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2136-75-6

Basic Information
CAS No.: 2136-75-6
Name: (FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE
Article Data: 27
Molecular Structure:
Molecular Structure of 2136-75-6 ((FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE)
Formula: C20H17 O P
Molecular Weight: 304.328
Synonyms: Acetaldehyde,(triphenylphosphoranylidene)- (6CI,7CI,8CI,9CI);(2-Oxoethylidene)triphenylphosphorane;(Formylmethylene)triphenylphosphorane;(Triphenylphosphoranylidene)acetaldehyde;2-(Triphenylphosphoranylidene)acetaldehyde;
EINECS: 218-375-6
Density: 1.162 g/cm3
Melting Point: 185-188 °C(lit.)
Boiling Point: 472.618 °C at 760 mmHg
Flash Point: 239.631 °C
Appearance: pink to brown crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 26.88000
LogP: 2.98160
Synthetic route
62942-43-2

formylmethyltriphenylphosphonium chloride

2136-75-6

(triphenylphosphoranylidene)acetaldehyde

Conditions
ConditionsYield
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
ConditionsYield
In benzene81%
1779-49-3

Methyltriphenylphosphonium bromide

109-94-4

formic acid ethyl ester

2136-75-6

(triphenylphosphoranylidene)acetaldehyde

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In nitromethane Heating;
19753-63-0

triphenylphosphonium bromide acetaldehyde

2136-75-6

(triphenylphosphoranylidene)acetaldehyde

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With base In water; dimethyl sulfoxide at 25℃; Kinetics; deprotonation;
603-35-0

triphenylphosphine

2136-75-6

(triphenylphosphoranylidene)acetaldehyde

Conditions
ConditionsYield
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
ConditionsYield
In benzene for 1h; Heating;100%
In ethyl acetate; benzene1.43 g (100%)
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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 

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