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CAS No.: | 22115-41-9 |
---|---|
Name: | 2-Cyanobenzyl bromide |
Article Data: | 22 |
Molecular Structure: | |
Formula: | C8H6BrN |
Molecular Weight: | 196.046 |
Synonyms: | o-Tolunitrile,a-bromo- (8CI);(2-Cyanophenyl)methyl bromide;1-(Bromomethyl)-2-cyanobenzene;2-(Bromomethyl)benzonitrile;2-Cyano-a-bromotoluene;2-Cyanobenzyl bromide;o-(Bromomethyl)benzonitrile;o-Cyanobenzyl bromide;a-Bromo-2-cyanotoluene;a-Bromo-o-tolunitrile;a-Bromo-o-toluonitrile; |
EINECS: | 231-555-8 |
Density: | 1.51g/cm3 |
Melting Point: | 72-74 °C(lit.) |
Boiling Point: | 264.6 °C at 760 mmHg |
Flash Point: | 113.8 °C |
Solubility: | Slightly soluble in water |
Appearance: | White to light yellow crystal powder |
Hazard Symbols: | C |
Risk Codes: | 34 |
Safety: | 26-36/37/39-45-28A |
Transport Information: | UN 3261 8/PG 2 |
PSA: | 23.79000 |
LogP: | 2.45318 |
2-Methylbenzonitrile
2-(bromomethyl)benzonitrile
Conditions | Yield |
---|---|
With dihydrogen peroxide; bromine In dichloromethane; water for 4h; Reflux; | 98% |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 90℃; for 2h; | 80% |
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 80 - 90℃; for 5.08333h; Inert atmosphere; | 69% |
2-(bromomethyl)benzonitrile
Conditions | Yield |
---|---|
With phosphorus tribromide In dichloromethane at 40℃; for 8h; Time; | 93% |
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-Ph2-3,4-bis(2,4,6-(t-Bu)3-phenylphophinidene)cyclobutene; zinc In various solvent(s) at 100℃; for 16h; | 60% |
B
2-(bromomethyl)benzonitrile
Conditions | Yield |
---|---|
With carbon tetrabromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine; tetrabutylammomium bromide; copper(I) bromide In N,N-dimethyl-formamide at 20℃; for 12h; Schlenk technique; Inert atmosphere; | A 52% B 13% |
2-Methylbenzonitrile
A
2-(dibromomethyl)benzonitrile
B
2-(bromomethyl)benzonitrile
Conditions | Yield |
---|---|
at 150 - 200℃; bei der Bromierung im Sonnenlicht; |
2-(bromomethyl)benzonitrile
Conditions | Yield |
---|---|
With hydrogen bromide at 100℃; im Druckrohr; |
B
2-(bromomethyl)benzonitrile
Conditions | Yield |
---|---|
With hydrogen bromide at 100℃; im geschlossenen Rohr; |
hydrogen bromide
A
2-(bromomethyl)benzonitrile
Conditions | Yield |
---|---|
at 100℃; im Druckrohr; |
2-cyanobenzyl chloride
2-(bromomethyl)benzonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: alcohol 2: fuming hydrobromic acid / 100 °C / im Druckrohr View Scheme | |
Multi-step reaction with 2 steps 1: alcohol 2: fuming hydrobromic acid / 100 °C / im geschlossenen Rohr View Scheme |
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The IUPAC name of o-Cyanobenzyl bromide is 2-(bromomethyl)benzonitrile. With the CAS registry number 22115-41-9, it is also named as benzonitrile, 2-(bromomethyl)-. The product's categories are benzyl bromide; benzyl; cyanide. It is white to light yellow crystal powder which should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.36; (4)ACD/LogD (pH 7.4): 2.36; (5)ACD/BCF (pH 5.5): 36.34; (6)ACD/BCF (pH 7.4): 36.34; (7)ACD/KOC (pH 5.5): 455.51; (8)ACD/KOC (pH 7.4): 455.51; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.588; (13)Molar Refractivity: 43.67 cm3; (14)Molar Volume: 129.7 cm3; (15)Polarizability: 17.31×10-24 cm3; (16)Surface Tension: 49.5 dyne/cm; (17)Enthalpy of Vaporization: 50.25 kJ/mol; (18)Vapour Pressure: 0.00961 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 194.968362; (21)MonoIsotopic Mass: 194.968362; (22)Topological Polar Surface Area: 23.8; (23)Heavy Atom Count: 10; (24)Complexity: 147.
Preparation of o-Cyanobenzyl bromide: It can be obtained by 2-methyl-benzonitrile. This reaction needs reagent NBS and AIBN and solvent CCl4 at temperature of 90 °C. The reaction time is 2 hours. The yield is 80%.
Uses of o-Cyanobenzyl bromide: It reacts with pyrrolidine to get 2-(1-Pyrrolidinyl-methyl)benzonitril. This reaction needs reagent solvent diethyl ether. The reaction time is 8 hours. The yield is 88 %.
When you are using this chemical, please be cautious about it as the following:
It can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must 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:BrCc1ccccc1C#N
2. InChI:InChI=1/C8H6BrN/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5H2
3. InChIKey:QGXNHCXKWFNKCG-UHFFFAOYAX