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2-Chlorobenzylamine is a chlorinated derivative of benzylamine, characterized as a colorless liquid with a slight amine odor. It is somewhat soluble in water, denser than water, and has a flash point of 192°F. The vapors are heavier than air and can severely irritate mucous membranes and the upper respiratory tract upon inhalation. Additionally, it may cause skin irritation, burns, and is a severe eye irritant, potentially leading to permanent damage or temporary blindness.

89-97-4

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89-97-4 Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorobenzylamine is used as a chemical intermediate for the synthesis of various pharmaceutical compounds due to its plasmin inhibitory activity and inhibition of bovine thrombin activity. These properties make it a valuable component in the development of drugs targeting blood clotting disorders and related conditions.
Used in Chemical Research:
As a chlorinated amine derivative, 2-Chlorobenzylamine is utilized in chemical research for studying reactions and mechanisms involving amines and halogens. Its unique chemical properties allow it to be a useful tool in understanding and developing new chemical processes and compounds.
Used in Organic Synthesis:
2-Chlorobenzylamine is employed as a reagent in organic synthesis, particularly for the preparation of various organic compounds. Its ability to participate in a range of chemical reactions, such as nucleophilic substitutions and addition reactions, makes it a versatile building block in the synthesis of complex organic molecules.
Used in Analytical Chemistry:
Due to its distinct chemical properties, 2-Chlorobenzylamine can be used in analytical chemistry as a reference compound or standard for the development and calibration of analytical methods. Its solubility and reactivity can be exploited to test and optimize techniques for the analysis of similar compounds.

Synthesis Reference(s)

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

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.

Check Digit Verification of cas no

The CAS Registry Mumber 89-97-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 9 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 89-97:
(4*8)+(3*9)+(2*9)+(1*7)=84
84 % 10 = 4
So 89-97-4 is a valid CAS Registry Number.
InChI:InChI=1/C7H8ClN/c8-7-4-2-1-3-6(7)5-9/h1-4H,5,9H2/p+1

89-97-4 Well-known Company Product Price

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  • Alfa Aesar

  • (A15594)  2-Chlorobenzylamine, 96%   

  • 89-97-4

  • 25g

  • 616.0CNY

  • Detail
  • Alfa Aesar

  • (A15594)  2-Chlorobenzylamine, 96%   

  • 89-97-4

  • 100g

  • 1901.0CNY

  • Detail
  • Alfa Aesar

  • (A15594)  2-Chlorobenzylamine, 96%   

  • 89-97-4

  • 500g

  • 7650.0CNY

  • Detail

89-97-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Chlorobenzylamine

1.2 Other means of identification

Product number -
Other names Benzenemethanamine, 2-chloro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:89-97-4 SDS

89-97-4Synthetic route

2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

Conditions
ConditionsYield
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-chlorobenzylazide

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

Conditions
ConditionsYield
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

1-chloro-2-(chloromethyl)benzene

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

Conditions
ConditionsYield
85.6%
With hexamethylenetetramine
With ammonium hydroxide
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

A

bis(2-chlorobenzyl)amine
65130-79-2

bis(2-chlorobenzyl)amine

B

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

Conditions
ConditionsYield
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

1-(2-chlorobenzyl)-3,4-diphenyl-1H-pyrrole-2,5-dione

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

Conditions
ConditionsYield
With water; sodium carbonate In acetonitrile at 80℃; for 10h;81%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

1-chloro-2-(chloromethyl)benzene
611-19-8

1-chloro-2-(chloromethyl)benzene

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

Conditions
ConditionsYield
With hydrogenchloride; ammonium hydroxide; sodium hydroxide In water; chlorobenzene80%
2-chloro benzaldehyde oxime
3717-28-0

2-chloro benzaldehyde oxime

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

Conditions
ConditionsYield
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

1-chloro-2-(chloromethyl)benzene

chlorobenzene
108-90-7

chlorobenzene

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

Conditions
ConditionsYield
With hydrogenchloride; ammonium hydroxide; sodium hydroxide; benzaldehyde62.8%
2-Chlorobenzonitrile
873-32-5

2-Chlorobenzonitrile

A

benzylamine
100-46-9

benzylamine

B

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

Conditions
ConditionsYield
With samarium diiodide; water In tetrahydrofuran for 0.0166667h; Ambient temperature;A 37%
B 62%
2-chlorobenzamide
609-66-5

2-chlorobenzamide

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

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

89-97-4Relevant articles and documents

Reusable Co-nanoparticles for general and selectiveN-alkylation of amines and ammonia with alcohols

Beller, Matthias,Gawande, Manoj B.,Jagadeesh, Rajenahally V.,Kadam, Ravishankar G.,Li, Xinmin,Ma, Zhuang,Petr, Martin,Zbo?il, Radek,Zhou, Bei

, p. 111 - 117 (2022/01/06)

A general cobalt-catalyzedN-alkylation of amines with alcohols by borrowing hydrogen methodology to prepare different kinds of amines is reported. The optimal catalyst for this transformation is prepared by pyrolysis of a specific templated material, which is generatedin situby mixing cobalt salts, nitrogen ligands and colloidal silica, and subsequent removal of silica. Applying this novel Co-nanoparticle-based material, >100 primary, secondary, and tertiary amines includingN-methylamines and selected drug molecules were conveniently prepared starting from inexpensive and easily accessible alcohols and amines or ammonia.

PROCESS FOR PREPARATION OF HALOGENATED BENZYLAMINE AND INTERMEDIATES THEROF

-

Page/Page column 19, (2020/08/13)

The present invention provides an improved process for the preparation of halogenated benzylamine having the formula I from halogenated benzonitriles, Formula I wherein, X1 is selected from group consisting of hydrogen, chloro or fluoro, provided atleast one X1 is chloro or fluoro.

Chemoselective reduction of nitro and nitrile compounds using an Fe3O4-MWCNTs?PEI-Ag nanocomposite as a reusable catalyst

Ansari, Sara,Khorshidi, Alireza,Shariati, Shahab

, p. 3554 - 3565 (2020/02/04)

Multi-walled carbon nanotubes (MWNTs) were modified with carboxylic acid functional groups (MWCNTs-(COOH)n) prior to decoration with Fe3O4 nanoparticles. A further modification step by polyethyleneimine (PEI) resulted in Fe3O4-MWCNTs?PEI which provided a suitable platform for coordination and in situ reduction of silver ions to obtain an Fe3O4-MWCNTs?PEI-Ag nanocomposite with highly dispersed Ag nanoparticles. The Fe3O4-MWCNTs?PEI-Ag hybrid material was characterized by various techniques such as Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA), and was used as an efficient catalyst for chemoselective reduction of nitroaromatic and nitrile compounds to their corresponding amines in aqueous solution at ambient temperature. Nitrofurazone, a cytotoxic antibiotic, as a non-aromatic example was also reduced selectively at the nitro group without reduction of the other functionalities in the presence of Fe3O4-MWCNTs?PEI-Ag. The catalyst was magnetically recoverable and maintained its activity for at least six cycles without considerable loss of efficiency.

Design, synthesis and the structure-activity relationship of agonists targeting on the ALDH2 catalytic tunnel

Cheng, Ming-Che,Lo, Wei-Chi,Chang, Yu-Wen,Lee, Shoei-Sheng,Chang, Chia-Chuan

, (2020/09/15)

ALDH2, a key enzyme in the alcohol metabolism process, detoxifies several kinds of toxic small molecular aldehydes, which induce severe organ damages. The development of novel Alda-1 type ALDH2 activators was mostly relied on HTS but not rational design so far. To clarify the structure–activity relationship (SAR) of the skeleton of Alda-1 analogs by synthesis of the least number of analogs, we prepared 31 Alda-1 analogs and 3 isoflavone derivatives and evaluated for their ALDH2-activating activity. Among these, the ALDH2-activating activity of mono-halogen-substituted (Cl and Br) N-piperonylbenzamides 3b and 3 k, and non-aromatic amides 8a-8c, were 1.5–2.1 folds higher than that of Alda-1 at 20 μM. The relationship between binding affinity in computer aided molecular docking model and the ALDH2-activating activity assays were clarified as follows: for Alda-1 analogs, with the formation of halogen bonds, the enzyme-activating activity was found to follow a specific regression curve within the range between ?5 kcal/mol and ?4 kcal/mol. For isoflavone derivatives, the basic moiety on the B ring enhance the activating activity. These results provide a new direction of utilizing computer-aided modeling to design novel ALDH2 agonists in the future.

Facile synthesis of controllable graphene-co-shelled reusable Ni/NiO nanoparticles and their application in the synthesis of amines under mild conditions

Cui, Zhibing,Liu, Jianguo,Liu, Qiying,Ma, Longlong,Singh, Thishana,Wang, Chenguang,Wang, Nan,Zhu, Yuting

supporting information, p. 7387 - 7397 (2020/11/19)

The primary objective of many researchers in chemical synthesis is the development of recyclable and easily accessible catalysts. These catalysts should preferably be made from Earth-abundant metals and have the ability to be utilised in the synthesis of pharmaceutically important compounds. Amines are classified as privileged compounds, and are used extensively in the fine and bulk chemical industries, as well as in pharmaceutical and materials research. In many laboratories and in industry, transition metal catalysed reductive amination of carbonyl compounds is performed using predominantly ammonia and H2. However, these reactions usually require precious metal-based catalysts or RANEY nickel, and require harsh reaction conditions and yield low selectivity for the desired products. Herein, we describe a simple and environmentally friendly method for the preparation of thin graphene spheres that encapsulate uniform Ni/NiO nanoalloy catalysts (Ni/NiO?C) using nickel citrate as the precursor. The resulting catalysts are stable and reusable and were successfully used for the synthesis of primary, secondary, tertiary, and N-methylamines (more than 62 examples). The reaction couples easily accessible carbonyl compounds (aldehydes and ketones) with ammonia, amines, and H2 under very mild industrially viable and scalable conditions (80 °C and 1 MPa H2 pressure, 4 h), offering cost-effective access to numerous functionalized, structurally diverse linear and branched benzylic, heterocyclic, and aliphatic amines including drugs and steroid derivatives. We have also demonstrated the scale-up of the heterogeneous amination protocol to gram-scale synthesis. Furthermore, the catalyst can be immobilized on a magnetic stirring bar and be conveniently recycled up to five times without any significant loss of catalytic activity and selectivity for the product.

Synthesis of oxalamides by acceptorless dehydrogenative coupling of ethylene glycol and amines and the reverse hydrogenation catalyzed by ruthenium

Ben-David, Yehoshoa,Diskin-Posner, Yael,Milstein, David,Zhou, Quan-Quan,Zou, You-Quan

, p. 7188 - 7193 (2020/07/23)

A sustainable, new synthesis of oxalamides, by acceptorless dehydrogenative coupling of ethylene glycol with amines, generating H2, homogeneously catalyzed by a ruthenium pincer complex, is presented. The reverse hydrogenation reaction is also accomplished using the same catalyst. A plausible reaction mechanism is proposed based on stoichiometric reactions, NMR studies, X-ray crystallography as well as observation of plausible intermediates.

Green and convenient protocols for the efficient reduction of nitriles and nitro compounds to corresponding amines with NaBH4 in water catalyzed by magnetically retrievable CuFe2O4 nanoparticles

Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein

, (2019/03/23)

Abstract: In this study, firstly, CuFe2O4 nanoparticles were prepared by a simple operation. The structure of the mentioned nanoparticles was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma-optical emission spectrometry, vibrating sample magnetometer and also Brunauer–Emmett–Teller and Barrett–Joyner–Halenda analyses. The prepared magnetically copper ferrite nanocomposite was successfully applied as a simple, cost-effective, practicable, and recoverable catalyst on the green, highly efficient, fast, base-free, and ligand-free reduction of nitriles and also on the affordable and eco-friendly reduction of nitro compounds with the broad substrate scope to the corresponding amines with NaBH4 in water at reflux in high to excellent yields. Graphical abstract: [Figure not available: see fulltext.].

A ppm level Rh-based composite as an ecofriendly catalyst for transfer hydrogenation of nitriles: Triple guarantee of selectivity for primary amines

Liu, Lei,Li, Jifan,Ai, Yongjian,Liu, Yuhong,Xiong, Jialiang,Wang, Hongdong,Qiao, Yijun,Liu, Wenrui,Tan, Shanchao,Feng, Shaofei,Wang, Kunpeng,Sun, Hongbin,Liang, Qionglin

, p. 1390 - 1395 (2019/03/26)

Hydrogenation of nitriles to afford amines under mild conditions is a challenging task with an inexpensive heterogeneous catalyst, and it is even more difficult to obtain primary amines selectively because of the accompanying self-coupling side reactions. An efficient catalytic system was designed as Fe3O4@nSiO2-NH2-RhCu@mSiO2 to prepare primary amines through the transfer hydrogenation of nitrile compounds with economical HCOOH as the hydrogen donor. The loading of rhodium in the catalyst could be at the ppm level, and the TOF reaches 6803 h-1 for Rh. This catalytic system has a wide substrate range including some nitriles that could not proceed in the previous literature. The experimental results demonstrate that the excellent selectivity for primary amines is guaranteed by three tactics, which are the strong active site, the inhibition of side products by the hydrogen source and the special pore structure of the catalyst. In addition, the catalyst could be reused ten times without activity loss through convenient magnetic recovery.

Chemo-selective reduction of nitro and nitrile compounds using Ni nanoparticles immobilized on hyperbranched polymer-functionalized magnetic nanoparticles

Tabatabaei Rezaei, Seyed Jamal,Mashhadi Malekzadeh, Asemeh,Poulaei, Sima,Ramazani, Ali,Khorramabadi, Hossein

, (2017/09/06)

The nitro and nitrile groups in aromatic and aliphatic compounds containing various reducible substituents such as carboxylic acid, ketone, aldehyde and halogen are selectively reduced to the corresponding amines in water as a green solvent with excellent yields by employing NaBH4 in the presence of Fe3O4@PAMAM/Ni(0)-b-PEG nanocatalyst. The morphology and structural features of the catalyst were characterized using various microscopic and spectroscopic techniques. The designed catalyst system because of it being covered with hydrophilic polymers is soluble in a wide range of solvents (e.g. water and ethanol) and suitable for immobilizing and stabilizing Ni nanoparticles in aqueous mediums. In addition, the catalyst can be easily recovered from a reaction mixture by applying an external magnetic field and can be reused up to six runs without significant loss of activity.

Synthesis of cobalt nanoparticles by pyrolysis of Vitamin B12: A non-noble-metal catalyst for efficient hydrogenation of nitriles

Ferraccioli, Raffaella,Borovika, Diana,Surkus, Annette-Enrica,Kreyenschulte, Carsten,Topf, Christoph,Beller, Matthias

, p. 499 - 507 (2018/02/07)

A facile preparation of vitamin B12-derived carbonaceous cobalt particles supported on ceria is reported. The resulting composite material is obtained upon wet impregnation of ceria with natural cyanocobalamin and consecutive pyrolysis under inert conditions. The novel catalyst shows good to excellent performance in the industrially relevant heterogeneous hydrogenation of nitriles to the corresponding primary amines.

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