Basic information Description References Safety Supplier Related
ChemicalBook >  Product Catalog >  Organic Chemistry >  Hydrocarbons and derivatives >  Aromatic hydrocarbons >  1-Methylnaphthalene

1-Methylnaphthalene

Basic information Description References Safety Supplier Related

1-Methylnaphthalene Basic information

Product Name:
1-Methylnaphthalene
Synonyms:
  • 1 Methyl Napthalene
  • ALPHA-METHYLNAPHTHALENE
  • A-METHYLNAPHTHALENE
  • femanumber3193
  • Methyl-1-naphthalene
  • Naphthalene,1-methyl-
  • naphthalene,alpha-methyl
  • FEMA 3193
CAS:
90-12-0
MF:
C11H10
MW:
142.2
EINECS:
201-966-8
Product Categories:
  • Bioactive Small Molecules
  • Building Blocks
  • Cell Biology
  • Chemical Synthesis
  • Alpha Sort
  • Chemical Class
  • Hydrocarbons
  • M
  • MAlphabetic
  • META - METHAnalytical Standards
  • NaphthalenesChemical Class
  • Neats
  • Volatiles/ Semivolatiles
  • Arenes
  • Building Blocks
  • Organic Building Blocks
  • Alphabetical Listings
  • Flavors and Fragrances
  • M-N
  • Naphthalenes
  • Organic Building Blocks
Mol File:
90-12-0.mol
More
Less

1-Methylnaphthalene Chemical Properties

Melting point:
−22 °C(lit.)
Boiling point:
240-243 °C(lit.)
Density 
1.001 g/mL at 25 °C(lit.)
vapor pressure 
2 hPa (25 °C)
FEMA 
3193 | 1-METHYLNAPHTHALENE
refractive index 
n20/D 1.615(lit.)
Flash point:
180 °F
storage temp. 
2-8°C
solubility 
0.026g/l
pka
37(at 25℃)
form 
Liquid
color 
Clear colorless to yellow
explosive limit
0.7-6.5%(V)
Water Solubility 
0.026 g/L (25 ºC)
JECFA Number
1335
BRN 
506793
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents, oxygen.
InChIKey
QPUYECUOLPXSFR-UHFFFAOYSA-N
CAS DataBase Reference
90-12-0(CAS DataBase Reference)
NIST Chemistry Reference
Naphthalene, 1-methyl-(90-12-0)
EPA Substance Registry System
1-Methylnaphthalene (90-12-0)
More
Less

Safety Information

Hazard Codes 
Xn,N,T
Risk Statements 
22-36/37/38-42/43-51/53-39/23/24/25-23/24/25-20/21/22
Safety Statements 
7-26-36/37/39-61-45-36/37-23-36
RIDADR 
UN 3082 9/PG 3
WGK Germany 
2
RTECS 
QJ9630000
Autoignition Temperature
984 °F
TSCA 
Yes
HazardClass 
9
PackingGroup 
III
HS Code 
29029080
Hazardous Substances Data
90-12-0(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 1840 mg/kg

MSDS

More
Less

1-Methylnaphthalene Usage And Synthesis

Description

1-methylnaphthalene is a polycyclic aromatic hydrocarbon (PAH). It is present in cigarette smoke, wood smoke, tar, asphalt, and at some hazardous waste sites.  
The main use of 1-methylnaphthalene is as a raw material for naphthoic acid, fluorescent whitening agents, and surfactants. It is also used as a raw material for dyestuff dispersants and heat transfer oils, and as a solvent for agricultural chemical. 1-methylnaphthalene is used to make other chemicals such as dyes and resins.

References

[1] https://www.atsdr.cdc.gov/toxprofiles/tp67.pdf
[2] https://www.env.go.jp

Description

1-Methylnaphthalene has an earthy, phenolic odor. 1-Methylnaphthalene is generally obtained from coal tar and petroleum oils.

Chemical Properties

1-Methylnaphthalene has an earthy, phenolic odor

Chemical Properties

Colorless liquid. Insoluble in water; soluble in alcoholand ether. Combustible.

Occurrence

Reported found in apple, grape, peach, strawberry, onion, peas, bell pepper, Gruyere and parmesan cheese, milk, white wine, cocoa, coffee, tea, filberts, peanuts, oats, soybeans, Japanese plum, beans, starfruit, trassi, tamarind, rice, buckwheat, wild rice, endive, nectarine, lamb’s lettuce, okra, crayfish, rooibus tea (Aspalathus linearis), capsicum peppers and milk products. Methylnaphthalene was identified as a volatile component of cassava, roasted filberts and nectarines. Assorted types of lima, pinto, red kidney, black, navy and mung beans, soybeans, split peas and lentils were found to contain 1-methylnaphthalene at concentrations ranging from 2.8 to 49.2 ppb.

Uses

Organic synthesis.

Definition

ChEBI: A methylnaphthalene carrying a methyl substituent at position 1.

Production Methods

Alkylnaphthalenes are formed as pyrolysis products in cigarette smoke. Some have been identified in commercial carbon paper. They are also the major components of the C10–C13 alkylnaphthalene concentrate fraction, which distills at 400–500F. A C11–C12 petroleum mixture of reformates that contained about 23% alkylnaphthalenes caused skin and eye effects. The toxicity of the alkylnaphthalenes to marine species is greater than that of the alkylbenzenes (85). The toxicity and the bioaccumulation increase with molecular weight. Nocardia cultures, isolated from soil, preferentially oxidized alkylnaphthalenes when methylated in the two positions. Methylnaphthalene can occur as the 1- or 2-, the alpha or the beta isomer. 1-Naphthalene, a flammable solid, has also been identified in the wastewater of coking operations, and in textile processing plants. Methylnaphthalene is used as a component in slow-release insecticides and in mole repellents. Workplace exposures to 18–32 mg/m3 for 2-methylnaphthalene have been reported.

Preparation

Generally obtained from coal tar and petroleum oils.

Aroma threshold values

Detection: 7.5 to 20 ppb.

Taste threshold values

Taste characteristics at 1 ppm: naphthyl-like with a medicinal nuance.

Synthesis Reference(s)

Journal of the American Chemical Society, 65, p. 295, 1943 DOI: 10.1021/ja01242a503
The Journal of Organic Chemistry, 53, p. 4466, 1988
Tetrahedron Letters, 29, p. 97, 1988

General Description

Colorless liquid. Freezing point -22°C (7.6°F). Boiling point 240-243°C (464-469°F). Flash point 82°C (180°F). Denser than water. Derived from coal tar and used in organic synthesis.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

1-Methylnaphthalene is sensitive to heat. Reacts with strong oxidizing agents. Incompatible with oxygen and peroxides .

Hazard

Moderate fire risk. Lower respiratory tractirritant and lung damage. Questionable carcinogen.

Health Hazard

Harmful if inhaled. Liquid causes irritation of the eyes and skin and skin photosensitization. Harmful if swallowed. Chronic exposure may cause liver or kidney damage.

Fire Hazard

1-Methylnaphthalene is combustible.

Carcinogenicity

The carcinogenic potential of 1- and 2-methyl was investigated in B6C3F1 mice. Female and male mice were given methylnaphthalene in their diets for 81 weeks. The results indicated that 1-methyl was a possible weak carcinogen in the lung of male but not female mice whereas 2-methyl did not possess unequivocal carcinogenic potential in these mice.

Purification Methods

Dry 1-methylnaphthalene for several days with CaCl2 or by prolonged refluxing with BaO. Fractionally distil it through a glass helices-packed column from sodium. Purify it further by solution in MeOH and precipitation of its picrate complex by adding to a saturated solution of picric acid in MeOH. The picrate, after crystallisation to constant melting point (m 140-141o) from MeOH, is dissolved in *benzene and extracted with aqueous 10% LiOH until the extract is colourless. Evaporation of the *benzene solution under vacuum gives 1-methylnaphthalene [Kloetzel & Herzog J Am Chem Soc 72 1991 1950]. However, neither the picrate nor the styphnate complexes satisfactorily separate 1-and 2-methylnaphthalenes. To achieve this, 2-methylnaphthalene (10.7g) in 95% EtOH (50mL) has been precipitated with 1,3,5-trinitrobenzene (7.8g) and this complex has been crystallised from MeOH to m 153-153.5o (m of the 2-methyl isomer is 124o). [Alternatively, 2,4,7-trinitrofluorenone in hot glacial acetic acid could be used, and the derivative (m 163-164o) is recrystallised from glacial acetic acid]. The 1-methylnaphthalene is regenerated by passing a soution of the complex in dry *benzene through a 15-in column of activated alumina and washing with *benzene/pet ether (b 35-60o) until the coloured band of the nitro compound had moved down near the end of the column. The complex can also be decomposed using tin and acetic-hydrochloric acids, followed by extraction with diethyl ether and *benzene; the extracts are washed successively with dilute HCl, strongly alkaline sodium hypophosphite, water, dilute HCl and water. [Soffer & Stewart J Am Chem Soc 74 567 1952.] It can be freed from anthracene by zone melting [Beilstein 5 IV 1687.]

1-MethylnaphthaleneSupplier

Hangzhou QiFei Chemical Co., Ltd. Gold
Tel
571-28950939-
Email
hzqifeihuagong@163.com;
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Alfa Aesar
Tel
400-610-6006; 021-67582000
Email
saleschina@alfa-asia.com
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386 / 800-988-0390
Email
Sales-CN@TCIchemicals.com
BeiJing Hwrk Chemicals Limted
Tel
0757-86311057-
Email
kennyrong@hwrkchemical.com