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Basic Information

Molecular Structure:
CAS No.:	132-75-2
Name:	1-Naphthyl acetonitrile
Article Data:	65

Formula:	C₁₂H₉N
Molecular Weight:	167.21
Synonyms:	1-Cyanomethylnaphthalene;1-Naphthylacetonitrile;2-(1-Naphthyl)acetonitrile;NSC 9844;a-Naphthylacetonitrile;1-Naphthaleneacetonitrile;
EINECS:	205-078-1
Density:	1.116 g/cm³
Melting Point:	33-35 °C(lit.)
Boiling Point:	323.9 °C at 760 mmHg
Flash Point:	180.3 °C
Appearance:	White crystalline powder
Hazard Symbols:	Xn
Risk Codes:	20/21/22-36/37/38-22
Safety:	26-37/39-24/25-37-36
PSA:	23.79000
LogP:	2.90588

Synthetic route

: C25H18N2O4

A: 132-75-2
naphthalen-1-ylacetonitrile

B: 92-92-2
biphenyl-4-carboxylic acid

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene Heating;	A 98% B 95%

: 139109-57-2
2-[(Z)-Hydroxyimino]-3-naphthalen-1-yl-propionic acid

: 132-75-2
naphthalen-1-ylacetonitrile

Conditions

Conditions	Yield
With 1,1'-carbonyldiimidazole In benzene 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h;	97%

: 86-86-2
1-Naphthylacetamide

: 132-75-2
naphthalen-1-ylacetonitrile

Conditions

Conditions	Yield
With trichloromethyl chloroformate In various solvent(s) 0-5 deg C then heated to 60 deg C, 5 min;	96%
With (dimethoxy)methylsilane; copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 20℃; for 12h; Sealed tube;	96%
With phosgene In tetrahydrofuran; toluene at 25℃; for 4h; Inert atmosphere;	91%

: 151-50-8
potassium cyanide

: 86-52-2
1-Chloromethylnaphthalene

: 132-75-2
naphthalen-1-ylacetonitrile

Conditions

Conditions	Yield
In acetonitrile at 60℃; for 3h; 18-crown-6 polyether;	96%

: 37630-26-5, 4735-49-3
β-(1-naphthyl)nitroethylene

: 132-75-2
naphthalen-1-ylacetonitrile

Conditions

Conditions	Yield
With titanium tetrachloride; tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction - 4 mA/cm2;	95%

: 90-11-9
1-Bromonaphthalene

: 1071-36-9
sodium cyanoacetate

: 132-75-2
naphthalen-1-ylacetonitrile

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)) In 1,3,5-trimethyl-benzene at 20 - 140℃; for 5.16667h; Inert atmosphere; Sealed tube; chemoselective reaction;	95%

: 13922-41-3
1-Naphthylboronic acid

: 107-14-2
chloroacetonitrile

: 132-75-2
naphthalen-1-ylacetonitrile

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 60℃; for 12h; Inert atmosphere; Sealed tube;	93%

: 133712-83-1
2-[(Z)-Hydroxyimino]-3-naphthalen-1-yl-propionic acid

: 132-75-2
naphthalen-1-ylacetonitrile

Conditions

Conditions	Yield
With 1,1'-oxalyldiimidazole In benzene 1.) r.t., 15 min, 2.) 68-70 deg C, 1 h;	90%

: 2-(3,4-dihydronaphthalen-1-yl)acetonitrile

: 132-75-2
naphthalen-1-ylacetonitrile

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 100℃; for 24h;	90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 100℃; for 24h;	90%

: 74607-42-4
Methylsulfanyl-naphthalen-1-yl-acetonitrile

: 132-75-2
naphthalen-1-ylacetonitrile

Conditions

Conditions	Yield
With acetic acid; zinc at 100℃; for 1h;	89%

Raw Materials

151-50-8

143-33-9

556-64-9

90-12-0

3163-27-7

1071-36-9

90-14-2

105-56-6

Downstream Products

2122-70-5

86-87-3

112399-65-2

86-86-2

835-31-4

22433-62-1

14271-86-4

2876-72-4

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Chemistry

Product Name: 1-Naphthyl acetonitrile (CAS NO.132-75-2)

Molecular Formula: C₁₂H₉N
Molecular Weight: 167.21g/mol
Mol File: 132-75-2.mol
EINECS: 205-078-1
Appearance: White to yellow solid or melt
Melting Point: 33-35 °C(lit.)
Boiling point: 323.9 °C at 760 mmHg
Flash Point: 180.3 °C
Density: 1.116 g/cm³
Refractive index: n20/D 1.6192(lit.)
Index of Refraction: 1.634
Molar Refractivity: 53.55 cm³
Molar Volume: 149.7 cm³
Surface Tension: 48.8 dyne/cm
Enthalpy of Vaporization: 58 kJ/mol
Vapour Pressure: 0.000255 mmHg at 25°C
XLogP3-AA: 2.9
H-Bond Donor: 0
H-Bond Acceptor: 1
Structure Descriptors of 1-Naphthyl acetonitrile (CAS NO.132-75-2):
IUPAC Name: 2-naphthalen-1-ylacetonitrile
Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2CC#N
InChI: InChI=1S/C12H9N/c13-9-8-11-6-3-5-10-4-1-2-7-12(10)11/h1-7H,8H2
InChIKey: OQRMWUNUKVUHQO-UHFFFAOYSA-N
Product Categories: Intermediates of Dyes and Pigments; Aromatic Nitriles

Uses

1-Naphthyl acetonitrile (CAS NO.132-75-2) is used in organic synthesis.

Toxicity Data With Reference

ivn-mus LD50:180 mg/kg

CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#03835 .

Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

Safety Profile

Poison by intravenous route. When heated to decomposition it emits toxic fumes of NO_x and CN⁻. See also NITRILES.
Safety Information of 1-Naphthyl acetonitrile (CAS NO.132-75-2):
Hazard Codes: Xn Harmful
Risk Statements: 20/21/22-36/37/38-22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R22:Harmful if swallowed.
Safety Statements: 26-37/39-24/25-37-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
S24/25:Avoid contact with skin and eyes.
S37:Wear suitable gloves.
S36:Wear suitable protective clothing.
RIDADR: 3276
WGK Germany: 3
RTECS: AM1240000
HazardClass: 6.1
PackingGroup: III

Specification

1-Naphthyl acetonitrile , its CAS NO. is 132-75-2, the synonyms are Acetonitrile, (1-naphthyl)- ; alpha-(1-Naphthyl)acetonitrile ; alpha-Naphthyl acetonitrile ; alpha-Naphthylacetonitrile ; 1-Naphthaleneacetonitrile ; 1-Naphthylacetonitrile .

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