2-Chlorobenzaldehyde Property

Melting point:

9-11 °C (lit.)

Boiling point:

209-215 °C (lit.)

Density 

1.248 g/mL at 25 °C (lit.)

vapor density 

4.84 (vs air)

vapor pressure 

1.27 mm Hg ( 50 °C)

refractive index 

n20/D 1.566(lit.)

Flash point:

190 °F

storage temp. 

Store in RT

solubility 

1.8g/l

form 

Liquid

color 

Clear colorless to light yellow

PH

2.9 (H2O)(saturated aqueous solution)

Water Solubility 

0.1-0.5 g/100 mL at 24 ºC

Sensitive 

Air Sensitive

BRN 

385877

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, iron, strong reducing agents. Moisture and light-sensitive.

LogP

2.44 at 25℃

CAS DataBase Reference

89-98-5(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 2-chloro-(89-98-5)

EPA Substance Registry System

2-Chlorobenzaldehyde (89-98-5)

Safety

Hazard Codes 

C,Xi

Risk Statements 

34

Safety Statements 

26-45

RIDADR 

UN 3265 8/PG 3

WGK Germany 

1

RTECS 

CU5075000

F 

8-9-23

Autoignition Temperature

746 °F

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29130000

Hazardous Substances Data

89-98-5(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 2160 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P363Wash contaminated clothing before reuse.

2-Chlorobenzaldehyde Chemical Properties,Usage,Production

Chemical Properties

2-Chlorobenzaldehyde is a colorless to yellowish liquid with a penetrating odor. Insoluble in water, soluble in benzene, alcohol and ether. 2-Chlorobenzaldehyde is considerably more resistant to oxidation than benzaldehyde. When it is heated with sodium sulfite solution under pressure, benzaldehyde-2-sulfonic acid forms.

Uses

2-Chlorobenzaldehyde has been used in generation of small focused library of diversely functionalized dihydropyrimidine derivatives via one-pot three-component Biginelli cyclocondensation of β-ketoesters, aldehydes and thioureas.

Uses

2-Chlorobenzaldehyde can be used to make alcohols, acids, and dyes; used in the rubber, tanning, and paper industries; used as an intermediate for optical brighteners, agricultural chemicals, and pharmaceuticals.It can also be used to prepare triphenyl methane and related dyes, organic intermediate.

Preparation

2-Chlorobenzaldehyde is produced mainly by chlorination of 2-chlorotoluene to form 2-chlorobenzal chloride, which is then subjected to acid hydrolysis. Metal salts, such as iron(III) chloride, are used as catalysts. The hydrolysis can also be accomplished using formic acid without a catalyst.
2-Chlorobenzaldehyde can also be produced by oxidation of 2-chlorobenzyl chloride with N-oxides of tertiary amines or with dilute nitric acid.
https://pubchem.ncbi.nlm.nih.gov/compound/2-Chlorobenzaldehyde

Application

2-Chlorobenzaldehyde is used acid zinc plating brightener, also be used for organic synthesis, agricultural pesticide and pharmaceutical industries. It is used to synthesize the acaricides clofentezine and flutenzine. 2-Chlorobenzaldehyde undergoes alkynylation with phenylacetylene in the presence of catalytic ligands and dimethylzinc at 0°C to form binaphthyl-derived amino alcohols.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 8037, 1993 DOI: 10.1016/S0040-4039(00)61444-2

General Description

2-chlorobenzaldehyde is a clear colorless to yellowish liquid. (NTP, 1992)

Air & Water Reactions

2-Chlorobenzaldehyde is moisture and light sensitive. Slightly water soluble.

Reactivity Profile

2-Chlorobenzaldehyde reacts with iron and strong oxidizers, strong bases and strong reducing agents.

Health Hazard

Symptoms of exposure to 2-Chlorobenzaldehyde may include skin, eye and upper respiratory tract irritation. This compound may cause skin, eye and respiratory tract irritation. When heated to decomposition it emits toxic fumes.

Fire Hazard

2-Chlorobenzaldehyde is combustible.

Safety Profile

Poison by intraperitoneal and intravenous routes. When heated to decomposition it emits toxic fumes of Cl-. See also ALDEHYDES and CHLORIDES.

Purification Methods

Wash it with 10% Na2CO3 solution, then fractionally distil it in the presence of a small amount of catechol as stabiliser. [Beilstein 7 H 233, 7 IV 561.]