5804-85-3

Basic information

• Product Name: DIETHYLALUMINUM CYANIDE SOLUTION
• Synonyms: DIETHYLALUMINUM CYANIDE SOLUTION;(cyano-C)diethylaluminium;DIETHYLALUMINUM CYANIDE SOLUTION, ~1 M I N TOLUENE;DIETHYLALUMINUM CYANIDE, 1.0M SOLUTION I N TOLUENE;Aluminum, (cyano-.kappa.C)diethyl-;Cyanodiethylaluminum;Diethylcyanoaluminum;Einecs 227-359-8
• CAS NO: 5804-85-3
• Molecular Formula: C5H10AlN
• Molecular Weight: 111.121138
• EINECS: 227-359-8
• Product Categories: Chemical Synthesis;Organoaluminum;Organometallic Reagents;Chemical Synthesis;Organometallic Reagents
• Mol File: 5804-85-3.mol
• Article Data: 0

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: 45 °F
• Appearance: /
• Density: 0.87 g/mL at 20 °C
• BRN: 3587410
• CAS DataBase Reference: DIETHYLALUMINUM CYANIDE SOLUTION(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYLALUMINUM CYANIDE SOLUTION(5804-85-3)
• EPA Substance Registry System: DIETHYLALUMINUM CYANIDE SOLUTION(5804-85-3)

Safety Data

• Hazard Codes: F,T+,N
• Statements: 11-26/27/28-32-38-48/20-50/53-63-65-67
• Safety Statements: 36/37-45-60-61-62-28-16
• RIDADR: UN 3123 6.1/PG 1
• WGK Germany: 2
• F: 10
• Hazardous Substances Data: 5804-85-3(Hazardous Substances Data)

Usage

Uses

DIETHYLALUMINUM CYANIDE SOLUTION Reagents used to hydrocyanate side chain ketones directed by aryl sulfinyl groups.1

InChI:InChI=1/2C2H5.CN.Al/c3*1-2;/h2*1H2,2H3;;/rC5H10AlN/c1-3-6(4-2)5-7/h3-4H2,1-2H3

Synthetic route

diethylaluminium cyanide (5804-85-3) + (RS,2R)-(-)-N-[(tert-butyldimethylsilyl)oxy]-2-phenylacetylidene-p-toluenesulfinamide (310435-48-4) → (RS,2S,3R)-(-)-N-(p-toluenesulfinyl)-2-amino-[(tert-butyldimethylsilyl)oxy]-3-phenylpropionitrile (310435-60-0)

Conditions	Yield
With isopropyl alcohol In tetrahydrofuran at -78 - 20℃; Addition;	100%

diethylaluminium cyanide (5804-85-3) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-[benzyl(cyclopropylcarbonyl)amino]-4'-cyano-1,4'-bipiperidine-1'-carboxylate (902472-98-4)

Conditions	Yield
Stage #1: N-benzyl-N-piperidin-4-ylcyclopropanecarboxamide; N-tert-butyloxycarbonylpiperidin-4-one With titanium(IV) isopropylate In dichloromethane at 20℃; for 72h; Stage #2: diethylaluminium cyanide In dichloromethane; toluene for 16h;	100%

C13H20N2O (306297-27-8) + diethylaluminium cyanide (5804-85-3) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → C24H36N4O3

Conditions	Yield
Stage #1: C13H20N2O; N-tert-butyloxycarbonylpiperidin-4-one With titanium(IV) isopropylate at 25℃; for 24h; Stage #2: diethylaluminium cyanide In toluene at 20℃; for 24h;	100%

rac-(4R,5S,6S)-1-benzyloxy-5,6-dihydroxy-5,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-azaspiro[3.5]non-8-ene-2,7-dione + diethylaluminium cyanide (5804-85-3) → rac-(4R,5S,6S,8R)-1-benzyloxy-8-bromo-9-cyano-5,6-dihydroxy-5,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-azaspiro[3.5]nonane-2,7-dione

Conditions	Yield
Stage #1: rac-(4R,5S,6S)-1-benzyloxy-5,6-dihydroxy-5,6-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-1-azaspiro[3.5]non-8-ene-2,7-dione; diethylaluminium cyanide In tetrahydrofuran at 0 - 80℃; for 3h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In tetrahydrofuran at 0 - 20℃; for 0.25h; Product distribution / selectivity;	100%

diethylaluminium cyanide (5804-85-3) + (S)-2-((2S,3S)-3-Trimethylsilanyl-oxiranyl)-hexan-2-ol (136233-98-2) → (E)-(S)-4-Hydroxy-4-methyl-oct-2-enenitrile (137024-39-6)

Conditions	Yield
In tetrahydrofuran for 2h; Heating;	99%

diethylaluminium cyanide (5804-85-3) + (R)-benzyl glycidol (14618-80-5) → (3R)-4-(benzyloxy)-3-hydroxybutanenitrile (934623-81-1)

Conditions	Yield
In toluene; benzene at 0 - 20℃;	99%

diethylaluminium cyanide (5804-85-3) + 2,3-epoxy-17-methyl-androstan-17-ol (968-54-7) → (2R,3S,5S,8R,9S,10S,13S,14S,17S)-3,17-Dihydroxy-10,13,17-trimethyl-hexadecahydro-cyclopenta[a]phenanthrene-2-carbonitrile (141691-37-4)

Conditions	Yield
In toluene for 4h; Ambient temperature;	98%

diethylaluminium cyanide (5804-85-3) + (1aβ,3α,3aα,6α,7aβ,7bβ)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>octahydro-6-methyl-5H-oxireno<1>benzopyran-5-one (98903-49-2, 98974-82-4, 106499-49-4) → (3R,4aR,5R,6R,8S,8aS)-8-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-methyl-2-oxo-octahydro-chromene-6-carbonitrile (106455-96-3)

Conditions	Yield
In tetrahydrofuran; toluene for 3h; Ambient temperature;	98%

11-oxatricyclo<4.4.1.01,6>undeca-3,8-diene (16573-72-1) + diethylaluminium cyanide (5804-85-3) → trans-8a-hydroxy-1,4,4a,5,8,8a-hexahydronaphthalene-4a-carbonitrile (335201-94-0)

Conditions	Yield
In dichloromethane at 20℃;	98%

diethylaluminium cyanide (5804-85-3) + (E)-N-benzylidene-2-methoxybenzenamine (5877-56-5) → α-[(2-methoxyphenyl)amino]-benzeneacetonitrile (60561-59-3)

Conditions	Yield
With (R)-1,1'-Bi-2-naphthol In toluene at -78 - -40℃; for 3h;	98%

diethylaluminium cyanide (5804-85-3) + (S)-1-[2-(p-tolylsulfinyl)phenyl]propan-2-one (794525-94-3) → [2S,(S)S]-2-hydroxy-2-methyl-3-[2-(p-tolylsulfinyl)phenyl]propanenitrile (854375-11-4)

Conditions	Yield
With ytterbium(III) triflate In tetrahydrofuran at -78℃; for 2h;	98%

diethylaluminium cyanide (5804-85-3) + (S)-3-methyl-1-[2-(p-tolylsulfinyl)phenyl]butan-2-one (794525-96-5) → [2R,(S)S]-2-hydroxy-3-methyl-2-[2-(p-tolylsulfinyl)benzyl]butanenitrile (877200-84-5)

Conditions	Yield
With ytterbium(III) triflate In tetrahydrofuran at -78℃; for 2h;	98%

diethylaluminium cyanide (5804-85-3) + (S)-1-[2-(p-tolylsulfinyl)phenyl]pentan-2-one (794525-95-4) → [2S,(S)S]-2-hydroxy-2-[2-(p-tolylsulfinyl)benzyl]pentanenitrile (877200-85-6)

Conditions	Yield
With ytterbium(III) triflate In tetrahydrofuran at -78℃; for 2h;	98%

diethylaluminium cyanide (5804-85-3) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + (S)-2-Methyl-1-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazine (306296-89-9) → 4-Cyano-4-{(S)-3-methyl-4-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (306296-99-1)

Conditions	Yield
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; (S)-2-Methyl-1-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazine With titanium(IV) isopropylate In dichloromethane at 20℃; for 24h; Stage #2: diethylaluminium cyanide In dichloromethane; toluene for 20h;	98%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; (S)-2-Methyl-1-[(S)-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazine; titanium(IV) isopropylate In dichloromethane at 20℃; for 24h; Stage #2: diethylaluminium cyanide In dichloromethane; toluene for 20h;	98%

diethylaluminium cyanide (5804-85-3) + trans-3-(tert-butyldiphenylsilyloxy)-6-oxa-bicyclo[3.1.0]hexane (817210-65-4) → (1RS,2SR,4RS)-4-(tert-butyl(diphenyl)silanyloxy)-2-hydroxycyclopentanecarbonitrile

Conditions	Yield
Stage #1: diethylaluminium cyanide; trans-3-(tert-butyldiphenylsilyloxy)-6-oxa-bicyclo[3.1.0]hexane In toluene at 0 - 20℃; Stage #2: With water; sodium fluoride In toluene at 0℃; for 1h;	98%

C20H32N3O2P (1186139-52-5) + diethylaluminium cyanide (5804-85-3) → C21H33N4O2P (1310539-58-2)

Conditions	Yield
Stage #1: diethylaluminium cyanide With isopropyl alcohol In tetrahydrofuran; toluene at -78 - 20℃; Strecker reaction; Inert atmosphere; Stage #2: C20H32N3O2P In tetrahydrofuran; toluene at -78℃; for 2h; Strecker reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	98%

C19H30N3OP (1186139-42-3) + diethylaluminium cyanide (5804-85-3) → C20H31N4OP (1310539-57-1)

Conditions	Yield
Stage #1: diethylaluminium cyanide With isopropyl alcohol In tetrahydrofuran; toluene at -78 - 20℃; Strecker reaction; Inert atmosphere; Stage #2: C19H30N3OP In tetrahydrofuran; toluene at -78℃; for 2h; Strecker reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	98%

C20H32N3OP + diethylaluminium cyanide (5804-85-3) → C21H33N4OP (1310539-64-0)

Conditions	Yield
Stage #1: diethylaluminium cyanide With isopropyl alcohol In tetrahydrofuran; toluene at -78 - 20℃; Strecker reaction; Inert atmosphere; Stage #2: C20H32N3OP In tetrahydrofuran; toluene at -78℃; for 2h; Strecker reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	98%

diethylaluminium cyanide (5804-85-3) + (1aα,3α,3aα,5α,7aβ,7bα)-(1,1-dimethylethyl)-<<1a,3,3a,5,7a,7b-hexahydro-5-methoxy-6-methyl-2H-oxireno<1>benzopyran-3-yl>oxy>dimethylsilane (98903-53-8, 106499-50-7) → (2R,4aS,5S,6R,8R,8aR)-8-(tert-Butyl-dimethyl-silanyloxy)-6-hydroxy-2-methoxy-3-methyl-4a,5,6,7,8,8a-hexahydro-2H-chromene-5-carbonitrile (106455-99-6)

Conditions	Yield
In dichloromethane; toluene at 0℃; for 3.5h;	97%

diethylaluminium cyanide (5804-85-3) + RS-4-(2,5-dimethoxyphenyl)-1-p-tolylsulfinyl-2-butanone (251447-03-7) → (2S,RS)-2-cyano-4-(2,5-dimethoxyphenyl)-1-(p-tolylsulfinyl)-2-butanol (251447-04-8)

Conditions	Yield
In tetrahydrofuran; toluene at -35℃; for 0.0833333h; Addition;	97%

4-Bromo-benzoic acid 3-((E)-4-acetoxy-2-methyl-but-2-enyloxy)-2-formyl-benzyl ester (857651-83-3) + diethylaluminium cyanide (5804-85-3) → 4-Bromo-benzoic acid 3-((E)-4-acetoxy-2-methyl-but-2-enyloxy)-2-(cyano-hydroxy-methyl)-benzyl ester (857652-16-5)

Conditions	Yield
In toluene at 0 - 25℃; for 1h;	97%

C31H27BrN3OP (1335230-80-2) + diethylaluminium cyanide (5804-85-3) → C32H28BrN4OP (1236163-03-3)

Conditions	Yield
Stage #1: diethylaluminium cyanide With (R)-phenylglycine; isopropyl alcohol In toluene at -78 - 20℃; Molecular sieve; Inert atmosphere; Stage #2: C31H27BrN3OP In toluene at -78℃; for 5h; Strecker reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	97%

C20H32N3OP (1186139-51-4) + diethylaluminium cyanide (5804-85-3) → C21H33N4OP (1310539-59-3)

Conditions	Yield
Stage #1: diethylaluminium cyanide With isopropyl alcohol In tetrahydrofuran; toluene at -78 - 20℃; Strecker reaction; Inert atmosphere; Stage #2: C20H32N3OP In tetrahydrofuran; toluene at -78℃; for 2h; Strecker reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	97%

C19H29ClN3OP (1186139-56-9) + diethylaluminium cyanide (5804-85-3) → C20H30ClN4OP (1310539-63-9)

Conditions	Yield
Stage #1: diethylaluminium cyanide With isopropyl alcohol In tetrahydrofuran; toluene at -78 - 20℃; Strecker reaction; Inert atmosphere; Stage #2: C19H29ClN3OP In tetrahydrofuran; toluene at -78℃; for 2h; Strecker reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	97%

C19H29ClN3OP (1186139-57-0) + diethylaluminium cyanide (5804-85-3) → C20H30ClN4OP (1310539-62-8)

Conditions	Yield
Stage #1: diethylaluminium cyanide With isopropyl alcohol In tetrahydrofuran; toluene at -78 - 20℃; Strecker reaction; Inert atmosphere; Stage #2: C19H29ClN3OP In tetrahydrofuran; toluene at -78℃; for 2h; Strecker reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	97%

C19H29FN3OP (1186139-58-1) + diethylaluminium cyanide (5804-85-3) → C20H30FN4OP (1310539-61-7)

Conditions	Yield
Stage #1: diethylaluminium cyanide With isopropyl alcohol In tetrahydrofuran; toluene at -78 - 20℃; Strecker reaction; Inert atmosphere; Stage #2: C19H29FN3OP In tetrahydrofuran; toluene at -78℃; for 2h; Strecker reaction; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	97%

isoquinoline (119-65-3) + diethylaluminium cyanide (5804-85-3) + 4-methoxy-benzoyl chloride (100-07-2) → 1,2-dihydro-2-(4-methoxybenzoyl)isoquinoline-1-carbonitrile (58021-73-1)

Conditions	Yield
In dichloromethane; toluene	96%

diethylaluminium cyanide (5804-85-3) + (R)-glycidyl tosylate (6746-81-2, 118712-54-2, 113826-06-5) → (S)-3-hydroxy-4-(p-toluenesulfonyloxy)butyronitrile (118712-64-4)

Conditions	Yield
In toluene for 0.333333h; Ambient temperature;	96%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + diethylaluminium cyanide (5804-85-3) → isophoronenitrile (7027-11-4)

Conditions	Yield
In hexane; toluene at 15 - 20℃; for 5h;	96%
In toluene at 20℃; for 1.5h; Addition;	91%

4-Bromo-benzoic acid 2-formyl-3-{(E)-4-[4-methoxy-6-methyl-1-(3-methyl-but-2-enyl)-2-oxo-cyclohex-3-enyl]-2-methyl-but-2-enyloxy}-benzyl ester (857651-85-5) + diethylaluminium cyanide (5804-85-3) → 4-Bromo-benzoic acid 2-(cyano-hydroxy-methyl)-3-{(E)-4-[4-methoxy-6-methyl-1-(3-methyl-but-2-enyl)-2-oxo-cyclohex-3-enyl]-2-methyl-but-2-enyloxy}-benzyl ester (857887-02-6)

Conditions	Yield
In toluene at 0℃; for 1h;	96%

Downstream Products

• 25017-78-1 3-cyano-2-cyclohexenone 
• 6398-50-1 6-methoxy-3,4-dihydronaphthalene-1-carbonitrile 
• 82742-17-4 1,6-anhydro-2-O-benzyl-4-C-cyano-4-deoxy-β-D-glucopyranose 
• 78705-84-7 4-Phenyl-but-3-ynenitrile 
• 106356-60-9 3-cyano-1,2-propanediol 1-O-p-nitrobenzoate 
• 124974-83-0 2-Ethyl-4-phenyl-3-butynenitrile 
• 141273-66-7 3β-(Benzoyloxy)-8β-bromo-4,4-dimethyl-7-oxo-5α-cholestane-14α-carbonitrile 
• 63546-69-0 3-Cyan-2-phenylthiocyclohexanon 
• 63546-68-9 4-Cyan-4-methyl-3-phenylthiopentan-2-on 
• 213113-51-0 Toluene-4-sulfonic acid (2S,3R,4R,5R)-3-cyano-4-hydroxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester 
• 220946-29-2 ((1S,2S,3S,4R)-1-Benzyl-4-cyano-2,3-dihydroxy-5-phenyl-pentyl)-carbamic acid tert-butyl ester 
• 272440-02-5 C₄₀H₅₁NO₇Si 
• 221660-80-6 (4-Cyclohexyl-piperazin-1-yl)-[4-((R)-4-methoxy-benzenesulfinyl)-phenyl]-acetonitrile 
• 221660-80-6 Sch 57790