(Triphenylphosphoranylidene)acetaldehyde supplier

Name
(FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE
EINECS 218-375-6
CAS No. 2136-75-6
Article Data27
CAS DataBase
Density 1.162 g/cm³
Solubility
Melting Point 185-188 °C(lit.)
Formula C₂₀H₁₇ O P
Boiling Point 472.618 °C at 760 mmHg
Molecular Weight 304.328
Flash Point 239.631 °C
Transport Information
Appearance pink to brown crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Acetaldehyde,(triphenylphosphoranylidene)- (6CI,7CI,8CI,9CI);(2-Oxoethylidene)triphenylphosphorane;(Formylmethylene)triphenylphosphorane;(Triphenylphosphoranylidene)acetaldehyde;2-(Triphenylphosphoranylidene)acetaldehyde;
PSA 26.88000
LogP 2.98160

Synthetic route

: 62942-43-2
formylmethyltriphenylphosphonium chloride

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

Conditions

Conditions	Yield
With sodium hydroxide In water at 20 - 30℃; for 0.5h;	97%
With water; sodium hydroxide at 20 - 60℃; for 3h; pH=> 9; Time;	96%
With triethylamine In ethanol for 1h;	1.24 g
With sodium hydroxide In dichloromethane; water at 0 - 10℃;
With sodium hydroxide In water pH=7-8;	4.1 g

: 19493-09-5
Methylenetriphenylphosphorane

: 109-94-4
formic acid ethyl ester

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

Conditions

Conditions	Yield
In benzene	81%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 109-94-4
formic acid ethyl ester

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

Conditions

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 1.5h; Stage #2: formic acid ethyl ester In diethyl ether at 20℃;	76%
With n-butyllithium In diethyl ether
With n-butyllithium

: 107-20-0
2-chloroethanal

: 603-35-0
triphenylphosphine

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

Conditions

Conditions	Yield
In chloroform; water for 24h; Reflux;	53%
In chloroform; water for 5h; Heating;	51%
With pyrographite 1.) reflux, 5 h, CHCl3, 2.) 30 min, room temp., water; Yield given. Multistep reaction;

: 603-35-0
triphenylphosphine

: 2032-35-1
Bromoacetaldehyde diethyl acetal

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

Conditions

Conditions	Yield
In nitromethane Heating;

: 19753-63-0
triphenylphosphonium bromide acetaldehyde

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

Conditions

Conditions	Yield
With n-butyllithium In 1,2-dimethoxyethane; hexane for 1h; Ambient temperature;
With sodium hydroxide In toluene at 5℃; for 3h; Temperature; Inert atmosphere;

: 90601-11-9
<2-(dimethylamino)vinyl>triphenylphosphonium chloride

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

Conditions

Conditions	Yield
With sodium hydroxide; sulfuric acid 1) H2O, benzene, CH2Cl2, 5 min, 2) H2O, benzene, CH2Cl2; Yield given. Multistep reaction;

: 47181-98-6
P-(formylmethyl)triphenylphosphonium cation

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

Conditions

Conditions	Yield
With base In water; dimethyl sulfoxide at 25℃; Kinetics; deprotonation;

: 603-35-0
triphenylphosphine

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 10 h / 80 °C 2: sulfuric acid; water / 2 h / 40 °C 3: sodium hydroxide / water / 0.5 h / 20 - 30 °C View Scheme

: 128995-63-1
2-cyano-3,3-bis(4-fluorophenyl)-2-propenal

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 130200-45-2
4-cyano-5,5-bis(4-fluorophenyl)-2,4-pentadienal

Conditions

Conditions	Yield
In benzene for 1h; Heating;	100%
In ethyl acetate; benzene	1.43 g (100%)

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 134578-05-5
methyl-4-(3-formyl-4-hydroxyphenylaminocarbonyl)butanoate

: 197707-54-3
methyl-4-[3-(2-formyl-(E)-ethenyl)-4-hydroxyphenylaminocarbonyl]butanoate

Conditions

Conditions	Yield
In dichloromethane at 25℃; for 2h;	100%

: 398489-26-4
tert-butyl 3-oxoazetidine-1-carboxylate

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 1223573-23-6
tert-butyl 3-(2-oxomethylene)azetidine-1-carboxylic acid

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 6h;	100%
In dichloromethane at 40℃; for 6h;	100%
In dichloromethane at 40℃;	99%

: 1394257-23-8
(S,Z)-2-(benzyloxy)dec-4-enal

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 1394257-22-7
(S,2E,6Z)-4-(benzyloxy)dodeca-2,6-dienal

Conditions

Conditions	Yield
In benzene at 60℃; for 4h; Wittig reaction; Inert atmosphere;	99%

: 624-48-6
dimethyl cis-but-2-ene-1,4-dioate

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: dimethyl 2-(2-(triphenyl phosphaneylidene)acetyl)succinate

Conditions

Conditions	Yield
With [Ir(dF(CF3)ppy)2(dtbbpy)]Cl In benzene for 16h; Sealed tube; Irradiation; Heating; Inert atmosphere;	99%

: 90178-78-2
2-nitro-4-cyano-benzaldehyde

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 104291-55-6
4-(4-Formyl-1,3-butadienyl)-3-nitrobenzonitril

Conditions

Conditions	Yield
In benzene for 4h; Heating;	96%

: 102919-04-0, 102854-75-1
benzyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 108182-76-9
benzyl (E)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enodialdo-1,4-furanoside

Conditions

Conditions	Yield
In benzene for 2.5h; Heating;	95%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 246545-41-5
(+)-(2R,3S)-2,3-epoxydodecanal

: (+)-(E)-(4R,5R)-4,5-epoxytetradec-2-enal

Conditions

Conditions	Yield
In toluene for 12h; Condensation; Heating;	95%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: (2RS,3RS)-3-(tert-butyldimethylsilyl)-2,3-epoxypropanal

: 5-(tert-butyldimethylsilyl)-4,5-epoxy-(E)-2-pentenal

Conditions

Conditions	Yield
In acetonitrile for 0.416667h; Heating;	95%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 3,3-diphenyloxirane carboxaldehyde

: C17H14O2

Conditions

Conditions	Yield
Inert atmosphere;	95%
In chloroform at 25℃; for 5h; Inert atmosphere;	1.6 g

: 112389-48-7
2',4',4"-tri-O-acetyldesmycosin

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 658684-19-6
C47H73NO17

Conditions

Conditions	Yield
In benzene at 80℃; for 2h; Wittig reaction;	94%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 109466-87-7
4-(trifluoromethyl)-2-nitrobenzaldehyde

: (E)-3-(2-nitro-4-(trifluoromethyl)phenyl)acrylaldehyde

Conditions

Conditions	Yield
In acetonitrile at 20℃;	94%

: 653-37-2
perfluorobenzaldehyde

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 849796-05-0
(E)-3-(perfluorophenyl)acrylaldehyde

Conditions

Conditions	Yield
In toluene at 80℃; for 1h; Wittig-Horner olefination;	93%

: 698-63-5
5-nitrofurane-2-carboxaldehyde

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 1874-22-2
3-(5-nitrofuran-2-yl)-2-propenal

Conditions

Conditions	Yield
In toluene for 6h; Reflux; Inert atmosphere;	93%
In dichloromethane at 20℃; Wittig Olefination;	30%

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: (E)-3-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propenal

Conditions

Conditions	Yield
In benzene for 1h; Heating;	92%

: 77823-89-3
methyl 2β-formyl-3β<(benzyloxycarbonyl)amino>-4-cyclohexene-α-carboxylate

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 77823-90-6, 98819-46-6, 98819-47-7
methyl 2β-<3-oxo-2(E)-propenyl>-3β<(benzyloxycarbonyl)amino>-4-cyclohexene-α-carboxylate

Conditions

Conditions	Yield
In toluene for 2h; Heating;	92%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 389121-76-0
((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetaldehyde

: 389121-79-3
(E)-4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-but-2-enal

Conditions

Conditions	Yield
	92%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 87884-14-8
methyl (2S)-2-[(tert-butoxy)carbonylamino]-4-oxobutanoate

: 116613-74-2
C12H19NO5

Conditions

Conditions	Yield
In tetrahydrofuran at 35℃; for 48h; Wittig reaction;	92%

: 1224702-13-9
C13H26O4Si

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: C15H28O4Si

Conditions

Conditions	Yield
In phenol for 17h; Wittig reaction; Reflux;	92%

: C64H110O17Si3

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: C66H112O17Si3

Conditions

Conditions	Yield
In toluene at 100℃; for 1h; Wittig Olefination; Inert atmosphere;	92%

: 2-((3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)methyl)benzaldehyde

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: (4bS*,5R*,6R*,11aR*)-6-hydroxy-11,13-dioxo-4b,6,11,12-tetrahydro-5H-6,11a-methanodibenzo[a,f]azulene-5-carbaldehyde

Conditions

Conditions	Yield
In dichloromethane at 50℃; for 7h;	92%

: 86363-76-0
(4R,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 86348-32-5
(E)-3-((4S,5S)-5-Benzhydryloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propenal

Conditions

Conditions	Yield
In benzene Ambient temperature;	91%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 99202-72-9, 99265-85-7, 106293-95-2, 106293-96-3
1,2:3,4:6,7-tri-O-isopropylidene-α-D-threo-D-galacto-octodialdo-1,5-pyranose

: 99202-73-0, 106400-53-7
(E)-8,9-dideoxy-1,2:3,4:6,7-tri-O-isopropylidene-α-D-threo-D-galacto-dec-8-enodialdo-1,5-pyranose

Conditions

Conditions	Yield
In benzene for 1.16667h; Heating;	91%
In benzene Heating;	91%

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: N-phenyl-acetimidoyl iodide

: [(E)-2-(Acetyl-phenyl-amino)-vinyl]-triphenyl-phosphonium; iodide

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 24h;	91%

: 874-69-1
N-phenylacetimidoyl chloride

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: [(E)-2-(Acetyl-phenyl-amino)-vinyl]-triphenyl-phosphonium; iodide

Conditions

Conditions	Yield
With sodium iodide In acetonitrile at 20℃; for 24h;	91%

: 1200-14-2
4-(n-butyl)benzaldehyde

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 20850-09-3
(E)-3-(4-butylphenyl)acrylaldehyde

Conditions

Conditions	Yield
In benzene for 30h; Heating;	90.6%

: 118875-10-8
3,3-bis(4-fluorophenyl)-2-(2-methyl-2H-tetrazol-5-yl)-2-propenal

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 130200-54-3
5,5-bis(4-fluorophenyl)-4-(2-methyl-2H-tetrazol-5-yl)-2,4-pentadienal

Conditions

Conditions	Yield
In benzene for 0.5h; Heating;	90.5%
	0.66 g (90.5%)

: 4933-77-1
(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 100759-67-9, 50256-79-6
(E)-6,7-didehydro-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octodialo-1,5-pyranose

Conditions

Conditions	Yield
In benzene for 12h; Heating;	90%
In benzene for 4.5h; Heating;	90%
In benzene Heating;	90%
In dichloromethane for 12h; Ambient temperature;	88%

: 76745-20-5
Methyl 5S-benzoyloxy-5-formylvalerate

: 2136-75-6
(triphenylphosphoranylidene)acetaldehyde

: 80335-91-7
Benzoic acid (E)-(S)-1-(3-methoxycarbonyl-propyl)-4-oxo-but-2-enyl ester

Conditions

Conditions	Yield
In benzene for 2h; Heating;	90%
In acetone for 5h; Heating;	54%

(Triphenylphosphoranylidene)acetaldehyde Specification

The Acetaldehyde,2-(triphenylphosphoranylidene)-, with the cas registry number 2136-75-6, has the IUPAC name of 2-(triphenyl-λ5-phosphanylidene)acetaldehyde. This is a kind of pink to brown crystalline powder, and is sensitive to air. Besides, it is combustible and incompatible with strong oxidizing agents, with the product categories including Wittig Reagents; Synthetic Organic Chemistry; Wittig & Horner-Emmons.

The physical properties of this chemical are as follows: (1)ACD/LogP: 3.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.36; (4)ACD/LogD (pH 7.4): 3.36; (5)ACD/BCF (pH 5.5): 209.5; (6)ACD/BCF (pH 7.4): 209.5; (7)ACD/KOC (pH 5.5): 1596.27; (8)ACD/KOC (pH 7.4): 1596.27; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 26.88; (13)Index of Refraction: 1.62; (14)Molar Refractivity: 92.08 cm³; (15)Molar Volume: 262 cm³; (16)Polarizability: 36.5 ×10^-24 cm³; (17)Surface Tension: 48.2 dyne/cm; (18)Density: 1.16 g/cm³; (19)Flash Point: 239.6 °C; (20)Enthalpy of Vaporization: 70.75 kJ/mol; (21)Boiling Point: 472.6 °C at 760 mmHg; (22)Vapour Pressure: 1.2E-08 mmHg at 25°C; (23)Exact Mass: 304.101702; (24)MonoIsotopic Mass: 304.101702; (25)Topological Polar Surface Area: 17.1; (26)Heavy Atom Count: 22; (27)Formal Charge: 0; (28)Complexity: 344.

Use of this chemical: 4-nitro-benzaldehyde could react with Acetaldehyde,2-(triphenylphosphoranylidene)- to produce 3t-(4-nitro-phenyl)-propenal, with the following condition: solvent: benzene.

When you are dealing with this kind of chemical, you should be much more careful and then take some measures to protect yourself. Being a kind of irritant chemical to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. Therefore, remember to wear suitable protective clothing, and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)P(=CC=O)(C2=CC=CC=C2)C3=CC=CC=C3
(2)InChI: InChI=1S/C20H17OP/c21-16-17-22(18-10-4-1-5-11-18,
19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-17H
(3)InChIKey: CQCAYWAIRTVXIY-UHFFFAOYSA-N

Product Name

(FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE

Synthetic route

(Triphenylphosphoranylidene)acetaldehyde Specification

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