(3-Bromophenyl)acetonitrile
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(3-Bromophenyl)acetonitrile
structure -
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CAS No:
31938-07-5
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Formula:
C8H6BrN
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Chemical Name:
(3-Bromophenyl)acetonitrile
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Synonyms:
Benzeneacetonitrile,3-bromo-;Acetonitrile,(m-bromophenyl)-;3-Bromobenzeneacetonitrile;m-Bromobenzyl cyanide;(3-Bromophenyl)acetonitrile;3-Bromobenzyl cyanide;1-Bromo-3-cyanomethylbenzene;3-Bromobenzylnitrile;2-(3-Bromophenyl)acetonitrile
- Categories:
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CAS No:
(3-Bromophenyl)acetonitrile Basic Attributes
196.04
196.04
2355439
250-867-6
DTXSID4075322
2926909090
Characteristics
23.8
2.6
White solid or colorless liquid.
1.5±0.1 g/cm3
26-29 °C
135-138 °C @ Press: 8 Torr
>110°C
1.573
Room temperature.
Safety Information
I
6.1
3449
3
36/37/38-20/21/22-20/21/22/36/37/38
36/37/39-26-26/36/37/39-36
AL8060000
Xn,Xi
Irritant
P261-P280-P305 + P351 + P338
H302 + H312 + H332-H315-H319-H335
|Warning|H302 (89.13%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
(3-Bromophenyl)acetonitrile Use and Manufacturing
To a flame dried 5L 3-neck flask equipped with a mechamical overhead stirrer under nitrogen was added diisopropylamine (78.60 mL, 0.56 mol, 2.2 eq) and 2 L of benzene. After cooling to 0-5 C., 1.6 M n-BuLi (351.0 mL, 0.56 mol, 2.2 eq) was added dropwise via addition funnel while keeping the temperature at 0-5 C. The LDA was stirred for 45 min. at 0-5 C. 3-Bromophenylacetonitrile (50.0 g, 0.26 mol, 1.0 eq) dissolved in 200 mL of benzene was added dropwise via addition funnel keeping the temperature at 0-5 C. The mixture was stirred an additional 15 min at this temperature. 2-Chlorobenzylthiocyanate (J. Am. Chem. Soc., 1954, 76, 585) (103.0 g, 0.56 mol, 2.2 eq) dissolved in 200 mL benzene was added dropwise via addition funnel keeping the temperature at 0-5 C. During the addition, a precipitate formed. The reaction was allowed to warm to room temperature and the mixture stirred overnight. The reaction was quenched by adding water and 200 mL 10% NaOH. The layers were separated, and the benzene layer extracted with 10% NaOH (3×1 L). The basic layers were collected and acidified with conc. HCl to pH 1-2. A precipitate formed. Methylene chloride was added to dissolve the precipitate. The layers were separated and the aqueous layer reextracted with methylene chloride (2×). The methylene chloride layers were collected, dried (MgSO4) and the solvent removed in vacuo to yield 65.32 g of 2-(3-bromophenyl)malononitrile as a yellow solid. Recrystallization from methylcyclohexane yielded two crops: crop 1, 42.86 g of orange crystals, m.p. 99.5-101.5 C.; crop 2, 2.18 g of orange crystals, m.p. 97.0-99.0 C. Combined yield 79.9%. 1H-NMR (CDCl3) delta: 7.67 (s, 1H); 7.63 (d, 1H, J=7 Hz); 7.47 (d, 1H, J=7 Hz); 7.39 (t, 1H, J=7 Hz); 5.08 (s, 1H).When the following commerically available compounds: a. 2-bromophenylacetonitrile (Aldrich Chemical), b. 3-bromophenylacetonitrile (Aldrich Chemical), c. 4-bromophenylacetonitrile (Aldrich Chemical), d. 2-chlorobenzylcyanide (Aldrich Chemical), e. 3-chlorobenzylcyanide (Aldrich Chemical), and f. 4-chlorobenzylcyanide (Aldrich Chemical)
For organic synthesis
Computed Properties
Molecular Weight:196.04
XLogP3:2.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:194.96836
Monoisotopic Mass:194.96836
Topological Polar Surface Area:23.8
Heavy Atom Count:10
Complexity:147
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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