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CAS No.: | 52509-14-5 |
---|---|
Name: | (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C22H22 O2 P . Br |
Molecular Weight: | 429.293 |
Synonyms: | Phosphonium,(1,3-dioxolan-2-ylmethyl)triphenyl-, bromide (9CI); (1,3-Dioxolan-2-ylmethyl)triphenylphosphoniumbromide |
EINECS: | 257-977-3 |
Density: | g/cm3 |
Melting Point: | 193-195 ºC |
Boiling Point: | °Cat760mmHg |
Flash Point: | °C |
Solubility: | Soluble in water (20°C). |
Appearance: | White Power |
Hazard Symbols: | |
Risk Codes: | R20/21/22;R36/37/38 |
Safety: | S26;S37/39 |
PSA: | 32.05000 |
LogP: | 0.35740 |
2-bromomethyl-1,3-dioxolane
triphenylphosphine
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
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; |
2-bromomethyl-1,3-dioxolane
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
In toluene for 48h; Reflux; | 33% |
4,15-diformyl[2.2]paracyclophane
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
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% |
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
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% |
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
p-(iodophenyl)carboxaldehyde
Conditions | Yield |
---|---|
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% |
mesytaldehyde
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
Conditions | Yield |
---|---|
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% |
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
5-((allyloxy)methyl)furan-2-carbaldehyde
Conditions | Yield |
---|---|
With sodium methylate In methanol; N,N-dimethyl-formamide at 70℃; for 48h; Wittig Olefination; Inert atmosphere; | 99% |
(E)-3-(methylthio)cinnamaldehyde
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
(2E,4E)-5-(3-(methylthio)phenyl)penta-2,4-dienal
Conditions | Yield |
---|---|
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% |
C17H26O
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
C19H28O
Conditions | Yield |
---|---|
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% |
quinoline-4-carboxaldehyde
(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
4-((E)-2-[1,3]Dioxolan-2-yl-vinyl)-quinoline
Conditions | Yield |
---|---|
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 |
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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
Hazard Codes: Xn
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 , 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.