Product Name

  • Name

    Chlorpropham

  • EINECS 202-925-7
  • CAS No. 101-21-3
  • Article Data18
  • CAS DataBase
  • Density 1.226 g/cm3
  • Solubility 0.009 g/100 ml very poor in water
  • Melting Point 41 °C
  • Formula C10H12ClNO2
  • Boiling Point 251.1 °C at 760 mmHg
  • Molecular Weight 213.664
  • Flash Point 105.7 °C
  • Transport Information UN 3077 9/PG 3
  • Appearance beige to brown solid
  • Safety Moderately toxic by ingestion and intraperitoneal routes. Questionable carcinogen with experimental neoplastigenic and teratogenic data. Human mutation data reported. An herbicide. When heated to decomposition it emits highly toxic fumes of Cl, NOx, and phosgene.
  • Risk Codes 22-51/53-36-20/21/22-11
  • Molecular Structure Molecular Structure of 101-21-3 (Chlorpropham)
  • Hazard Symbols HarmfulXn,DangerousN,FlammableF
  • Synonyms IsopropylN-(3-chlorophenyl)carbamate;Isopropyl N-(m-chlorophenyl)carbamate;Isopropylm-chlorocarbanilate;Keim-Stop;Liro CIPC;Metoxon;Mirvale;NSC 29466;Nexoval;Preventol;Preventol 56;Triherbicide CIPC;Y 3;m-Chlorocarbanilicacid isopropyl ester;Carbamic acid,N-(3-chlorophenyl)-, 1-methylethyl ester;Carbamicacid, (3-chlorophenyl)-, 1-methylethyl ester (9CI);Carbanilic acid, m-chloro-,isopropyl ester (6CI,7CI,8CI);Bud Nip;Bygran;CI-IPC;CIPC;Chlor IFC;ChlorIFK;Chlor IPC;Chloro-IPC;Cl-IFK;Elbanil;Furloe;Furloe 3EC;IPCPC;Isopropyl 3-chlorocarbanilate;
  • PSA 38.33000
  • LogP 3.36990

Synthetic route

1-azido-3-chlorobenzene
3296-06-8

1-azido-3-chlorobenzene

carbon monoxide
201230-82-2

carbon monoxide

isopropyl alcohol
67-63-0

isopropyl alcohol

CHLORPROPHAM
101-21-3

CHLORPROPHAM

Conditions
ConditionsYield
With triethylamine; palladium dichloride In N,N-dimethyl acetamide at 70℃; under 760.051 Torr; for 24h; Schlenk technique;94%
potassium cyanate
590-28-3

potassium cyanate

1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

isopropyl alcohol
67-63-0

isopropyl alcohol

CHLORPROPHAM
101-21-3

CHLORPROPHAM

Conditions
ConditionsYield
With copper(l) iodide; 2-(2,6-dimethylphenyl-amino)-2-oxoacetic acid potassium salt at 110℃; for 24h; Inert atmosphere;85%
di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

3-chloro-aniline
108-42-9

3-chloro-aniline

CHLORPROPHAM
101-21-3

CHLORPROPHAM

Conditions
ConditionsYield
With copper diacetate at 20℃; for 1h; Inert atmosphere;81%
potassium cyanate
590-28-3

potassium cyanate

3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

isopropyl alcohol
67-63-0

isopropyl alcohol

CHLORPROPHAM
101-21-3

CHLORPROPHAM

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; 2-((2-methylnaphthalen-1-yl)amino)-2-oxoacetic acid at 100℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;67%
carbon monoxide
201230-82-2

carbon monoxide

3-chloro-aniline
108-42-9

3-chloro-aniline

isopropyl alcohol
67-63-0

isopropyl alcohol

CHLORPROPHAM
101-21-3

CHLORPROPHAM

Conditions
ConditionsYield
With Oxone; chloro(1,5-cyclooctadiene)rhodium(I) dimer In toluene at 20 - 100℃; Schlenk technique; Cooling with liquid nitrogen;50%
3-chloro-aniline
108-42-9

3-chloro-aniline

CHLORPROPHAM
101-21-3

CHLORPROPHAM

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride / water / 0 °C
1.2: 0.17 h
2.1: palladium dichloride; triethylamine / N,N-dimethyl acetamide / 24 h / 70 °C / 760.05 Torr / Schlenk technique
View Scheme
2-(2-methylphenyl)pyridine
10273-89-9

2-(2-methylphenyl)pyridine

CHLORPROPHAM
101-21-3

CHLORPROPHAM

C22H22N2O2

C22H22N2O2

Conditions
ConditionsYield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 24h; Inert atmosphere;92%
CHLORPROPHAM
101-21-3

CHLORPROPHAM

isopropyl 3-hydroxycarbanilate
2610-61-9

isopropyl 3-hydroxycarbanilate

Conditions
ConditionsYield
In water at 20℃; Kinetics; Quantum yield; Decomposition; Oxidation; UV-irradiation;70%
CHLORPROPHAM
101-21-3

CHLORPROPHAM

isopropyl chloroformate
108-23-6

isopropyl chloroformate

(3-chloro-phenyl)-μ-imido-dicarbonic acid diisopropyl ester
109846-95-9

(3-chloro-phenyl)-μ-imido-dicarbonic acid diisopropyl ester

formaldehyd
50-00-0

formaldehyd

CHLORPROPHAM
101-21-3

CHLORPROPHAM

Isopropyl-N-chloromethyl-N-(3-chlorophenyl)-carbamate
39074-64-1

Isopropyl-N-chloromethyl-N-(3-chlorophenyl)-carbamate

Conditions
ConditionsYield
With thionyl chloride
oxalyl dichloride
79-37-8

oxalyl dichloride

CHLORPROPHAM
101-21-3

CHLORPROPHAM

(3-chloro-phenyl)-oxazolidinetrione
7038-95-1

(3-chloro-phenyl)-oxazolidinetrione

Conditions
ConditionsYield
In toluene for 6h; Heating;
Methoxyacetyl chloride
38870-89-2

Methoxyacetyl chloride

CHLORPROPHAM
101-21-3

CHLORPROPHAM

(3-Chloro-phenyl)-(2-methoxy-acetyl)-carbamic acid isopropyl ester
6733-21-7

(3-Chloro-phenyl)-(2-methoxy-acetyl)-carbamic acid isopropyl ester

Conditions
ConditionsYield
(i) NaH, (ii) /BRN= 1740244/; Multistep reaction;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

benzyl(methyl)carbamic chloride
32366-02-2

benzyl(methyl)carbamic chloride

C19H21ClN2O3

C19H21ClN2O3

Conditions
ConditionsYield
(i) NaH, (ii) /BRN= 2831794/; Multistep reaction;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

N-methyl-N-cyclohexylaminocarbonyl chloride
35028-38-7

N-methyl-N-cyclohexylaminocarbonyl chloride

C18H25ClN2O3

C18H25ClN2O3

Conditions
ConditionsYield
(i) NaH, (ii) /BRN= 6313397/; Multistep reaction;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

acetic anhydride
108-24-7

acetic anhydride

Acetyl-(3-chloro-phenyl)-carbamic acid isopropyl ester
5833-26-1

Acetyl-(3-chloro-phenyl)-carbamic acid isopropyl ester

Conditions
ConditionsYield
With sulfuric acid Heating;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

(3-Chloro-phenyl)-(4-nitro-benzoyl)-carbamic acid isopropyl ester
5833-29-4

(3-Chloro-phenyl)-(4-nitro-benzoyl)-carbamic acid isopropyl ester

Conditions
ConditionsYield
(i) NaH, (ii) /BRN= 473192/; Multistep reaction;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

diphenylcarbamic chloride
83-01-2

diphenylcarbamic chloride

C23H21ClN2O3

C23H21ClN2O3

Conditions
ConditionsYield
(i) NaH, (ii) /BRN= 515312/; Multistep reaction;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

Trichloroacetyl chloride
76-02-8

Trichloroacetyl chloride

(3-Chloro-phenyl)-(2,2,2-trichloro-acetyl)-carbamic acid isopropyl ester
6075-41-8

(3-Chloro-phenyl)-(2,2,2-trichloro-acetyl)-carbamic acid isopropyl ester

Conditions
ConditionsYield
(i) NaH, (ii) /BRN= 774120/; Multistep reaction;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

m-nitrobenzoic acid chloride
121-90-4

m-nitrobenzoic acid chloride

(3-Chloro-phenyl)-(3-nitro-benzoyl)-carbamic acid isopropyl ester

(3-Chloro-phenyl)-(3-nitro-benzoyl)-carbamic acid isopropyl ester

Conditions
ConditionsYield
(i) NaH, toluene, (ii) /BRN= 777186/; Multistep reaction;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

N,N-Dimethylcarbamoyl chloride
79-44-7

N,N-Dimethylcarbamoyl chloride

C13H17ClN2O3
5833-28-3

C13H17ClN2O3

Conditions
ConditionsYield
(i) NaH, (ii) /BRN= 878197/; Multistep reaction;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

3-Methylbenzoyl chloride
1711-06-4

3-Methylbenzoyl chloride

(3-Chloro-phenyl)-(3-methyl-benzoyl)-carbamic acid isopropyl ester
5833-30-7

(3-Chloro-phenyl)-(3-methyl-benzoyl)-carbamic acid isopropyl ester

Conditions
ConditionsYield
(i) NaH, (ii) /BRN= 878419/; Multistep reaction;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

A

isopropyl carbamate
1746-77-6

isopropyl carbamate

B

(2-Hydroxy-5-chlorophenyl)carbamic acid isopropyl ester
27898-06-2

(2-Hydroxy-5-chlorophenyl)carbamic acid isopropyl ester

C

Isopropyl-3-chlor-5-hydroxycarbanilat
34061-87-5

Isopropyl-3-chlor-5-hydroxycarbanilat

D

3-chloro-aniline
108-42-9

3-chloro-aniline

Conditions
ConditionsYield
Kinetics; Decomposition; Oxidation; ultrasonication;
CHLORPROPHAM
101-21-3

CHLORPROPHAM

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C10H12ClNO2*2C42H70O35

C10H12ClNO2*2C42H70O35

Conditions
ConditionsYield
In ethanol; water at 70℃; for 24h;

Chlorpropham 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. 55.(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) . EPA Genetic Toxicology Program.

Chlorpropham Specification

Basic Information of Chlorpropham:
The Chlorpropham, with the CAS registry number 101-21-3, is also known as Isopropyl N-(3-chlorophenyl)carbamate; Isopropyl 3-chlorocarbanilate. It belongs to the product categories of Amides;Building Blocks;C8 to C20+;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks.This chemical's molecular formula is C10H12ClNO2 and molecular weight is 213.66.Its EINECS number is 202-925-7. What's more,Its systematic name is Chlorpropham. It is a carbamate that is used as an herbicide and as a plant growth regulator.It is beige to brown chunky solid,and it is Stable. Incompatible with strong acids, strong bases, strong oxidizing agents. Chlorpropham is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.

Physical properties about Chlorpropham are:
(1)ACD/LogP: 3.569; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.57; (4)ACD/LogD (pH 7.4): 3.57; (5)ACD/BCF (pH 5.5): 303.84; (6)ACD/BCF (pH 7.4): 303.84; (7)ACD/KOC (pH 5.5): 2082.96; (8)ACD/KOC (pH 7.4): 2082.96; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.561; (13)Molar Refractivity: 56.389 cm3; (14)Molar Volume: 174.219 cm3; (15)Surface Tension: 41.9949989318848 dyne/cm; (16)Density: 1.226 g/cm3; (17)Flash Point: 105.653 °C; (18)Enthalpy of Vaporization: 48.838 kJ/mol; (19)Boiling Point: 251.086 °C at 760 mmHg; (20)Vapour Pressure: 0.0209999997168779 mmHg at 25°C;

Safety Information of Chlorpropham:
The Chlorpropham is highly Flammable. It is harmful by inhalation, in contact with skin and if swallowed ,and irritating to the eyes And it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.When you use it, wear suitable protective clothing and gloves .Avoid release to the environment. Refer to special instructions safety data sheet.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES:Clc1cc(NC(=O)OC(C)C)ccc1;
(2)Std. InChI:InChI=1S/C10H12ClNO2/c1-7(2)14-10(13)12-9-5-3-4-8(11)6-9/h3-7H,1-2H3,(H,12,13);
(3)Std. InChIKey:CWJSHJJYOPWUGX-UHFFFAOYSA-N.

The toxicity data of Chlorpropham as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
duck LD50 unreported > 2gm/kg (2000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C73, 1991.
mammal (species unspecified) LD50 unreported 3gm/kg (3000mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 200, 1971.
mouse LD50 intraperitoneal 2600mg/kg (2600mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 175, Pg. 496, 1981.
mouse LD50 oral 3650mg/kg (3650mg/kg)   Food Additives and Contaminants. Vol. 16, Pg. 173, 1999.
rabbit LD50 oral 5gm/kg (5000mg/kg)   Pharmacological Reviews. Vol. 14, Pg. 225, 1962.
rat LD50 intraperitoneal 700mg/kg (700mg/kg)   Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 175, Pg. 496, 1981.
rat LD50 oral 1200mg/kg (1200mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Archives of Environmental Health. Vol. 19, Pg. 621, 1969.
rat LD50 unreported 3350mg/kg (3350mg/kg)   Environmental Quality and Safety, Supplement. Vol. 3, Pg. 618, 1975.

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