89-98-5

Basic information

• Product Name: 2-Chlorobenzaldehyde
• Synonyms: 2-chloorbenzaldehyde;2-Chlorbenzaldehyd;2-chloro-benzaldehyd;2-Clorobenzaldeide;Benzaldehyde, o-chloro-;Benzaldehyde,2-chloro-;-Chloroformylbenzene;o-Chloorbenzaldehyde
• CAS NO: 89-98-5
• Molecular Formula: C₇H₅ClO
• Molecular Weight: 140.57
• EINECS: 201-956-3
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);C7Alphabetic;Aldehydes;C;Carbonyl Compounds;CH;C7;Aromatics;Pesticides intermediate;Pyridines
• Mol File: 89-98-5.mol
• Article Data: 424

Chemical Properties

• Melting Point: 9-11 °C(lit.)
• Boiling Point: 209-215 °C(lit.)
• Flash Point: 190 °F
• Appearance: Clear colorless to light yellow/Liquid
• 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.)
• Storage Temp.: -20?C Freezer
• Solubility: 1.8g/l
• Water Solubility: 0.1-0.5 g/100 mL at 24 ºC
• Sensitive: Air Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, iron, strong reducing agents. Moisture and light-s
• BRN: 385877
• CAS DataBase Reference: 2-Chlorobenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorobenzaldehyde(89-98-5)
• EPA Substance Registry System: 2-Chlorobenzaldehyde(89-98-5)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 1
• RTECS: CU5075000
• F: 8-9-23
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 89-98-5(Hazardous Substances Data)

Usage

Chemical Description

2-chlorobenzaldehyde is an organic compound with a chlorinated benzene ring and an aldehyde functional group.

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

Different sources of media describe the Uses of 89-98-5 differently. You can refer to the following data:
1. 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.
2. 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.]

InChI:InChI=1/C7H5ClO/c8-7-4-2-1-3-6(7)5-9/h1-5H

Synthetic route

2-Chlorobenzyl alcohol (17849-38-6) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With n-butyltriphenylphosphonium permanganate In acetonitrile at 20℃; for 0.25h;	100%
With ferric nitrate; barium(II) chloride at 90℃; for 0.166667h;	100%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In dichloromethane; water under 760.051 Torr; for 4h; Green chemistry;	100%

2-chlorobenzyl trimethylsilyl ether (150480-30-1) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With nitrogen dioxide at 20℃; for 1h;	100%
With 2,6-dicarboxypyridinium fluorochromate In acetonitrile at 20℃; for 0.1h;	98%
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate In acetonitrile for 0.116667h; Reflux;	98%

1,1-diacetoxy-1-(2-chlorophenyl)methane (13086-95-8) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With water; silica sulfate In benzene for 0.0333333h; Heating;	99%
With potassium tert-butylate; 3-Dimethylaminophenol In tetrahydrofuran for 0.0833333h;	98%
With sodium hydrogen sulfate; PEG-2000 at 70℃; for 0.5h;	96%

2-chlorobenzamide (609-66-5) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With samarium diiodide; phosphoric acid In tetrahydrofuran for 0.000833333h; Ambient temperature;	99%
With lithium-tris(diethylamino)hydridoaluminate In tetrahydrofuran for 12h; Ambient temperature;	68%

2-CHLOROBENZYLAMINE (89-97-4) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccasefrom Trametes versicolor; oxygen In water at 30℃; for 24h; pH=4.5; Enzymatic reaction;	99%
With 3-carboxypyridinium dichromate In acetonitrile at 20℃; for 0h;	93%
With zinc dichromate trihydrate at 20℃; grinding; neat (no solvent); chemoselective reaction;	90%

2-chloro benzaldehyde oxime (3717-28-0) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With Cr-MCM-41 zeolite on silica gel for 0.0833333h; microwave irradiation;	98%
With molybdenum(V) chloride; zinc In acetonitrile at 20℃; for 0.166667h;	95%
With tris[trinitratocerium(IV)] paraperiodate at 90℃; for 0.166667h;	95%

2-(2-chlorophenyl)-1,3-dithiolane (83521-68-0) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With silica gel; copper(II) nitrate In tetrachloromethane for 0.25h; Ambient temperature;	98%
With dimethyl sulfoxide at 20℃; for 2h; Solvent;	89%

2-(2-chlorophenyl)-1,3-dithiane (69849-09-8) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With silica gel; copper(II) nitrate In tetrachloromethane for 1h; Ambient temperature;	98%
With silica gel; iodic acid at 20℃; for 0.0208333h;	93%
With quinolinium monofluorochromate(VI) In acetonitrile for 4h; Heating;	92%
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile for 2.13333h; Heating;	88%
With water In 1,4-dioxane at 100℃; for 48h; Inert atmosphere;	78%

2-Chlorobenzyl alcohol (17849-38-6) + nitrobenzene (98-95-3) → 2-chlorobenzalaniline (32347-02-7, 5877-49-6) + 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With α,α,α-trifluorotoluene; titanium(IV) oxide In dodecane under 750.075 Torr; for 3h; Darkness; Inert atmosphere; Irradiation;	A 96.98% B n/a

2-methylchlorobenzene (95-49-8) → 2-chloro-benzaldehyde (89-98-5) + 1-bromomethyl-2-chlorobenzene (611-17-6) + ortho-chlorobenzoic acid (118-91-2)

Conditions	Yield
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 95℃; for 0.666667h; Kinetics; Mechanism; Rate constant; other time; other temperature; various concentrations of Co(OAc)2 and NaBr;	A n/a B n/a C 96%
With oxygen; cobalt(II) acetate; sodium bromide In acetic acid at 95℃; for 0.666667h;	A n/a B n/a C 95%

2-chlorobenzaldehyde phenylhydrazone (34158-76-4) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.1h; Heating;	96%
With NTPPPODS In water; acetonitrile for 0.25h; Reflux;	95%
With caro's acid; silica gel In dichloromethane for 1.25h; Heating;	90%

o-chlorobenzoyl chloride (609-65-4) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With 1-benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate In hexane; chloroform for 1.5h; Heating;	95%
With hydrogenchloride; samarium; tributylphosphine In acetonitrile at -20℃; for 1h;	92%
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In hexane; dichloromethane for 0.16h; Ambient temperature;	89%

2-(2-chloro-phenyl)-[1,3]oxathiolane (99586-81-9) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With t-butyl thionitrite In acetonitrile at 0℃; for 0.6h;	95%
With Iron(III) nitrate nonahydrate at 90℃; for 0.166667h;	95%

2-[(2-chlorophenyl)methylene]hydrazinecarboxamide (5315-85-5, 120445-39-8) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With NTPPPODS In water; acetonitrile for 0.333333h; Reflux;	95%
With bis(trimethylsilyl)chromate; Montmorillonite K10 for 0.0333333h; Solid phase reaction; Cleavage; microwave irradiation;	92%
With clayfen (montmorillonite K-10, Fe(NO3)3*9H2O) for 0.0333333h; microwave irradiation;	88%

2-(2'-chlorophenyl)-1,3-dioxolane (7366-47-4) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With carbon tetrabromide In water; acetonitrile at 45℃; for 6h; sonication;	95%
With water; β‐cyclodextrin at 20℃; for 6h;	94%
With caro's acid; silica gel In acetonitrile at 20℃; for 1h;	84%
With sodium tetrahydroborate; nickel(II) chloride hexahydrate In methanol for 3h; chemoselective reaction;	77%

2-chlorobenzaldehyde dimethyl acetal (70380-66-4) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
perchloric acid In methanol; water at 25 - 30℃; for 0.25h;	95%
With water In methanol at 25 - 30℃; for 0.25h;	95%
With chloroacetate buffer; sodium dodecyl-sulfate In water at 25℃; pH=2.77 - 2.96; Kinetics;

2-(2-chlorobenzyloxy)tetrahydro-2H-pyran (512180-26-6) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With NTPPPODS In acetonitrile for 0.133333h; Reflux;	95%
With 2,6-dicarboxypyridinium chlorochromate In acetonitrile at 20℃; for 0.166667h;	92%
With allyltriphenylphopsphonium peroxodisulfate In acetonitrile for 0.333333h; Heating;	91%
With dipotassium peroxodisulfate; molybdenum trioxide In water; acetonitrile for 0.34h; Reflux;	82%
With trichloroisocyanuric acid In acetonitrile Reflux;

2-chlorostyrene (2039-87-4) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With iron(III) trifluoromethanesulfonate; 2-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)-6-((4R,5R)-1-((4-(tert-butyl)phenyl)sulfonyl)-4,5-diphenylimidazolidin-2-yl)pyridine; oxygen In 1,2-dichloro-ethane at 70℃; under 760.051 Torr; for 6h; Green chemistry; chemoselective reaction;	95%
With dihydrogen peroxide In water at 100℃; for 4h;	89%
With tetrabutylammonium perchlorate; oxygen; platinum In nitromethane at 20℃; Electrolysis;	79%

2-methylchlorobenzene (95-49-8) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With Xylaria polymorpha laccase; 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonate) diammonium salt In 1,4-dioxane at 20℃; for 1.5h; pH=4.5; Green chemistry; Enzymatic reaction;	94%
With dipotassium peroxodisulfate; ferrocene; iron(II) acetylacetonate In water; acetonitrile at 80℃; for 6h;	92%
With laccase of Pleurotus ostreatus MTCC-1801; 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt In 1,4-dioxane at 20℃; pH=4.5; Enzymatic reaction;	89%

2'-chloro-benzeneacetic acid (2444-36-2) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile at 25℃; for 10h; UV-irradiation;	94%
With potassium 12-tungstocobaltate(III) In water; acetonitrile for 0.25h; Microwave irradiation;	92%
With 1H-imidazole; sodium periodate; {Mn(III)[5,10,15,20-tetrakis(4-H2N-Ph)porphyrin]}polystyrene In acetonitrile at 20℃; for 4h;	90%

ortho-chlorobenzoic acid (118-91-2) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h;	93%

N’-(2-chlorobenzylidene)-4-methylbenzenesulfonohydrazide (107135-19-3) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With silica gel; copper(II) nitrate In tetrachloromethane for 0.166667h; Heating;	93%
With Cr-MCM-41 zeolite on silica gel for 0.0833333h; microwave irradiation;	93%

1-chloro-2-(chloromethyl)benzene (611-19-8) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With dihydrogen peroxide; trimethylamine In water for 1h; Reflux;	93%
Stage #1: 1-chloro-2-(chloromethyl)benzene With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide In water for 0.0833333h; Reflux; Stage #2: With dihydrogen peroxide In water for 2h;	92%
With sodium nitrate; acetic acid In water for 4h; Reflux;	90%

1-bromomethyl-2-chlorobenzene (611-17-6) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With dihydrogen peroxide In ethanol for 3.5h; Heating;	93%
Stage #1: 1-bromomethyl-2-chlorobenzene With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water for 0.0833333h; Reflux; Stage #2: With dihydrogen peroxide In water for 2h;	91%
With potassium hydrogencarbonate; dimethyl sulfoxide for 0.05h; Microwave irradiation;	83%
Multi-step reaction with 2 steps 1: 20percent NaOH / 4 h 2: CH2Cl2 / 18 h / 60 - 70 °C / Irradiation View Scheme

(DL)-o-chlorophenyl-1,2-ethanediol (32345-65-6, 133082-13-0, 59365-60-5) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With tert-butylhypochlorite; lead acetate; dibenzoyl peroxide In toluene at 20℃; for 0.75h;	93%
With dimanganese decacarbonyl In toluene at 120℃; Sealed tube;	91%
With oxygen; sodium carbonate In water at 20℃; for 5h; Irradiation; Green chemistry;	77%

o-chlorobenzyl acetate (22184-24-3) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With methanol; potassium permanganate In ethyl acetate at 25℃; for 20h;	92%

2-chlorobenzaldoxime (3717-26-8, 3717-27-9, 3717-28-0) → 2-chloro-benzaldehyde (89-98-5)

Conditions	Yield
With N-bromobis(p-toluenesulfonyl)amine In tetrachloromethane at 20℃; for 2h;	90%

Upstream product

• 91-22-5 quinoline 
• 99-65-0 meta-dinitrobenzene 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 497-19-8 sodium carbonate 
• 873-32-5 2-Chlorobenzonitrile 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 94489-25-5 (2RS,3SR)-3-(2-chloro-phenyl)-2-cyano-2,3-epoxy-propionic acid 
• 95-49-8 2-methylchlorobenzene 
• 64-18-6 formic acid 
• 100-97-0 hexamethylenetetramine 
• 611-17-6 1-bromomethyl-2-chlorobenzene 
• 64-17-5 ethanol 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 13086-95-8 1,1-diacetoxy-1-(2-chlorophenyl)methane 

Downstream Products

• 6238-67-1 α-(2-chlorophenyl)-2-pyridylmethanol 
• 6772-77-6 (E)-2-[2-(chlorophenyl)vinyl]pyridine 
• 107922-87-2 (2-chloro-benzyl)-(3-morpholino-propyl)-amine 
• 5462-00-0 3-((Ξ)-2-chloro-benzylidene)-dihydro-furan-2-one 
• 67288-79-3 3,5-bis-(2-chloro-benzylidene)-1-methyl-piperidin-4-one 
• 14258-47-0 2-(2-chloro-styryl)-6-methyl-pyran-4-one 
• 100623-08-3 2-(2-chloro-trans-styryl)-6-methyl-pyran-4-thione 
• 46883-26-5 3-(2-chloro-benzylidene)-2-methyl-3H-indole 
• 6318-36-1 (E,Z)-5-(2-chlorophenylmethylene)-4-oxo-2-thioxothiazolidine 
• 35558-97-5 thiophene-2-carboxylic acid-(2-chloro-benzylidenehydrazide) 
• 110157-00-1 [4]pyridyl-acetic acid-(2-chloro-benzylidenehydrazide) 
• 29813-94-3 2-(2-chloro-benzylidene)-6,7-dihydroxy-benzofuran-3-one 
• 92796-71-9 2-anilino-5-(2-chloro-benzylidene)-thiazol-4-one 
• 58486-89-8 2-phenyl-5-[1-(2-chlorophenyl)-meth-(Z)-ylidene]-3,5-dihydro-imidazol-4-one 

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