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63-25-2

Basic Information
CAS No.: 63-25-2
Name: Carbaryl
Molecular Structure:
Molecular Structure of 63-25-2 (Carbaryl)
Formula: C12H11NO2
Molecular Weight: 201.22
Synonyms: Karbaryl;Atoxan;Dicarbament 23,969;Carbatox 75;1-Naftylester kyseliny methylkarbaminove [Czech];N-Methyl-alpha-naphthylurethan;Murvin;Hexavin;Karbaryl [Polish];Suleo;ENT-23969;XLR-Plus;Denapon;N-Methyl-alpha-naphthylcarbamate;Menaphtam;alpha-Naphthalenyl methylcarbamate;Karbaspray;EPA Pesticide Chemical Code 056801;Experimental Insecticide 7744;Methylcarbamate 1-naphthol;N-Metil-1-naftil-carbammato [Italian];1-Naphthalenol, methylcarbamate;Cekubaryl;ENT 23,969;Carbatox-75;Sewin;N-Methyl-1-naftyl-carbamaat;N-Methylcarbamate de 1-naphtyle [French];Vioxan;Monsur;Carylderm;Latka 7744 [Czech];Carbamic acid, methyl-, 1-naphthyl ester;Dicarbam;Bug master;Carbaril [Italian];N-Methyl-.alpha.-naphthylurethan;Carbamine;UC 7744;1-Naphthyl-N-methyl-karbamat [German];N-Metil-1-naftil-carbammato;Vetox;Tricarnam;.alpha.-Naftyl-N-methylkarbamat;Thinsec;1-Naphthalenol, methylcarbamate (9CI);Methylcarbamate 1-naphthalenol;Carbatox-60;Panam;Caprolin;1-Naphthalenol methylcarbamate;Toxan;Septene;Sevin;Carbavur;Carbaril [INN];Laivin;Seffein;N-Methyl-1-naphthyl carbamate;Suvamil;
EINECS: 200-555-0
Density: 1.183 g/cm3
Melting Point: 142-146 °C(lit.)
Boiling Point: 329.3 °C at 760 mmHg
Flash Point: 153 °C
Solubility: 0.00826 g/100 mL in water
Appearance: colourless solid
Hazard Symbols: HarmfulXn, DangerousN, FlammableF
Risk Codes: 22-40-50-67-65-50/53-38-11
Safety: 22-24-36/37-46-61-2-62-60
Transport Information: UN 2811 6.1/PG 3
PSA: 38.33000
LogP: 2.94890
Synthetic route
6642-30-4

methyl N-methylcarbamate

90-15-3

α-naphthol

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
With trichlorophosphate at 60℃; for 7h; Mechanism; analogous reaction of other carbamates;88%
With trichlorophosphate at 60℃; for 7h;88%
22013-97-4

N-methyl-thiocarbamic acid S-methyl ester

90-15-3

α-naphthol

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
With triethylamine In toluene for 4h; Reflux;80%
With zinc(II) chloride In benzene for 21h; Heating;50%
90-15-3

α-naphthol

124-38-9

carbon dioxide

74-89-5

methylamine

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
Stage #1: carbon dioxide; methylamine With N-ethyl-N,N-diisopropylamine In dichloromethane at -40℃; for 0.75h;
Stage #2: α-naphthol With trichlorophosphate In dichloromethane
Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane
80%
132905-86-3

Carbonic acid chloromethyl ester naphthalen-1-yl ester

74-89-5

methylamine

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
In hexane; water for 2h; Ambient temperature;75.4%
90-15-3

α-naphthol

4-methyl-1H-imidazole-2-carboxamide

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 18h; Reagent/catalyst; Time; Inert atmosphere;65%
123-39-7

N-Methylformamide

90-15-3

α-naphthol

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; 1,10-Phenanthroline; copper diacetate In decane at 20℃; for 2h; Molecular sieve; Inert atmosphere;45%
817-73-2

ethyl N-methylthiocarbamate

90-15-3

α-naphthol

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
With trichlorophosphate at 60℃; for 8h;33%
90-15-3

α-naphthol

624-83-9

methyl isocyanate

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
With pyridine; benzene
In Dimethyldisulphide at 20℃; for 0.166667h;
90-15-3

α-naphthol

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / Et3N / CH2Cl2 / 1.67 h / 5 °C
2: 75.4 percent / H2O; hexane / 2 h / Ambient temperature
View Scheme
96-31-1

N,N'-Dimethylurea

90-15-3

α-naphthol

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
With Isopropylbenzene; methanesulfonic acid In water; toluene
With Isopropylbenzene; methanesulfonic acid In water; toluene
105-40-8

Ethyl N-methylcarbamate

90-15-3

α-naphthol

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
With trichlorophosphate In water; toluene
With trichlorophosphate In water; toluene
With phosphorus tribromide In 1,1-dichloroethane
75-44-5

phosgene

90-15-3

α-naphthol

63-25-2

1-naphthalenol methylcarbamate

Conditions
ConditionsYield
With methylamine In toluene
50-00-0

formaldehyd

63-25-2

1-naphthalenol methylcarbamate

39073-17-1

Chloromethyl-methyl-carbamic acid naphthalen-1-yl ester

Conditions
ConditionsYield
With thionyl chloride
63-25-2

1-naphthalenol methylcarbamate

74-89-5

methylamine

Conditions
ConditionsYield
aluminium In water; acetonitrile Product distribution; Irradiation; influence of aluminum foil;;
63-25-2

1-naphthalenol methylcarbamate

A

90-15-3

α-naphthol

B

74-89-5

methylamine

Conditions
ConditionsYield
With water; aluminum oxide In methanol at 57℃; Mechanism; other temperature, flow velocity;
63-25-2

1-naphthalenol methylcarbamate

5266-96-6

Carbaryl methylol

Conditions
ConditionsYield
With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride; dihydrogen peroxide for 0.5h; Ambient temperature;
63-25-2

1-naphthalenol methylcarbamate

90-15-3

α-naphthol

Conditions
ConditionsYield
With rabbit serum albumin at 37℃; for 5h; pH=7.4; Enzyme kinetics;
With bovin serum albumin Kinetics; aq. buffer; Enzymatic reaction;
With potassium hydroxide at 20℃; under 760.051 Torr; Electrochemical reaction; Inert atmosphere;
With sodium hydroxide In water at 80℃; for 10h;
63-25-2

1-naphthalenol methylcarbamate

A

90-15-3

α-naphthol

B

130-15-4

[1,4]naphthoquinone

C

(phthalic acid-O-)yl N-methylcarbamate

Conditions
ConditionsYield
With dihydrogen peroxide; iron(II); sodium chloride at 24.7℃; Product distribution; Activation energy; Further Variations:; Temperatures; var. ratio of reagents; Electrochemical reaction;
With dihydrogen peroxide; iron; sodium chloride In water at 25℃; Activation energy; Product distribution; Further Variations:; Temperatures; Electrolysis;
63-25-2

1-naphthalenol methylcarbamate

67271-09-4

N,N'-bis-(dibutylamino)disulfide

67316-53-4

1-naphthyl (dibutylaminothio)methylcarbamate

Conditions
ConditionsYield
With sulfuryl dichloride; triethylamine In hexane; water
63-25-2

1-naphthalenol methylcarbamate

C18H16N2O3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water
2: hydrogenchloride; sodium nitrite / water
View Scheme
63-25-2

1-naphthalenol methylcarbamate

3019-88-3

sodium naphtholate

Conditions
ConditionsYield
With sodium hydroxide In water
624-92-0

Dimethyldisulphide

63-25-2

1-naphthalenol methylcarbamate

137-41-7

potassium N-methyldithiocarbamate

Conditions
ConditionsYield
With potassium hydroxide In water; acetonitrile for 0.0111111h; Time; Microwave irradiation;
63-25-2

1-naphthalenol methylcarbamate

C76H66N6O6

C12H11NO2*C76H66N6O6

Conditions
ConditionsYield
In ethanol
7647-01-0

hydrogenchloride

63-25-2

1-naphthalenol methylcarbamate

(S)-1-((2-acetamidoethyl)thio)-4-methyl-1-oxopentan-2-yl (R)-3-((tert-butoxycarbonyl)amino)-2-methylpropanoate

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol
7647-01-0

hydrogenchloride

63-25-2

1-naphthalenol methylcarbamate

(S)-1-((2-acetamidoethyl)thio)-4-methyl-1-oxopentan-2-yl 3-((tert-butoxycarbonyl)amino)-2,2-dimethylpropanoate

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol
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    63-25-2 Carbaryl

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Chemistry

IUPAC Name: naphthalen-1-yl N-methylcarbamate 
Empirical Formula: C12H11NO2
Molecular Weight: 201.2212g/mol
EINECS: 200-555-0 
Structure of Carbaril (CAS NO.63-25-2):

Index of Refraction: 1.611
Molar Refractivity: 59.03 cm3
Molar Volume: 169.9 cm3
Polarizability: 23.4×10-24cm3
Surface Tension: 45.1 dyne/cm
Density: 1.183 g/cm3
Flash Point: 153 °C
Enthalpy of Vaporization: 57.18 kJ/mol 
Melting point: 142 ºC
Boiling Point: 329.3 °C at 760 mmHg
Vapour Pressure: 0.000179 mmHg at 25°C 
Water solubility: Insoluble. 0.00826 g/100 mL 
Product Categories: Nitrogen Compounds;Organic Building Blocks;Protected Amines;AcaricidesAlphabetic;CA - CGPesticides;CarbamatesMethod Specific;Endocrine Disruptors (Draft)Method Specific;C;EPA;Insecticides;Oeko-Tex Standard 100;Pesticides;Pesticides&Metabolites;AcaricidesPesticides;PesticidesAlphabetic;SA - SM;S;AcaricidesPesticides&Metabolites;Alpha sort;CAlphabetic;PesticidesPesticides&Metabolites;Plant growth regulators
Canonical SMILES: CNC(=O)OC1=CC=CC2=CC=CC=C21
InChI: InChI=1S/C12H11NO2/c1-13-12(14)15-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14)
InChIKey: CVXBEEMKQHEXEN-UHFFFAOYSA-N

History

 Carbaryl is a colorless white crystalline solid commonly sold under the brand name Sevin, a trademark of the Bayer Company. Union Carbide discovered carbaryl and introduced it commercially in 1958. Bayer purchased Aventis CropScience in 2002, a company that included Union Carbide pesticide operations.
 

Uses

 Carbaryl is used chiefly as an insecticide.

Toxicity Data With Reference

1.    

skn-rbt 12 mg/24H SEV

    JAFCAU    Journal of Agricultural and Food Chemistry. 9 (1961),30.
2.    

eye-rbt 500 mg/24H MOD

    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,164.
3.    

mmo-sat 250 µg/plate

    RPZHAW    Roczniki Panstwowego Zakladu Higieny. 30 (1979),81.
4.    

mma-hmn:fbr 1 µmol/L

    MUREAV    Mutation Research. 42 (1977),161.
5.    

dns-hmn:fbr 1 µmol/L

    MUREAV    Mutation Research. 42 (1977),161.
6.    

cyt-hmn:emb 40 µg/kg

    ZDVKAP    Zdravookhranenie. Public Health. 20 (4)(1977),14.
7.    

orl-man TDLo:500 mg/kg:PNS

    NEURAI    Neurology. 37 (1987),1229.
8.    

orl-rat LD50:230 mg/kg

    TXAPA9    Toxicology and Applied Pharmacology. 11 (1967),546.
9.    

skn-rat LD50:4000 mg/kg

    85DPAN    Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel Werner Perkow,Berlin, Germany.: Verlag Paul Parey,1971/76.
10.    

ipr-rat LD50:64 mg/kg

    PSEBAA   

Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 12 , 1976,p. 37.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Community Right-To-Know List.

Safety Profile

Hazard Codes: HarmfulXn,DangerousN,FlammableF
Risk Statements: 22-40-50-67-65-50/53-38-11
R22:Harmful if swallowed. 
R40:Limited evidence of a carcinogenic effect. 
R50:Very toxic to aquatic organisms. 
R67:Vapours may cause drowsiness and dizziness. 
R65:Harmful: may cause lung damage if swallowed. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R38:Irritating to skin. 
R11:Highly flammable. .
Safety Statements: 22-24-36/37-46-61-2-62-60 
S22:Do not breathe dust. 
S24:Avoid contact with skin. 
S36/37:Wear suitable protective clothing and gloves. 
S46:If swallowed, seek medical advice immediately and show this container or label. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets. 
S2:Keep out of the reach of children. 
S62:If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. 
S60:This material and its container must be disposed of as hazardous waste.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: FC5950000
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion, intravenous, intraperitoneal, and possibly other routes. Human systemic effects by ingestion: sensory change involving peripheral nerves and muscle weakness. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. An eye and severe skin irritant. Absorbed by all routes, although skin absorption is slow. No accumulation in tissue. Symptoms include blurred vision, headache, stomachache, vomiting. Symptoms similar to but less severe than those due to parathion. A reversible cholinesterase inhibitor. See also CARBAMATES and ESTERS. When heated to decomposition it emits toxic fumes of NOx.    

 

Standards and Recommendations

OSHA PEL: TWA 5 mg/m3
ACGIH TLV: TWA 5 mg/m3; Not Classifiable as a Human Carcinogen
DFG MAK: 5 mg/m3
NIOSH REL: (Carbaryl) TWA 5 mg/m3

Analytical Methods

For occupational chemical analysis use OSHA: #ID-63 or NIOSH: Carbaryl, 5006.

Specification

  Carbaril , its cas register number is 63-25-2. It also can be called 1-Naphthalenol methylcarbamate ; 1-Naphthol methylcarbamate ; 1-Naphthyl N-methylcarbamate ; Arylam ; Dicarbam ; Bug Master ; Carbamec ; Carbamine ; Carbatox ; Carbomate ; Carpolin ; Carylderm ; Cekubaryl ; Clinicide ; Denapon ; Derbac ; Devicarb ; Hexavin ; Karbaspray ; Murvin ; NAC ; OMS 29, UC 7744 ; Padrin ; Panam ; Patrin ; Ravyon ; Savit ; Seffein ; Septene ; Sevimol ; Sevin ; Tercyl; Thinsec ; Tornado ; Tricarnam . Carbaril (CAS NO.63-25-2) is a colourless solid.