89-97-4

Basic information

• Product Name: 2-Chlorobenzylamine
• Synonyms: RARECHEM AL BW 0012;RARECHEM AL BW 0027;TIMTEC-BB SBB004151;TIMTEC-BB SBB004154;P-CHLOROBENZYLAMINE;O-CHLOROBENZYLAMINE;OCAM;ORTHO-CHLOROBENZYLAMINE
• CAS NO: 89-97-4
• Molecular Formula: C₇H₈ClN
• Molecular Weight: 141.6
• EINECS: 203-245-3
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amine;Amines;C7;Nitrogen Compounds;amine series
• Mol File: 89-97-4.mol
• Article Data: 42

Chemical Properties

• Melting Point: 227-228 °C(Solv: N,N-dimethylformamide (68-12-2))
• Boiling Point: 215 °C(lit.)
• Flash Point: 195 °F
• Appearance: Clear yellow/Liquid
• Density: 1.173 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0772mmHg at 25°C
• Refractive Index: n20/D 1.562(lit.)
• Storage Temp.: -20°C
• PKA: 8.52±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 907186
• CAS DataBase Reference: 2-Chlorobenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chlorobenzylamine(89-97-4)
• EPA Substance Registry System: 2-Chlorobenzylamine(89-97-4)

Safety Data

• Hazard Codes: C,Xi
• Statements: 36/37/38-34-37
• Safety Statements: 26-36/37/39-45-36
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• F: 9-23
• TSCA: T
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 89-97-4(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

2-Chlorobenzylamine is a chlorinated derivative of benzylamine. 2-Chlorobenzylamine showed plasmin inhibitory activity as well as inhibition of bovine thrombin activity.

Synthesis Reference(s)

The Journal of Organic Chemistry, 36, p. 1710, 1971 DOI: 10.1021/jo00811a036

General Description

A colorless liquid with a slight amine odor. Somewhat soluble in water. Denser than water. Flash point 192°F. Vapors are heavier than air. Inhalation of vapors may severely irritate mucous membranes and upper respiratory tract. May severely irritate and possible burn skin. Severe eye irritant. May cause permanent damage or temporary blindness.

Air & Water Reactions

Somewhat soluble in water.

Reactivity Profile

2-CHLOROBENZYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

InChI:InChI=1/C7H8ClN/c8-7-4-2-1-3-6(7)5-9/h1-4H,5,9H2/p+1

Synthetic route

2-Chlorobenzonitrile (873-32-5) → 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
With sodium tetrahydroborate In water at 95℃; for 1h; chemoselective reaction;	95%
With [Ru(H)(BH4)(CO)(PPh3)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2 yl)methyl)propylamine)]; hydrogen In isopropyl alcohol at 130℃; for 3h; Inert atmosphere; Autoclave;	92%
With ammonium hydroxide; hydrogen In water; isopropyl alcohol at 60 - 80℃; under 7500.75 Torr;	90%

2-chlorobenzylazide (63777-70-8) → 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
With hydrogen; palladium In methanol for 24h;	91%
With hydrogen; palladium In methanol at 20℃; for 24h;	91%
With ammonium chloride; zinc In ethanol; water

1-chloro-2-(chloromethyl)benzene (611-19-8) → 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
	85.6%
With hexamethylenetetramine
With ammonium hydroxide

2-Chlorobenzonitrile (873-32-5) → bis(2-chlorobenzyl)amine (65130-79-2) + 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In ethanol at 20℃; for 0.0833333h;	A 7% B 82%
With nickel; decalin Hydrogenation;

1-(2-chlorobenzyl)-3,4-diphenyl-1H-pyrrole-2,5-dione → 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
With water; sodium carbonate In acetonitrile at 80℃; for 10h;	81%

2-chloro-benzaldehyde (89-98-5) + 1-chloro-2-(chloromethyl)benzene (611-19-8) → 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
With hydrogenchloride; ammonium hydroxide; sodium hydroxide In water; chlorobenzene	80%

2-chloro benzaldehyde oxime (3717-28-0) → 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
With hydrogenchloride; zinc In ethanol; water at 0 - 90℃; for 1h;	78%
Stage #1: 2-chloro benzaldehyde oxime With hydrogenchloride In ethanol; water at 20℃; for 0.25h; Stage #2: With zinc In ethanol; water for 1h; Reflux; Stage #3:	72%

1-chloro-2-(chloromethyl)benzene (611-19-8) + chlorobenzene (108-90-7) → 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
With hydrogenchloride; ammonium hydroxide; sodium hydroxide; benzaldehyde	62.8%

2-Chlorobenzonitrile (873-32-5) → benzylamine (100-46-9) + 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
With samarium diiodide; water In tetrahydrofuran for 0.0166667h; Ambient temperature;	A 37% B 62%

2-chlorobenzamide (609-66-5) → 2-CHLOROBENZYLAMINE (89-97-4)

Conditions	Yield
With sodium tetrahydroborate; lithium chloride In diethylene glycol dimethyl ether at 162℃; for 4h;	55%
With lithium aluminium tetrahydride; diethyl ether

Upstream product

• 408530-64-3 2-chlorobenzalchloroimine 
• 89-98-5 2-chloro-benzaldehyde 
• 609-66-5 2-chlorobenzamide 
• 64-17-5 ethanol 
• 3717-26-8 (E)-2-chlorobenzaldehyde oxime 
• 64-19-7 acetic acid 
• 63777-70-8 2-chlorobenzylazide 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 108-90-7 chlorobenzene 
• 74805-32-6 2-(2-chlorobenzyl)isoindoline-1,3-dione 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 873-32-5 2-Chlorobenzonitrile 
• 3717-28-0 2-chloro benzaldehyde oxime 
• 7664-93-9 sulfuric acid 

Downstream Products

• 20366-86-3 (2-chloro-benzyl)-(7⁽⁹⁾H-purin-6-yl)-amine 
• 131132-58-6 3-(2-Chlorobenzyl)-2-phenylthiazolidin-4-one 
• 63867-37-8 N,N'-Bis-<2-chlor-benzyl>-dithiooxamid 
• 7577-85-7 N-(2-Chlor-benzyl)-exo-cis-7-oxa-bicyclo<2.2.1>-heptan-2,3-dicarbonimid 
• 70059-60-8 (2-chloro-benzyl)-(5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidin-4-yl)-amine 
• 10175-31-2 1-(2-chlorophenyl)-N,N-dimethylmethanamine 
• 55247-33-1 (2-Chloro-benzyl)-[2-(4-chloro-phenoxy)-ethyl]-amine 
• 33312-08-2 N,N'-bis-(2-chloro-benzyl)-3,3'-disulfanediyl-bis-propionamide 
• 56000-49-8 2-(2-Chloro-benzylamino)-2-[(Z)-hydroxyimino]-N,N-dimethyl-acetamide 
• 59815-52-0 4-chloro-3-o-chlorobenzylsulfamoylbenzoic acid 
• 70325-42-7 4-[4-chloro-3-(2-chlorobenzylsulfamoyl)-phenyl]-4-oxobutanoic acid 
• 7006-80-6 N,N'-Di(2-chlorobenzyl)cyclohexane-trans-1,4-bis(carboxamide) 
• 59815-82-6 4'-Chloro-3'-o-chlorobenzylsulfamoylacetophenone 
• 19380-83-7 N¹-(o-Chlorbenzyl)-N³-aminoguanidin 

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