrofuran under Ar; dropwise addn. of soln. of alcohol to the ether; fractionated; elem. anal.;	70%

ethyl [2]alcohol (925-93-9) + C11H7F3O3S (1013936-27-0) → C12H10(2)H2O

Conditions	Yield
[Cp*RuCl(η2-SMe)]2 at 20℃; for 4h;	67%

sodium tetrahydroborate (16940-66-2) + (+/-)-dicyano{2,2,3,3,7,7,8,8,12,12,13,13,17,17,18,18-hexadecamethyl-2,3,7,8,12,13,17,18-octahydro-1H,21H-10,20-diaza-porphinato}cobalt(III) + ethyl [2]alcohol (925-93-9) → Co(C34H50(2)HN6) (95762-90-6)

Conditions	Yield
In ethyl [2]alcohol 48 h at r.t.; filtered, washed (EtOH/H2O 1:1 then H2O), dried (80°C, 72 h, 0.01 Torr);	66%

ethyl [2]alcohol (925-93-9) + methyl 5-chloropyrazine-2-carboxylate (33332-25-1) → ethyl 5-d-pyrazine-2-carboxylate

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate; deuterium at 20℃; under 6000.6 Torr; for 1h; Sealed tube;	65%

lithium aluminium deuteride + bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] + ethyl [2]alcohol (925-93-9) → [(η5-C5Me5)Ru(μ-D)4Ru(η5-C5Me5)]

Conditions	Yield
In diethyl ether under argon, addn. of Al-compound to a stirred suspn. of Ru-complex at -78°C, slow warming to room temperature, stirring for 5 h, cooling again to -78°C, addn. of EtOD, warming to room temperature, stirring for 12 h; removing solvent (reduced pressure), extn. of residue (toluene), filtn., concg. filtrate, chromy. (alumina);	63%

ethyl [2]alcohol (925-93-9) + 3-Bromo-2-cyclopropyl-2-ethylsulfanylcarbonyl-propionic acid ethyl ester → C11H17(2)HO4

Conditions	Yield
With cyanocobalamin	60%

bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] + ethyl [2]alcohol (925-93-9) → (C5(CH3)5)Ru(H)2(2)H2Ru(C5(CH3)5)

Conditions	Yield
With LiAlH4 In diethyl ether under argon, addn. of Al-compound to a stirred suspn. of Ru-complex at -78°C, slow warming to room temperature, stirring for 5 h, cooling again to -78°C, addn. of EtOD, warming to room temperature, stirring for 12 h; removing solvent (reduced pressure), extn. of residue (toluene), filtn., concg. filtrate, chromy. (alumina);	60%

ethyl [2]alcohol (925-93-9) + 4-methyliminomethyl-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl (89148-76-5) + copper dichloride → [(C3N2)(CH3)4(O)(CH(OCH2CH3)N(2)H(CH3))]CuCl2 (89140-56-7)

Conditions	Yield
In ethyl [2]alcohol for 1-24 h; ppt. filtered off, washed (ethanol-d); elem. anal.;	60%

ethyl [2]alcohol (925-93-9) + 3,6-dibromopyrazine-2-carboxylic acid methyl ester (13301-04-7) → ethyl 3,6-d2-pyrazine-2-carboxylate

Conditions	Yield
With 5%-palladium/activated carbon; water-d2; sodium carbonate; deuterium at 20℃; under 6000.6 Torr; for 1h; Sealed tube;	60%

ethyl [2]alcohol (925-93-9) + 1-phenylbut-3-yn-2-one (31739-46-5) → C12H10(2)H2O

Conditions	Yield
[Cp*RuCl(η2-SMe)2RuCp*(OH2)]OSO2CF3 at 60℃; for 2h;	56%

sodium borodeuteride + ethyl [2]alcohol (925-93-9) + tris(2-diphenylphosphinoethyl)phosphine (23582-03-8) + iron(II) chloride → {(P(CH2CH2P(C6H5)2)3)Fe(H)2} (128973-37-5) + {(P(CH2CH2P(C6H5)2)3)Fe((2)H)(H)} + {(P(CH2CH2P(C6H5)2)3)Fe((2)H)2}

Conditions	Yield
In tetrahydrofuran (N2) or (Ar) excess of NaBD4; addn. of C2H5OD, NMR;	A 20% B 25% C 55%

sodium borodeuteride + (+/-)-dicyano{2,2,3,3,7,7,8,8,12,12,13,13,17,17,18,18-hexadecamethyl-2,3,7,8,12,13,17,18-octahydro-1H,21H-10,20-diaza-porphinato}cobalt(III) + ethyl [2]alcohol (925-93-9) → Co(C34H50(2)HN6) (95762-90-6)

Conditions	Yield
In ethyl [2]alcohol 48 h at r.t.; filtered, washed (EtOH/H2O 1:1 then H2O), dried (80°C, 72 h, 0.01 Torr);	53%

Upstream product

• 141-52-6 sodium ethanolate 
• 555-75-9 aluminum ethoxide 
• 78-10-4 tetraethoxy orthosilicate 
• 811-98-3 d⁽⁴⁾-methanol 
• 141-78-6 ethyl acetate 
• 75041-78-0 N-pivaloyl proline 
• 105-54-4 butanoic acid ethyl ester 
• 125347-82-2 1-acetyl-prolin-ethyl ester 
• 5524-57-2 ethyl 2-(2,4,6-trimethylphenyl)-2-oxoacetate 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 78-09-1 orthocarbonic acid tetraethyl ester 
• 64-17-5 ethanol 
• 352-93-2 diethyl sulphide 
• 2219-52-5 ethylene glycol-d2 

Downstream Products

• 676-55-1 methane-d2 
• 676-80-2 methane-d3 
• 19804-64-9 trans-(3-methyl-3-phenyloxiran-2-yl)(phenyl)methanone 
• 19804-64-9 cis-(3-methyl-3-phenyloxiran-2-yl)(phenyl)methanone 
• 64-17-5 ethanol 
• 1455-13-6 deuteromethanol 
• 60051-46-9 ethyl-2-deuterio-2-phenylpropanoate 
• 21370-59-2 (Z)-β-deuteriostyrene 
• 108-67-8 mesitylene cation radical 
• 128973-37-5 {(P(CH₂CH₂P(C₆H₅)2)3)Fe(H)2} 

Relevant articles and documents

An Improved Procedure for the Preparation of Very Pure Ethanol-OD

Changed molar ratio of starting materials and prolonged reaction times in the deuterolysis of tetraethylorthosilicate gave yields of pure (>99.5percent) ethanol-OD (relative to starting D2O) nearly twice of that of a literature procedure. - Keywords: Deuterolysis; Ethanol-OD; Methanol-OD; Tetraethylorthosilicate

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Isotope Effects in the Solvolysis of Sterically Hindered Arenesulfonyl Chlorides

Solvent isotope effects in the ethanolysis of sterically hindered arenesulfonyl chlorides ruled out a proton transfer in the rate-determining step and agreed with a SN2 mechanism involving at least a second solvent molecule in the transition state (TS). The lack of a secondary kinetic isotope effect in the o-alkyl groups allows us to disregard the possible contribution of σ-π hyperconjugation. The measured activation parameters are consistent with a SN2 mechanism involving the participation of solvent molecules in the TS, possibly forming a cyclic TS through a chain of solvent molecules.

Synthesis, reactivity and catalytic properties of the allenylidene [Ru(C=C=CPh2)Cp(PTA)(PPh3)](CF3SO3) (PTA = 1,3,5-triaza-7-phosphaadamantane)

The reactivity of [RuCpCl(PTA)(PPh3)] with HC≡CPh and HC≡CC(OH)PPh2 has been studied. The reaction with the phenylacetylene did not provide the desired vinylidene ruthenium complex but as a collateral result the complex [RuCp(DMSO-κS)(PTA)(PPh 3)](CF3SO3) (1) was obtained by reaction of [RuCpCl(PTA)(PPh3)] with Ag(CF3SO3) in DMSO. Reaction of [RuCpCl(PTA)(PPh3)] with HC≡CC(OH)PPh2 provided the Ruthenium(II) diphenyl-allenylidene complex [Ru(C=C=CPh 2)Cp(PTA)(PPh3)](CF3SO3) (2) that was characterized by NMR, IR spectroscopy and elemental analysis. The chemistry of the new diphenyl-allenylidene ruthenium complex has been studied towards a variety of small molecules such as water, O2, n-propylamine, cyclohexylamine and ethanethiol. From the reaction of 2 with the amines and thiol, two isomers are obtained respectively but only one of them could be isolated and characterized. The allenylidene complex was found to be a useful catalyst for the trans-etherification of 1,4-butanedioldivinyl-ether, ethoxyethene and 1-methoxycyclohexa-1,3-diene