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Sodium hydride
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7646-69-7 Usage

Physical properties

Sodium hydride belongs to ionic crystals, salt compounds in which the hydrogen is negative monovalent ions. When heating, it is unstable, decomposition without melting, hydrolysis reaction of sodium hydride with water to prepare sodium hydroxide and hydrogen. Pure sodium hydride is silver needle-like crystals, commercially available sodium hydride merchandise usually is subtle gray crystalline powder, the proportion of sodium hydride is 25% to 50% dispersed in oil. The relative density is 0.92. Sodium hydride is crystalline rock salt type structure (lattice constant a = 0.488nm), and as lithium hydride in ionic crystalline, hydrogen ion is existent in anion form. Heat of formation is 69.5kJ · mol-1, at the high temperature of 800 ℃, it decomposes into metallic sodium and hydrogen; decomposes explosively in water; reacts violently with lower alcohols;dissolves in molten sodium and molten sodium hydroxide; insoluble in liquid ammonia, benzene, carbon tetrachloride and carbon disulfide.

Safety Profile

The powder ignites spontaneously in air. Flammable when exposed to heat or flame. Potentially explosive reaction with water, diethyl succinate + ethyltrifluoroacetate (above 60℃), dimethyl sulfoxide + heat, sulfur dioxide. Ignition or violent reaction with dimethylformamide (above 50℃), ethyl 2,2,3-trifluoropropionate, oxygen (at 230℃). Incompatible with acetylene + moisture, glycerin, halogens, sulphur. Normal fire extinguishers are unsuitable, use sand, ashes, solurn chloride. The commercial material may contain traces of sodium. When heated to decomposition it emits toxic fumes of Na2O. See also HYDRIDES.

Fire Hazard

FLAMMABLE. MAY EXPLODE ON CONTACT WITH WATER. Accidental contact with water used to extinguish surrounding fire will result in the release of hydrogen gas and possible explosion.

General Description

A silvery to whitish powder or slurry in oil. Used to make other chemicals.

Storage Characteristics

Treasury ventilation low-temperature drying, stored separately from oxidants, halogens, strong acids.

Preparation

Sodium hydride is prepared by passing hydrogen gas into molten sodium metal dispersed in oil. Alternatively, the hydride can be made by passing hydrogen into sodium dispersed over the surface of an inert solid, such as, hydrocarbon above 200°C 2Na + H2 → 2NaH

Hazard

Dangerous fire risk, reacts violently with water evolving hydrogen. Irritant.

Air & Water Reactions

Highly flammable. Ignites or explodes in contact with air of high humidity [Bretherick 1979 p. 107]. Reacts violently with water producing a caustic solution (NaOH) and hydrogen (H2). Heat of reaction may ignite the hydrogen.

Definition

sodium hydride: A white crystallinesolid, NaH; cubic; r.d. 0.92; decomposesabove 300°C (slow);completely decomposed at 800°C.Sodium hydride is prepared by thereaction of pure dry hydrogen withsodium at 350°C. Electrolysis ofsodium hydride in molten LiCl/KClleads to the evolution of hydrogen;this is taken as evidence for the ionicnature of NaH and the presence ofthe hydride ion (H–). It reacts violentlywith water to give sodium hydroxideand hydrogen, with halogensto give the halide and appropriatehydrogen halide, and ignites spontaneouslywith oxygen at 230°C. It is apowerful reducing agent with severallaboratory applications.

Reactivity Profile

Sodium hydride is a powerful reducing agent. Attacks SiO2 in glass. Ignites on contact with gaseous F2, Cl2, Br2, and I2 (the last at temperatures exceeding 100°C), especially in the presence of moisture, to form HF, HCl, HBr, and HI [Mellor 2:483 1946-47]. Reacts with sulfur to give Na2S and H2S [Bretherick 1979 p. 107]. Can react explosively with dimethyl sulfoxide [Chem. Eng. News 44(24):7 1966]. Reacts vigorously with acetylene, even at -60°C [Mellor 2:483 1946-47]. Spontaneously flammable in fluorine. Reaction with dimethylformamide, when heated, runs away [Chem. Eng. News, 1982, 60(28), 5]. Initiates a polymerization reaction in ethyl-2,2,3-trifluoropropionate such that the ester decomposed violently [Bretherick 5th ed. 1995]. Presence in the reaction of diethyl succinate and ethyl trifluoroacetate, has twice caused explosions [Chem. Brit., 1983, 19, 645].

Flammability hazard characteristics

Encountering Water or moist air to emit hydrogen and can be combustible

Chemical Properties

Grey solid

Uses

Sodium hydride can be used for condensation and alkylation reaction and can be used as a polymerization catalyst, used for the manufacture of drug synthetic and used in fragrance industry, used for manufacturing boron hydrides, used as metal surface rust, reducing agents, condensing agent, desiccant and Clay Johnson's reagents. Used as a condensing agent, an alkylating agent and a reducing agent, etc. It is an important reductant for Pharmaceutical, perfumes, dyes, but also as a drying agent, an alkylating agent, etc.

Related chemical reaction

Sodium hydride is a strong reducing agent, For example, titanium tetrachloride can reduced to metallic titanium at 400 ℃: TiCl4 == 4NaH + Ti + 4NaCl + 2H2. At atmospheric pressure and heated to 425 ℃, it decomposes to generate hydrogen gas. And it can violently react with water, even causes a fire, and produces sodium hydroxide and hydrogen. It reacts with liquild ammonia to prepare amine salt (sodium amide) and hydrogen. NaH + NH3-(H2) → NaNH2 + H2. At a high temperature, sodium hydride also reacts with halogen, sulfur vapor, sulfur dioxide and carbon dioxide. It is highly reductive, liberates the metal from metal oxides, metal chlorides. TiCl4 + 4NaH → Ti + NaCl + 2H2. Sodium hydride reacts with boron trifluoride to generate diborane. 2BF3 + 6NaH → B2H6 + 6NaF. Sodium hydride is stable in dry air below 230 ℃, over this temperature it will burn into sodium oxide. If there is the presence of trace amounts of sodium, even at low temperatures it is also easy to fire. When firing, water and organic fire extinguishing agent must not be used.

Uses

At low temperatures where reducing properties of sodium are undesirable as in the condensation of ketones and aldehydes with acid esters; in solution with molten sodium hydroxide for the reduction of oxide scale on metals; at high temperatures as a reducing agent and reduction catalyst.

Production Methods

Sodium hydride, reactive with water yielding hydrogen gas and NaOH solution, formed by reaction of sodium and hydrogen at about 360 °C (680 °F). Used as a powerful reducing agent.

Physical properties

Silvery needles; refractive index 1.470; density 0.92 g/cm3; decomposes at 800°C; decomposes explosively in water; reacts violently with lower alcohols; dissolves in molten sodium and molten sodium hydroxide; insoluble in liquid ammonia, benzene, carbon tetrachloride and carbon disulfide.

Health Hazard

SOLID: Will burn skin and eyes. Harmful if swallowed.
InChI:InChI=1/Na.H/rHNa/h1H

7646-69-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (S0481)  Sodium Hydride (60%, dispersion in Paraffin Liquid)   7646-69-7 100g 280.00CNY Detail
TCI America (S0481)  Sodium Hydride (60%, dispersion in Paraffin Liquid)   7646-69-7 500g 595.00CNY Detail
Alfa Aesar (13431)  Sodium hydride, 57-63% oil dispersion    7646-69-7 50g 313.0CNY Detail
Alfa Aesar (13431)  Sodium hydride, 57-63% oil dispersion    7646-69-7 500g 1586.0CNY Detail
Alfa Aesar (13431)  Sodium hydride, 57-63% oil dispersion    7646-69-7 *2x1kg 6271.0CNY Detail
Alfa Aesar (H36490)  Sodium hydride, ca 60% dispersion in oil, in solvent solublebags    7646-69-7 50g 555.0CNY Detail
Alfa Aesar (H36490)  Sodium hydride, ca 60% dispersion in oil, in solvent solublebags    7646-69-7 100g 667.0CNY Detail
Alfa Aesar (H36490)  Sodium hydride, ca 60% dispersion in oil, in solvent solublebags    7646-69-7 500g 1984.0CNY Detail
Aldrich (223441)  Sodiumhydride  dry, 95% 7646-69-7 223441-10G 548.73CNY Detail
Aldrich (223441)  Sodiumhydride  dry, 95% 7646-69-7 223441-50G 2,230.02CNY Detail
Aldrich (223441)  Sodiumhydride  dry, 95% 7646-69-7 223441-250G 8,903.70CNY Detail
Aldrich (223441)  Sodiumhydride  dry, 95% 7646-69-7 223441-1KG 25,155.00CNY Detail

7646-69-7SDS

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 Sodium hydride

1.2 Other means of identification

Product number -
Other names HNa

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:7646-69-7 SDS

7646-69-7Synthetic route

hydrogen
1333-74-0

hydrogen

sodium
7440-23-5

sodium

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In tetrahydrofuran heating under increasing H2-pressure (from about 7 to 35atm) to 250-350°C;;98%
In further solvent(s) heating in mineral oil or in another hydrocarbon (high b.p.) under increasing H2-pressure (from about 7 to 35atm) to 250-350°C;;98%
In paraffin heating under increasing H2-pressure (from about 7 to 35atm) to 250-350°C;;98%
sodium
7440-23-5

sodium

monosilane
7440-21-3

monosilane

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
With naphthalene In 1,2-dimethoxyethane byproducts: H2, SiH2; stirring a mixture of sodium, naphthalene and DME for 1 h, addn. of silane under argon; filtn., washing (ether in a vac. at 288 K for 14 h), elem. anal.;97.8%
hydrogen
1333-74-0

hydrogen

sodium acetylide

sodium acetylide

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) heating the powdered carbide in an autoclave (H2 pressure: 500atm)in a H2-stream to 650°C;; 72% NaH;;86%
In neat (no solvent) heating the powdered carbide in an autoclave (H2 pressure: 500atm)in a H2-stream to 650°C;; 72% NaH;;86%
monosilane
7440-21-3

monosilane

A

sodium disilanyl
139508-55-7

sodium disilanyl

B

2-sodium trisilanyl
139508-56-8

2-sodium trisilanyl

C

2-sodium isotetrasilanyl
139508-57-9

2-sodium isotetrasilanyl

D

sodium hydride
7646-69-7

sodium hydride

E

sodiumsilanyl

sodiumsilanyl

Conditions
ConditionsYield
With sodium In diethylene glycol Under N2, filling of SiH4 in an evacuated flask with a freshly prepd. Na dispersion at -30 or 25°C under magnetic stirring. End of react. is reached after 3 days.; Concg. in vac. under stirring, filtn. (NaH), addn. of benzylchloride, GC.;A 17.7%
B 1.6%
C 0%
D 2.1%
E 78.6%
With Na on activated charcoal In 1,2-dimethoxyethane Under N2, filling of SiH4 in an evacuated flask with a freshly prepd. Na dispersion at -30 or 25°C under magnetic stirring. End of react. is reached after 3 days.; Concg. in vac. under stirring, filtn. (NaH), addn. of benzylchloride, GC.;A 30.4%
B 4.6%
C <1
D 0%
E 65%
With sodium In 1,2-dimethoxyethane Under N2, filling of SiH4 in an evacuated flask with a freshly prepd. Na dispersion at -30 or 25°C under magnetic stirring. End of react. is reached after 3 days.; Concg. in vac. under stirring, filtn. (NaH), addn. of benzylchloride, GC.;A 25.4-28.6
B 1.2-3.5
C <1
D 0-25.1
E 48.3-68.2
titanium doped sodium aluminium hydride

titanium doped sodium aluminium hydride

A

hydrogen
1333-74-0

hydrogen

B

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) byproducts: Al; dehydrogenation: 160°C, against 0.1 MPa for 3 h; detd. of H2 with Sieverts type volumetric apparatus; XRD;A 4%
B n/a
sodium alanate

sodium alanate

A

hydrogen
1333-74-0

hydrogen

B

sodium hydride
7646-69-7

sodium hydride

C

aluminium
7429-90-5

aluminium

Conditions
ConditionsYield
titanium(III) chloride at 200 - 250℃; under 760.051 Torr; Product distribution / selectivity; Neat (no solvent); Balled milled;
In neat (no solvent, solid phase) decompd. at heating;
sodium nitride

sodium nitride

hydrogen
1333-74-0

hydrogen

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) byproducts: NH3; at about 120°C;;
sodium azide

sodium azide

hydrogen

hydrogen

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) reaction of H2 with NaN3 at 300°C (under no circumstances 375°C); using of activated H2 is advantageous;;
In neat (no solvent) reaction of H2 with NaN3 at 300°C (under no circumstances 375°C); using of activated H2 is advantageous;;
sodium azide

sodium azide

hydrogen
1333-74-0

hydrogen

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) heated in a H2-stream;;
In neat (no solvent) heated in a H2-stream;;
In neat (no solvent) byproducts: NH3; begin of react. at about 250°C;;
water
7732-18-5

water

sodium
7440-23-5

sodium

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) with over-heated H2O-vapor between 250 and 400°C;;
In neat (no solvent) with over-heated H2O-vapor between 250 and 400°C;;
hydrogen
1333-74-0

hydrogen

disodium cyanamide
20611-81-8

disodium cyanamide

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) heating the powdered Na-compound in an autoclave (H2 pressure: 500atm)in a H2-stream to 650°C;;
In neat (no solvent) heating the powdered Na-compound in an autoclave (H2 pressure: 500atm)in a H2-stream to 650°C;;
triphenyl boron sodium

triphenyl boron sodium

A

triphenylborane
960-71-4

triphenylborane

B

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
With methanol In diethyl ether byproducts: CH3ONa; on addn. of ether/methanol to suspension of ((C6H5)3B)Na in ether;;
With methanol In diethyl ether byproducts: CH3ONa; on addn. of ether/methanol to suspension of ((C6H5)3B)Na in ether;;
Hg(b),Na(0.1-0.8) (W%)

Hg(b),Na(0.1-0.8) (W%)

hydrogen
1333-74-0

hydrogen

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) anodic decompn. of Na-amalgame (prepared by electrolysis of aq. Na-salt solns. at 80-90°C), at 250-300°C in a Na-halogenide/NaOH-melt (cathode: Ni or Fe or Ni-alloy or Fe-alloy), react. of Na with H2;;
In neat (no solvent) anodic decompn. of Na-amalgame (prepared by electrolysis of aq. Na-salt solns. at 80-90°C), at 250-300°C in a Na-halogenide/NaOH-melt (cathode: Ni or Fe or Ni-alloy or Fe-alloy), react. of Na with H2;;
NaC5H11-n
1822-71-5

NaC5H11-n

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In n-heptane decompn. at ambient temp., N2-atmosphere;;
In n-heptane decompn. at ambient temp., N2-atmosphere;;
sodium chloride
7647-14-5

sodium chloride

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
With hydrogen byproducts: HCl; ΔH = 62.04 cal/mol;
methane
34557-54-5

methane

sodium chloride
7647-14-5

sodium chloride

A

hydrogenchloride
7647-01-0

hydrogenchloride

B

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent)
Na3AlH6, α

Na3AlH6, α

A

hydrogen
1333-74-0

hydrogen

B

sodium hydride
7646-69-7

sodium hydride

C

aluminium
7429-90-5

aluminium

Conditions
ConditionsYield
In neat (no solvent, solid phase) above 180°C; powder XRD;
In neat (no solvent, solid phase) heating; 228°C; DSC;
manganese
7439-96-5

manganese

sodium hydroxide
1310-73-2

sodium hydroxide

A

sodium
7440-23-5

sodium

B

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
600-700°C, N2 or H2 flow; the product was separated;
sodium
7440-23-5

sodium

A

sodium acetylide

sodium acetylide

B

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
With methane In gas Kinetics; (gas space temp.: 500 and 465°, Na temp.: 500 and 450° orgas space temp.: 340 - 445°, Na temp.: 395°); gas chromy.;
hydrogen

hydrogen

sodium
7440-23-5

sodium

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) free Na reacts in H-atmosphere during glow discharge;;
calcium In neat (no solvent) passing H over pure Na in a Fe-ship in a refractory glass tube; addition of Ca-splinters accelerates the process;; NaH smoke floculates between two condensers; not pure;;
In neat (no solvent) Electrolysis; Na anode;Ni cathode;;
sodium
7440-23-5

sodium

sodium hydroxide
1310-73-2

sodium hydroxide

A

sodium oxide

sodium oxide

B

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
in system NaOH-K-Na-KOH;
In neat (no solvent) at 400°C in a closed Ni-tube;;
In neat (no solvent) at 400°C in a closed Ni-tube;;
sodium
7440-23-5

sodium

acetylene
74-86-2

acetylene

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) catalytic decomposition of C2H2 by molten Na leads to the formation of H; this reacts with Na at 100-550°C;;
In neat (no solvent) catalytic decomposition of C2H2 by molten Na leads to the formation of H; this reacts with Na at 100-550°C;;
ethene
74-85-1

ethene

sodium
7440-23-5

sodium

A

sodium carbide

sodium carbide

B

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) byproducts: polyethylene; polymerization of C2H4 during reaction of ethine with molten Na;;
hydrogenchloride
7647-01-0

hydrogenchloride

sodium
7440-23-5

sodium

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In gas in highly dild. flames of Na-vapor and hydrogen halide;;
In gas in highly dild. flames of Na-vapor and hydrogen halide;;
methanol
67-56-1

methanol

sodium
7440-23-5

sodium

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
byproducts: hydroxy-methyl radicals;
hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

sodium
7440-23-5

sodium

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In gas in highly dild. flames of Na-vapor and hydrogen halide;;
In gas in highly dild. flames of Na-vapor and hydrogen halide;;
hydrogen iodide
10034-85-2

hydrogen iodide

sodium
7440-23-5

sodium

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In gas in highly dild. flames of Na-vapor and hydrogen halide;;
In gas in highly dild. flames of Na-vapor and hydrogen halide;;
hydrogen

hydrogen

disodium
25681-79-2

disodium

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent, gas phase) byproducts: Na; reacn. in crossing region of Na2 molecular beam and H-atom beam; QMS, LIF;
sodium amide

sodium amide

hydrogen

hydrogen

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) byproducts: NH3; reaction of dry H2 with NaNH2 at 300°C;;
In neat (no solvent) byproducts: NH3; reaction of dry H2 with NaNH2 at 300°C;;
sodium oxide

sodium oxide

hydrogen

hydrogen

sodium hydride
7646-69-7

sodium hydride

Conditions
ConditionsYield
In neat (no solvent) reduction of Na2O with H at 170-180°C;;
sodium hydride
7646-69-7

sodium hydride

palladium
7440-05-3

palladium

sodium palladium hydrate

sodium palladium hydrate

Conditions
ConditionsYield
In neat (no solvent) 2:1 molar mixture of educts, 700K;100%
In neat (no solvent, solid phase) according to: W. Bronger, P. Mueller, D. Schmitz, H. Spittank, Z. anorg. allg. Chem. 516 (1984) 35; heating reaction mixt. (molar ratio NaH:Pd=4:1) in H2 atmosphere (360°C, 6 h); X-ray anal.;
calcium hydride
7789-78-8

calcium hydride

magnesium hydride

magnesium hydride

potassium metaborate

potassium metaborate

sodium hydride
7646-69-7

sodium hydride

A

potassium borohydride

potassium borohydride

B

magnesium oxide

magnesium oxide

Conditions
ConditionsYield
In neat (no solvent, solid phase) ball milled at room temp., 120 min; extd. (ethylenediamine) under Ar; filtered; ethylenediamine evapd. at room temp. under 0.05 MPa; XRD;A 100%
B n/a
arachno-6,8-S2B7H9
63115-77-5

arachno-6,8-S2B7H9

sodium hydride
7646-69-7

sodium hydride

acetonitrile
75-05-8

acetonitrile

hypho-CH3CNS2B7H8Na

hypho-CH3CNS2B7H8Na

Conditions
ConditionsYield
In tetrahydrofuran byproducts: H2; distn. of THF into mixt. of NaH and B-complex, warming to room temp., filtration and conc. after H2 evolution (vac.), addn. of predried CH3CN, refluxing overnight; evapn. (vac.);100%
tris(triphenylphosphinegold)oxonium fluoroborate

tris(triphenylphosphinegold)oxonium fluoroborate

1,3-diphenyl-2,8-dihydrocyclopenta[a]indene
33836-49-6

1,3-diphenyl-2,8-dihydrocyclopenta[a]indene

sodium hydride
7646-69-7

sodium hydride

2,4-dihydro-1,3-diphenyl(triphenylphosphinegold)cyclopenta{b}indene

2,4-dihydro-1,3-diphenyl(triphenylphosphinegold)cyclopenta{b}indene

Conditions
ConditionsYield
In tetrahydrofuran Ar atmosphere; stirring suspn. of Au-complex, org. ligand and NaH at 0 to -10°C for 1 h 45 min; addn. of several crystals of PPh3; filtration, evapn. to dryness (vac.); residue washing (pentane), dissoln. (THF), addn. to cold pentane (stirring), pptn.; ppt. sepn., washing (pentane), drying; elem. anal.;100%
tris(triphenylphosphinegold)oxonium fluoroborate

tris(triphenylphosphinegold)oxonium fluoroborate

sodium hydride
7646-69-7

sodium hydride

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

A

2P(C6H5)3*Au(1+)*BF4(1-)=(P(C6H5)3)2AuBF4

2P(C6H5)3*Au(1+)*BF4(1-)=(P(C6H5)3)2AuBF4

B

gold(I) cyanide
506-65-0

gold(I) cyanide

Conditions
ConditionsYield
In tetrahydrofuran stirring suspn. of all substances in abs. THF for 4 h; ppt. sepn., washing (THF, water and ether) and drying gave AuCN; soln. dild. with petroleum ether and cooled to 0°C; ppt. sepn. and washing with petroleum ether gave Au-complex;A 100%
B 67%
{(C5H5)Fe(C5H4C3H3N2)}*B((C3H2N2C5H4)Fe(C5H5))(C8H14)

{(C5H5)Fe(C5H4C3H3N2)}*B((C3H2N2C5H4)Fe(C5H5))(C8H14)

sodium hydride
7646-69-7

sodium hydride

Na(1+)*{((C5H5)Fe(C5H4C3H2N2))2B(C8H14)}(1-)=Na{((C5H5)Fe(C5H4C3H2N2))2B(C8H14)}

Na(1+)*{((C5H5)Fe(C5H4C3H2N2))2B(C8H14)}(1-)=Na{((C5H5)Fe(C5H4C3H2N2))2B(C8H14)}

Conditions
ConditionsYield
In benzene to soln. of Fe-B-compd. was added NaH, stirred for 2 h at room temp.; filtn., evapn.;100%
IrOs(H)2(CO)3((C6H5)2PCH2P(C6H5)2)2(1+)*BF4(1-) = {IrOs(H)2(CO)3(((C6H5)2P)2CH2)2}BF4
132939-86-7

IrOs(H)2(CO)3((C6H5)2PCH2P(C6H5)2)2(1+)*BF4(1-) = {IrOs(H)2(CO)3(((C6H5)2P)2CH2)2}BF4

sodium hydride
7646-69-7

sodium hydride

IrOs(H)2(CO)3((C6H4)C6H5PCH2P(C6H5)2)((C6H5)2PCH2P(C6H5)2)
132959-03-6

IrOs(H)2(CO)3((C6H4)C6H5PCH2P(C6H5)2)((C6H5)2PCH2P(C6H5)2)

Conditions
ConditionsYield
In tetrahydrofuran (Ar); added THF to NaH and Ir-complex; stirred vigorously for 1 h; evapd. (vac.); (31)P NMR, IR;100%
tris(acetonitrile)tricarbonylmolybdenum(0)
15038-48-9, 17731-95-2

tris(acetonitrile)tricarbonylmolybdenum(0)

sodium hydride
7646-69-7

sodium hydride

3-diphenylphosphanyl-2-diphenylphosphanylmethyl-2-methyl-1-propanethiol
161202-62-6

3-diphenylphosphanyl-2-diphenylphosphanylmethyl-2-methyl-1-propanethiol

Na(1+)*(CO)3Mo(C29H29P2S)(1-)*2C4H8O=Na[(CO)3Mo(C29H29P2S)]*2C4H8O

Na(1+)*(CO)3Mo(C29H29P2S)(1-)*2C4H8O=Na[(CO)3Mo(C29H29P2S)]*2C4H8O

Conditions
ConditionsYield
In tetrahydrofuran Ar atmosphere, addn. of NaH to soln. of ligand at 0°C, stirring (30 min), addn. of solid Mo complex, stirring (30 min); concn., washing (petroleum ether (40/60), ultrasonication), removement of solvent (vacuum);100%
C2B7H13
17653-38-2

C2B7H13

sodium hydride
7646-69-7

sodium hydride

acrylonitrile
107-13-1

acrylonitrile

endo/exo-6-(NCCH2CH2)-arachno-6,8-C2B7H12
679838-36-9, 680224-29-7

endo/exo-6-(NCCH2CH2)-arachno-6,8-C2B7H12

Conditions
ConditionsYield
In 1,2-dimethoxyethane under N2 atm. arachno-6,8-C2B7H13 was dissolved in DME and cooled to 0°C, NaH was added, react. mixt. was warmed to room temp., filtered,cooled to 0°C, acrylonitrile was added dropwise and stirred for 12 h; HCl-Et2O was added at 0°C, allowed to warm to room temp., soln. was filtered, were evapd. in vacuo, and dried in vacuo; elem. anal.;100%
tris(acetonitrile)tricarbonylmolybdenum(0)
15038-48-9, 17731-95-2

tris(acetonitrile)tricarbonylmolybdenum(0)

(CH3OCH2)C(CH2P(C6H5)2)(CH2SH)2
215854-12-9

(CH3OCH2)C(CH2P(C6H5)2)(CH2SH)2

sodium hydride
7646-69-7

sodium hydride

2Na(1+)*(CO)3Mo(C18H21OPS2)(2-)*2C4H8O=Na2[(CO)3Mo(C18H21OPS2)]*2C4H8O

2Na(1+)*(CO)3Mo(C18H21OPS2)(2-)*2C4H8O=Na2[(CO)3Mo(C18H21OPS2)]*2C4H8O

Conditions
ConditionsYield
In tetrahydrofuran Ar atmosphere, addn. of NaH to soln. of ligand at 0°C, stirring (30 min), addn. of solid Mo complex, stirring (30 min); concn., washing (petroleum ether (40/60), ultrasonication), removement of solvent (vacuum);100%
tetrahydrofuran
109-99-9

tetrahydrofuran

1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-dimethyl-1,4,8,11-tetraazacyclotetradecane
1428144-91-5

1,8-bis(2-hydroxy-3,5-di-tert-butylbenzyl)-4,11-dimethyl-1,4,8,11-tetraazacyclotetradecane

sodium hydride
7646-69-7

sodium hydride

Na2{(tBu2PhO)2Me2Cyclam}
1428144-92-6

Na2{(tBu2PhO)2Me2Cyclam}

Conditions
ConditionsYield
at 20℃; Inert atmosphere;100%
tetrahydrofuran
109-99-9

tetrahydrofuran

B-(2-pyridyl)-9-borabicyclo[3.3.1]nonane hydrogen chloride salt
1607013-48-8

B-(2-pyridyl)-9-borabicyclo[3.3.1]nonane hydrogen chloride salt

sodium hydride
7646-69-7

sodium hydride

Na[B-(2-pyridyl)-9-borabicyclo[3.3.1]nonane]*2THF

Na[B-(2-pyridyl)-9-borabicyclo[3.3.1]nonane]*2THF

Conditions
ConditionsYield
for 12h; Inert atmosphere; Schlenk technique; Glovebox;100%
NH-pyrazole
288-13-1

NH-pyrazole

sodium hydride
7646-69-7

sodium hydride

phenylboronic acid
98-80-6

phenylboronic acid

sodium phenyltris(pyrazolyl)borate
80583-77-3

sodium phenyltris(pyrazolyl)borate

Conditions
ConditionsYield
at 200℃; for 0.25h; Microwave irradiation; Inert atmosphere;100%
Trimethyl borate
121-43-7

Trimethyl borate

sodium hydride
7646-69-7

sodium hydride

sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

Conditions
ConditionsYield
Heating;99.5%
In neat (no solvent) 1mol B(OCH3)3, 4mol NaH, 225-275°C;; 90-96% NaBH4;;94%
In neat (no solvent) 1mol B(OCH3)3, 4mol NaH, 225-275°C;; 90-96% NaBH4;;94%
boric acid trimethylester tetrahydrofuranate

boric acid trimethylester tetrahydrofuranate

Tetrahydro-furan; compound with trifluoroborane

Tetrahydro-furan; compound with trifluoroborane

sodium hydride
7646-69-7

sodium hydride

sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

Conditions
ConditionsYield
In tetrahydrofuran byproducts: NaF; addn. of B(OCH3)3*THF to NaH at 60-65°C (stirring, N2-atmosphere), NaH dissolves, boiling, cooling to ambient temp., addn. of BF3*THF, distn. of THF and B(OCH3), extractn. of residue with isopropyl amine;; pure product;;99%
In tetrahydrofuran byproducts: NaF; addn. of B(OCH3)3*THF to NaH at 60-65°C (stirring, N2-atmosphere), NaH dissolves, boiling, cooling to ambient temp., addn. of BF3*THF, distn. of THF and B(OCH3), extractn. of residue with isopropyl amine;; pure product;;99%
2,3-bis(trimethylsilyl)-2,3-dicarba-nido-hexaborane(8)
91686-41-8

2,3-bis(trimethylsilyl)-2,3-dicarba-nido-hexaborane(8)

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

sodium hydride
7646-69-7

sodium hydride

Na(1+)*(CH3)2NCH2CH2N(CH3)2*B4H5C2(Si(CH3)3)2(1-) = Na(((CH3)2NCH2)2)(Si(CH3)3)2C2B4H5

Na(1+)*(CH3)2NCH2CH2N(CH3)2*B4H5C2(Si(CH3)3)2(1-) = Na(((CH3)2NCH2)2)(Si(CH3)3)2C2B4H5

Conditions
ConditionsYield
In further solvent(s) byproducts: H2; addn. of B-compd. in TMEDA to mixt. of NaH and TMEDA (-78°C, vac.); filtration (vac.), solvent removal (vac.); recrystn. (hexane); elem. anal.;99%
(1,2-bis[1,3-dioxan-2-yl]-3,4-bis[trimethylsilyl]cyclobutadiene)cyclopentadienylcobalt
464926-60-1

(1,2-bis[1,3-dioxan-2-yl]-3,4-bis[trimethylsilyl]cyclobutadiene)cyclopentadienylcobalt

sodium hydride
7646-69-7

sodium hydride

(1,2-bis[1,3-dioxan-2-yl]cyclobutadiene)cyclopentadienylcobalt
406498-73-5

(1,2-bis[1,3-dioxan-2-yl]cyclobutadiene)cyclopentadienylcobalt

Conditions
ConditionsYield
With Me4NF In dimethyl sulfoxide under inert atmosphere, Schlenk techniques; Co complex, NaH and Me4NF (molar ratio 2.4:1:19.3) dissolved in dry Me2SO; heated to 50°C overnight; aq. workup with ethyl ether; chromd. (silica gel, hexanes-ethyl acetate);99%
Ir(H)(Cl)CH3OC6H2(CH2P(C4H9)2)2
471255-34-2

Ir(H)(Cl)CH3OC6H2(CH2P(C4H9)2)2

Ir(Cl)CH3OC6H2(CH2P(C4H9)2)CH2P(C4H9)C(CH3)2CH2

Ir(Cl)CH3OC6H2(CH2P(C4H9)2)CH2P(C4H9)C(CH3)2CH2

hydrogen
1333-74-0

hydrogen

sodium hydride
7646-69-7

sodium hydride

(p-OMetBu4PCP)IrH4
471255-35-3

(p-OMetBu4PCP)IrH4

Conditions
ConditionsYield
With NaH In tetrahydrofuran Sonication; complexes in THF were treated with 100% excess of NaH, the mixt. was stirred at room temp. for 1 h under H2 atm., sonicated for 6 h with intermittent cooling and stirring, stirred for 24 h at room temp.; filtered, THF was removed by a stream of H2;99%
tetrahydrofuran
109-99-9

tetrahydrofuran

La2(O-2,6-i-Pr2C6H3)6

La2(O-2,6-i-Pr2C6H3)6

2,6-diisopropylphenol
2078-54-8

2,6-diisopropylphenol

sodium hydride
7646-69-7

sodium hydride

(THF)La(O-2,6-i-Pr2C6H3)2(μ-O-2,6-i-Pr2C6H3)2Na(THF)2
172918-17-1

(THF)La(O-2,6-i-Pr2C6H3)2(μ-O-2,6-i-Pr2C6H3)2Na(THF)2

Conditions
ConditionsYield
In tetrahydrofuran; toluene Ar-atmosphere; addn. of La-compd. (in PhMe) to mixt. of diisopropylphenol and NaH (in THF) with stirring, stirring for 72 h at room temp.; filtration (Celite), removal of volatiles (vac.), washing (hexane), extn. into PhMe, filtration (Celite), vol. reduction (vac.), crystn. (-40°C, overnight); elem. anal.;99%
[diruthenium(μ-CN(Me)2)(μ-CO)(CO)(NHCCMe3CC(Ph)(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)2)(μ-CO)(CO)(NHCCMe3CC(Ph)(Cp)2]CF3SO3

sodium hydride
7646-69-7

sodium hydride

[diruthenium(μ-CN(Me)2)(μ-CO)(CO)(NNaCCMe3CC(Ph))(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)2)(μ-CO)(CO)(NNaCCMe3CC(Ph))(Cp)2]CF3SO3

Conditions
ConditionsYield
In not given (N2), mixed; not isolated, detected by IR;99%
[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NHCCMe3CCH)(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NHCCMe3CCH)(Cp)2]CF3SO3

sodium hydride
7646-69-7

sodium hydride

[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NNaCCMe3CCH)(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NNaCCMe3CCH)(Cp)2]CF3SO3

Conditions
ConditionsYield
In not given (N2), mixed; not isolated, detected by IR;99%
[diruthenium(μ-CN(Me)2)(μ-CO)(CO)(NHCCMe3CC(p-tolyl))(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)2)(μ-CO)(CO)(NHCCMe3CC(p-tolyl))(Cp)2]CF3SO3

sodium hydride
7646-69-7

sodium hydride

[diruthenium(μ-CN(Me)2)(μ-CO)(CO)(NNaCCMe3CC(p-tolyl))(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)2)(μ-CO)(CO)(NNaCCMe3CC(p-tolyl))(Cp)2]CF3SO3

Conditions
ConditionsYield
In not given (N2), mixed; not isolated, detected by IR;99%
[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NHCCMe3CC(Ph)(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NHCCMe3CC(Ph)(Cp)2]CF3SO3

sodium hydride
7646-69-7

sodium hydride

[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NNaCCMe3CC(Ph))(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NNaCCMe3CC(Ph))(Cp)2]CF3SO3

Conditions
ConditionsYield
In not given (N2), mixed; not isolated, detected by IR;99%
[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NHCCMe3CCC(Me)CH2(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NHCCMe3CCC(Me)CH2(Cp)2]CF3SO3

sodium hydride
7646-69-7

sodium hydride

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NNaCCMe3CCC(Me)CH2)(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NNaCCMe3CCC(Me)CH2)(Cp)2]CF3SO3

Conditions
ConditionsYield
In not given (N2), mixed; not isolated, detected by IR;99%
[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NHCCMe3CC(p-tolyl))(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NHCCMe3CC(p-tolyl))(Cp)2]CF3SO3

sodium hydride
7646-69-7

sodium hydride

[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NNaCCMe3CC(p-tolyl))(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(benzyl))(μ-CO)(CO)(NNaCCMe3CC(p-tolyl))(Cp)2]CF3SO3

Conditions
ConditionsYield
In not given (N2), mixed; not isolated, detected by IR;99%
[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NHCCMe3CCBu)(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NHCCMe3CCBu)(Cp)2]CF3SO3

sodium hydride
7646-69-7

sodium hydride

diruthenium(μ-CN(Me)(xylyl)(μ-CO)(CO)(NNaCCMe3CCBu)(Cp)2]CF3SO3

diruthenium(μ-CN(Me)(xylyl)(μ-CO)(CO)(NNaCCMe3CCBu)(Cp)2]CF3SO3

Conditions
ConditionsYield
In not given (N2), mixed; not isolated, detected by IR;99%
[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NHCCMe3CC(Ph)(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NHCCMe3CC(Ph)(Cp)2]CF3SO3

sodium hydride
7646-69-7

sodium hydride

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NNaCCMe3CC(Ph))(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NNaCCMe3CC(Ph))(Cp)2]CF3SO3

Conditions
ConditionsYield
In not given (N2), mixed; not isolated, detected by IR;99%
[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NHCCMe3CC(p-tolyl))(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NHCCMe3CC(p-tolyl))(Cp)2]CF3SO3

sodium hydride
7646-69-7

sodium hydride

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NNaCCMe3CC(p-tolyl))(Cp)2]CF3SO3

[diruthenium(μ-CN(Me)(xylyl))(μ-CO)(CO)(NNaCCMe3CC(p-tolyl))(Cp)2]CF3SO3

Conditions
ConditionsYield
In not given (N2), mixed; not isolated, detected by IR;99%
[Bu3NH][1-ammonia-closo-dodecaborate]

[Bu3NH][1-ammonia-closo-dodecaborate]

sodium hydride
7646-69-7

sodium hydride

sodium amino-closo-dodecaborate

sodium amino-closo-dodecaborate

Conditions
ConditionsYield
In tetrahydrofuran refluxed; filtered, evapd., washed (Et2O);99%
In tetrahydrofuran refluxing (Bu3NH)(B12H11NH3) with 2 equiv. NaH in THF; solvent was evapd., residue was washed with Et2O;99%
[Ph(pz)Bt(tBu)]H

[Ph(pz)Bt(tBu)]H

sodium hydride
7646-69-7

sodium hydride

sodium phenyl(pyrazolyl)bis((tert-butylthio)methyl)borate

sodium phenyl(pyrazolyl)bis((tert-butylthio)methyl)borate

Conditions
ConditionsYield
In tetrahydrofuran NaH added to soln. of Ph(pz)Bt(tBu)H;99%
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