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104-88-1

Basic Information
CAS No.: 104-88-1
Name: 4-Chlorobenzaldehyde
Article Data: 1303
Molecular Structure:
Molecular Structure of 104-88-1 (4-Chlorobenzaldehyde)
Formula: C7H5ClO
Molecular Weight: 140.569
Synonyms: Benzaldehyde, p-chloro-;Benzaldehyde, 4-chloro-;4-chloro benzaldehyde;4-chloroBenzaldehyde;p-chlorobenzenecarboxaldehyde;4-Chlorobenzaldehyde (PCBA);Para-chlorobenzaldehyde;p-Chlorobenzenecarboxaldehyde;p-Chlorobenzaldehyde;
EINECS: 203-247-4
Density: 1.243 g/cm3
Melting Point: 46 °C
Boiling Point: 213.713 °C at 760 mmHg
Flash Point: 87.778 °C
Solubility: 935 mg/L (20 °C) in water
Appearance: colourless to light yellow crystalline powder
Hazard Symbols: FlammableF; CorrosiveC; DangerousN; HarmfulXn; IrritantXi
Risk Codes: 22-36/37/38-51/53
Safety: 26-61-37/39-36
Transport Information: UN 1219 3/PG 2
PSA: 17.07000
LogP: 2.15250
Synthetic route
873-76-7

para-Chlorobenzyl alcohol

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With oxygen; perruthenate modified mesoporous silicate MCM-41 In toluene at 80℃; for 1h; Oxidation;100%
With n-butyltriphenylphosphonium permanganate In acetonitrile at 20℃; for 0.25h;100%
With butyltriphenylphosphonium chlorochromate In acetonitrile for 0.75h; Heating;100%
62102-59-4

2-(4-chlorophenyl)-1,3-benzodithiole

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran for 0.25h; Ambient temperature;100%

Sodium; 6-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-hexanoate

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde;100%
13086-93-6

(acetyloxy)(4-chlorophenyl)methyl acetate

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With [NO(1+)*18-crown-6*H(NO3)2(1-)]; silica gel In dichloromethane at 20℃; for 0.0833333h;100%
With poly(4-vinylpyridine)-supported sulfuric acid In acetonitrile at 50℃; for 0.75h; Green chemistry;100%
With bismuth(III) chloride In chloroform for 0.416667h; deprotection; Heating;99%
14856-74-7

4-chlorobenzyltrimethylsilyl ether

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With nitrogen dioxide at 20℃; for 0.0833333h;100%
With trichloroisocyanuric acid In acetonitrile for 0.166667h; Reflux;100%
With NTPPPODS In acetonitrile for 0.0666667h; Reflux;99%
18484-03-2

2-(4-chlorobenzyloxy)tetrahydro-2H-pyran

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With aluminium trichloride; benzyltriphenylphosphonium chlorate In acetonitrile at 20℃; for 1h;100%
With allyltriphenylphopsphonium peroxodisulfate In acetonitrile for 0.333333h; Heating;99%
With N-Bromosuccinimide; β‐cyclodextrin In acetone at 20℃; for 0.5h;95%

(E)-2-(4-chlorobenzylidene)hydrazine carboxamide

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With caro's acid; silica gel In dichloromethane for 0.133333h; Heating;100%
7335-27-5

ethyl 4-chlorobenzoate

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
Stage #1: ethyl 4-chlorobenzoate With morpholine; diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 3.16667h; Inert atmosphere;
Stage #2: With diisobutylaluminium hydride In tetrahydrofuran; hexane at 0℃; for 0.166667h; Inert atmosphere;
99%
With phenylsilane; cobalt(II) diacetate tetrahydrate; sodium triethylborohydride In 1,2-dimethoxyethane; toluene at 25℃; for 15h; Inert atmosphere; Schlenk technique;84%
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃;83%
619-56-7

4-chlorobenzamide

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With samarium diiodide; phosphoric acid In tetrahydrofuran for 0.000833333h; Ambient temperature;99%
1073-67-2

4-vinylbenzyl chloride

104-88-1

4-chlorobenzaldehyde

Conditions
ConditionsYield
With sodium periodate; C53H44As2N2O3Ru In water; ethyl acetate; acetonitrile at 25℃; for 0.5h;99%
With sodium periodate; C22H23ClIN2Os(1+)*F6P(1-) In water; tert-butyl alcohol at 60℃; for 1h; Schlenk technique; Inert atmosphere;99%
With sodium periodate; C18H15ClFN2Ru(1+)*Cl(1-) In water; tert-butyl alcohol at 60℃; for 1h; Catalytic behavior; Schlenk technique; Inert atmosphere;99%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The CAS registry number of p-Chlorobenzaldehyde is 104-88-1. Its EINECS registry number is 203-247-4. The IUPAC name is 4-chlorobenzaldehyde. In addition, the molecular formula is C7H5ClO and the molecular weight is 140.57. It is also called benzaldehyde, 4-chloro-. What's more, it is a kind of colourless to light yellow crystalline powder and belongs to the classes of Fine Chemical & Intermediates; Aromatic Aldehydes & Derivatives (substituted); Benzaldehyde; Aldehydes; C7; Carbonyl Compounds. Besides, it should be stored in sealed container, and put in a cool and dry place. The storage place must stay away from oxidant, the fire and heat source.

Physical properties about this chemical are: (1)ACD/LogP: 2.21; (2)ACD/LogD (pH 5.5): 2.21; (3)ACD/LogD (pH 7.4): 2.21; (4)ACD/BCF (pH 5.5): 28.158; (5)ACD/BCF (pH 7.4): 28.158; (6)ACD/KOC (pH 5.5): 379.525; (7)ACD/KOC (pH 7.4): 379.525; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 17.07 Å2; (11)Index of Refraction: 1.585; (12)Molar Refractivity: 37.901 cm3; (13)Molar Volume: 113.05 cm3; (14)Polarizability: 15.025 ×10-24cm3; (15)Surface Tension: 42.238 dyne/cm; (16)Density: 1.243 g/cm3; (17)Flash Point: 87.778 °C; (18)Enthalpy of Vaporization: 45.003 kJ/mol; (19)Boiling Point: 213.713 °C at 760 mmHg; (20)Vapour Pressure: 0.162 mmHg at 25°C.

Preparation of p-Chlorobenzaldehyde: it can be prepared by 4-chloro-benzaldehyde oxime. This reaction will need reagent poly[N-(4-pyridinumdichromate)-p-styrenesulphonamide] and solvent acetonitrile. The reaction time is 2 hours by heating. The yield is about 90%.

p-Chlorobenzaldehyde can be prepared by 4-chloro-benzaldehyde oxime

Uses of p-Chlorobenzaldehyde: it can be used as medicine and dye intermediates. And it can react with phenylboronic acid to get biphenyl-4-carbaldehyde. This reaction is a kind of suzuki reaction. It will need reagent K2CO3, catalyst Tedicyp/[PdCl(C3H5)]2 and solvent xylene. The reaction time is 20 hours at reaction temperature of 130 °C. The yield is about 25%.

p-Chlorobenzaldehyde can react with phenylboronic acid to get biphenyl-4-carbaldehyde

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes, respiratory system and skin. Moreover, it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. In addition, you should avoid release to the environment and you can refer to special instructions safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(ccc1C=O)Cl
(2)InChI: InChI=1/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H
(3)InChIKey: AVPYQKSLYISFPO-UHFFFAOYAQ

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 1400mg/kg (1400mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(2), Pg. 50, 1987.
rat LC inhalation > 473mg/m3/4H (473mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(2), Pg. 50, 1987.
rat LD50 oral 1575mg/kg (1575mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(2), Pg. 50, 1987.