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(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide
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Name

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide

 EINECS 257-977-3
CAS No. 52509-14-5 Density g/cm3
PSA 32.05000 LogP 0.35740
Solubility Soluble in water (20°C). Melting Point 193-195 ºC
Formula C22H22 O2 P . Br Boiling Point °Cat760mmHg
Molecular Weight 429.293 Flash Point °C
Transport Information N/A Appearance White Power
Safety S26;S37/39 Risk Codes R20/21/22;R36/37/38   
Molecular Structure Molecular Structure of 52509-14-5 ((1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide) Hazard Symbols
Synonyms

Phosphonium,(1,3-dioxolan-2-ylmethyl)triphenyl-, bromide (9CI); (1,3-Dioxolan-2-ylmethyl)triphenylphosphoniumbromide

Article Data 5

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide Synthetic route

4360-63-8

2-bromomethyl-1,3-dioxolane

603-35-0

triphenylphosphine

52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In isopropyl alcohol at 60 - 65℃; for 3h; Inert atmosphere; Green chemistry;99.1%
In toluene for 24h; Heating / reflux;54%
at 120℃; for 24h;
4360-63-8

2-bromomethyl-1,3-dioxolane

52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In toluene for 48h; Reflux;33%
288156-11-6

4,15-diformyl[2.2]paracyclophane

52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

4,15-bis[(E)-2-formylvinyl]-[2.2]paracyclophane

Conditions
ConditionsYield
Stage #1: 4,15-diformyl[2.2]paracyclophane; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran at 2℃; for 16h;		100%
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

4,15-bis[(1E,3E)-4-formylbuta-1,3-dienyl][2.2]paracyclophane

(2E,4E,6E)-7-[12-((1E,3E,5E)-7-Oxo-hepta-1,3,5-trienyl)-tricyclo[8.2.2.24,7]hexadeca-1(13),4(16),5,7(15),10(14),11-hexaen-5-yl]-hepta-2,4,6-trienal

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; 4,15-bis[(1E,3E)-4-formylbuta-1,3-dienyl][2.2]paracyclophane With potassium tert-butylate In tetrahydrofuran at 20℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran at 2℃; for 16h;		100%
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

15164-44-0

p-(iodophenyl)carboxaldehyde

(E)-3-(4-iodophenyl)acrylaldehyde

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; p-(iodophenyl)carboxaldehyde With 18-crown-6 ether; sodium hydride In tetrahydrofuran at 25℃; for 14h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 25℃; for 6h;		100%
With 18-crown-6 ether; sodium hydride In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;78.7%
487-68-3

mesytaldehyde

52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

2-(2,4,6-trimethylstyryl)-1,3-dioxolane

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: mesytaldehyde In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere;		100%
52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

113675-57-3

5-((allyloxy)methyl)furan-2-carbaldehyde

C11H12O3

Conditions
ConditionsYield
With sodium methylate In methanol; N,N-dimethyl-formamide at 70℃; for 48h; Wittig Olefination; Inert atmosphere;99%
1421970-17-3

(E)-3-(methylthio)cinnamaldehyde

52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

1421970-16-2

(2E,4E)-5-(3-(methylthio)phenyl)penta-2,4-dienal

Conditions
ConditionsYield
Stage #1: (E)-3-(methylthio)cinnamaldehyde; (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With sodium methylate In methanol at 25℃; Wittig Olefination; Inert atmosphere;
Stage #2: With iodine In methanol; acetone for 12h; Inert atmosphere; Reflux;		96.2%
860032-97-9

C17H26O

52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

1254522-05-8

C19H28O

Conditions
ConditionsYield
Stage #1: (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: C17H26O In tetrahydrofuran at 20℃; Wittig reaction; Inert atmosphere;
Stage #3: With oxalic acid In tetrahydrofuran; water		96%
4363-93-3

quinoline-4-carboxaldehyde

52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

172678-77-2

4-((E)-2-[1,3]Dioxolan-2-yl-vinyl)-quinoline

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -35 - 10℃; for 4h;95%
With lithium methanolate In methanol; N,N-dimethyl-formamide at 70 - 80℃; for 4h;
With potassium tert-butylate In tetrahydrofuran

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide Chemical Properties

Molecular Structure of (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide (CAS NO.1530-45-6):

IUPAC Name: 1,3-dioxolan-2-ylmethyl(triphenyl)phosphanium bromide 
Empirical Formula: C22H22BrO2P
Molecular Weight: 429.2866
H bond acceptors: 2
H bond donors: 0
Freely Rotating Bonds: 5
Polar Surface Area: 18.46Å2
Melting point: 193-195 °C(lit.)
Sensitive: Hygroscopic
InChI
InChI=1/C22H22O2P.BrH/c1-4-10-19(11-5-1)25(18-22-23-16-17-24-22,20-12-6-2-7-13-20)21-14-8-3-9-15-21;/h1-15,22H,16-18H2;1H/q+1;/p-1
Smiles
[BrH-].C1COC(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)O1
EINECS: 257-977-3
Product Categories: Dioxanes & Dioxolanes; Dioxolanes; Phosphonium Compounds; Synthetic Organic Chemistry; Wittig & Horner-Emmons Reaction; Wittig Reaction; C-C Bond Formation; Olefination; Wittig Reagents

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
HS Code: 29329970

(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide Specification

  (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide , with CAS number of 1530-45-6, can be called phosphonium, (1,3-dioxolan-2-ylmethyl)triphenyl-, bromide (1:1) . It is a white to light brown granular powder.

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