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| CAS No.: | 28446-72-2 | ||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|
| Name: | 4-CHLOROCINNAMONITRILE | ||||||||||
| Molecular Structure: | |||||||||||
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| Formula: | C9H6 Cl N | ||||||||||
| Molecular Weight: | 163.606 | ||||||||||
| Synonyms: | Cinnamonitrile,p-chloro- (6CI,7CI,8CI); 3-(4-Chlorophenyl)acrylonitrile;3-(4-Chlorophenyl)propenenitrile; 4-Chlorocinnamonitrile; NSC 636921; NSC636944; p-Chlorocinnamonitrile; b-(4-Chlorophenyl)acrylonitrile | ||||||||||
| Density: | 1.205g/cm3 | ||||||||||
| Melting Point: |
55-70 °C(lit.) |
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| Boiling Point: | 293.9°Cat760mmHg | ||||||||||
| Flash Point: | 130.9°C | ||||||||||
| Hazard Symbols: |
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| Risk Codes: | 20/21/22-36/37/38 | ||||||||||
| Safety: |
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| PSA: | 23.79000 | ||||||||||
| LogP: | 2.87678 | ||||||||||

| Conditions | Yield |
|---|---|
| With P(HNCH2CH2)(i-PrNCH2CH2)2N at 40℃; for 3h; | 96% |
| With tetrabutylammomium bromide; oxygen for 8h; electrolysis; | 58% |

diethyl 1-cyanomethylphosphonate


4-chlorobenzaldehyde


4-chlorocinnamonitrile

| Conditions | Yield |
|---|---|
| With HT-O-t-Bu In N,N-dimethyl-formamide for 2.5h; Wadsworth-Emmons reaction; Heating; | 93% |

4-chlorobenzaldehyde


C14H29BrNSb

A

4-chlorocinnamonitrile

B

(RS)-3-(4-chlorophenyl)-3-hydroxypropionitrile

| Conditions | Yield |
|---|---|
| With n-butyllithium In tetrahydrofuran at -78℃; for 2h; | A 6% B 92% |


| Conditions | Yield |
|---|---|
| With IMes-Pd(dmba)Cl; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 18h; Heck-Mizoroki reaction; Inert atmosphere; | 88% |
| With palladium diacetate; potassium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 125 - 127℃; Heck Reaction; Inert atmosphere; | 47% |
| With tetrabutyl-ammonium chloride; palladium diacetate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 40℃; |

4-chlorobenzaldehyde


acetonitrile

A

4-chlorocinnamonitrile

B

(RS)-3-(4-chlorophenyl)-3-hydroxypropionitrile

| Conditions | Yield |
|---|---|
| With P(MeNCH2CH2)3N; magnesium sulfate at 0℃; for 6h; Product distribution; other reagent, temperature, reaction time; | A 4 % Spectr. B 82% |


diethyl 1-cyanomethylphosphonate


4-chlorobenzaldehyde

A

4-chlorocinnamonitrile

B

(E)-diethyl 1-cyano-2-(4-chlorophenyl)-vinylphosphonate

| Conditions | Yield |
|---|---|
| With aluminum oxide at 100℃; for 2h; Yield given; | A n/a B 70% |
| With aluminum oxide at 100℃; for 2h; Yields of byproduct given; | A n/a B 70% |


para-Chlorobenzyl alcohol


cyanomethylene triphenylphosphorane

A

bis(4-chlorobenzyl) ether

B

4-chlorocinnamonitrile

C

3-(4-chlorophenyl)propanenitrile

D

4-chlorobenzaldehyde

| Conditions | Yield |
|---|---|
| With 1,3-bis-(diphenylphosphino)propane; caesium carbonate; bis(1,5-cyclooctadiene)diiridium(I) dichloride In toluene at 150℃; for 72h; | A n/a B n/a C 66% D n/a |


1-[(E)-2-bromoethenyl]-4-chlorobenzene


4-chlorocinnamonitrile

| Conditions | Yield |
|---|---|
| With [bmim]BF4; sodium carbonate; N,N`-dimethylethylenediamine; palladium dichloride for 0.266667h; microwave irradiation; | 65% |

(Z)-1-bromo-2-(4-chlorophenyl)ethylene


4-chlorocinnamonitrile

| Conditions | Yield |
|---|---|
| With [bmim]BF4; sodium carbonate; N,N`-dimethylethylenediamine; palladium dichloride for 0.3h; microwave irradiation; | 63% |

3-(4-chlorophenyl)-1-phenylprop-2-en-1-one

A

4-chlorocinnamonitrile

B

3-(4-Chloro-phenyl)-5-oxo-5-phenyl-pentanenitrile

C

benzoic acid

D

para-chlorobenzoic acid

| Conditions | Yield |
|---|---|
| With potassium superoxide In acetonitrile for 0.25h; Irradiation; | A 2% B 55% C 10% D 7% |
