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5-(Aminomethyl)-2-chloropyridine

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Name

5-(Aminomethyl)-2-chloropyridine

EINECS -0
CAS No. 97004-04-1 Density 1.244 g/cm3
PSA 38.91000 LogP 1.89400
Solubility N/A Melting Point 28-34 °C
Formula C6H7ClN2 Boiling Point 254.2 °C at 760 mmHg
Molecular Weight 142.588 Flash Point 107.6 °C
Transport Information UN 2811 6.1/PG 3 Appearance white to off-white crystal
Safety 26-36/37/39-45-20 Risk Codes 25-37/38-41-43-34
Molecular Structure Molecular Structure of 97004-04-1 (5-(Aminomethyl)-2-chloropyridine) Hazard Symbols ToxicT, CorrosiveC
Synonyms

((2-Chloropyridin-5-yl)methyl)amine;((6-Chloropyridin-3-yl)methyl)amine;(2-Chloro-5-pyridyl)methylamine;(6-Chloro-3-pyridyl)methylamine;(6-Chloropyridin-3-yl)methanamine;1-(6-Chloropyridin-3-yl)methanamine;2-Chloro-5-(aminomethyl)pyridine;3-Aminomethyl-6-chloropyridine;5-(Aminomethyl)-2-chloropyridine;6-Chloro-3-(aminomethyl)pyridine;6-Chloro-3-pyridinemethanamine;

Article Data 15

5-(Aminomethyl)-2-chloropyridine Synthetic route

1080018-12-7

1,3,5-tris[(2-chloropyridin-5-yl)methyl]-1,3,5-perhydrotriazine

97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
Stage #1: 1,3,5-tris[(2-chloropyridin-5-yl)methyl]-1,3,5-trihydrotriazine With hydrogenchloride; water In methanol at 75 - 80℃; for 6h;
Stage #2: With sodium hydroxide In methanol; chloroform; water
95%
Stage #1: 1,3,5-tris[(2-chloropyridin-5-yl)methyl]-1,3,5-trihydrotriazine With hydrogenchloride In methanol at 75 - 80℃; for 6h;
Stage #2: With sodium hydroxide In methanol; chloroform; water Product distribution / selectivity;
95%
3731-52-0

3-Aminomethylpyridine

75-44-5

phosgene

sodium tungstate

97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide; trimethylamine In hydrogenchloride; chloroform; water87%
33252-28-7

6-chloronicotinonitrile

A

3731-52-0

3-Aminomethylpyridine

B

23100-12-1

6-chloronicotinylaldehyde

C

bis(6-chloro-3-pyridylmethyl)amine

D

97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 760 Torr; for 5h; Reduction;A 3%
B 5%
C 8%
D 75%
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 912 - 1064 Torr; for 9h; Product distribution; Further Variations:; Catalysts; Pressures; Temperatures; Reduction;A 2%
B 1%
C 2%
D 73%
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 912 - 1064 Torr; Reduction;A 2%
B 2%
C 2%
D 73%
With hydrogen; Raney Nickel R-100 In methanol; ammonium hydroxide at 25℃; under 760 Torr; for 9h; Product distribution; Further Variations:; Catalysts; Pressures; Solvents; Temperatures; Hydrogenation;A 11%
B 3%
C 17%
D 59%
33252-28-7

6-chloronicotinonitrile

A

3731-52-0

3-Aminomethylpyridine

B

bis(6-chloro-3-pyridylmethyl)amine

C

97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
With ammonia; hydrogen; Sponge Ni In ethanol at 50℃; under 760 Torr; for 1.5h; Reduction;A 17%
B 3%
C 62%
70258-18-3

2-chloro-5-(chloromethyl)pyridine

97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
With ammonium hydroxide; sodium hydroxide In acetonitrile
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: hydrazine hydrate / ethanol / Reflux
View Scheme
Stage #1: 2-chloro-5-(chloromethyl)pyridine With hexamethylenetetramine In acetonitrile for 6.16667h; Reflux;
Stage #2: With hydrogenchloride In methanol; water at 60 - 100℃; for 4h; Temperature;
With sodium hydroxide In ethanol; acetonitrile
120739-60-8

((2-chloro-5-pyridinyl)methyl)isoindol-1,3-dione

97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 5h; Reflux;
With hydrazine hydrate In ethanol Reflux;9.5 g
33252-28-7

6-chloronicotinonitrile

97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
With potassium borohydride In ethanol at 25 - 40℃; for 2.25h;
With ammonia; hydrogen In methanol at 20℃; for 12h;
136918-14-4

phthalimide

70258-18-3

2-chloro-5-(chloromethyl)pyridine

97004-04-1

5-(aminomethyl)-2-chloropyridine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;
24424-99-5

di-tert-butyl dicarbonate

97004-04-1

5-(aminomethyl)-2-chloropyridine

285119-72-4

(6-chloropyridin-3-ylmethyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
With sodium hydroxide In dichloromethane at 20℃; for 16h;99%
With triethylamine In dichloromethane at 0 - 20℃; for 1h;98%
407-25-0

trifluoroacetic anhydride

97004-04-1

5-(aminomethyl)-2-chloropyridine

169506-55-2

C8H6ClF3N2O

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 1h;100%

5-(Aminomethyl)-2-chloropyridine Specification

The IUPAC name of 5-(Aminomethyl)-2-chloropyridine is (6-chloropyridin-3-yl)methanamine. With the CAS registry number 97004-04-1, it is also named as 6-Chloro-3-pyridinemethanamine. The product's categories are Pyridine; Aminomethyl's; Pyridines; C6 Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks. Besides, it is white to off-white crystal, which should be stored in closed containers in a cool, dry warehouse away from oxidizing agents and acids. In addition, its molecular formula is C6H7ClN2 and molecular weight is 142.59.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.96; (4)ACD/LogD (pH 7.4): -0.26; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 9.78; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.571; (13)Molar Refractivity: 37.69 cm3; (14)Molar Volume: 114.5 cm3; (15)Surface Tension: 48.9 dyne/cm; (16)Density: 1.244 g/cm3; (17)Flash Point: 107.6 °C; (18)Melting point: 28-34 °C; (19)Enthalpy of Vaporization: 49.16 kJ/mol; (20)Boiling Point: 254.2 °C at 760 mmHg; (21)Vapour Pressure: 0.0175 mmHg at 25 °C.

Preparation of 5-(Aminomethyl)-2-chloropyridine: this chemical can be produced by the reaction of 5-Aminomethyl-2-chloropyridine and Hexamethylenetetramine. This reaction needs Acetonitrile and Methanol.

Uses of 5-(Aminomethyl)-2-chloropyridine: this chemical is an intermediate of acetaniprid. Furthermore, it can react with S-Methyl-isothionitrourea to get N-(6-Chloropyridin-3-ylmethyl)-N'-nitroguanidine.



This reaction needs Ethanol at temperature of 80 °C for 3 hours. The yield is 84 %.

When you are using this chemical, please be cautious about it as the following: it is toxic if swallowed. When using, please do not eat or drink. It also may cause burns. Moreover, it is irritating to respiratory system and skin. And it is risk of serious damage to the eyes that may cause sensitization by skin contact. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. Additionally, you should wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)SMILES: Clc1ncc(cc1)CN
(2)InChI: InChI=1/C6H7ClN2/c7-6-2-1-5(3-8)4-9-6/h1-2,4H,3,8H2
(3)InChIKey: XPARFBOWIYMLMY-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C6H7ClN2/c7-6-2-1-5(3-8)4-9-6/h1-2,4H,3,8H2
(5)Std. InChIKey: XPARFBOWIYMLMY-UHFFFAOYSA-N

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